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US20230157350A1 - Delivery systems and methods of making the same - Google Patents

Delivery systems and methods of making the same Download PDF

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Publication number
US20230157350A1
US20230157350A1 US17/905,567 US202117905567A US2023157350A1 US 20230157350 A1 US20230157350 A1 US 20230157350A1 US 202117905567 A US202117905567 A US 202117905567A US 2023157350 A1 US2023157350 A1 US 2023157350A1
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US
United States
Prior art keywords
cooling agent
delivery system
aerosol
generating material
delivery
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
US17/905,567
Inventor
Ignacio Suarez YANEZ
Ianto DAVIES
Zohal KURDOGHLEE
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
British American Tobacco Investments Ltd IFI
Nicoventures Trading Ltd
Original Assignee
British American Tobacco Investments Ltd IFI
Nicoventures Trading Ltd
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Filing date
Publication date
Application filed by British American Tobacco Investments Ltd IFI, Nicoventures Trading Ltd filed Critical British American Tobacco Investments Ltd IFI
Publication of US20230157350A1 publication Critical patent/US20230157350A1/en
Assigned to Nicoventures Trading Limited reassignment Nicoventures Trading Limited ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: LAI, SAM, HUANG, CHING TING, HUNG, Hsi Kai, YANG, RICK
Pending legal-status Critical Current

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    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24DCIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D1/00Cigars; Cigarettes
    • A24D1/002Cigars; Cigarettes with additives, e.g. for flavouring
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24CMACHINES FOR MAKING CIGARS OR CIGARETTES
    • A24C5/00Making cigarettes; Making tipping materials for, or attaching filters or mouthpieces to, cigars or cigarettes
    • A24C5/005Treatment of cigarette paper
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24CMACHINES FOR MAKING CIGARS OR CIGARETTES
    • A24C5/00Making cigarettes; Making tipping materials for, or attaching filters or mouthpieces to, cigars or cigarettes
    • A24C5/01Making cigarettes for simulated smoking devices
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24DCIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D1/00Cigars; Cigarettes
    • A24D1/02Cigars; Cigarettes with special covers
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24DCIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D1/00Cigars; Cigarettes
    • A24D1/02Cigars; Cigarettes with special covers
    • A24D1/025Cigars; Cigarettes with special covers the covers having material applied to defined areas, e.g. bands for reducing the ignition propensity
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24DCIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D1/00Cigars; Cigarettes
    • A24D1/04Cigars; Cigarettes with mouthpieces or filter-tips
    • A24D1/045Cigars; Cigarettes with mouthpieces or filter-tips with smoke filter means
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24DCIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D1/00Cigars; Cigarettes
    • A24D1/20Cigarettes specially adapted for simulated smoking devices
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24DCIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D1/00Cigars; Cigarettes
    • A24D1/22Cigarettes with integrated combustible heat sources, e.g. with carbonaceous heat sources
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24DCIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
    • A24D3/02Manufacture of tobacco smoke filters
    • A24D3/0204Preliminary operations before the filter rod forming process, e.g. crimping, blooming
    • A24D3/0212Applying additives to filter materials
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24DCIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
    • A24D3/02Manufacture of tobacco smoke filters
    • A24D3/0204Preliminary operations before the filter rod forming process, e.g. crimping, blooming
    • A24D3/0212Applying additives to filter materials
    • A24D3/022Applying additives to filter materials with liquid additives, e.g. application of plasticisers
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24DCIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
    • A24D3/02Manufacture of tobacco smoke filters
    • A24D3/0204Preliminary operations before the filter rod forming process, e.g. crimping, blooming
    • A24D3/0212Applying additives to filter materials
    • A24D3/0225Applying additives to filter materials with solid additives, e.g. incorporation of a granular product
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24DCIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
    • A24D3/04Tobacco smoke filters characterised by their shape or structure
    • A24D3/048Tobacco smoke filters characterised by their shape or structure containing additives
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24DCIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
    • A24D3/06Use of materials for tobacco smoke filters
    • A24D3/061Use of materials for tobacco smoke filters containing additives entrapped within capsules, sponge-like material or the like, for further release upon smoking
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24DCIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
    • A24D3/17Filters specially adapted for simulated smoking devices
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24FSMOKERS' REQUISITES; MATCH BOXES; SIMULATED SMOKING DEVICES
    • A24F40/00Electrically operated smoking devices; Component parts thereof; Manufacture thereof; Maintenance or testing thereof; Charging means specially adapted therefor
    • A24F40/40Constructional details, e.g. connection of cartridges and battery parts
    • A24F40/42Cartridges or containers for inhalable precursors
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24FSMOKERS' REQUISITES; MATCH BOXES; SIMULATED SMOKING DEVICES
    • A24F40/00Electrically operated smoking devices; Component parts thereof; Manufacture thereof; Maintenance or testing thereof; Charging means specially adapted therefor
    • A24F40/20Devices using solid inhalable precursors

Definitions

  • the present invention relates to delivery systems, including combustible aerosol provision systems and non-combustible aerosol provision systems, as well as methods of manufacturing the same.
  • a delivery system comprising an aerosol-generating material and a cooling agent WS-3, wherein the cooling agent WS-3 is included in an amount to provide delivery of, on average, at least about 1.5 ⁇ g of WS-3 in a 35 mL puff.
  • the WS-3 is included in an amount to provide delivery of, on average, no more than about 100 ⁇ g of WS-3 in a 35 mL puff.
  • the delivery system does not comprise an additive that provides any clearly noticeable smell or taste in addition to that of the aerosol-generating material.
  • the delivery system does not comprise a further cooling agent in addition to the cooling agent WS-3.
  • the delivery system is a combustible aerosol provision system comprising a rod of aerosol-generating material and WS-3 is included in an amount to provide delivery of, on average, at least 1.5 ⁇ g of WS-3 in a puff under the ISO smoking regime.
  • the combustible aerosol provision system comprises WS-3 in an amount to provide delivery of, on average, at least about 25 ⁇ g WS-3 in a puff of aerosol generated under the ISO smoking regime.
  • the combustible aerosol provision system comprises WS-3 in an amount to provide delivery of no greater than 100 ⁇ g WS-3 in a puff of aerosol generated under the ISO smoking regime.
  • the delivery system is a non-combustible aerosol provision system and WS-3 is included in an amount to provide delivery of, on average, at least 1.5 ⁇ g of WS-3 in a puff under the HCI smoking regime.
  • the non-combustible aerosol provision system comprises WS-3 in an amount to provide delivery of, on average, at least about 2 ⁇ g WS-3 in a puff of aerosol generated under the HCI smoking regime.
  • the non-combustible aerosol provision system comprises WS-3 in an amount to provide delivery of no greater than 100 ⁇ g WS-3 in a puff of aerosol generated under the HCI smoking regime.
  • the amount of cooling agent WS-3 included in the delivery system is at least 0.1 mg or at least 0.3 mg per delivery system.
  • the amount of cooling agent WS-3 included in the delivery system is at least 1 mg per delivery system.
  • the amount of cooling agent WS-3 included in the delivery system is no greater than 10 mg or no greater than 5 mg or no greater than 2.5 mg per delivery system.
  • the amount of cooling agent WS-3 included in the delivery system is at least 60 ⁇ g per 1 mg of tar delivered by the delivery system.
  • the amount of cooling agent WS-3 included in the delivery system is no greater than 10 mg or no greater than 5 mg per 1 mg of tar delivered by the delivery system.
  • the amount of cooling agent WS-3 included in the delivery system is at least 0.8 mg per 1 g of aerosol-generating material.
  • the amount of cooling agent WS-3 included in the delivery system is no greater than 15 mg or no greater than 11 mg per 1 g of aerosol-generating material.
  • the cooling agent WS-3 is present in the aerosol-generating material.
  • the cooling agent WS-3 is applied to the aerosol-generating material.
  • the cooling agent WS-3 is applied to the aerosol-generating material by spraying a solution of the cooling agent WS-3 onto the aerosol-generating material, or by adding the cooling agent WS-3 to the aerosol-generating material in solid form, such as in the form of a powder.
  • the cooling agent WS-3 is added to the wrapper surrounding the aerosol-generating material.
  • the delivery system comprises a filter and wherein the cooling agent WS-3 is present in said filter.
  • the cooling agent WS-3 is applied to the filter material.
  • the cooling agent WS-3 is applied to the filter material by spraying a solution of the cooling agent WS-3 onto the filter material, or by adding the cooling agent WS-3 to the filter material in solid form, such as in the form of a powder.
  • a method of making a delivery system as described herein comprising incorporating the cooling agent WS-3 into the delivery system in an amount to provide a cooling sensation without providing any clearly noticeable smell or taste in addition to that of the aerosol-generating material.
  • the method comprises applying the cooling agent WS-3 to the aerosol-generating material.
  • the method comprises applying the cooling agent WS-3 to the aerosol-generating material by spraying a solution of the cooling agent WS-3 onto the aerosol-generating material, or applying the cooling agent WS-3 to the aerosol-generating material in solid form, such as in the form of a powder.
  • the method comprises applying the cooling agent WS-3 to at least a portion of the wrapper surrounding the aerosol-generating material.
  • the method comprises incorporating the cooling agent WS-3 into a filter of the delivery system.
  • the method comprises applying the cooling agent WS-3 to the filter material.
  • the method comprises applying the cooling agent WS-3 to the filter material by spraying a solution of the cooling agent WS-3 onto the filter material, or applying the cooling agent WS-3 to the filter material in solid form, such as in the form of a powder.
  • cooling agent WS-3 to provide a cooling sensation to the user of a delivery system without imparting a characteristic flavor, wherein an amount of, on average, at least about 1.5 ⁇ g of WS-3 is delivered in a 35 mL puff.
  • FIG. 1 is a schematic side view of a combustible aerosol provision system according to embodiments of the invention.
  • FIG. 2 is an exploded view of a combustible aerosol provision system according to an embodiment of the invention wherein the WS-3 cooling agent is included as a patch on the wrapper circumscribing the aerosol-generating material.
  • delivery system is intended to encompass systems that deliver at least one substance to a user, and includes:
  • the invention relates to delivery systems comprising aerosol-generating material and a cooling agent WS-3 in an amount sufficient to provide a cooling effect or a cleansing sensation.
  • the invention relates to delivery systems that do not provide any clearly noticeable smell or taste in addition to that of the aerosol-generating material.
  • the aerosol-generating material comprises tobacco
  • the WS-3 provides a cooling or cleansing sensation without providing any clearly noticeably smell or taste other than one of tobacco.
  • the object of the development work that led to the present invention was to develop delivery systems that provide a cooling sensation without imparting any characteristic flavoring attributes.
  • Menthol is an example of an additive that imparts a characteristic flavor.
  • menthol When included in a delivery system, menthol produces three different sensations, namely: the menthol taste or flavor; freshness; and a cooling sensation which is as a result of menthol's ability to chemically trigger the cold-sensitive TRPM8 receptors.
  • Menthol cigarettes were first developed in the 1920s. They are constructed similarly to non-mentholated cigarettes, but include up to 3.5% by weight menthol.
  • Combustible aerosol provision systems which burn aerosol-generating material, such as combustible cigarettes, progressively burn the substrate during a smoking session. That is, a lit cigarette gradually burns the substrate therein from the lit end, towards the mouth end.
  • the menthol may be included in the aerosol-generating material, the filter, and/or the tipping paper.
  • the menthol may be incorporated for a number of reasons, such as its cooling sensory effect and/or its mint taste.
  • the user will perceive a relatively constant cooling sensory effect and/or mint taste throughout a smoking session, as portions of menthol disposed throughout the combustible cigarette are gradually volatilized.
  • WS-3 is a cooling agent that acts as a TRPM8 receptor agonist, providing an intense and lingering cooling trigeminal effect.
  • WS-3 Alternative names include: Cyclohexanecarboxamide; N-ethyl-2-(isopropyl)-5-methylcyclohexane carboxamide; ethyl methane carboxamide (INCI); N-ethyl-5-methyl-2-(1-methylethyl) cyclohexanecarboxamide; N-ethyl-2-(isopropyl)-5-methylcyclohexane carboxamide; N-ethyl-p-methane-3-carboxamide. Its molecular formula is C 13 H 25 NO.
  • WS-3 in delivery systems.
  • the amount of WS-3 included in delivery systems has been generally too low for any cooling sensation to be detected by inhalation. This is because WS-3 is usually combined with a flavor, such as menthol, or with a second cooling agent and the effect sought is as a result of this combination of sensory agents.
  • cooling agent WS-3 in the appropriate amount can provide a cooling or cleansing sensation with the absence of any minty or other characteristic flavor upon use of the delivery system.
  • WS-3 is an agent that does not migrate within the delivery system or packaging during storage.
  • Menthol for example, is highly volatile and migrates following its incorporation into the delivery system unless it is contained or encapsulated in some way.
  • the menthol in a pack of mentholated cigarettes, for example, is contained by an outer plastic packaging film. Within this packaging film, the menthol migrates and equilibrates. However, once this outer packaging film is removed (upon opening the pack for the first time), the menthol will begin to be lost. This migration and loss of the volatile menthol needs to be factored in when deciding how much menthol to include in each delivery system and where to apply it. It also means that the menthol delivery may vary depending on where the menthol is located when the delivery system is used.
  • the stable WS-3 does not migrate and so the amount of WS-3 included in the delivery system will correlate closely with the amount that is delivered to the consumer when the delivery system is used. This means that greater significance is attached to the amount of WS-3 incorporated into the delivery system, as well as where and how it is incorporated.
  • the invention provides a delivery system comprising an aerosol-generating material and a cooling agent WS-3, wherein the cooling agent WS-3 is included in an amount to provide delivery of, on average, at least about 1.5 ⁇ g of WS-3 in a 35 mL puff.
  • the average amount of WS-3 in a puff refers to the average amount in a puff that provides a cooling or cleansing sensation.
  • the invention includes embodiments in which WS-3 provides a cooling or cleansing sensation in only selected, predetermined puffs.
  • the WS-3 is included in an amount to provide delivery of, on average, no more than about 100 ⁇ g of WS-3 in a 35 mL puff.
  • the suitable amount of WS-3 is included in the delivery system to provide a discernible cooling effect.
  • the delivery system including the WS-3 does not provide any clearly noticeable smell or taste in addition to that of the aerosol-generating material.
  • the effect of the cooling agent achieved using the present invention is more subtle still and, rather than providing an overt cooling effect, it provides the user with a cleansing sensation or impression.
  • the cleansing sensation may provide the user with a cool and/or clean aftertaste.
  • the delivery system does not comprise any other additive that provides any clearly noticeable smell or taste in addition to that of the aerosol-generating material.
  • the delivery system does not comprise any further cooling agent in addition to the cooling agent WS-3.
  • the WS-3 is included in an amount to provide delivery of, on average, at least 1.5 ⁇ g of WS-3 in a puff under the ISO smoking regime.
  • the ISO smoking regime is based on a 35 mL puff volume, 2 second puff duration, 60 second puff interval, and no vent blocking.
  • a combustible aerosol provision system comprises sufficient WS-3 to provide delivery of, on average, at least about 1.7, 2, 2.5, 3, 3.5, 4, 4.5, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, or at least 95 ⁇ g WS-3 in a puff of aerosol generated by the combustible aerosol provision system under the ISO smoking regime.
  • the maximum amount of WS-3 delivered in a puff of aerosol generated by the combustible aerosol provision system under the ISO smoking regime is about 100 ⁇ g.
  • a combustible aerosol provision system includes sufficient WS-3 to provide delivery of, on average, no more than 100 ⁇ g WS-3 in a puff, no more than about 95, 90, 85, 80, 75, 70, 65, or no more than about 60 ⁇ g WS-3 in a puff under an ISO smoking regime.
  • the WS-3 is included in an amount to provide delivery of, on average, at least about 1.5 ⁇ g WS-3 in a puff of aerosol generated by the product under the HCI smoking regime.
  • the HCI smoking regime is based on a 55 mL puff volume, 2 second puff duration, and 30 second puff interval with vents blocked.
  • the non-combustible aerosol provision system comprises sufficient WS-3 to provide delivery of, on average, at least 2 ⁇ g WS-3 in a puff of aerosol generated by the non-combustible aerosol provision system under the HCI smoking regime.
  • the maximum amount of WS-3 delivered in a puff of aerosol generated by the non-combustible aerosol provision system under the HCI smoking regime is about 100 ⁇ g.
  • Inclusion of WS-3 in these amounts provides delivery of the WS-3 cooling agent to the consumer in an amount that provides a cooling or cleansing sensation with the absence of any minty or other characteristic flavor upon use of the delivery system.
  • a combustible aerosol provision system includes sufficient WS-3 to provide delivery of, on average, at least about 30 ⁇ g WS-3 in a puff, at least about 35 ⁇ g, at least about 40 ⁇ g, at least about 45 ⁇ g, at least about 50 ⁇ g, at least about 55 ⁇ g, at least about 60 ⁇ g, at least about 65 ⁇ g, at least about 70 ⁇ g, at least about 75 ⁇ g, at least about 80 ⁇ g WS-3 in a puff under the ISO smoking regime.
  • a combustible aerosol provision system includes sufficient WS-3 to provide delivery of, on average, no more than 100 ⁇ g WS-3 in a puff, no more than 95 ⁇ g, 90 ⁇ g, 85 ⁇ g, 80 ⁇ g, 75 ⁇ g, 70 ⁇ g, 65 ⁇ g, or no more than about 60 ⁇ g WS-3 in a puff under the ISO smoking regime.
  • the estimated rate of transfer of WS-3 from the combustible aerosol provision system to the aerosol generated upon combustion is between about 1 and about 2% per 1 mg of tar or nicotine-free dry particulate material (NFDPM) under the ISO smoking regime.
  • the rate of WS-3 transfer from the combustible aerosol provision system to the aerosol is approximately 1.2% per 1 mg of tar or NFDPM
  • the following calculations can be made.
  • 21 mg of WS-3 needs to be evenly distributed along the rod of aerosol-generating material.
  • 2 mg of WS-3 needs to be included in a localized manner, for example, as a patch or band positioned at an appropriate position along the rod of aerosol-generating material.
  • a combustible aerosol provision system comprising from about 0.1 mg to about 5 mg WS-3, or from about 0.3 mg to about 2.5 mg WS-3. In some embodiments, a combustible aerosol provision system is provided comprising up to about 10 mg of WS-3.
  • a combustible aerosol provision system comprises WS-3 localized towards or at the filter end of the rod of aerosol-generating material so as to provide a cooling or cleansing sensation during the last few puffs when the combustible aerosol provision system is used.
  • the localized WS-3 provides delivery of, on average, at least 1.5 ⁇ g of WS-3 in a puff under the ISO smoking regime.
  • the ISO smoking regime is based on a 35 mL puff volume, 2 second puff duration, 60 second puff interval, and no vent blocking.
  • a liquid formulation comprising WS-3 is printed onto the wrapper that circumscribes the rod of aerosol-generating material.
  • Any suitable printing process may be used, such as a rotary-gravure printing process.
  • the WS-3 is printed on the entire wrapper to provide a cooling or cleansing sensation throughout the use of the combustible aerosol provision system.
  • only one or more portions of the wrapper has WS-3 applied to it with other portions of the wrapper being free of cooling agent, thereby providing localized WS-3 which provides a cooling or cleansing sensation when the localized area of the WS-3 on the wrapper is heated.
  • the cooling agent may be provided as one or more bands on the wrapper. Depending on where the band or bands are located and their width, the cooling or cleansing sensation can be experienced at different points during use of the aerosol provision system, and for different durations.
  • the WS-3 is provided in a band having a width of at least about 0.1 mm, at least about 1 mm. at least about 5 mm, at least about 7 mm, at least about 10 mm, at least about 15 mm, at least about 20 mm, or at least about 25 mm. In some embodiments, the WS-3 is provided in a band having a width of up to about 73 mm, up to about 60 mm, up to about 50 mm, up to about 45 mm, up to about 40 mm, up to about 35 mm, up to about 30 mm, or up to about 25 mm.
  • the WS-3 is printed in the form of a patch or band towards or at the filter end of the rod of aerosol-generating material. This will release the WS-3 and create or deliver the cooling or cleansing sensation towards the end of the use of the combustible aerosol provision system, for example, during the last 4, 3, 2, or 1 puffs.
  • the printed area is positioned so that it forms a band having a width of 21 mm at the filter end of the assembled combustible aerosol provision system.
  • the 21 mm printed band of WS-3 is expected to provide a cooling sensation for the last 3 puffs.
  • the printed band contains at least 0.5 mg of WS-3.
  • the printed band for example a band having a width of 21 mm, contains 1 mg, 1.5 mg, 2 mg, 2.5 mg or 3 mg WS-3 to provide a cooling sensation for the final few puffs.
  • the printed area of the wrapper may exclude the edge of the wrapper where glue is applied to form a lap seam.
  • the combustible aerosol provision system is a cigarette.
  • the cigarette may comprise a rod of tobacco material circumscribed by a paper wrapper, and a filter.
  • the WS-3 is included in the cigarette applied to the wrapper.
  • the WS-3 is applied as a band on the wrapper.
  • a cigarette may, in some embodiments, comprise a band on the wrapper comprising from about 0.1 mg to about 5 mg WS-3, or from about 0.3 mg to about 2.5 mg WS-3.
  • the band may the applied, for example, by a rotary-gravure printing process.
  • a non-combustible aerosol provision system including a charge of aerosol-generating material that is heated to form an aerosol but is not combusted, includes sufficient WS-3 to provide delivery of, on average, at least about 1.5 ⁇ g WS-3 in a puff, at least about 2 ⁇ g, at least about 2.5 ⁇ g, at least about 3 ⁇ g, at least about 4 ⁇ g, at least about 5 ⁇ g, at least about 6 ⁇ g, at least about 7 ⁇ g, at least about 8 ⁇ g, at least about 9 ⁇ g, at least about 10 ⁇ g, at least about 12 ⁇ g, at least about 15 ⁇ g, at least about 20 ⁇ g, at least about 25 ⁇ g, or at least about 30 ⁇ g WS-3 in a puff under the HCI smoking regime.
  • a non-combustible aerosol provision system includes sufficient WS-3 to provide delivery of, on average, no more than about 100 ⁇ g WS-3 in a puff, no more than about 95 ⁇ g, no more than about 90 ⁇ g, no more than about 85 ⁇ g, no more than about 80 ⁇ g, no more than about 75 ⁇ g, no more than about 70 ⁇ g, no more than about 65 ⁇ g, no more than about 60 ⁇ g, no more than about 55 ⁇ g, or no more than about 50 ⁇ g WS-3 in a puff under the HCI smoking regime.
  • the estimated rate of transfer of WS-3 from the non-combustible aerosol provision system to the aerosol generated upon heating the aerosol-generating material is between about 5 and about 35% under the HCI smoking regime.
  • the rate of WS-3 transfer is approximately 5%
  • the following calculation can be made. In order to deliver 25 ⁇ g WS-3 in each of the 9 puffs provided by a non-combustible aerosol provision system, 4.5 mg of WS-3 needs to be evenly distributed within the aerosol-generating material. In an embodiment where the rate of WS-3 transfer is approximately 35%, the following calculation can be made. In order to deliver approximately 36 ⁇ g WS-3 per puff in each of the 9 puffs provided by a non-combustible aerosol provision system, 0.925 mg of WS-3 needs to be evenly distributed within the aerosol-generating material.
  • the amount of cooling agent WS-3 included in the delivery system may be expressed as a total weight of WS-3 per delivery system.
  • a delivery system includes at least about 1 mg of cooling agent WS-3.
  • a delivery system includes no more than about 10 mg or no more than about 5 mg of cooling agent WS-3.
  • the delivery system is a King Size cigarette, having a length of approximately 83 mm.
  • the delivery system includes at least about 1, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 3, 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 4, 4.1, 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8 or at least about 4.9 mg of WS-3 per delivery system.
  • the delivery system includes no more than about 5, 4.9, 4.8, 4.7, 4.6, 4.5, 4.4, 4.3, 4.2, 4.1, 4, 3.9, 3.8, 3.7, 3.6, 3.5, 3.4, 3.3, 3.2, 3.1, 3, 2.9, 2.8, 2.7, 2.6, 2.5, 2.4, 2.3, 2.2, 2.1, 2, 1.9, 1.8, 1.7, 1.6, 1.5, 1.4, 1.3, 1.2, or no more than about 1.1 mg of WS-3 per delivery system. In some embodiments, the delivery system includes about 1 mg, about 2 mg or about 3 mg of WS-3.
  • the amount of cooling agent WS-3 included in the delivery system may be expressed as a total weight of the WS-3 per mg of tar delivered by the delivery systems upon use.
  • a delivery system includes at least 60 ⁇ g of WS-3 per 1 mg of tar delivered by the delivery system upon use.
  • a delivery system includes no more than about 5 mg of WS-3 per 1 mg of tar delivered by the delivery system upon use.
  • the tar delivery of the delivery system is that which is measured using the ISO machine smoking regime, which involves a 35 ml puff volume, a puff duration of 2 seconds, and a puff frequency of once per minute, with ventilation holes open and with smoking continuing to a fixed length from the tipping paper or filter.
  • the delivery system includes at least about 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 3, 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 4, 4.1, 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8 or at least about 4.9 mg of WS-3 per 1 mg of tar delivered by the delivery system.
  • the delivery system includes no more than about 10 mg or no more than about 5, 4.9, 4.8, 4.7, 4.6, 4.5, 4.4, 4.3, 4.2, 4.1, 4, 3.9, 3.8, 3.7, 3.6, 3.5, 3.4, 3.3, 3.2, 3.1, 3, 2.9, 2.8, 2.7, 2.6, 2.5, 2.4, 2.3, 2.2, 2.1, 2, 1.9, 1.8, 1.7, 1.6, 1.5, 1.4, 1.3, 1.2, 1.1, 1, 0.9, 0.8, 0.7, 0.6, 0.5, 0.4, 0.3, 0.2, or no more than about 0.1 mg of WS-3 per 1 mg of tar delivered by the delivery system.
  • the amount of cooling agent WS-3 included in the delivery system may be expressed as a total weight of the WS-3 per mg of aerosol-generating material in the delivery system.
  • the delivery system is a King Size cigarette, having a length of approximately 83 mm.
  • the delivery system includes at least about 0.8, 0.9, 1, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 3, 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 4, 4.1, 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8, 4.9, 5, 5.1, 5.2, 5.3, 5.4, 5.5, 5.6, 5.7, 5.8, 5.9, 6, 6.1, 6.2, 6.3, 6.4, 6.5, 6.6, 6.7, 6.8, 6.9, 7, 7.1, 7.2, 7.3, 7.4, 7.5, 7.6, 7.7, 7.8 or at least about 7.9 mg of WS-3 per 1 g of aerosol-generating material the delivery system.
  • the delivery system includes no more than about 15 mg or no more than about 11, 10.5, 10, 9.5, 9, 8.5, 8, 7.9, 7.8, 7.7, 7.6, 7.5, 7.4, 7.3, 7.2, 7.1, 7, 6.9, 6.8, 6.7, 6.6, 6.5, 6.4, 6.3, 6.2, 6.1, 6, 5.9, 5.8, 5.7, 5.6, 5.5, 5.4, 5.3, 5.2, 5.1, 5, 4.9, 4.8, 4.7, 4.6, 4.5, 4.4, 4.3, 4.2, 4.1, 4, 3.9, 3.8, 3.7, 3.6, 3.5, 3.4, 3.3, 3.2, 3.1, 3, 2.9, 2.8, 2.7, 2.6, 2.5, 2.4, 2.3, 2.2, 2.1, 2, 1.9, 1.8, 1.7, 1.6, 1.5, or no more than about 1.4 mg of WS-3 per 1 g of aerosol-generating material in the delivery system.
  • a delivery system includes at least about 1.4 mg WS-3 per 1
  • the WS-3 cooling agent may be added to the delivery system or to constituents of the delivery system in the form of a solution.
  • WS-3 is readily soluble in alcohol, such as ethanol, and in DMSO (dimethyl sulphoxide) and so in some embodiments, the WS-3 is added to the delivery system in the form of a solution, the solvent comprising alcohol, such as ethanol, and/or DMSO.
  • alcohol such as ethanol
  • DMSO dimethyl sulphoxide
  • the solution comprising WS-3 and a solvent further comprises a humectant such as propylene glycol, glycerol, or other glycols.
  • a humectant such as propylene glycol, glycerol, or other glycols.
  • the inclusion of the humectant in the WS-3 solution has the benefit of lowering the flash point of the solution. This is of particular benefit when the solvent is an alcohol such as ethanol.
  • a humectant such as propylene glycol
  • a combination of alcohol or DMSO and the humectant is preferred as such a combination reduces the total volume of liquid required to solubilize a given amount of WS-3, since the solubility of WS-3 is higher in the solvents than in humectants such as propylene glycol.
  • the solution used to add WS-3 to the delivery system comprises WS-3 solubilized in an alcohol with a humectant.
  • the solvent is ethanol and/or the humectant is propylene glycol.
  • the solution comprises 1 part propylene glycol, 2 parts ethanol and 3 parts WS-3.
  • the proportions of the components may be adjusted with the solution still being suitable to add the WS-3 to the delivery system. Indeed, different solutions are used to add WS-3 to delivery systems in the Examples below.
  • a solution with the ratio mentioned above is used to apply the WS-3 and propylene glycol to the aerosol-generating material of a delivery system. 6 mg of the solution is used to add 3 mg of WS-3 to the aerosol-generating material.
  • the solutions comprising WS-3 are added to the delivery system by spraying.
  • the solution may be sprayed onto the aerosol-generating material before it is incorporated into the delivery system.
  • the solution may be applied evenly onto the aerosol-generating material or it may be applied to provide a specific distribution of the solution and therefore of the WS-3 within the aerosol-generating material and in the delivery system.
  • the WS-3 cooling agent should be included in the delivery system in a manner so as to allow delivery of the WS-3 to the consumer during use of the delivery system.
  • delivery of the WS-3 cooling agent is by inhalation.
  • the WS-3 to be delivered to the consumer is included in the aerosol generated by the delivery system and inhaled by the consumer. Accordingly, the WS-3 is incorporated in the delivery system so that it is entrained in the aerosol.
  • the cooling agent WS-3 is present in the aerosol-generating material. In some embodiments, the cooling agent WS-3 is applied to the aerosol-generating material. As the delivery system is used, the WS-3 is volatilized and is entrained in the aerosol flow through the delivery system. Research suggests that WS-3 is a stable molecule and is not transformed and does not react with other chemicals in the aerosol. This is despite the high temperatures seen in the rods of aerosol-generating material in combustible aerosol provision system, such as cigarettes. This is also despite the relatively low volatility of the WS-3 compared to some cooling agents used in delivery systems, such as menthol.
  • the WS-3 is applied to the aerosol-generating material before or as the aerosol-generating material is incorporated in to a rod of aerosol-generating material for inclusion in a delivery system.
  • the WS-3 may be added to the aerosol-generating material rod after it has been formed, for example by injecting the WS-3 into the rod of aerosol-generating material.
  • the cooling agent WS-3 is applied to the aerosol-generating material by spraying a solution of the cooling agent WS-3 onto the aerosol-generating material. Suitable solutions have been discussed above. This application of a WS-3 solution can help to ensure that the WS-3 is evenly distributed throughout the aerosol-generating material.
  • the cooling agent WS-3 may be added to the aerosol-generating material in solid form, such as in the form of a powder.
  • the WS-3 When the WS-3 is applied to the aerosol-generating material, the WS-3 is gradually released and entrained in the aerosol as the delivery system is used and the aerosol-generating material is heated.
  • the cooling agent WS-3 is included by being applied to the wrapper surrounding the aerosol-generating material. This may be in addition to or instead of applying the WS-3 to the aerosol-generating material or to one or more other parts of the delivery system.
  • the WS-3 may be applied to the wrapper in the form of a solution or in solid form, for example in powder form. Particles of WS-3 may be attached to the wrapper using an adhesive.
  • the WS-3 is present on the inner surface of the wrapper, which faces the aerosol-generating material in the delivery system.
  • the WS-3 is applied to a discrete layer of sheet material which is disposed on or adjacent to the wrapper surrounding the aerosol-generating material.
  • the cooling agent WS-3 may be uniformly distributed along the rod of aerosol-generating material.
  • the cooling or cleansing effect is to be provided at specific, predetermined points during use of the delivery system, this may be achieved by the localized provision of the cooling agent.
  • the cooling agent WS-3 may be applied to only part of the rod of aerosol-generating material, namely the part that is heated or combusted during the latter stages of using the delivery system.
  • the cooling agent In the case of a combustible aerosol provision system, the cooling agent would be located toward the filter end of the rod of aerosol-generating material.
  • One convenient way to achieve this is by providing a patch or band of the cooling agent on or adjacent to the wrapper surrounding the rod of aerosol-generating material.
  • the delivery system includes a filter and the cooling agent WS-3 is included in the filter. This may be in addition to or instead of including the WS-3 in the aerosol-generating material of the delivery system.
  • the WS-3 is applied to the filter material.
  • the WS-3 may be applied to the filter material before or as the filter material is incorporated in to a filter of filter element for inclusion in a delivery system.
  • the WS-3 may be applied to the filter material in the form of a solution or in solid form, for example in powder form.
  • the WS-3 may be added to the filter or filter element after it has been formed, for example by injecting the WS-3 into the filter.
  • the cooling agent WS-3 is included in the filter by being applied to the wrapper surrounding the filter material. This may be in addition to or instead of applying the WS-3 to the filter material or to other parts of the delivery system.
  • the WS-3 may be applied to the wrapper in the form of a solution or in solid form, for example in powder form. Particles of WS-3 may be attached to the wrapper using an adhesive.
  • the WS-3 is present on the inner surface of the wrapper, which faces the filter material in the delivery system.
  • the delivery system may include a sensate on at least a portion of its surface, to provide further sensations to the user during use.
  • a sensate may be provided on the surface at the mouth end of the system, localized where the system is in contact with the user's lips upon use. The sensate may be selected to complement the cooling or cleansing sensation provided by the WS-3 as discussed herein.
  • a combustible aerosol provision system 1 comprises a filter 2 and a cylindrical rod of aerosol-generating material 3 .
  • the rod of aerosol-generating material 3 is aligned with the filter 2 such that one end of the rod of aerosol-generating material 3 abuts the end of the filter 2 .
  • the filter 2 is filter material 4 wrapped in a plug wrap 5 and the plug of aerosol-generating material 6 , such as tobacco, is circumscribed by a paper wrapper 7 to form the rod of aerosol-generating material 3 .
  • the rod of aerosol-generating material 3 is joined to the filter 2 by tipping paper 8 in a conventional manner.
  • the plug of aerosol-generating material comprises tobacco to which the cooling agent WS-3 has been applied, in accordance with an embodiment of the invention described herein.
  • the embodiment shown in FIG. 2 includes the cooling agent WS-3 provided in the form of a patch 9 at a first position along the length of the wrapper 7 that will circumscribe the plug of aerosol-generating material to form the rod of aerosol-generating material.
  • the patch 9 is positioned toward the mouth end of the rod of aerosol-generating material 3 and, upon use of the combustible aerosol provision system, the patch will release the cooling agent as it is heated, so that the cooling agent is delivered during the final few puffs of the delivery system only.
  • the cooling agent patch may be located at an alternative position along the length of the rod of aerosol-generating material, multiple patches may be provided, or a single patch may extend a greater length along the rod, and may even extend the entire length of the rod of aerosol-generating material.
  • Combustible aerosol provision systems may conform to any size or dimensions known for combustible aerosol provision systems.
  • tobacco refers to the material typically found in the tobacco rod of a combustible aerosol provision system such as a cigarette, or in tobacco-containing aerosol-generating material of a non-combustible aerosol provision system.
  • tobacco includes tobacco lamina, tobacco stem, expanded tobacco, reconstituted tobacco, extruded tobacco, tobacco substitutes, and filler materials.
  • the term “tobacco” includes any part and any related by-product, such as for example the leaves or stems, of any member of the genus Nicotiana .
  • the tobacco material is from the species Nicotiana tabacum .
  • the tobacco material is one or more selected from the group consisting of: cut stem, cut lamina, leaf lamina, small lamina, stem fibers, short stem and long stem.
  • Any type, style and/or variety of tobacco may be treated.
  • tobacco which may be used include, but are not limited to, Virginia, Burley, Oriental, Comum, Amarelinho and Maryland tobaccos, and blends of any of these types.
  • the skilled person will be aware that the treatment of different types, styles and/or varieties will result in tobacco with different organoleptic properties.
  • the delivery systems comprise a filter.
  • the filter may represent any filter configuration known in the art.
  • Filters for delivery systems typically comprise one or more of fibrous cellulose acetate, polypropylene material, polyethylene material, or gathered paper material.
  • the filter may, in some embodiments, comprise an adsorbent material, such as activated carbon.
  • the filter may include on or more capsules.
  • the capsule may comprise an aerosol modifying agent, such as a flavor, where permitted by local regulations.
  • the aerosol modifying agent is not another cooling agent other than WS-3 and/or is not a flavor providing any clearly noticeable smell or taste in addition to that of the aerosol-generating material
  • flavor and “flavorant” refer to materials which, where local regulations permit, may be used to create a desired taste or aroma in a product for adult consumers. They may include extracts (e.g., licorice, hydrangea, Japanese white bark magnolia leaf, chamomile, fenugreek, clove, menthol, Japanese mint, aniseed, cinnamon, herb, wintergreen, cherry, berry, peach, apple, Drambuie, bourbon, scotch, whiskey, spearmint, peppermint, lavender, cardamon, celery, cascarilla, nutmeg, sandalwood, bergamot, geranium, honey essence, rose oil, vanilla, lemon oil, orange oil, cassia, caraway, cognac, jasmine, ylang-ylang, sage, fennel, piment, ginger, anise, coriander, coffee, or a mint oil from any species of the genus Mentha),
  • extracts e.g.,
  • the objective of experimental work conducted was to demonstrate the discrimination between cooling agents and a characterizing flavor, which is defined as a ‘clearly noticeable smell or taste other than one of tobacco, resulting from an additive or a combination of additives’.
  • Test cigarettes were produced using the following amounts of WS-3 applied to the aerosol-generating material in the tobacco rod in the form of a solution:
  • the WS-3 solutions were made using the following solvents (PG is propylene glycol and EtOH is ethanol):
  • the cooling sensation in the cooling agent samples was significant higher than both control products.
  • Statistical PCA analysis confirms the ANOVA results and shows a clear differentiation of the both cooling agent samples (WS-3 and WS-23) from the menthol loaded products.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Cigarettes, Filters, And Manufacturing Of Filters (AREA)
  • Manufacture Of Tobacco Products (AREA)

Abstract

The disclosure relates to delivery systems including aerosol-generating material and a cooling agent WS-3 in an amount sufficient to provide a cooling effect. In particular, the disclosure relates to delivery systems that do not provide any clearly noticeable smell or taste other than one of tobacco.

Description

    PRIORITY CLAIM
  • The present application is a National Phase entry of PCT Application No. PCT/PCT/GB2021/050530, filed Mar. 3, 2021, which claims priority from GB Application No. 2011177.9, filed Jul. 20, 2020 and GB Application No. 2003093.8, filed Mar. 4, 2020, each of which is hereby fully incorporated herein by reference.
  • TECHNICAL FIELD
  • The present invention relates to delivery systems, including combustible aerosol provision systems and non-combustible aerosol provision systems, as well as methods of manufacturing the same.
  • BACKGROUND
  • It is known to use cooling agents in delivery systems in order to provide desired cooling and/or taste sensations when the delivery system is used.
  • SUMMARY
  • In accordance with some embodiments described herein, there is provided a delivery system comprising an aerosol-generating material and a cooling agent WS-3, wherein the cooling agent WS-3 is included in an amount to provide delivery of, on average, at least about 1.5 μg of WS-3 in a 35 mL puff.
  • In some embodiments, the WS-3 is included in an amount to provide delivery of, on average, no more than about 100 μg of WS-3 in a 35 mL puff.
  • In some embodiments, the delivery system does not comprise an additive that provides any clearly noticeable smell or taste in addition to that of the aerosol-generating material.
  • In some embodiments, the delivery system does not comprise a further cooling agent in addition to the cooling agent WS-3.
  • In some embodiments, the delivery system is a combustible aerosol provision system comprising a rod of aerosol-generating material and WS-3 is included in an amount to provide delivery of, on average, at least 1.5 μg of WS-3 in a puff under the ISO smoking regime.
  • In some embodiments, the combustible aerosol provision system comprises WS-3 in an amount to provide delivery of, on average, at least about 25 μg WS-3 in a puff of aerosol generated under the ISO smoking regime.
  • In some embodiments, the combustible aerosol provision system comprises WS-3 in an amount to provide delivery of no greater than 100 μg WS-3 in a puff of aerosol generated under the ISO smoking regime.
  • In some embodiments, the delivery system is a non-combustible aerosol provision system and WS-3 is included in an amount to provide delivery of, on average, at least 1.5 μg of WS-3 in a puff under the HCI smoking regime.
  • In some embodiments, the non-combustible aerosol provision system comprises WS-3 in an amount to provide delivery of, on average, at least about 2 μg WS-3 in a puff of aerosol generated under the HCI smoking regime.
  • In some embodiments, the non-combustible aerosol provision system comprises WS-3 in an amount to provide delivery of no greater than 100 μg WS-3 in a puff of aerosol generated under the HCI smoking regime.
  • In some embodiments, the amount of cooling agent WS-3 included in the delivery system is at least 0.1 mg or at least 0.3 mg per delivery system.
  • In some embodiments, the amount of cooling agent WS-3 included in the delivery system is at least 1 mg per delivery system.
  • In some embodiments, the amount of cooling agent WS-3 included in the delivery system is no greater than 10 mg or no greater than 5 mg or no greater than 2.5 mg per delivery system.
  • In some embodiments, the amount of cooling agent WS-3 included in the delivery system is at least 60 μg per 1 mg of tar delivered by the delivery system.
  • In some embodiments, the amount of cooling agent WS-3 included in the delivery system is no greater than 10 mg or no greater than 5 mg per 1 mg of tar delivered by the delivery system.
  • In some embodiments, the amount of cooling agent WS-3 included in the delivery system is at least 0.8 mg per 1 g of aerosol-generating material.
  • In some embodiments, the amount of cooling agent WS-3 included in the delivery system is no greater than 15 mg or no greater than 11 mg per 1 g of aerosol-generating material.
  • In some embodiments, the cooling agent WS-3 is present in the aerosol-generating material.
  • In some embodiments, the cooling agent WS-3 is applied to the aerosol-generating material.
  • In some embodiments, the cooling agent WS-3 is applied to the aerosol-generating material by spraying a solution of the cooling agent WS-3 onto the aerosol-generating material, or by adding the cooling agent WS-3 to the aerosol-generating material in solid form, such as in the form of a powder.
  • In some embodiments, the cooling agent WS-3 is added to the wrapper surrounding the aerosol-generating material.
  • In some embodiments, the delivery system comprises a filter and wherein the cooling agent WS-3 is present in said filter.
  • In some embodiments, the cooling agent WS-3 is applied to the filter material.
  • In some embodiments, the cooling agent WS-3 is applied to the filter material by spraying a solution of the cooling agent WS-3 onto the filter material, or by adding the cooling agent WS-3 to the filter material in solid form, such as in the form of a powder.
  • In some embodiments described herein, there is provided a method of making a delivery system as described herein, comprising incorporating the cooling agent WS-3 into the delivery system in an amount to provide a cooling sensation without providing any clearly noticeable smell or taste in addition to that of the aerosol-generating material.
  • In some embodiments, the method comprises applying the cooling agent WS-3 to the aerosol-generating material.
  • In some embodiments, the method comprises applying the cooling agent WS-3 to the aerosol-generating material by spraying a solution of the cooling agent WS-3 onto the aerosol-generating material, or applying the cooling agent WS-3 to the aerosol-generating material in solid form, such as in the form of a powder.
  • In some embodiments, the method comprises applying the cooling agent WS-3 to at least a portion of the wrapper surrounding the aerosol-generating material.
  • In some embodiments, the method comprises incorporating the cooling agent WS-3 into a filter of the delivery system.
  • In some embodiments, the method comprises applying the cooling agent WS-3 to the filter material.
  • In some embodiments, the method comprises applying the cooling agent WS-3 to the filter material by spraying a solution of the cooling agent WS-3 onto the filter material, or applying the cooling agent WS-3 to the filter material in solid form, such as in the form of a powder.
  • In some embodiments described herein, there is provided a use of the cooling agent WS-3 to provide a cooling sensation to the user of a delivery system without imparting a characteristic flavor, wherein an amount of, on average, at least about 1.5 μg of WS-3 is delivered in a 35 mL puff.
  • BRIEF DESCRIPTION OF THE DRAWINGS
  • Embodiments of the invention will now be described, by way of example only, with reference to the accompanying drawings, in which:
  • FIG. 1 is a schematic side view of a combustible aerosol provision system according to embodiments of the invention.
  • FIG. 2 is an exploded view of a combustible aerosol provision system according to an embodiment of the invention wherein the WS-3 cooling agent is included as a patch on the wrapper circumscribing the aerosol-generating material.
  • DETAILED DESCRIPTION OF THE DRAWINGS
  • As used herein, the term “delivery system” is intended to encompass systems that deliver at least one substance to a user, and includes:
      • “combustible aerosol provision systems”, such as cigarettes, cigarillos, cigars, and tobacco for pipes or for roll-your-own or for make-your-own cigarettes (whether based on tobacco, tobacco derivatives, expanded tobacco, reconstituted tobacco, tobacco substitutes or other smokeable material); and
      • “non-combustible aerosol provision systems” that release compounds from an aerosol-generating material without combusting the aerosol-generating material, such as electronic cigarettes, tobacco heating products, and hybrid systems to generate aerosol using a combination of aerosol-generating materials.
  • The invention relates to delivery systems comprising aerosol-generating material and a cooling agent WS-3 in an amount sufficient to provide a cooling effect or a cleansing sensation. In particular, the invention relates to delivery systems that do not provide any clearly noticeable smell or taste in addition to that of the aerosol-generating material. Where the aerosol-generating material comprises tobacco, the WS-3 provides a cooling or cleansing sensation without providing any clearly noticeably smell or taste other than one of tobacco.
  • The object of the development work that led to the present invention was to develop delivery systems that provide a cooling sensation without imparting any characteristic flavoring attributes.
  • Menthol is an example of an additive that imparts a characteristic flavor. When included in a delivery system, menthol produces three different sensations, namely: the menthol taste or flavor; freshness; and a cooling sensation which is as a result of menthol's ability to chemically trigger the cold-sensitive TRPM8 receptors.
  • Menthol cigarettes were first developed in the 1920s. They are constructed similarly to non-mentholated cigarettes, but include up to 3.5% by weight menthol.
  • Combustible aerosol provision systems which burn aerosol-generating material, such as combustible cigarettes, progressively burn the substrate during a smoking session. That is, a lit cigarette gradually burns the substrate therein from the lit end, towards the mouth end. When such delivery systems incorporate menthol, the menthol may be included in the aerosol-generating material, the filter, and/or the tipping paper. The menthol may be incorporated for a number of reasons, such as its cooling sensory effect and/or its mint taste. If the menthol is incorporated uniformly in the aerosol-generating material of a combustible cigarette, for instance, the user will perceive a relatively constant cooling sensory effect and/or mint taste throughout a smoking session, as portions of menthol disposed throughout the combustible cigarette are gradually volatilized.
  • Many synthetic derivatives of menthol have been used in personal hygiene products. Some of the most commercially successful compounds were generated by Wilkinson Sword Ltd. in the 1970s, and they include WS-3. WS-3 is a cooling agent that acts as a TRPM8 receptor agonist, providing an intense and lingering cooling trigeminal effect.
  • Figure US20230157350A1-20230525-C00001
  • Alternative names for WS-3 include: Cyclohexanecarboxamide; N-ethyl-2-(isopropyl)-5-methylcyclohexane carboxamide; ethyl methane carboxamide (INCI); N-ethyl-5-methyl-2-(1-methylethyl) cyclohexanecarboxamide; N-ethyl-2-(isopropyl)-5-methylcyclohexane carboxamide; N-ethyl-p-methane-3-carboxamide. Its molecular formula is C13H25NO.
  • It has previously been proposed to include WS-3 in delivery systems. However, the amount of WS-3 included in delivery systems has been generally too low for any cooling sensation to be detected by inhalation. This is because WS-3 is usually combined with a flavor, such as menthol, or with a second cooling agent and the effect sought is as a result of this combination of sensory agents.
  • It has now been surprisingly found that inclusion of the cooling agent WS-3 in a delivery system in the appropriate amount can provide a cooling or cleansing sensation with the absence of any minty or other characteristic flavor upon use of the delivery system.
  • As indicated in the experimental work set out below, other cooling agents did not provide only the desired cooling or cleansing sensation but also added mint or other non-tobacco flavor, which rendered their inclusion undesirable in the present invention.
  • In contrast to menthol and some other cooling agents that have previously been used in delivery systems, WS-3 is an agent that does not migrate within the delivery system or packaging during storage. Menthol, for example, is highly volatile and migrates following its incorporation into the delivery system unless it is contained or encapsulated in some way. The menthol in a pack of mentholated cigarettes, for example, is contained by an outer plastic packaging film. Within this packaging film, the menthol migrates and equilibrates. However, once this outer packaging film is removed (upon opening the pack for the first time), the menthol will begin to be lost. This migration and loss of the volatile menthol needs to be factored in when deciding how much menthol to include in each delivery system and where to apply it. It also means that the menthol delivery may vary depending on where the menthol is located when the delivery system is used.
  • In contrast, the stable WS-3 does not migrate and so the amount of WS-3 included in the delivery system will correlate closely with the amount that is delivered to the consumer when the delivery system is used. This means that greater significance is attached to the amount of WS-3 incorporated into the delivery system, as well as where and how it is incorporated.
  • Amount of Cooling Agent
  • As discussed above, the invention provides a delivery system comprising an aerosol-generating material and a cooling agent WS-3, wherein the cooling agent WS-3 is included in an amount to provide delivery of, on average, at least about 1.5 μg of WS-3 in a 35 mL puff.
  • For the avoidance of doubt, where reference is made herein to the average amount of WS-3 in a puff, this refers to the average amount in a puff that provides a cooling or cleansing sensation. As discussed herein, the invention includes embodiments in which WS-3 provides a cooling or cleansing sensation in only selected, predetermined puffs.
  • In some embodiments, the WS-3 is included in an amount to provide delivery of, on average, no more than about 100 μg of WS-3 in a 35 mL puff.
  • In some embodiments, the suitable amount of WS-3 is included in the delivery system to provide a discernible cooling effect. The delivery system including the WS-3 does not provide any clearly noticeable smell or taste in addition to that of the aerosol-generating material.
  • In some embodiments, the effect of the cooling agent achieved using the present invention is more subtle still and, rather than providing an overt cooling effect, it provides the user with a cleansing sensation or impression. In particular, the cleansing sensation may provide the user with a cool and/or clean aftertaste.
  • In some embodiments, the delivery system does not comprise any other additive that provides any clearly noticeable smell or taste in addition to that of the aerosol-generating material.
  • In some embodiments, the delivery system does not comprise any further cooling agent in addition to the cooling agent WS-3.
  • In embodiments where the delivery system is a combustible aerosol provision system, such as a cigarette, the WS-3 is included in an amount to provide delivery of, on average, at least 1.5 μg of WS-3 in a puff under the ISO smoking regime. The ISO smoking regime is based on a 35 mL puff volume, 2 second puff duration, 60 second puff interval, and no vent blocking.
  • In some embodiments, a combustible aerosol provision system comprises sufficient WS-3 to provide delivery of, on average, at least about 1.7, 2, 2.5, 3, 3.5, 4, 4.5, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, or at least 95 μg WS-3 in a puff of aerosol generated by the combustible aerosol provision system under the ISO smoking regime. In some embodiments, the maximum amount of WS-3 delivered in a puff of aerosol generated by the combustible aerosol provision system under the ISO smoking regime is about 100 μg. In some embodiments, a combustible aerosol provision system includes sufficient WS-3 to provide delivery of, on average, no more than 100 μg WS-3 in a puff, no more than about 95, 90, 85, 80, 75, 70, 65, or no more than about 60 μg WS-3 in a puff under an ISO smoking regime.
  • In embodiments where the delivery system is a non-combustible aerosol provision system, the WS-3 is included in an amount to provide delivery of, on average, at least about 1.5 μg WS-3 in a puff of aerosol generated by the product under the HCI smoking regime. The HCI smoking regime is based on a 55 mL puff volume, 2 second puff duration, and 30 second puff interval with vents blocked.
  • In some embodiments, the non-combustible aerosol provision system comprises sufficient WS-3 to provide delivery of, on average, at least 2 μg WS-3 in a puff of aerosol generated by the non-combustible aerosol provision system under the HCI smoking regime. In some embodiments, the maximum amount of WS-3 delivered in a puff of aerosol generated by the non-combustible aerosol provision system under the HCI smoking regime is about 100 μg.
  • Inclusion of WS-3 in these amounts provides delivery of the WS-3 cooling agent to the consumer in an amount that provides a cooling or cleansing sensation with the absence of any minty or other characteristic flavor upon use of the delivery system.
  • In some embodiments, a combustible aerosol provision system includes sufficient WS-3 to provide delivery of, on average, at least about 30 μg WS-3 in a puff, at least about 35 μg, at least about 40 μg, at least about 45 μg, at least about 50 μg, at least about 55 μg, at least about 60 μg, at least about 65 μg, at least about 70 μg, at least about 75 μg, at least about 80 μg WS-3 in a puff under the ISO smoking regime.
  • In some embodiments, a combustible aerosol provision system includes sufficient WS-3 to provide delivery of, on average, no more than 100 μg WS-3 in a puff, no more than 95 μg, 90 μg, 85 μg, 80 μg, 75 μg, 70 μg, 65 μg, or no more than about 60 μg WS-3 in a puff under the ISO smoking regime.
  • The estimated rate of transfer of WS-3 from the combustible aerosol provision system to the aerosol generated upon combustion is between about 1 and about 2% per 1 mg of tar or nicotine-free dry particulate material (NFDPM) under the ISO smoking regime.
  • In an embodiment where the rate of WS-3 transfer from the combustible aerosol provision system to the aerosol is approximately 1.2% per 1 mg of tar or NFDPM, the following calculations can be made. In order to deliver 36 μg WS-3 in each puff provided by a 1 mg tar cigarette providing 7 puffs, 21 mg of WS-3 needs to be evenly distributed along the rod of aerosol-generating material. In order to deliver approximately 50 μg WS-3 in 3 predetermined puffs provided by a 6.1 mg tar cigarette including WS-3, 2 mg of WS-3 needs to be included in a localized manner, for example, as a patch or band positioned at an appropriate position along the rod of aerosol-generating material.
  • In some embodiments, a combustible aerosol provision system is provided comprising from about 0.1 mg to about 5 mg WS-3, or from about 0.3 mg to about 2.5 mg WS-3. In some embodiments, a combustible aerosol provision system is provided comprising up to about 10 mg of WS-3.
  • In some embodiments, a combustible aerosol provision system comprises WS-3 localized towards or at the filter end of the rod of aerosol-generating material so as to provide a cooling or cleansing sensation during the last few puffs when the combustible aerosol provision system is used. In some embodiments the localized WS-3 provides delivery of, on average, at least 1.5 μg of WS-3 in a puff under the ISO smoking regime. The ISO smoking regime is based on a 35 mL puff volume, 2 second puff duration, 60 second puff interval, and no vent blocking.
  • In a particular embodiment, a liquid formulation comprising WS-3 is printed onto the wrapper that circumscribes the rod of aerosol-generating material. Any suitable printing process may be used, such as a rotary-gravure printing process.
  • In some embodiments, the WS-3 is printed on the entire wrapper to provide a cooling or cleansing sensation throughout the use of the combustible aerosol provision system. In other embodiments, only one or more portions of the wrapper has WS-3 applied to it with other portions of the wrapper being free of cooling agent, thereby providing localized WS-3 which provides a cooling or cleansing sensation when the localized area of the WS-3 on the wrapper is heated. In some embodiments, the cooling agent may be provided as one or more bands on the wrapper. Depending on where the band or bands are located and their width, the cooling or cleansing sensation can be experienced at different points during use of the aerosol provision system, and for different durations.
  • In some embodiments, the WS-3 is provided in a band having a width of at least about 0.1 mm, at least about 1 mm. at least about 5 mm, at least about 7 mm, at least about 10 mm, at least about 15 mm, at least about 20 mm, or at least about 25 mm. In some embodiments, the WS-3 is provided in a band having a width of up to about 73 mm, up to about 60 mm, up to about 50 mm, up to about 45 mm, up to about 40 mm, up to about 35 mm, up to about 30 mm, or up to about 25 mm.
  • In some embodiments, the WS-3 is printed in the form of a patch or band towards or at the filter end of the rod of aerosol-generating material. This will release the WS-3 and create or deliver the cooling or cleansing sensation towards the end of the use of the combustible aerosol provision system, for example, during the last 4, 3, 2, or 1 puffs. In some particular embodiments, the printed area is positioned so that it forms a band having a width of 21 mm at the filter end of the assembled combustible aerosol provision system. Based on a combustible aerosol provision system with a rod of aerosol-generating material having a length of 58 mm and providing an average of 8 puffs, the 21 mm printed band of WS-3 is expected to provide a cooling sensation for the last 3 puffs. In some embodiments, the printed band contains at least 0.5 mg of WS-3. In some particular embodiments, the printed band, for example a band having a width of 21 mm, contains 1 mg, 1.5 mg, 2 mg, 2.5 mg or 3 mg WS-3 to provide a cooling sensation for the final few puffs. The printed area of the wrapper may exclude the edge of the wrapper where glue is applied to form a lap seam.
  • In some embodiments, the combustible aerosol provision system is a cigarette. For example, the cigarette may comprise a rod of tobacco material circumscribed by a paper wrapper, and a filter. In some embodiments, the WS-3 is included in the cigarette applied to the wrapper. In some embodiments, the WS-3 is applied as a band on the wrapper. Thus, a cigarette may, in some embodiments, comprise a band on the wrapper comprising from about 0.1 mg to about 5 mg WS-3, or from about 0.3 mg to about 2.5 mg WS-3. The band may the applied, for example, by a rotary-gravure printing process.
  • In some embodiments, a non-combustible aerosol provision system including a charge of aerosol-generating material that is heated to form an aerosol but is not combusted, includes sufficient WS-3 to provide delivery of, on average, at least about 1.5 μg WS-3 in a puff, at least about 2 μg, at least about 2.5 μg, at least about 3 μg, at least about 4 μg, at least about 5 μg, at least about 6 μg, at least about 7 μg, at least about 8 μg, at least about 9 μg, at least about 10 μg, at least about 12 μg, at least about 15 μg, at least about 20 μg, at least about 25 μg, or at least about 30 μg WS-3 in a puff under the HCI smoking regime.
  • In some embodiments, a non-combustible aerosol provision system includes sufficient WS-3 to provide delivery of, on average, no more than about 100 μg WS-3 in a puff, no more than about 95 μg, no more than about 90 μg, no more than about 85 μg, no more than about 80 μg, no more than about 75 μg, no more than about 70 μg, no more than about 65 μg, no more than about 60 μg, no more than about 55 μg, or no more than about 50 μg WS-3 in a puff under the HCI smoking regime.
  • The estimated rate of transfer of WS-3 from the non-combustible aerosol provision system to the aerosol generated upon heating the aerosol-generating material is between about 5 and about 35% under the HCI smoking regime.
  • In an embodiment where the rate of WS-3 transfer is approximately 5%, the following calculation can be made. In order to deliver 25 μg WS-3 in each of the 9 puffs provided by a non-combustible aerosol provision system, 4.5 mg of WS-3 needs to be evenly distributed within the aerosol-generating material. In an embodiment where the rate of WS-3 transfer is approximately 35%, the following calculation can be made. In order to deliver approximately 36 μg WS-3 per puff in each of the 9 puffs provided by a non-combustible aerosol provision system, 0.925 mg of WS-3 needs to be evenly distributed within the aerosol-generating material.
  • The amount of cooling agent WS-3 included in the delivery system may be expressed as a total weight of WS-3 per delivery system. In some embodiments, a delivery system includes at least about 1 mg of cooling agent WS-3. In some embodiments, a delivery system includes no more than about 10 mg or no more than about 5 mg of cooling agent WS-3. In some of these embodiments, the delivery system is a King Size cigarette, having a length of approximately 83 mm. In some embodiments, the delivery system includes at least about 1, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 3, 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 4, 4.1, 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8 or at least about 4.9 mg of WS-3 per delivery system. In some embodiments, the delivery system includes no more than about 5, 4.9, 4.8, 4.7, 4.6, 4.5, 4.4, 4.3, 4.2, 4.1, 4, 3.9, 3.8, 3.7, 3.6, 3.5, 3.4, 3.3, 3.2, 3.1, 3, 2.9, 2.8, 2.7, 2.6, 2.5, 2.4, 2.3, 2.2, 2.1, 2, 1.9, 1.8, 1.7, 1.6, 1.5, 1.4, 1.3, 1.2, or no more than about 1.1 mg of WS-3 per delivery system. In some embodiments, the delivery system includes about 1 mg, about 2 mg or about 3 mg of WS-3.
  • Alternatively or in addition, the amount of cooling agent WS-3 included in the delivery system may be expressed as a total weight of the WS-3 per mg of tar delivered by the delivery systems upon use. In some embodiments a delivery system includes at least 60 μg of WS-3 per 1 mg of tar delivered by the delivery system upon use. In some embodiments a delivery system includes no more than about 5 mg of WS-3 per 1 mg of tar delivered by the delivery system upon use. In these embodiments, the tar delivery of the delivery system is that which is measured using the ISO machine smoking regime, which involves a 35 ml puff volume, a puff duration of 2 seconds, and a puff frequency of once per minute, with ventilation holes open and with smoking continuing to a fixed length from the tipping paper or filter. In some embodiments, the delivery system includes at least about 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 3, 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 4, 4.1, 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8 or at least about 4.9 mg of WS-3 per 1 mg of tar delivered by the delivery system. In some embodiments, the delivery system includes no more than about 10 mg or no more than about 5, 4.9, 4.8, 4.7, 4.6, 4.5, 4.4, 4.3, 4.2, 4.1, 4, 3.9, 3.8, 3.7, 3.6, 3.5, 3.4, 3.3, 3.2, 3.1, 3, 2.9, 2.8, 2.7, 2.6, 2.5, 2.4, 2.3, 2.2, 2.1, 2, 1.9, 1.8, 1.7, 1.6, 1.5, 1.4, 1.3, 1.2, 1.1, 1, 0.9, 0.8, 0.7, 0.6, 0.5, 0.4, 0.3, 0.2, or no more than about 0.1 mg of WS-3 per 1 mg of tar delivered by the delivery system.
  • Alternatively or in addition, the amount of cooling agent WS-3 included in the delivery system may be expressed as a total weight of the WS-3 per mg of aerosol-generating material in the delivery system. In some of these embodiments, the delivery system is a King Size cigarette, having a length of approximately 83 mm. In some embodiments, the delivery system includes at least about 0.8, 0.9, 1, 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 2, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 3, 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 4, 4.1, 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8, 4.9, 5, 5.1, 5.2, 5.3, 5.4, 5.5, 5.6, 5.7, 5.8, 5.9, 6, 6.1, 6.2, 6.3, 6.4, 6.5, 6.6, 6.7, 6.8, 6.9, 7, 7.1, 7.2, 7.3, 7.4, 7.5, 7.6, 7.7, 7.8 or at least about 7.9 mg of WS-3 per 1 g of aerosol-generating material the delivery system. In some embodiments, the delivery system includes no more than about 15 mg or no more than about 11, 10.5, 10, 9.5, 9, 8.5, 8, 7.9, 7.8, 7.7, 7.6, 7.5, 7.4, 7.3, 7.2, 7.1, 7, 6.9, 6.8, 6.7, 6.6, 6.5, 6.4, 6.3, 6.2, 6.1, 6, 5.9, 5.8, 5.7, 5.6, 5.5, 5.4, 5.3, 5.2, 5.1, 5, 4.9, 4.8, 4.7, 4.6, 4.5, 4.4, 4.3, 4.2, 4.1, 4, 3.9, 3.8, 3.7, 3.6, 3.5, 3.4, 3.3, 3.2, 3.1, 3, 2.9, 2.8, 2.7, 2.6, 2.5, 2.4, 2.3, 2.2, 2.1, 2, 1.9, 1.8, 1.7, 1.6, 1.5, or no more than about 1.4 mg of WS-3 per 1 g of aerosol-generating material in the delivery system. In some embodiments a delivery system includes at least about 1.4 mg WS-3 per 1 g of aerosol-generating material. In some embodiments a delivery system includes no more than about 8 mg WS-3 per 1 g of aerosol-generating material.
  • Solvent
  • The WS-3 cooling agent may be added to the delivery system or to constituents of the delivery system in the form of a solution.
  • WS-3 is readily soluble in alcohol, such as ethanol, and in DMSO (dimethyl sulphoxide) and so in some embodiments, the WS-3 is added to the delivery system in the form of a solution, the solvent comprising alcohol, such as ethanol, and/or DMSO.
  • In some embodiments, the solution comprising WS-3 and a solvent further comprises a humectant such as propylene glycol, glycerol, or other glycols. In addition to being a convenient means of including the humectant in the delivery system, the inclusion of the humectant in the WS-3 solution has the benefit of lowering the flash point of the solution. This is of particular benefit when the solvent is an alcohol such as ethanol.
  • Whilst in some embodiments a humectant, such as propylene glycol, may be used as the solvent (without an alcohol or DMSO), a combination of alcohol or DMSO and the humectant is preferred as such a combination reduces the total volume of liquid required to solubilize a given amount of WS-3, since the solubility of WS-3 is higher in the solvents than in humectants such as propylene glycol.
  • In some embodiments, the solution used to add WS-3 to the delivery system comprises WS-3 solubilized in an alcohol with a humectant. In some embodiments, the solvent is ethanol and/or the humectant is propylene glycol. In one particular embodiment, the solution comprises 1 part propylene glycol, 2 parts ethanol and 3 parts WS-3. Obviously, the proportions of the components may be adjusted with the solution still being suitable to add the WS-3 to the delivery system. Indeed, different solutions are used to add WS-3 to delivery systems in the Examples below.
  • In one particular embodiment, a solution with the ratio mentioned above is used to apply the WS-3 and propylene glycol to the aerosol-generating material of a delivery system. 6 mg of the solution is used to add 3 mg of WS-3 to the aerosol-generating material.
  • In some embodiments, the solutions comprising WS-3 are added to the delivery system by spraying. For example, the solution may be sprayed onto the aerosol-generating material before it is incorporated into the delivery system. The solution may be applied evenly onto the aerosol-generating material or it may be applied to provide a specific distribution of the solution and therefore of the WS-3 within the aerosol-generating material and in the delivery system.
  • Location
  • In order to provide the desired effect of the invention, the WS-3 cooling agent should be included in the delivery system in a manner so as to allow delivery of the WS-3 to the consumer during use of the delivery system.
  • In some embodiments, delivery of the WS-3 cooling agent is by inhalation. Thus, the WS-3 to be delivered to the consumer is included in the aerosol generated by the delivery system and inhaled by the consumer. Accordingly, the WS-3 is incorporated in the delivery system so that it is entrained in the aerosol.
  • In some embodiments, the cooling agent WS-3 is present in the aerosol-generating material. In some embodiments, the cooling agent WS-3 is applied to the aerosol-generating material. As the delivery system is used, the WS-3 is volatilized and is entrained in the aerosol flow through the delivery system. Research suggests that WS-3 is a stable molecule and is not transformed and does not react with other chemicals in the aerosol. This is despite the high temperatures seen in the rods of aerosol-generating material in combustible aerosol provision system, such as cigarettes. This is also despite the relatively low volatility of the WS-3 compared to some cooling agents used in delivery systems, such as menthol.
  • In some embodiments, the WS-3 is applied to the aerosol-generating material before or as the aerosol-generating material is incorporated in to a rod of aerosol-generating material for inclusion in a delivery system. Alternatively, the WS-3 may be added to the aerosol-generating material rod after it has been formed, for example by injecting the WS-3 into the rod of aerosol-generating material.
  • In some embodiments, the cooling agent WS-3 is applied to the aerosol-generating material by spraying a solution of the cooling agent WS-3 onto the aerosol-generating material. Suitable solutions have been discussed above. This application of a WS-3 solution can help to ensure that the WS-3 is evenly distributed throughout the aerosol-generating material. Alternatively or additionally, the cooling agent WS-3 may be added to the aerosol-generating material in solid form, such as in the form of a powder.
  • When the WS-3 is applied to the aerosol-generating material, the WS-3 is gradually released and entrained in the aerosol as the delivery system is used and the aerosol-generating material is heated.
  • In some embodiments, the cooling agent WS-3 is included by being applied to the wrapper surrounding the aerosol-generating material. This may be in addition to or instead of applying the WS-3 to the aerosol-generating material or to one or more other parts of the delivery system. Once again, the WS-3 may be applied to the wrapper in the form of a solution or in solid form, for example in powder form. Particles of WS-3 may be attached to the wrapper using an adhesive. In some embodiments, the WS-3 is present on the inner surface of the wrapper, which faces the aerosol-generating material in the delivery system.
  • In other embodiments, the WS-3 is applied to a discrete layer of sheet material which is disposed on or adjacent to the wrapper surrounding the aerosol-generating material.
  • In some embodiments, it is possible to control the delivery of the cooling or cleansing sensation to the consumer by controlling the location of the cooling agent WS-3 along the aerosol-generating rod. Where a consistent delivery of a cooling or cleansing sensation is desired, the cooling agent may be uniformly distributed along the rod of aerosol-generating material. Where the cooling or cleansing effect is to be provided at specific, predetermined points during use of the delivery system, this may be achieved by the localized provision of the cooling agent. For example, in order to provide a cooling or cleansing sensation in the last few puffs of the delivery system, the cooling agent WS-3 may be applied to only part of the rod of aerosol-generating material, namely the part that is heated or combusted during the latter stages of using the delivery system. In the case of a combustible aerosol provision system, the cooling agent would be located toward the filter end of the rod of aerosol-generating material. One convenient way to achieve this is by providing a patch or band of the cooling agent on or adjacent to the wrapper surrounding the rod of aerosol-generating material.
  • In some embodiments, the delivery system includes a filter and the cooling agent WS-3 is included in the filter. This may be in addition to or instead of including the WS-3 in the aerosol-generating material of the delivery system.
  • In some embodiments, the WS-3 is applied to the filter material. For example, the WS-3 may be applied to the filter material before or as the filter material is incorporated in to a filter of filter element for inclusion in a delivery system. Once again, the WS-3 may be applied to the filter material in the form of a solution or in solid form, for example in powder form. Alternatively, the WS-3 may be added to the filter or filter element after it has been formed, for example by injecting the WS-3 into the filter.
  • In some embodiments, the cooling agent WS-3 is included in the filter by being applied to the wrapper surrounding the filter material. This may be in addition to or instead of applying the WS-3 to the filter material or to other parts of the delivery system. Once again, the WS-3 may be applied to the wrapper in the form of a solution or in solid form, for example in powder form. Particles of WS-3 may be attached to the wrapper using an adhesive. In some embodiments, the WS-3 is present on the inner surface of the wrapper, which faces the filter material in the delivery system.
  • In some embodiments, in addition to including the WS-3 so that it is delivered in the aerosol generated and delivered to the user, the delivery system may include a sensate on at least a portion of its surface, to provide further sensations to the user during use. For example, a sensate may be provided on the surface at the mouth end of the system, localized where the system is in contact with the user's lips upon use. The sensate may be selected to complement the cooling or cleansing sensation provided by the WS-3 as discussed herein.
  • Referring to FIGS. 1 and 2 , for the purpose of illustration and not limitation, a combustible aerosol provision system 1 according to exemplary embodiments of the invention comprises a filter 2 and a cylindrical rod of aerosol-generating material 3. The rod of aerosol-generating material 3 is aligned with the filter 2 such that one end of the rod of aerosol-generating material 3 abuts the end of the filter 2. The filter 2 is filter material 4 wrapped in a plug wrap 5 and the plug of aerosol-generating material 6, such as tobacco, is circumscribed by a paper wrapper 7 to form the rod of aerosol-generating material 3. The rod of aerosol-generating material 3 is joined to the filter 2 by tipping paper 8 in a conventional manner.
  • In the embodiment illustrated in FIG. 1 , the plug of aerosol-generating material comprises tobacco to which the cooling agent WS-3 has been applied, in accordance with an embodiment of the invention described herein.
  • The embodiment shown in FIG. 2 includes the cooling agent WS-3 provided in the form of a patch 9 at a first position along the length of the wrapper 7 that will circumscribe the plug of aerosol-generating material to form the rod of aerosol-generating material. In the illustrated embodiment, the patch 9 is positioned toward the mouth end of the rod of aerosol-generating material 3 and, upon use of the combustible aerosol provision system, the patch will release the cooling agent as it is heated, so that the cooling agent is delivered during the final few puffs of the delivery system only.
  • In other embodiments (not illustrated) the cooling agent patch may be located at an alternative position along the length of the rod of aerosol-generating material, multiple patches may be provided, or a single patch may extend a greater length along the rod, and may even extend the entire length of the rod of aerosol-generating material.
  • Combustible aerosol provision systems according to the present invention may conform to any size or dimensions known for combustible aerosol provision systems.
  • As used herein, the term “tobacco” refers to the material typically found in the tobacco rod of a combustible aerosol provision system such as a cigarette, or in tobacco-containing aerosol-generating material of a non-combustible aerosol provision system. For example, tobacco includes tobacco lamina, tobacco stem, expanded tobacco, reconstituted tobacco, extruded tobacco, tobacco substitutes, and filler materials.
  • As used herein, the term “tobacco” includes any part and any related by-product, such as for example the leaves or stems, of any member of the genus Nicotiana. In some embodiments, the tobacco material is from the species Nicotiana tabacum. In some embodiments, the tobacco material is one or more selected from the group consisting of: cut stem, cut lamina, leaf lamina, small lamina, stem fibers, short stem and long stem.
  • Any type, style and/or variety of tobacco may be treated. Examples of tobacco which may be used include, but are not limited to, Virginia, Burley, Oriental, Comum, Amarelinho and Maryland tobaccos, and blends of any of these types. The skilled person will be aware that the treatment of different types, styles and/or varieties will result in tobacco with different organoleptic properties.
  • In some embodiments, the delivery systems comprise a filter. The filter may represent any filter configuration known in the art. Filters for delivery systems typically comprise one or more of fibrous cellulose acetate, polypropylene material, polyethylene material, or gathered paper material.
  • The filter may, in some embodiments, comprise an adsorbent material, such as activated carbon. In some embodiments, the filter may include on or more capsules. The capsule may comprise an aerosol modifying agent, such as a flavor, where permitted by local regulations. In some embodiments, the aerosol modifying agent is not another cooling agent other than WS-3 and/or is not a flavor providing any clearly noticeable smell or taste in addition to that of the aerosol-generating material
  • As used herein, the terms “flavor” and “flavorant” refer to materials which, where local regulations permit, may be used to create a desired taste or aroma in a product for adult consumers. They may include extracts (e.g., licorice, hydrangea, Japanese white bark magnolia leaf, chamomile, fenugreek, clove, menthol, Japanese mint, aniseed, cinnamon, herb, wintergreen, cherry, berry, peach, apple, Drambuie, bourbon, scotch, whiskey, spearmint, peppermint, lavender, cardamon, celery, cascarilla, nutmeg, sandalwood, bergamot, geranium, honey essence, rose oil, vanilla, lemon oil, orange oil, cassia, caraway, cognac, jasmine, ylang-ylang, sage, fennel, piment, ginger, anise, coriander, coffee, or a mint oil from any species of the genus Mentha), flavor enhancers, bitterness receptor site blockers, sensorial receptor site activators or stimulators, sugars and/or sugar substitutes (e.g., sucralose, acesulfame potassium, aspartame, saccharine, cyclamates, lactose, sucrose, glucose, fructose, sorbitol, or mannitol), and other additives such as charcoal, chlorophyll, minerals, botanicals, or breath freshening agents. They may be imitation, synthetic or natural ingredients or blends thereof. They may be in any suitable form, for example, oil, liquid, or powder.
  • Experimental
  • The objective of experimental work conducted was to demonstrate the discrimination between cooling agents and a characterizing flavor, which is defined as a ‘clearly noticeable smell or taste other than one of tobacco, resulting from an additive or a combination of additives’.
  • Test cigarettes were produced using the following amounts of WS-3 applied to the aerosol-generating material in the tobacco rod in the form of a solution:
  • TABLE 1
    WS-3
    Total amount of concentration Total amount of
    WS-3 applied in solution solution applied
    [mg] [%] [mg]
    0.24 6.00 4
    0.78 19.50 4
    1.00 25.00 4
    2.00 25.00 8
    3.00 37.50 8
  • The WS-3 solutions were made using the following solvents (PG is propylene glycol and EtOH is ethanol):
  • TABLE 2
    WS-3 conc’n
    in solution
    [%] Solvent 1 Solvent 2 Solvent 3
    6.00 PG 100% PG 50%/EtOH 50% EtOH 100%
    19.50 PG 100% PG 50%/EtOH 50% EtOH 100%
    25.00 PG 100% PG 50%/EtOH 50% EtOH 100%
    25.00 PG 100% PG 50%/EtOH 50% EtOH 100%
    37.50 PG 50%/EtOH 50% PG 50%/EtOH 50% EtOH 100%
  • Various cigarettes were prepared and smoked so that the (1) menthol-family flavor intensity; (2) cooling sensation; and (3) tobacco taste intensity could each be evaluated by testers on a 1 to 10 scale (N=28).
  • TABLE 3
    Menthol-Family Cooling Tobacco Taste
    Sample Flavor Intensity Sensation Intensity
    Tobacco Control 0.4 0.5 5.7
    no additive
    Tobacco Control 0.3 0.5 5.8
    (Virginia Sample) -
    no additive
    Menthol Control 4.1 4.8 3.1
    (low) 1.5 mg
    menthol
    Menthol Control 7.0 7.6 2.1
    (medium) 3.5 mg
    menthol
    Menthol Control 8.0 8.8 1.4
    (high) 5.0 mg
    menthol
    Test sample 0.8 3.3 4.5
    1 - 1.0 mg WS-3
    Test sample 2.2 4.2 3.9
    2 - 1.0 mg WS-23
  • With a score of less than 1 for menthol-family flavor intensity, the data showed that WS-3 provided a cooling sensation without the menthol flavor. Indeed, ANOVA statistics (shown in FIG. 1 ) show significantly lower menthol flavor intensities of all cooling agent loaded samples vs. menthol loaded samples. In particular, WS-3 was not statistically different in the attribute menthol flavor to both of the control samples (which included no menthol).
  • The cooling sensation in the cooling agent samples was significant higher than both control products. Statistical PCA analysis confirms the ANOVA results and shows a clear differentiation of the both cooling agent samples (WS-3 and WS-23) from the menthol loaded products.
  • Further samples were analyzed using “Sniffing Analysis”, an applied sensory method for the assessment of characterizing flavors of standard products, by sniffing the tobacco itself, without combusting it, using a method as provided in the international standard ISO 13299. The data is set out in Tables 4 and 5, showing the results of Quantitative Descriptive Profiling (QDP), providing a score of between 0 and 5 for perception of the different tobacco typical and non-tobacco typical flavor notes
  • TABLE 4
    Tobacco Typical Flavor Notes
    Sample Tobacco Smoky Roasted Haylike Black Tea Woody Earthy Animalic
    WS-3 (1 mg) 3.9 0.0 0.7 1.1 0.0 1.3 0.3 0.1
    WS-23 (1 mg) 3.5 0.1 0.7 0.9 0.1 1.0 0.3 0.1
    Control 4.1 0.1 1.0 1.3 0.1 1.4 0.2 0.1
    (no flavor)
    Menthol 0.6 0.0 0.1 0.0 0.0 0.1 0.0 0.0
    (4 mg)
  • TABLE 5
    Non-Tobacco Typical Flavor Notes
    Sample Vanilla Caramel Honey Fruity Floral Minty Citrus Cacao Licorice Spicy Alcoholic
    WS-3 (1 mg) .3 .1 .1 .1 .0 .0 .0 .2 .0 .1 .0
    WS-23 (1 mg) .3 .1 .1 .2 .1 .7 .2 .1 .0 .0 .0
    Control .2 .1 .1 .2 .0 .1 .1 .0 .0 .0 .0
    (no flavor)
    Menthol .1 .1 .1 .0 .0 .9 .0 .0 .0 .0 .1
    (4 mg)
  • A critical intensity of a Mean >1.0 is highlighted in bold in Tables 4 and 5. On the 0-5 category scale, none of the prototype cigarette of “W53” or “WS23” show any critical intensity above 1.0 for the Non-Tobacco Typical Flavor Notes (see Table 5).
  • Only the menthol-loaded cigarette was described as having a highly intensive minty flavor at 4.9 on the scoring scale. According to the results of the smoking analysis, very low minty notes were described even for the “control” non-flavored cigarette. “WS23” shows with 0.7 points an uncritical but detectable minty flavor (Table 5).
  • The “Tobacco Typical Flavor Notes” are more or less similar detectable in the “control” cigarette as well as in the prototypes “WS-3” and “WS-23” (see Table 4). That means that the tobacco aromas dominate the flavor in all cigarettes, except for the menthol-loaded one. These results of the QDP fit very well to the smoking analysis. That proves also the validity of both methods.
  • From the data, it may be concluded that the inclusion of “WS-23” could be identified in the smoking analysis as well as in the sniffing analysis as a substance imparting a very low, but detectable minty/menthol flavor. In contrast, the data suggest that inclusion of the “WS-3” cooling agent provides a cooling sensation without menthol flavor. The data shows that WS-3 provides minimal non-tobacco flavors and so is preferred when an additive is sought that provides a cooling or cleansing sensation without any clearly noticeable or discernible smell or taste other than one of tobacco.
  • The various embodiments described herein are presented only to assist in understanding and teaching the claimed features. These embodiments are provided as a representative sample of embodiments only, and are not exhaustive and/or exclusive. It is to be understood that advantages, embodiments, examples, functions, features, structures, and/or other aspects described herein are not to be considered limitations on the scope of the invention as defined by the claims or limitations on equivalents to the claims, and that other embodiments may be utilized and modifications may be made without departing from the scope of the claimed invention. Various embodiments of the invention may suitably comprise, consist of, or consist essentially of, appropriate combinations of the disclosed elements, components, features, parts, steps, means, etc., other than those specifically described herein. In addition, this disclosure may include other inventions not presently claimed, but which may be claimed in future.

Claims (33)

1. A delivery system comprising:
aerosol-generating material; and
a cooling agent WS-3, wherein the cooling agent WS-3 is included in an amount to provide delivery of, on average, at least about 1.5 μg of the cooling agent WS-3 in a 35 mL puff.
2. The delivery system according to claim 1, wherein the cooling agent WS-3 is included in an amount to provide delivery of, on average, no more than about 100 μg of the cooling agent WS-3 in a 35 mL puff.
3. The delivery system according to claim 1, wherein the delivery system does not comprise an additive that provides any clearly noticeable smell or taste in addition to that of the aerosol-generating material.
4. The delivery system according to claim 1, wherein the delivery system does not comprise a further cooling agent in addition to the cooling agent WS-3.
5. The delivery system according to claim 1, wherein the delivery system is a combustible aerosol provision system comprising a rod of the aerosol-generating material and the cooling agent WS-3 is included in an amount to provide delivery of, on average, at least 1.5 μg of the cooling agent WS-3 in a puff under an International Standards Organization (ISO) smoking regime.
6. The delivery system according to claim 5, wherein the combustible aerosol provision system comprises the cooling agent WS-3 in an amount to provide delivery of, on average, at least about 25 μg of the cooling agent WS-3 in a puff of aerosol generated under the ISO smoking regime.
7. The delivery system according to claim 5, wherein the combustible aerosol provision system comprises the cooling agent WS-3 in an amount to provide delivery of no greater than 100 μg of the cooling agent WS-3 in a puff of aerosol generated under the ISO smoking regime.
8. The delivery system according to claim 1, wherein the delivery system is a non-combustible aerosol provision system and the cooling agent WS-3 is included in an amount to provide delivery of, on average, at least 1.5 μg of the cooling agent WS-3 in a puff under a Health Canada Intense (HCI) smoking regime.
9. The delivery system according to claim 8, wherein the non-combustible aerosol provision system comprises the cooling agent WS-3 in an amount to provide delivery of, on average, at least about 2 μg of the cooling agent WS-3 in a puff of aerosol generated under the HCI smoking regime.
10. The delivery system according to claim 8, wherein the non-combustible aerosol provision system comprises the cooling agent WS-3 in an amount to provide delivery of no greater than 100 μg of the cooling agent WS-3 in a puff of aerosol generated under the HCI smoking regime.
11. The delivery system according to claim 1, wherein the amount of the cooling agent WS-3 included in the delivery system is at least 0.1 mg or at least 0.3 mg per delivery system.
12. The delivery according to claim 1, wherein the amount of the cooling agent WS-3 included in the delivery system is at least 1 mg per delivery system.
13. The delivery system according to claim 1, wherein the amount of the cooling agent WS-3 included in the delivery system is no greater than 10 mg or no greater than 5 mg or no greater than 2.5 mg per delivery system.
14. The delivery system according to claim 5, wherein the amount of the cooling agent WS-3 included in the delivery system is at least 60 μg per 1 mg of tar delivered by the delivery system.
15. The delivery system according to claim 5, wherein the amount of the cooling agent WS-3 included in the delivery system is no greater than 10 mg or no greater than 5 mg per 1 mg of tar delivered by the delivery system.
16. The delivery system according to claim 1, wherein the amount of the cooling agent WS-3 included in the delivery system is at least 0.8 mg per 1 g of aerosol-generating material.
17. The delivery system according to claim 1, wherein the amount of the cooling agent WS-3 included in the delivery system is no greater than 15 mg or no greater than 11 mg per 1 g of aerosol-generating material.
18. The delivery system according to claim 1, wherein the cooling agent WS-3 is present in the aerosol-generating material.
19. The delivery system according to claim 18, wherein the cooling agent WS-3 is applied to the aerosol-generating material.
20. The delivery system according to claim 19, wherein the cooling agent WS-3 is applied to the aerosol-generating material by spraying a solution of the cooling agent WS-3 onto the aerosol-generating material, or by adding the cooling agent WS-3 to the aerosol-generating material in solid form.
21. The delivery system according to claim 18, wherein the cooling agent WS-3 is added to a wrapper surrounding the aerosol-generating material.
22. The delivery system according to claim 1, wherein the delivery system comprises a filter and wherein the cooling agent WS-3 is present in the filter.
23. The delivery system according to claim 22, wherein the cooling agent WS-3 is applied to the filter.
24. The delivery system according to claim 23, wherein the cooling agent WS-3 is applied to the filter by spraying a solution of the cooling agent WS-3 onto the filter, or by adding the cooling agent WS-3 to the filter in solid form.
25. A method of making the delivery system according to claim 1, comprising:
incorporating the cooling agent WS-3 into the delivery system in an amount to provide a cooling sensation without providing any clearly noticeable smell or taste in addition to that of the aerosol-generating material.
26. The method according to claim 25, further comprising applying the cooling agent WS-3 to the aerosol-generating material.
27. The method according to claim 26, further comprising applying the cooling agent WS-3 to the aerosol-generating material by spraying a solution of the cooling agent WS-3 onto the aerosol-generating material, or applying the cooling agent WS-3 to the aerosol-generating material in solid form.
28. The method according to claim 25, further comprising applying the cooling agent WS-3 to at least a portion of a wrapper surrounding the aerosol-generating material.
29. The method according to claim 25, further comprising incorporating the cooling agent WS-3 into a filter of the delivery system.
30. The method according to claim 29, further comprising applying the cooling agent WS-3 to the filter.
31. The method according to claim 30, further comprising applying the cooling agent WS-3 to the filter by spraying a solution of the cooling agent WS-3 onto the filter, or applying the cooling agent WS-3 to the filter in solid form.
32. A method of use of a cooling agent WS-3 to provide a cooling sensation to the user of a delivery system without imparting a characteristic flavor, wherein an amount of, on average, at least about 1.5 μg of WS-3 is delivered in a 35 mL puff.
33. The method according to claim 32, wherein the delivery system does not comprise an additive that provides any clearly noticeable smell or taste in addition to that of the aerosol-generating material.
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CN118541041A (en) * 2022-12-09 2024-08-23 韩国烟草人参公社 Cooling mass comprising cooling agent and aerosol-generating article comprising same
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US12496061B2 (en) 2022-01-20 2025-12-16 Neochord, Inc. Minimally invasive heart valve repair in a beating heart

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