WO2016026911A2 - Methods for forming aerosol-generating substrates having a reduced amount of tobacco specific nitrosamines - Google Patents

Methods for forming aerosol-generating substrates having a reduced amount of tobacco specific nitrosamines Download PDF

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Publication number
WO2016026911A2
WO2016026911A2 PCT/EP2015/069091 EP2015069091W WO2016026911A2 WO 2016026911 A2 WO2016026911 A2 WO 2016026911A2 EP 2015069091 W EP2015069091 W EP 2015069091W WO 2016026911 A2 WO2016026911 A2 WO 2016026911A2
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WO
WIPO (PCT)
Prior art keywords
tobacco
aerosol
generating substrate
amount
slurry
Prior art date
Application number
PCT/EP2015/069091
Other languages
French (fr)
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WO2016026911A3 (en
Inventor
Gerhard Lang
Jan Carlos HUFNAGEL
Original Assignee
Philip Morris Products S.A.
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 Philip Morris Products S.A. filed Critical Philip Morris Products S.A.
Priority to EP15753036.1A priority Critical patent/EP3182844B1/en
Priority to JP2017508991A priority patent/JP6602845B2/en
Priority to US15/504,487 priority patent/US20170238597A1/en
Priority to BR112017001255-3A priority patent/BR112017001255B1/en
Priority to PL15753036T priority patent/PL3182844T3/en
Priority to ES15753036.1T priority patent/ES2690876T3/en
Priority to RU2017108898A priority patent/RU2685845C2/en
Priority to CN201580042554.0A priority patent/CN106714587B/en
Priority to KR1020177002813A priority patent/KR102486705B1/en
Publication of WO2016026911A2 publication Critical patent/WO2016026911A2/en
Publication of WO2016026911A3 publication Critical patent/WO2016026911A3/en

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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
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/22—Treatment of tobacco products or tobacco substitutes by application of electric or wave energy or particle radiation
    • 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
    • A24B15/16—Chemical features of tobacco products or tobacco substitutes of tobacco substitutes
    • A24B15/167—Chemical features of tobacco products or tobacco substitutes of tobacco substitutes in liquid or vaporisable form, e.g. liquid compositions for electronic cigarettes
    • 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
    • A24B15/241—Extraction of specific substances
    • A24B15/243—Nicotine
    • 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
    • A24B15/241—Extraction of specific substances
    • A24B15/245—Nitrosamines
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24F—SMOKERS' REQUISITES; MATCH BOXES; SIMULATED SMOKING DEVICES
    • A24F40/00—Electrically operated smoking devices; Component parts thereof; Manufacture thereof; Maintenance or testing thereof; Charging means specially adapted therefor
    • A24F40/10—Devices using liquid inhalable precursors

Definitions

  • the present invention relates to methods of forming aerosol-generating substrates having a reduced amount of tobacco-specific nitrosamines.
  • the aerosol-generating substrates formed according to the present invention find particular application as substrates for electrical smoking systems.
  • a known electrically operated smoking system comprises a shell and a replaceable mouthpiece wherein the shell comprises an electric power supply and electric circuitry.
  • the mouthpiece comprises a liquid storage portion, a capillary wick having a first end that extends into the liquid storage portion for contact with liquid therein, and a heating element for heating a second end of the capillary wick.
  • liquid is transferred from the liquid storage portion towards the heating element by capillary action in the wick. Liquid at the second end of the wick is vaporised by the heating element.
  • a known electrically operated smoking system comprises a resistively heated ceramic heater blade that is inserted into a tobacco rod to generate an aerosol comprising volatile compounds contained within the tobacco.
  • Cast leaf tobacco products are formed by casting and drying a tobacco slurry.
  • Liquid nicotine formulations and tobacco slurries are typically derived from cured tobacco materials.
  • liquid nicotine formulations and heated tobacco products formed from tobacco slurries may be undesirably contaminated with tobacco-specific nitrosamines (TSNAs), such as /V-nitrosonornicotine (NNN), 4-(methylnitrosamino)-1 -(3-pyridyl)-1 -butanone (NNK), N- nitrosoanatabine (NAT) and /V-Nitrosoanabasine (NAB).
  • TSNAs tobacco-specific nitrosamines
  • NNN /V-nitrosonornicotine
  • NNK 4-(methylnitrosamino)-1 -(3-pyridyl)-1 -butanone
  • NAT N- nitrosoanatabine
  • NAB /V-Nitrosoanabasine
  • a known method for reducing TSNA contamination of nicotine purified from cured tobacco materials includes chemical treatment of the tobacco plants prior to harvest to increase antioxidant production and prevent TSNA formation during curing.
  • the process of treating the tobacco plants is time consuming, costly, and care must be taken to prevent environmental contamination with the chemicals used.
  • the present invention provides a method of forming an aerosol- generating substrate, the method comprising providing a liquid nicotine source containing at least one tobacco-specific nitrosamine, mixing the liquid nicotine source with a solvent and at least one aerosol former to form an aerosol-generating substrate, and irradiating the aerosol-generating substrate with ultraviolet light to reduce the amount of the at least one tobacco-specific nitrosamine.
  • aerosol-generating substrate refers to a substrate capable of releasing volatile compounds, which can form an aerosol.
  • the aerosols generated from aerosol- generating substrates according to the invention may be visible or invisible and may include vapours (for example, fine particles of substances, which are in a gaseous state, that are ordinarily liquid or solid at room temperature) as well as gases and liquid droplets of condensed vapours.
  • the method according to the first aspect of the present invention advantageously eliminates the need for chemical removal processes.
  • the method according to the first aspect of the present invention may therefore be cheaper, produce little or no waste, and minimise any health and environmental concerns when compared to existing processes.
  • the present invention utilises UV irradiation of an aerosol-generating substrate comprising a liquid nicotine source it can be applied to solutions of nicotine already separated from the tobacco plant material. This is in contrast to known methods, such as the chemical treatment method described above that requires treatment of the tobacco plant during cultivation and prior to harvest, and other known methods that attempt to reduce TSNA content by optimising the conditions under which the harvested tobacco is cured.
  • the solvent may comprise water or an organic solvent. Additionally, or alternatively, the at least one aerosol former may comprise at least one of propylene glycol and glycerin.
  • the ultraviolet irradiance of the aerosol- generating substrate is preferably at least about 4 milliwatts per square centimetre, more preferably at least about 40 milliwatts per square centimetre, most preferably at least about 400 milliwatts per square centimetre.
  • UV irradiance at or above these levels can provide significant reduction of the amount of the one or more TSNAs within a relatively short time period.
  • the irradiation level of a fluid can be determined using a UV radiometer.
  • the UV irradiance step preferably comprises irradiating the aerosol-generating substrate with ultraviolet light for less than about 180 minutes, more preferably less than about 120 minutes, yet more preferably less than about 60 minutes, most preferably less than about 30 minutes. Irradiating the aerosol-generating substrate with ultraviolet light for a period within these ranges can provide significant reduction in the amount of the one or more TSNAs. These time periods refer to the total duration of the UV irradiation and the total duration may be a single consecutive period of irradiance, or two or more discrete periods of irradiance.
  • the irradiating step comprises irradiating the aerosol- generating substrate with UV light for 30 minutes
  • the irradiance may be conducted in a single 30 minute step, or in two separate steps each of 15 minutes long.
  • increasing the UV irradiance will yield a higher reduction in TSNA content over a fixed time period. Therefore, to optimise the efficiency of the TSNA reduction process, a high UV irradiance is preferably used to minimise the total time required to reduce the TSNA content to a desired level.
  • the amount of the at least one tobacco-specific nitrosamine present in the aerosol-generating substrate after the irradiation step is preferably less than about 75 percent by weight of the amount of the at least one tobacco-specific nitrosamine present in the aerosol-generating substrate before the irradiation step, more preferably less than about 50 percent by weight of the amount of the at least one tobacco-specific nitrosamine present in the aerosol-generating substrate before the irradiation step, most preferably less than about 25 percent by weight of the amount of the at least one tobacco-specific nitrosamine present in the aerosol-generating substrate before the irradiation step.
  • the reduction in the amount of the at least one tobacco-specific nitrosamine can be increased by increasing at least one of the irradiance and the duration of the irradiating step.
  • the amount of the at least one tobacco-specific nitrosamine present in the aerosol- generating substrate decreases in a generally exponential manner during the period of irradiation.
  • the present invention provides a method of forming an aerosol-generating substrate, the method comprising providing a tobacco slurry containing at least one tobacco-specific nitrosamine, irradiating the tobacco slurry with ultraviolet light to reduce the amount of the at least one tobacco-specific nitrosamine, and drying the tobacco slurry to form an aerosol-generating substrate.
  • the method according to the second aspect of present invention advantageously eliminates the need for chemical removal processes.
  • the method according to the second aspect of the present invention may therefore be cheaper, produce little or no waste, and minimise any health and environmental concerns when compared to existing processes.
  • the present invention utilises UV irradiation of a tobacco slurry it can be applied to tobacco plant material that has already been harvested and processed. This is in contrast to known methods, such as the chemical treatment method described above that requires treatment of the tobacco plant during cultivation and prior to harvest, and other known methods that attempt to reduce TSNA content by optimising the conditions under which the harvested tobacco is cured.
  • the tobacco slurry may be cast and dried to form a cast leaf tobacco.
  • the tobacco slurry may be irradiated before casting, after casting, or both.
  • Such a method may be advantageous in that it would allow for integration of an apparatus capable of irradiating the slurry directly into a casting line.
  • the term "cast leaf tobacco” refers to a homogenised tobacco material typically formed by casting a tobacco slurry comprising particulate tobacco and one or more binders onto a conveyor belt or other surface, drying the cast slurry to form a sheet of homogenised tobacco material and removing the sheet of homogenised tobacco material from the support surface.
  • the ultraviolet irradiance of the tobacco slurry is preferably at least about 4 milliwatts per square centimetre, more preferably at least about 40 milliwatts per square centimetre, most preferably at least about 400 milliwatts per square centimetre.
  • UV irradiance at or above these levels can provide significant reduction of the amount of the one or more TSNAs within a relatively short time period.
  • the irradiation level of a fluid can be determined using a UV radiometer.
  • the UV irradiance step preferably comprises irradiating the tobacco slurry with ultraviolet light for less than about 180 minutes, more preferably less than about 120 minutes, yet more preferably less than about 60 minutes, most preferably less than about 30 minutes. Irradiating the tobacco slurry with ultraviolet light for a period within these ranges can provide significant reduction in the amount of the one or more TSNAs.
  • These time periods refer to the total duration of the UV irradiation and the total duration may be a single consecutive period of irradiance, or two or more discrete periods of irradiance.
  • the irradiance may be conducted in a single 30 minute step, or in two separate steps each of 15 minutes long.
  • the total irradiation time may be varied according to the thickness of the tobacco slurry. That is, the total irradiation time may be increased as the thickness of the tobacco slurry is increased.
  • a high UV irradiance is preferably used to minimise the total time required to reduce the TSNA content to a desired level.
  • the amount of the at least one tobacco-specific nitrosamine present in the tobacco slurry after the irradiation step is preferably less than about 75 percent by weight of the amount of the at least one tobacco-specific nitrosamine present in the tobacco slurry before the irradiation step, more preferably less than about 50 percent by weight of the amount of the at least one tobacco-specific nitrosamine present in the tobacco slurry before the irradiation step, most preferably less than about 25 percent by weight of the amount of the at least one tobacco-specific nitrosamine present in the tobacco slurry before the irradiation step.
  • the reduction in the amount of the at least one tobacco-specific nitrosamine can be increased by increasing at least one of the irradiance and the duration of the irradiating step.
  • the amount of the at least one tobacco-specific nitrosamine present in the tobacco slurry decreases in a generally exponential manner during the period of irradiation.
  • the ultraviolet light used in the irradiating step preferably has a peak intensity at a wavelength of at least about 315 nanometres, more preferably at least about 335 nanometres, most preferably at least about 350 nanometres.
  • the ultraviolet light preferably has a peak intensity at a wavelength of less than about 400 nanometres, more preferably less than about 390 nanometres, most preferably less than about 380 nanometres.
  • the ultraviolet light has a peak intensity at a wavelength of between about 315 nanometres and about 400 nanometres, more preferably between about 335 nanometres and about 390 nanometres, most preferably between about 350 nanometres and about 380 nanometres.
  • the ultraviolet light may have a peak intensity at a wavelength of about 365 nanometres.
  • UV light having a peak intensity at a wavelength within these ranges falls within the UV-A portion of the ultraviolet spectrum, which the present inventors have recognised provides effective reduction of TSNAs and is optimised for transmission through glass and common UV transparent polymeric packaging materials. Therefore, methods in accordance with these embodiments are particularly suited for the treatment of aerosol- generating substrates or tobacco slurries that are housed within a glass container, or housed within a container comprising a glass window through which the UV light is transmitted. Use of radiation having a shorter wavelength is undesirable, as it may result in undesirable chemical decomposition of the nicotine.
  • the present invention provides an aerosol-generating substrate formed using the method according to either the first aspect of the invention or the second aspect of the invention, in accordance with any of the embodiments described above.
  • N-nitrosonornicotine N-nitrosonornicotine
  • NNK 4-(methylnitrosamino)-1 -(3-pyridyl)-1 - butanone (NNK) (380 and 613 nanograms per millilitre, respectively) were added to three different liquid aerosol-generating substrates each consisting of nicotine, glycerin, propylene glycol and water (2:10:68:20, 2:39:39:20 and 2:68:10:20 by weight). Aliquots of these solutions were placed in clear glass vials and irradiated for a specified time (0, 15, 30, 60, 120 or 240 minutes) with ultraviolet radiation (wavelength of 365 nanometres; lamp nominal power of 8 watts; distance to lamp of 3 centimetres).
  • NNN and NNK content was analyzed.
  • the UV irradiation caused a time-dependent decrease of NNK and NNN in all three nicotine/glycerin/propylene-glycol/water mixtures. Nicotine concentrations were not affected.
  • the nitrosamine decay is approximately exponential with respect to irradiation time.
  • Half-lives for NNN and NNK were in the ranges of 30-50 minutes and 60-70 minutes, respectively. The results are illustrated in Figures 1 to 3.
  • a sample sheet of cast tobacco slurry having a thickness of 0.20 to 0.22 millimetres after drying to 195 to 200 grams per square metre was irradiated for 150 minutes, each, on both sides with UV light at a wavelength of 365 nanometres and an intensity of 4.5 milliwatts per square centimetre.
  • the irradiated cast leaf sample and a non-irradiated control were analysed for NNK, NNN, and nicotine content by mass spectroscopy. As compared to the control, the irradiated sample indicated no effect on nicotine content, a reduction of 12 percent in NNK content, and a reduction of 26 percent in NNN content.

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Abstract

There is provided a method of forming an aerosol-generating substrate, the method comprising providing a liquid nicotine source containing at least one tobacco-specific nitrosamine, mixing the liquid nicotine source with a solvent and at least one aerosol former to form an aerosol-generating substrate,and irradiating the aerosol-generating substrate with ultraviolet light to reduce the amount of the at least one tobacco-specific nitrosamine. Also provided is a method of forming an aerosol-generating substrate, the method comprising providing a tobacco slurry containing at least one tobacco-specific nitrosamine, irradiating the tobacco slurry with ultraviolet light to reduce the amount of the at least one tobacco-specific nitrosamine, and drying the tobacco slurry to form an aerosol-generating substrate.

Description

METHODS FOR FORMING AEROSOL-GENERATING SUBSTRATES HAVING A REDUCED AMOUNT OF TOBACCO-SPECIFIC NITROSAMINES
The present invention relates to methods of forming aerosol-generating substrates having a reduced amount of tobacco-specific nitrosamines. The aerosol-generating substrates formed according to the present invention find particular application as substrates for electrical smoking systems.
Electrically operated smoking systems that vaporise a liquid nicotine formulation to form an aerosol that is inhaled by a user are known in the art. For example, a known electrically operated smoking system comprises a shell and a replaceable mouthpiece wherein the shell comprises an electric power supply and electric circuitry. The mouthpiece comprises a liquid storage portion, a capillary wick having a first end that extends into the liquid storage portion for contact with liquid therein, and a heating element for heating a second end of the capillary wick. In use, liquid is transferred from the liquid storage portion towards the heating element by capillary action in the wick. Liquid at the second end of the wick is vaporised by the heating element.
Electrically operated smoking systems that heat a tobacco product, such as a cast leaf tobacco product, are also known. For example, a known electrically operated smoking system comprises a resistively heated ceramic heater blade that is inserted into a tobacco rod to generate an aerosol comprising volatile compounds contained within the tobacco. Cast leaf tobacco products are formed by casting and drying a tobacco slurry.
Liquid nicotine formulations and tobacco slurries are typically derived from cured tobacco materials. As such, liquid nicotine formulations and heated tobacco products formed from tobacco slurries may be undesirably contaminated with tobacco-specific nitrosamines (TSNAs), such as /V-nitrosonornicotine (NNN), 4-(methylnitrosamino)-1 -(3-pyridyl)-1 -butanone (NNK), N- nitrosoanatabine (NAT) and /V-Nitrosoanabasine (NAB).
A known method for reducing TSNA contamination of nicotine purified from cured tobacco materials includes chemical treatment of the tobacco plants prior to harvest to increase antioxidant production and prevent TSNA formation during curing. However, the process of treating the tobacco plants is time consuming, costly, and care must be taken to prevent environmental contamination with the chemicals used.
It would therefore be desirable to provide a method of reducing or eliminating TSNA contamination of nicotine that overcomes these difficulties associated with known methods of TSNA reduction.
According to a first aspect, the present invention provides a method of forming an aerosol- generating substrate, the method comprising providing a liquid nicotine source containing at least one tobacco-specific nitrosamine, mixing the liquid nicotine source with a solvent and at least one aerosol former to form an aerosol-generating substrate, and irradiating the aerosol-generating substrate with ultraviolet light to reduce the amount of the at least one tobacco-specific nitrosamine.
As used herein, the term "aerosol-generating substrate" refers to a substrate capable of releasing volatile compounds, which can form an aerosol. The aerosols generated from aerosol- generating substrates according to the invention may be visible or invisible and may include vapours (for example, fine particles of substances, which are in a gaseous state, that are ordinarily liquid or solid at room temperature) as well as gases and liquid droplets of condensed vapours.
By using ultraviolet (UV) light to reduce the amount of one or more TSNAs in an aerosol- generating substrate containing a liquid nicotine source, the method according to the first aspect of the present invention advantageously eliminates the need for chemical removal processes. The method according to the first aspect of the present invention may therefore be cheaper, produce little or no waste, and minimise any health and environmental concerns when compared to existing processes. Furthermore, since the present invention utilises UV irradiation of an aerosol-generating substrate comprising a liquid nicotine source it can be applied to solutions of nicotine already separated from the tobacco plant material. This is in contrast to known methods, such as the chemical treatment method described above that requires treatment of the tobacco plant during cultivation and prior to harvest, and other known methods that attempt to reduce TSNA content by optimising the conditions under which the harvested tobacco is cured.
The solvent may comprise water or an organic solvent. Additionally, or alternatively, the at least one aerosol former may comprise at least one of propylene glycol and glycerin.
In any of the embodiments described above, the ultraviolet irradiance of the aerosol- generating substrate is preferably at least about 4 milliwatts per square centimetre, more preferably at least about 40 milliwatts per square centimetre, most preferably at least about 400 milliwatts per square centimetre. UV irradiance at or above these levels can provide significant reduction of the amount of the one or more TSNAs within a relatively short time period. The irradiation level of a fluid can be determined using a UV radiometer.
Additionally, or alternatively, the UV irradiance step preferably comprises irradiating the aerosol-generating substrate with ultraviolet light for less than about 180 minutes, more preferably less than about 120 minutes, yet more preferably less than about 60 minutes, most preferably less than about 30 minutes. Irradiating the aerosol-generating substrate with ultraviolet light for a period within these ranges can provide significant reduction in the amount of the one or more TSNAs. These time periods refer to the total duration of the UV irradiation and the total duration may be a single consecutive period of irradiance, or two or more discrete periods of irradiance. For example, in those embodiments in which the irradiating step comprises irradiating the aerosol- generating substrate with UV light for 30 minutes, the irradiance may be conducted in a single 30 minute step, or in two separate steps each of 15 minutes long. Generally, increasing the UV irradiance will yield a higher reduction in TSNA content over a fixed time period. Therefore, to optimise the efficiency of the TSNA reduction process, a high UV irradiance is preferably used to minimise the total time required to reduce the TSNA content to a desired level. In any of the embodiments described above, the amount of the at least one tobacco-specific nitrosamine present in the aerosol-generating substrate after the irradiation step is preferably less than about 75 percent by weight of the amount of the at least one tobacco- specific nitrosamine present in the aerosol-generating substrate before the irradiation step, more preferably less than about 50 percent by weight of the amount of the at least one tobacco-specific nitrosamine present in the aerosol-generating substrate before the irradiation step, most preferably less than about 25 percent by weight of the amount of the at least one tobacco-specific nitrosamine present in the aerosol-generating substrate before the irradiation step. Generally, the reduction in the amount of the at least one tobacco-specific nitrosamine can be increased by increasing at least one of the irradiance and the duration of the irradiating step. For a given irradiance, the amount of the at least one tobacco-specific nitrosamine present in the aerosol- generating substrate decreases in a generally exponential manner during the period of irradiation.
According to a second aspect, the present invention provides a method of forming an aerosol-generating substrate, the method comprising providing a tobacco slurry containing at least one tobacco-specific nitrosamine, irradiating the tobacco slurry with ultraviolet light to reduce the amount of the at least one tobacco-specific nitrosamine, and drying the tobacco slurry to form an aerosol-generating substrate.
By using ultraviolet (UV) light to reduce the amount of one or more TSNAs in an aerosol- generating substrate formed from a tobacco slurry, the method according to the second aspect of present invention advantageously eliminates the need for chemical removal processes. The method according to the second aspect of the present invention may therefore be cheaper, produce little or no waste, and minimise any health and environmental concerns when compared to existing processes. Furthermore, since the present invention utilises UV irradiation of a tobacco slurry it can be applied to tobacco plant material that has already been harvested and processed. This is in contrast to known methods, such as the chemical treatment method described above that requires treatment of the tobacco plant during cultivation and prior to harvest, and other known methods that attempt to reduce TSNA content by optimising the conditions under which the harvested tobacco is cured.
The tobacco slurry may be cast and dried to form a cast leaf tobacco. In this case, the tobacco slurry may be irradiated before casting, after casting, or both. Such a method may be advantageous in that it would allow for integration of an apparatus capable of irradiating the slurry directly into a casting line.
As used herein, the term "cast leaf tobacco" refers to a homogenised tobacco material typically formed by casting a tobacco slurry comprising particulate tobacco and one or more binders onto a conveyor belt or other surface, drying the cast slurry to form a sheet of homogenised tobacco material and removing the sheet of homogenised tobacco material from the support surface.
In any of the embodiments described above, the ultraviolet irradiance of the tobacco slurry is preferably at least about 4 milliwatts per square centimetre, more preferably at least about 40 milliwatts per square centimetre, most preferably at least about 400 milliwatts per square centimetre. UV irradiance at or above these levels can provide significant reduction of the amount of the one or more TSNAs within a relatively short time period. The irradiation level of a fluid can be determined using a UV radiometer.
Additionally, or alternatively, the UV irradiance step preferably comprises irradiating the tobacco slurry with ultraviolet light for less than about 180 minutes, more preferably less than about 120 minutes, yet more preferably less than about 60 minutes, most preferably less than about 30 minutes. Irradiating the tobacco slurry with ultraviolet light for a period within these ranges can provide significant reduction in the amount of the one or more TSNAs. These time periods refer to the total duration of the UV irradiation and the total duration may be a single consecutive period of irradiance, or two or more discrete periods of irradiance. For example, in those embodiments in which the irradiating step comprises irradiating the tobacco slurry with UV light for 30 minutes, the irradiance may be conducted in a single 30 minute step, or in two separate steps each of 15 minutes long. The total irradiation time may be varied according to the thickness of the tobacco slurry. That is, the total irradiation time may be increased as the thickness of the tobacco slurry is increased.
Generally, increasing the UV irradiance will yield a higher reduction in TSNA content over a fixed time period. Therefore, to optimise the efficiency of the TSNA reduction process, a high UV irradiance is preferably used to minimise the total time required to reduce the TSNA content to a desired level. In any of the embodiments described above, the amount of the at least one tobacco-specific nitrosamine present in the tobacco slurry after the irradiation step is preferably less than about 75 percent by weight of the amount of the at least one tobacco-specific nitrosamine present in the tobacco slurry before the irradiation step, more preferably less than about 50 percent by weight of the amount of the at least one tobacco-specific nitrosamine present in the tobacco slurry before the irradiation step, most preferably less than about 25 percent by weight of the amount of the at least one tobacco-specific nitrosamine present in the tobacco slurry before the irradiation step. Generally, the reduction in the amount of the at least one tobacco- specific nitrosamine can be increased by increasing at least one of the irradiance and the duration of the irradiating step. For a given irradiance, the amount of the at least one tobacco-specific nitrosamine present in the tobacco slurry decreases in a generally exponential manner during the period of irradiation. ln any of the embodiments described above, in accordance with the first aspect or the second aspect of the present invention, the ultraviolet light used in the irradiating step preferably has a peak intensity at a wavelength of at least about 315 nanometres, more preferably at least about 335 nanometres, most preferably at least about 350 nanometres. Additionally, or alternatively, the ultraviolet light preferably has a peak intensity at a wavelength of less than about 400 nanometres, more preferably less than about 390 nanometres, most preferably less than about 380 nanometres. In particularly preferred embodiments, the ultraviolet light has a peak intensity at a wavelength of between about 315 nanometres and about 400 nanometres, more preferably between about 335 nanometres and about 390 nanometres, most preferably between about 350 nanometres and about 380 nanometres. The ultraviolet light may have a peak intensity at a wavelength of about 365 nanometres. UV light having a peak intensity at a wavelength within these ranges falls within the UV-A portion of the ultraviolet spectrum, which the present inventors have recognised provides effective reduction of TSNAs and is optimised for transmission through glass and common UV transparent polymeric packaging materials. Therefore, methods in accordance with these embodiments are particularly suited for the treatment of aerosol- generating substrates or tobacco slurries that are housed within a glass container, or housed within a container comprising a glass window through which the UV light is transmitted. Use of radiation having a shorter wavelength is undesirable, as it may result in undesirable chemical decomposition of the nicotine.
According to a third aspect, the present invention provides an aerosol-generating substrate formed using the method according to either the first aspect of the invention or the second aspect of the invention, in accordance with any of the embodiments described above.
Example 1
Defined concentrations of N-nitrosonornicotine (NNN) and 4-(methylnitrosamino)-1 -(3-pyridyl)-1 - butanone (NNK) (380 and 613 nanograms per millilitre, respectively) were added to three different liquid aerosol-generating substrates each consisting of nicotine, glycerin, propylene glycol and water (2:10:68:20, 2:39:39:20 and 2:68:10:20 by weight). Aliquots of these solutions were placed in clear glass vials and irradiated for a specified time (0, 15, 30, 60, 120 or 240 minutes) with ultraviolet radiation (wavelength of 365 nanometres; lamp nominal power of 8 watts; distance to lamp of 3 centimetres). After irradiation the samples were diluted ten-fold with water and their nicotine, NNN and NNK content was analyzed. The UV irradiation caused a time-dependent decrease of NNK and NNN in all three nicotine/glycerin/propylene-glycol/water mixtures. Nicotine concentrations were not affected. The nitrosamine decay is approximately exponential with respect to irradiation time. Half-lives for NNN and NNK were in the ranges of 30-50 minutes and 60-70 minutes, respectively. The results are illustrated in Figures 1 to 3.
Example 2
A sample sheet of cast tobacco slurry having a thickness of 0.20 to 0.22 millimetres after drying to 195 to 200 grams per square metre was irradiated for 150 minutes, each, on both sides with UV light at a wavelength of 365 nanometres and an intensity of 4.5 milliwatts per square centimetre. After further drying and cutting, the irradiated cast leaf sample and a non-irradiated control were analysed for NNK, NNN, and nicotine content by mass spectroscopy. As compared to the control, the irradiated sample indicated no effect on nicotine content, a reduction of 12 percent in NNK content, and a reduction of 26 percent in NNN content.

Claims

Claims
1 . A method of forming an aerosol-generating substrate, the method comprising:
providing a liquid nicotine source containing at least one tobacco-specific nitrosamine; mixing the liquid nicotine source with a solvent and at least one aerosol former to form an aerosol-generating substrate; and
irradiating the aerosol-generating substrate with ultraviolet light to reduce the amount of the at least one tobacco-specific nitrosamine.
2. A method according to claim 1 , wherein the solvent comprises water.
3. A method according to claim 1 or 2, wherein the at least one aerosol former comprises at least one of propylene glycol and glycerin.
4. A method according to claim 1 , 2 or 3, wherein the ultraviolet irradiance of the aerosol- generating substrate is at least 4 milliwatts per square centimetre.
5. A method according to any preceding claim, wherein the aerosol-generating substrate is irradiated with ultraviolet light for less than 60 minutes.
6. A method according to any preceding claim, wherein the amount of the at least one tobacco-specific nitrosamine present in the aerosol-generating substrate after the irradiation step is less than 75 percent by weight of the amount of the at least one tobacco-specific nitrosamine present in the aerosol-generating substrate before the irradiation step.
7. A method of forming an aerosol-generating substrate, the method comprising:
providing a tobacco slurry containing at least one tobacco-specific nitrosamine;
irradiating the tobacco slurry with ultraviolet light to reduce the amount of the at least one tobacco-specific nitrosamine; and
drying the tobacco slurry to form an aerosol-generating substrate.
8. A method according to claim 7, further comprising a step of casting the tobacco slurry before the step of drying the tobacco slurry, and wherein the step of casting the tobacco slurry is performed before or after the step of irradiating the tobacco slurry.
9. A method according to claim 7 or 8, wherein the ultraviolet irradiance of the tobacco slurry is at least 4 milliwatts per square centimetre.
10. A method according to claim 7, 8 or 9, wherein the tobacco slurry is irradiated with ultraviolet light for less than 60 minutes.
1 1 . A method according to any of claims 7 to 10, wherein the amount of the at least one tobacco-specific nitrosamine present in the tobacco slurry after the irradiation step is less than 75 percent by weight of the amount of the at least one tobacco-specific nitrosamine present in the tobacco slurry before the irradiation step.
12. A method according to any preceding claim, wherein the ultraviolet light has a peak intensity at a wavelength of between 315 nanometres and 400 nanometres.
13. A method according to any preceding claim, wherein the ultraviolet light has a peak intensity at a wavelength of between 350 nanometres and 380 nanometres.
An aerosol-generating substrate formed according to the method of any preceding claim
PCT/EP2015/069091 2014-08-20 2015-08-19 Methods for forming aerosol-generating substrates having a reduced amount of tobacco specific nitrosamines WO2016026911A2 (en)

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EP15753036.1A EP3182844B1 (en) 2014-08-20 2015-08-19 Method for reducing the amount of tobacco specific nitrosamines in liquids containing nicotine
JP2017508991A JP6602845B2 (en) 2014-08-20 2015-08-19 A method for forming aerosol-generating substrates with reduced amounts of tobacco-specific nitrosamines
US15/504,487 US20170238597A1 (en) 2014-08-20 2015-08-19 Methods for forming aerosol-generating substrates having a reduced amount of tobacco specific nitrosamines
BR112017001255-3A BR112017001255B1 (en) 2014-08-20 2015-08-19 METHOD FOR FORMATION OF AEROSOL GENERATING SUBSTRATES HAVING A REDUCED QUANTITY OF TOBACCO-SPECIFIC NITROSAMINES
PL15753036T PL3182844T3 (en) 2014-08-20 2015-08-19 Method for reducing the amount of tobacco specific nitrosamines in liquids containing nicotine
ES15753036.1T ES2690876T3 (en) 2014-08-20 2015-08-19 Methods for forming aerosol generating substrates that have a reduced amount of tobacco-specific nitrosamines
RU2017108898A RU2685845C2 (en) 2014-08-20 2015-08-19 Methods for forming aerosol-generating substrates having a reduced amount of tobacco specific nitrosamines
CN201580042554.0A CN106714587B (en) 2014-08-20 2015-08-19 Method for forming an aerosol-generating substrate having a reduced amount of tobacco-specific nitrosamines
KR1020177002813A KR102486705B1 (en) 2014-08-20 2015-08-19 Methods for forming aerosol-generating substrates having a reduced amount of tobacco-specific nitrosamines

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