WO2021176215A1

WO2021176215A1 - Delivery systems and methods of making the same

Info

Publication number: WO2021176215A1
Application number: PCT/GB2021/050530
Authority: WO
Inventors: Ignacio Suarez YANEZ; Ianto DAVIES; Zohal KURDOGHLEE
Original assignee: British American Tobacco (Investments) Limited
Priority date: 2020-03-04
Filing date: 2021-03-03
Publication date: 2021-09-10
Also published as: US20230157350A1; EP4114211A1; GB202011177D0; GB202003093D0; JP2023516169A; KR20220148895A; CA3169947A1; BR112022017819A2

Abstract

Delivery systems and methods of making the same 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. In particular, the invention relates to delivery systems that do not provide any clearly noticeable smell or taste other than one of tobacco.

Description

Delivery systems and methods of making the same 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 pg 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 too pg 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 pg 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 pg 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 pg 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 pg 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 pg 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 pg 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 pg 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 flavour, wherein an amount of, on average, at least about 1.5 pg 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:

Figure 1 is a schematic side view of a combustible aerosol provision system according to embodiments of the invention. Figure 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 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 flavouring attributes.

Menthol is an example of an additive that imparts a characteristic flavour. When included in a delivery system, menthol produces three different sensations, namely: the menthol taste or flavour; 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 maybe 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 volatilised.

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.

WS-3

Alternative names for WS-3 include: Cyclohexanecarboxamide; N-ethyl-2-(isopropyl)- 5-methylcyclohexane carboxamide; ethyl methane carboxamide (INCI); N-ethyl-5- methyl-2-(i-methyl ethyl) cyclohexanecarboxamide; N-ethyl-2-(isopropyl)-5- methyl cyclohexane carboxamide; N-ethyl-p-methane-3-carboxamide. Its molecular formula is C_I3H₂₅NO. 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 flavour, 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 flavour 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 flavour, 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 pg 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 pg 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 pg 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 pg 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 too pg. In some embodiments, a combustible aerosol provision system includes sufficient WS-3 to provide delivery of, on average, no more than too pg WS-3 in a puff, no more than about 95, 90, 85, 80, 75, 70, 65, or no more than about 60 pg 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 pg 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 pg 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 pg. 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 flavour 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 pg WS-3 in a puff, at least about 35 pg, at least about 40 pg, at least about 45 pg, at least about 50 pg, at least about 55 pg, at least about 60 pg, at least about 65 pg, at least about 70 pg, at least about 75 pg, at least about 80 pg 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 too pg WS-3 in a puff, no more than 95 pg, 90 pg, 85 pg, 80 pg, 75 pg, 70 pg, 65 pg, or no more than about 60 pg 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 pg WS-3 in each puff provided by a l 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 pg 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 localised 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 localised 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 localised WS-3 provides delivery of, on average, at least 1.5 pg 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 maybe 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 localised WS-3 which provides a cooling or cleansing sensation when the localised 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 of2i 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 pg WS-3 in a puff, at least about 2 pg, at least about 2.5 pg, at least about 3 pg, at least about 4 pg, at least about 5 pg, at least about 6 pg, at least about 7 pg, at least about 8 pg, at least about 9 pg, at least about 10 pg, at least about 12 pg, at least about 15 pg, at least about 20 pg, at least about 25 pg, or at least about 30 pg 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 pg WS-3 in a puff, no more than about 95 pg, no more than about 90 pg, no more than about 85 pg, no more than about 80 pg, no more than about 75 pg, no more than about 70 pg, no more than about 65 pg, no more than about 60 pg, no more than about 55 pg, or no more than about 50 pg 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 pg 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 pg 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-h 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-h 4, 3-9, 3-8, 3-7, 3-6, 3-5, 3-4, 3-3, 3-2, 3-h 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 2mg 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 pg 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-h 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 maybe 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-h 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-b 5, 4-9, 4-8, 4-7, 4-6, 4-5, 4-4, 4-3, 4-2, 4-b 4, 3-9, 3-8, 3-7, 3-6, 3-5, 3-4, 3-3, 3-2, 3-h 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 solubilise 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 solubilised 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 maybe 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 volatilised 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 maybe 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 maybe achieved by the localised 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, localised 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 Figures 1 and 2, for the purpose of illustration and not limitation, a combustible aerosol provision system1 according to exemplary embodiments of the invention comprises a filter2 and a cylindrical rod of aerosol-generating material3.

The rod of aerosol-generating material3 is aligned with the filter2 such that one end of the rod of aerosol-generating material3 abuts the end of the filter2. The filter2 is filter material4 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 Figure 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 Figure 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 fibres, 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, Co mum,

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 flavour, 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 flavour providing any clearly noticeable smell or taste in addition to that of the aerosol-generating material

As used herein, the terms “flavour” and “flavourant” refer to materials which, where local regulations permit, maybe 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), flavour 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. Exp erimental

The objective of experimental work conducted was to demonstrate the discrimination between cooling agents and a characterising flavour, 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

The WS-3 solutions were made using the following solvents (PG is propylene glycol and EtOH is ethanol):

Table 2

Various cigarettes were prepared and smoked so that the (1) menthol-family flavour 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

With a score of less than l for menthol-family flavour intensity, the data showed that WS-3 provided a cooling sensation without the menthol flavour. Indeed, ANOVA statistics (shown in Figure 1) show significantly lower menthol flavour intensities of all cooling agent loaded samples vs. menthol loaded samples. In particular, WS-3 was not statistically different in the attribute menthol flavour 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 analysed using “Sniffing Analysis”, an applied sensoiy method for the assessment of characterising flavours 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 o and 5 for perception of the different tobacco typical and non-tobacco typical flavour notes

Table 4

Table 5

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 “WS3” or “WS23” show any critical intensity above 1.0 for the Non-Tobacco Typical Flavour Notes (see Table 5).

Only the menthol-loaded cigarette was described as having a highly intensive minty flavour 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-flavoured cigarette. “WS23” shows with 0.7 points an uncritical but detectable minty flavour (Table 5). The “Tobacco Typical Flavour 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 flavour 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 flavour. In contrast, the data suggest that inclusion of the “WS-3” cooling agent provides a cooling sensation without menthol flavour. The data shows that WS-3 provides minimal non-tobacco flavours 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 utilised 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

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 pg of WS-3 in a 35 mL puff.

2. A delivery system as claimed in claim 1, wherein the WS-3 is included in an amount to provide delivery of, on average, no more than about 100 pg of WS-3 in a 35 mL puff.

3. A delivery system as claimed in any one of the preceding claims, 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. A delivery system as claimed in any one of the preceding claims, wherein the delivery system does not comprise a further cooling agent in addition to the cooling agent WS-3.

5. A delivery system as claimed in any one of the preceding claims, wherein 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 pg of WS-3 in a puff under the ISO smoking regime.

6. A delivery system as claimed in claim 5, wherein the combustible aerosol provision system comprises WS-3 in an amount to provide delivery of, on average, at least about 25 pg WS-3 in a puff of aerosol generated under the ISO smoking regime.

7. A delivery system as claimed in claim 5 or claim 6, wherein the combustible aerosol provision system comprises WS-3 in an amount to provide delivery of no greater than too pg WS-3 in a puff of aerosol generated under the ISO smoking regime.

8. A delivery system as claimed in any one of claims 1 to 4, wherein 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 pg of WS-3 in a puff under the HCI smoking regime.

9. A delivery system as claimed in claim 8, wherein the non-combustible aerosol provision system comprises WS-3 in an amount to provide delivery of, on average, at least about 2 pg WS-3 in a puff of aerosol generated under the HCI smoking regime.

10. A delivery system as claimed in claim 8 or claim 9, wherein the non-combustible aerosol provision system comprises WS-3 in an amount to provide delivery of no greater than 100 pg WS-3 in a puff of aerosol generated under the HCI smoking regime.

11. A delivery system as claimed in any one of the preceding claims, wherein 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.

12. A delivery system as claimed in any one of the preceding claims, wherein the amount of cooling agent WS-3 included in the delivery system is at least 1 mg per delivery system.

13. A delivery system as claimed in any one of the preceding claims, wherein 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.

14. A delivery system as claimed in any one of claims 5 to 7, wherein the amount of cooling agent WS-3 included in the delivery system is at least 60 pg per 1 mg of tar delivered by the delivery system.

15. A delivery system as claimed in any one of claims 5 to 7 or 14, wherein 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.

16. A delivery system as claimed in any one of the preceding claims, wherein 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.

17. A delivery system as claimed in any one of the preceding claims, wherein 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.

18. A delivery system as claimed in any one of the preceding claims, wherein the cooling agent WS-3 is present in the aerosol-generating material.

19. A delivery system as claimed in claim 18, wherein the cooling agent WS-3 is applied to the aerosol-generating material.

20. A delivery system as claimed in 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, such as in the form of a powder.

21. A delivery system as claimed in claim 18, wherein the cooling agent WS-3 is added to the wrapper surrounding the aerosol-generating material.

22. A delivery system as claimed in any one of the preceding claims, wherein the delivery system comprises a filter and wherein the cooling agent WS-3 is present in said filter.

23. A delivery system as claimed in claim 22, wherein the cooling agent WS-3 is applied to the filter material.

24. A delivery system as claimed in claim 23, wherein 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.

25. A method of making a delivery system as claimed in any one of claims 1 to 24, 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. A method as claimed in claim 25, comprising applying the cooling agent WS-3 to the aerosol-generating material.

27. A method as claimed in claim 26, 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, such as in the form of a powder.

28. A method as claimed in claim 25, comprising applying the cooling agent WS-3 to at least a portion of a wrapper surrounding the aerosol-generating material.

29. A method as claimed in any one of claims 25 to 28, comprising incorporating the cooling agent WS-3 into a filter of the delivery system.

30. A method as claimed in claim 29, comprising applying the cooling agent WS-3 to the filter material.

31. A method as claimed in claim 30, comprising 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.

32. Use of the cooling agent WS-3 to provide a cooling sensation to the user of a delivery system without imparting a characteristic flavour, wherein an amount of, on average, at least about 1.5 pg of WS-3 is delivered in a 35 mL puff.

33. A use as claimed in 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.