JP7562689B2 - Delivery system and method for making same - Patents.com - Google Patents

Description

The present invention relates to delivery systems, including combustible aerosol delivery systems and non-combustible aerosol delivery systems, and methods for manufacturing the same.

It is known to use cooling agents in delivery systems to provide a desired cooling and/or taste sensation when the delivery system is in use.

According to some embodiments described herein, a delivery system is provided that includes an aerosol generating material and a cooling agent WS-3, the cooling agent WS-3 being present in an amount that results in the delivery of an average of at least about 1.5 μg of WS-3 per 35 mL puff.

In some embodiments, WS-3 is included in an amount that results in the delivery of an average of about 100 μg or less of WS-3 per 35 mL puff.

In some embodiments, the delivery system does not contain additives that impart a noticeable odor or taste in addition to the odor or taste of the aerosol-forming material.

In some embodiments, the delivery system does not include any additional coolants in addition to the coolant WS-3.

In some embodiments, the delivery system is a combustible aerosol delivery system that includes a rod of aerosol-generating material, and WS-3 is included in an amount that results in the delivery of an average of at least 1.5 μg of WS-3 per puff under ISO smoking techniques.

In some embodiments, the combustible aerosol delivery system includes WS-3 in an amount that results in the delivery of an average of at least about 25 μg of WS-3 per puff of aerosol generated under ISO smoking techniques.

In some embodiments, the combustible aerosol delivery system contains WS-3 in an amount that results in the delivery of 100 μg or less of WS-3 in one puff of aerosol generated under ISO smoking techniques.

In some embodiments, the delivery system is a non-combustible aerosol delivery system and the WS-3 is included in an amount that results in the delivery of an average of at least 1.5 μg of WS-3 per puff under an HCI smoking technique.

In some embodiments, the non-combustible aerosol delivery system includes WS-3 in an amount that results in the delivery of an average of at least about 2 μg of WS-3 per puff of aerosol generated under an HCI smoking technique.

In some embodiments, the non-combustible aerosol delivery system includes WS-3 in an amount that results in the delivery of 100 μg or less of WS-3 in one puff of aerosol generated under HCI smoking.

In some embodiments, the amount of coolant WS-3 contained 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 coolant WS-3 contained in the delivery system is at least 1 mg per delivery system.

In some embodiments, the amount of coolant WS-3 contained in the delivery system is 10 mg or less, or 5 mg or less, or 2.5 mg or less per delivery system.

In some embodiments, the amount of coolant WS-3 contained in the delivery system is at least 60 μg per mg of tar delivered by the delivery system.

In some embodiments, the delivery system contains no more than 10 mg or no more than 5 mg of coolant WS-3 per mg of tar delivered by the delivery system.

In some embodiments, the delivery system contains at least 0.8 mg of coolant WS-3 per gram of aerosol-generating material.

In some embodiments, the delivery system contains no more than 15 mg or no more than 11 mg of coolant WS-3 per gram of aerosol-forming material.

In some embodiments, the coolant WS-3 is present in the aerosol generating material.

In some embodiments, the coolant WS-3 is applied to the aerosol generating material.

In some embodiments, the coolant WS-3 is applied to the aerosol-generating material by spraying a solution of the coolant WS-3 onto the aerosol-generating material or by adding the coolant WS-3 in a solid form, e.g., in powder form, to the aerosol-generating material.

In some embodiments, the coolant WS-3 is added to a wrapper that surrounds the aerosol-generating material.

In some embodiments, the delivery system includes a filter and the coolant WS-3 is present in the filter.

In some embodiments, the coolant WS-3 is applied to the filter material.

In some embodiments, the coolant WS-3 is applied to the filter material by spraying a solution of the coolant WS-3 onto the filter material or by adding the coolant WS-3 in a solid form, e.g., in powder form, to the filter material.

In some embodiments described herein, a method of making a delivery system described herein is provided that includes incorporating a cooling agent, WS-3, into the delivery system in an amount that provides a cooling sensation without imparting a noticeable odor or taste in addition to the odor or taste of the aerosol-generating material.

In some embodiments, the method includes applying a coolant, WS-3, to the aerosol-generating material.

In some embodiments, the method includes applying the coolant WS-3 to the aerosol-generating material by spraying a solution of the coolant WS-3 onto the aerosol-generating material or by applying the coolant WS-3 in a solid form, e.g., powder form, to the aerosol-generating material.

In some embodiments, the method includes applying the coolant WS-3 to at least a portion of a wrapper that surrounds the aerosol-generating material.

In some embodiments, the method includes incorporating the coolant WS-3 into a filter of the delivery system.

In some embodiments, the method includes applying a coolant, WS-3, to the filter material.

In some embodiments, the method includes applying the coolant WS-3 to the filter material by spraying a solution of the coolant WS-3 onto the filter material or by applying the coolant WS-3 to the filter material in a solid form, e.g., in powder form.

In some embodiments described herein, there is provided the use of a cooling agent WS-3 to provide a cooling sensation to a user of a delivery system without imparting a characteristic fragrance, wherein an average amount of WS-3 of at least about 1.5 μg is delivered in one 35 mL puff.

Embodiments of the invention will now be described, by way of example only, with reference to the accompanying drawings, in which:

1 is a schematic side view of a combustible aerosol delivery system according to an embodiment of the present invention. FIG. 1 is an exploded view of a combustible aerosol delivery system according to an embodiment of the present invention, in which the WS-3 coolant is included as a patch of a wrapper that surrounds the aerosol-generating material.

As used herein, the term "delivery system" is intended to encompass a system that delivers at least one substance to a user;
"Combustible aerosol delivery systems" include, for example, tobacco (whether based on tobacco, tobacco derivatives, expanded tobacco, reconstituted tobacco, tobacco substitutes, or other smokable materials) for cigarettes, cigarillos, cigars, and pipes, or for rolled or hand-made cigarettes, and "non-combustible aerosol delivery systems" that release compounds from an aerosol-forming material without combusting the aerosol-forming material, such as electronic cigarettes, tobacco heating products, and hybrid systems for generating aerosol using a combination of aerosol-forming materials.

The present invention relates to a delivery system that includes an aerosol-generating material and a cooling agent, WS-3, in an amount sufficient to provide a cooling or refreshing effect. In particular, the present invention relates to a delivery system that does not impart a noticeable odor or taste in addition to the odor or taste of the aerosol-generating material. When the aerosol-generating material includes tobacco, WS-3 provides a cooling or refreshing sensation without imparting a noticeable odor or taste other than the odor or taste of tobacco.

The objective of the research and development that led to this invention was to develop a delivery system that would provide a cooling sensation without imparting any distinctive flavoring properties.

Menthol is an example of an additive that imparts a characteristic flavor. When included in a delivery system, menthol produces three distinct sensations: menthol taste or flavor, freshness, and a cooling sensation as a result of menthol's ability to chemically trigger the cold-sensitive TRPM8 receptor.

Menthol cigarettes were first developed in the 1920s. Menthol cigarettes are constructed similarly to non-menthol cigarettes, but contain up to 3.5% menthol by weight.

A combustible aerosol delivery system that burns an aerosol-generating material, such as a combustible cigarette, burns the substrate gradually during a smoking session. That is, a lit cigarette burns the substrate therein gradually from the lit end to the mouth end. When such a delivery system incorporates menthol, the menthol may be included in the aerosol-generating material, the filter and/or the tipping paper. Menthol may be incorporated for several reasons, such as its cooling effect and/or its minty taste. For example, when menthol is uniformly incorporated into the aerosol-generating material of a combustible cigarette, the portion of the menthol located throughout the combustible cigarette gradually volatilizes, so that the user experiences a relatively consistent cooling effect and/or minty taste during a smoking session.

Many synthetic derivatives of menthol are used in personal hygiene products. Some of the most commercially successful compounds were produced by Willkinson Sword Ltd. in the 1970s and include WS-3, a cooling agent that acts as a TRPM8 receptor agonist, producing a potent and long-lasting cooling trigeminal effect.

Other names for WS-3 include cyclohexanecarboxamide, N-ethyl-2-(isopropyl)-5-methylcyclohexanecarboxamide, ethylmethanecarboxamide (INCI), N-ethyl-5-methyl-2-(1-methylethyl)cyclohexanecarboxamide, N-ethyl-2-(isopropyl)-5-methylcyclohexanecarboxamide, and N-ethyl-p-methane-3-carboxamide. Its molecular formula is C ₁₃ H ₂₅ NO.

The inclusion of WS-3 in delivery systems has previously been proposed. However, the amount of WS-3 included in delivery systems has generally been too small to provide a detectable cooling sensation upon inhalation. This is because WS-3 is usually combined with a flavoring or secondary cooling agent, such as menthol, and the desired effect is the result of this combination of sensates.

Surprisingly, it has been found that the inclusion of cooling agent WS-3 in an appropriate amount in a delivery system can provide a cooling or refreshing sensation without the presence of any mint or other characteristic flavor upon use of the delivery system.

As shown in the experimental work presented below, other cooling agents not only provided the desired cooling or refreshing sensation, but also added mint or other non-tobacco flavors, making their inclusion in the present invention undesirable.

In contrast to menthol and some other coolants that have been used in delivery systems to date, WS-3 is an agent that does not migrate within the delivery system or packaging during storage. For example, menthol is highly volatile and will migrate after incorporation into a delivery system unless contained or encapsulated in some way. For example, the menthol in a pack of menthol-containing cigarettes is contained in an outer plastic wrapping film. Within this wrapping film, the menthol migrates and equilibrates. However, once this outer wrapping film is removed (when the pack is opened for the first time), menthol begins to be lost. This migration and loss of volatile menthol must be considered when determining the amount of menthol to include in each delivery system and where it will be applied. This also means that menthol delivery may vary depending on where the menthol is located when the delivery system is in use.

In contrast, stable WS-3 does not migrate, so the amount of WS-3 contained in the delivery system will closely correlate with the amount delivered to the consumer when the delivery system is used. This means that the amount of WS-3 incorporated within the delivery system, and where and how the WS-3 is incorporated, is more important.

Amount of Coolant As noted above, the present invention provides a delivery system comprising an aerosol-forming material and a coolant, WS-3, wherein the coolant, WS-3, is present in an amount that results in the delivery of an average of at least about 1.5 μg of WS-3 in one 35 mL puff.

For the avoidance of doubt, when reference is made herein to the average amount of WS-3 in a puff, this means the average amount in a puff that provides a cooling or refreshing sensation. As discussed herein, the present invention includes embodiments in which WS-3 provides a cooling or refreshing sensation only in a selected, pre-determined puff.

In some embodiments, WS-3 is included in an amount that results in the delivery of an average of about 100 μg or less of WS-3 per 35 mL puff.

In some embodiments, a suitable amount of WS-3 is included in the delivery system to provide a discernible cooling effect. Delivery systems containing WS-3 do not impart a noticeable odor or taste in addition to the odor or taste of the aerosol-generating material.

In some embodiments, the cooling effect achieved using the present invention is more subtle, providing a cooling sensation or impression to the user rather than providing an obvious cooling effect. In particular, the cooling sensation may provide the user with a cool and/or clean aftertaste.

In some embodiments, the delivery system does not contain other additives that impart a noticeable odor or taste in addition to the odor or taste of the aerosol-forming material.

In some embodiments, the delivery system does not include any additional coolants in addition to the coolant WS-3.

In embodiments where the delivery system is a combustible aerosol delivery system such as a cigarette, WS-3 is included in an amount that results in the delivery of at least 1.5 μg of WS-3 per puff on average under the ISO smoking method. The ISO smoking method is based on a 35 mL puff volume, a 2 second puff duration, a 60 second interval between puffs, and no vent blockage.

In some embodiments, the combustible aerosol delivery system includes sufficient WS-3 to provide for the 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 of WS-3 in one puff of aerosol generated by the combustible aerosol delivery system under an ISO smoking method. In some embodiments, the maximum amount of WS-3 delivered in one puff of aerosol generated by the combustible aerosol delivery system under an ISO smoking method is about 100 μg. In some embodiments, the combustible aerosol delivery system includes sufficient WS-3 to provide for the 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 of WS-3 in one puff of aerosol generated by the combustible aerosol delivery system under an ISO smoking method. In some embodiments, the combustible aerosol delivery system contains sufficient WS-3 to result in delivery of, on average, no more than 100 μg of WS-3 per puff, or no more than about 95, 90, 85, 80, 75, 70, 65, or about 60 μg of WS-3 per puff under the ISO smoking method.

In embodiments where the delivery system is a non-combustible aerosol delivery system, WS-3 is included in an amount that results in the delivery of an average of at least about 1.5 μg of WS-3 per puff of aerosol generated by the product under an HCI smoking regime. The HCI smoking regime is based on a 55 mL puff volume with the vent blocked, a 2 second puff duration, and a 30 second interval between puffs.

In some embodiments, the non-combustible aerosol delivery system includes sufficient WS-3 to deliver, on average, at least 2 μg of WS-3 in one puff of aerosol generated by the non-combustible aerosol delivery system under HCI smoking. In some embodiments, the maximum amount of WS-3 delivered in one puff of aerosol generated by the non-combustible aerosol delivery system under HCI smoking is about 100 μg.

The inclusion of these amounts of WS-3 provides the consumer with delivery of a cooling or refreshing amount of WS-3 cooling agent without the presence of any mint or other characteristic flavors upon use of the delivery system.

In some embodiments, the combustible aerosol delivery system contains sufficient WS-3 to result in delivery of at least about 30 μg of WS-3, 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, or at least about 80 μg of WS-3 on average per puff under ISO smoking techniques.

In some embodiments, the combustible aerosol delivery system contains sufficient WS-3 to result in the delivery of, on average, no more than 100 μg WS-3, 95 μg, 90 μg, 85 μg, 80 μg, 75 μg, 70 μg, 65 μg, or about 60 μg WS-3 per puff under ISO smoking techniques.

The estimated transfer rate of WS-3 from the combustible aerosol delivery system to the aerosol generated during combustion is about 1 to about 2% per mg of tar or nicotine free dry particulate matter (NFDPM) under ISO smoking methods.

In an embodiment in which the transfer rate of WS-3 from the combustible aerosol delivery system to the aerosol is about 1.2% per mg of tar or NFDPM, the following calculations can be made: To deliver 36 μg of WS-3 per puff provided by a 1 mg tar cigarette to provide 7 puffs, 21 mg of WS-3 would need to be evenly distributed along the rod of aerosol-generating material. To deliver approximately 50 μg of WS-3 in a predetermined 3 puffs provided by a 6.1 mg tar cigarette containing WS-3, 2 mg of WS-3 would need to be included locally, e.g., as a patch or band appropriately positioned along the rod of aerosol-generating material.

In some embodiments, a combustible aerosol delivery system is provided that contains about 0.1 mg to about 5 mg of WS-3, or about 0.3 mg to about 2.5 mg of WS-3. In some embodiments, a combustible aerosol delivery system is provided that contains up to about 10 mg of WS-3.

In some embodiments, the combustible aerosol delivery system includes WS-3 localized toward or at the filter end of the rod of aerosol-generating material to provide a cooling or refreshing sensation during the last few puffs when the combustible aerosol delivery system is used. In some embodiments, the localized WS-3 results in the delivery of at least 1.5 μg of WS-3 per puff, on average, under an ISO smoking technique. The ISO smoking technique is based on a 35 mL puff volume, a 2 second puff duration, a 60 second interval between puffs, and no vent blockage.

In certain embodiments, a liquid formulation including WS-3 is printed onto a wrapper that surrounds 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 refreshing sensation throughout use of the combustible aerosol delivery system. In other embodiments, the WS-3 is applied to only one or more portions of the wrapper, with other portions of the wrapper being free of cooling agent, thereby providing localized WS-3 that provides a cooling or refreshing sensation when localized areas of the WS-3 on the wrapper are heated. In some embodiments, the cooling agent may be provided as one or more bands on the wrapper. Depending on the location of the one or more bands and their width, the cooling or refreshing sensation may occur at different times and for different durations during use of the aerosol delivery system.

In some embodiments, 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, 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, WS-3 is printed in the form of a patch or band towards or on the filter end of the rod of aerosol generating material. This releases the WS-3 to generate or deliver a cooling or refreshing sensation towards the end of use of the combustible aerosol delivery system, for example during the last 4 puffs, 3 puffs, 2 puffs, or 1 puff. In some specific embodiments, the printed area is arranged to form a band having a width of 21 mm at the filter end of the assembled combustible aerosol delivery system. Based on a combustible aerosol delivery system having a rod of aerosol generating material with a length of 58 mm and providing an average of 8 puffs, a 21 mm band of printed WS-3 is expected to provide a cooling sensation in the last 3 puffs. In some embodiments, the printed band contains at least 0.5 mg of WS-3. In some specific 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 of WS-3 to provide a cooling sensation in the last few puffs. The printed area of the wrapper may exclude the edges of the wrapper where adhesive is applied to form the lap seam.

In some embodiments, the combustible aerosol delivery system is a cigarette. For example, the cigarette may include a rod of tobacco material surrounded by a paper wrapper and a filter. In some embodiments, WS-3 is included in the cigarette applied to the wrapper. In some embodiments, the WS-3 is applied as a band in the wrapper. Thus, the cigarette may include a band in the wrapper that includes, in some embodiments, about 0.1 mg to about 5 mg of WS-3, or about 0.3 mg to about 2.5 mg of WS-3. The band may be applied, for example, by a rotary gravure printing process.

In some embodiments, a non-combustible aerosol delivery system that includes a charge of aerosol-generating material that is heated to form an aerosol but not combusted contains sufficient WS-3 to result in delivery of, on average, at least about 1.5 μg of WS-3 per puff under an HCI smoking technique, 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 of WS-3.

In some embodiments, the non-combustible aerosol delivery system contains sufficient WS-3 to result in delivery of about 100 μg or less of WS-3, about 95 μg or less, about 90 μg or less, about 85 μg or less, about 80 μg or less, about 75 μg or less, about 70 μg or less, about 65 μg or less, about 60 μg or less, about 55 μg or less, or about 50 μg or less of WS-3 per puff on average under HCl smoking techniques.

The estimated transfer rate of WS-3 into the aerosol generated when heating the aerosol-forming material from a non-combustible aerosol delivery system is about 5 to about 35% under the HCl smoking method.

In an embodiment where the WS-3 transfer rate is about 5%, the following calculation can be made: 4.5 mg of WS-3 needs to be uniformly distributed within the aerosol generating material to deliver 25 μg of WS-3 in each of 9 puffs delivered by the non-combustible aerosol delivery system. In an embodiment where the WS-3 transfer rate is about 35%, the following calculation can be made: 0.925 mg of WS-3 needs to be uniformly distributed within the aerosol generating material to deliver about 36 μg of WS-3 in each of 9 puffs delivered by the non-combustible aerosol delivery system.

The amount of coolant WS-3 contained in the delivery system may be expressed as the total weight of WS-3 per delivery system. In some embodiments, the delivery system contains at least about 1 mg of coolant WS-3. In some embodiments, the delivery system contains no more than about 10 mg or no more than about 5 mg of coolant WS-3. In some of these embodiments, the delivery system is a king size cigarette having a length of about 83 mm. In some embodiments, the delivery system comprises 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 comprises 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 mg or less, or about 1.1 mg or less of WS-3 per delivery system. In some embodiments, the delivery system comprises about 1 mg, about 2 mg, or about 3 mg of WS-3.

Alternatively or additionally, the amount of coolant WS-3 contained in the delivery system may be expressed as the total weight of WS-3 per mg of tar delivered by the delivery system in use. In some embodiments, the delivery system comprises at least 60 μg of WS-3 per mg of tar delivered by the delivery system in use. In some embodiments, the delivery system comprises about 5 mg or less of WS-3 per mg of tar delivered by the delivery system in use. In these embodiments, the tar delivery of the delivery system is measured using an ISO machine smoking method, which includes a 35 ml puff volume, a 2 second puff duration, and a puff frequency of one puff per minute, with the vent open and smoking continuing through a length of tipping paper or filter. In some embodiments, the delivery system comprises 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 mg, or at least about 4.9 mg of WS-3 per mg of tar delivered by the delivery system. In some embodiments, the delivery system comprises 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 mg or less, or about 0.1 mg or less of WS-3 per mg of tar delivered by the delivery system.

Alternatively or additionally, the amount of coolant WS-3 included in the delivery system may be expressed as a total weight of 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 about 83 mm. In some embodiments, the delivery system is a king size cigarette having a length of about 83 mm. In some embodiments, the delivery system is a WS-3 containing 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 mg, or at least about 7.9 mg of WS-3. In some embodiments, the delivery system comprises 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 mg or less, or about 1.4 mg or less of WS-3. In some embodiments, the delivery system comprises at least about 1.4 mg of WS-3 per mg of aerosol-generating material in the delivery system. In some embodiments, the delivery system comprises about 8 mg or less of WS-3 per mg of aerosol-generating material in the delivery system.

The solvent WS-3 coolant may be added in solution form to the delivery system, or to a component of the delivery system.

WS-3 is readily soluble in alcohols such as ethanol and DMSO (dimethyl sulfoxide), so in some embodiments, WS-3 is added to the delivery system in the form of a solution, and the solvent includes an 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 glycol. In addition to being a convenient means of including a humectant in the delivery system, including a humectant in the WS-3 solution has the advantage of lowering the flash point of the solution. This is particularly beneficial when the solvent is an alcohol, such as ethanol.

In some embodiments, a humectant such as propylene glycol may be used as a solvent (without alcohol or DMSO), but such combinations are preferred because the solubility of WS-3 is higher in the solvent than in a humectant such as propylene glycol, thereby reducing the total amount of liquid required to solubilize a given amount of WS-3.

In some embodiments, the solution used to add WS-3 to the delivery system includes WS-3 solubilized in alcohol along with a wetting agent. In some embodiments, the solvent is ethanol and/or the wetting agent is propylene glycol. In one particular embodiment, the solution includes 1 part propylene glycol, 2 parts ethanol, and 3 parts WS-3. Obviously, the ratio of ingredients may be adjusted to provide a solution suitable for adding WS-3 to the delivery system. Indeed, in the following examples, various solutions are used to add WS-3 to the delivery system.

In one particular embodiment, WS-3 and propylene glycol are applied to the aerosol generating material of the delivery system using the ratio solutions described above. 3 mg of WS-3 is added to the aerosol generating material using 6 mg of solution.

In some embodiments, the solution containing WS-3 is 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 uniformly to the aerosol-generating material, or may be applied to provide a specific distribution of the solution, and thus the WS-3, within the aerosol-generating material and within the delivery system.

Location In order to provide the desired benefits of the present invention, the WS-3 refrigerant should be included in the delivery system to allow for delivery of the WS-3 to the consumer during use of the delivery system.

In some embodiments, delivery of the WS-3 coolant is by inhalation. Thus, the WS-3 delivered to the consumer is contained in the aerosol generated by the delivery system and inhaled by the consumer. Thus, the WS-3 is incorporated into the delivery system so that it is entrained in the aerosol.

In some embodiments, the coolant WS-3 is present in the aerosol generating material. In some embodiments, the coolant WS-3 is applied to the aerosol generating material. When the delivery system is used, the WS-3 volatilizes and is entrained in the aerosol flow through the delivery system. Research suggests that WS-3 is a stable molecule and does not transform or react with other chemicals in the aerosol. This is despite the high temperatures found in the rod of aerosol generating material in a combustible aerosol delivery system such as a cigarette. This is also despite the relatively low volatility of WS-3 compared to some coolants used in delivery systems such as menthol.

In some embodiments, WS-3 is applied to the aerosol-generating material before or as the aerosol-generating material is incorporated into the rod of aerosol-generating material for inclusion in a delivery system. Alternatively, WS-3 may be added to the rod of aerosol-generating material after the rod of aerosol-generating material is formed, for example, by injecting WS-3 into the rod of aerosol-generating material.

In some embodiments, the coolant WS-3 is applied to the aerosol-generating material by spraying a solution of the coolant WS-3 onto the aerosol-generating material. Suitable solutions are described above. This application of the WS-3 solution can help ensure that the WS-3 is evenly distributed throughout the aerosol-generating material. Alternatively or additionally, the coolant WS-3 may be added to the aerosol-generating material in solid form, for example in powder form.

When WS-3 is applied to an aerosol-forming material, a delivery system is used and the WS-3 is gradually released and entrained in the aerosol as the aerosol-forming material is heated.

In some embodiments, the coolant WS-3 is included by being applied to a wrapper that surrounds the aerosol-generating material. This may be in addition to, or instead of, applying WS-3 to the aerosol-generating material or one or more other parts of the delivery system. Again, the WS-3 may be applied to the wrapper in solution form 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 that faces the aerosol-generating material in the delivery system.

In other embodiments, WS-3 is applied to a separate layer of a sheet material placed adjacent to or on a wrapper surrounding the aerosol-generating material.

In some embodiments, it is possible to control the delivery of the cooling or refreshing sensation to the consumer by controlling the location of the coolant WS-3 along the aerosol-generating rod. If a consistent delivery of a cooling or refreshing sensation is desired, the coolant may be distributed evenly along the rod of aerosol-generating material. If the cooling or refreshing effect is to be provided at a specific, pre-determined point during use of the delivery system, this can be achieved by localized delivery of the coolant. For example, to provide a cooling or refreshing sensation in the last few puffs of the delivery system, the coolant WS-3 may be applied to only a portion of the rod of aerosol-generating material, i.e., the portion that will be heated or combusted later in use of the delivery system. In the case of a combustible aerosol delivery system, the coolant is located towards the filter end of the rod of aerosol-generating material. One convenient way to achieve this is by providing a patch or band of coolant in a wrapper surrounding or adjacent to the rod of aerosol-generating material.

In some embodiments, the delivery system includes a filter and the coolant WS-3 is included in the filter. This may be in addition to or instead of including WS-3 in the aerosol-forming material of the delivery system.

In some embodiments, WS-3 is applied to the filter material. For example, WS-3 may be applied to the filter material before or as the filter material is incorporated into a filter of a filter element for inclusion in a delivery system. Again, WS-3 may be applied to the filter material in solution form or in solid form, such as powder form. Alternatively, WS-3 may be added to the filter or filter element after the filter or filter element is formed, for example by injection into the filter.

In some embodiments, the coolant WS-3 is included in the filter by being applied to a wrapper that surrounds the filter material. This may be in addition to or instead of applying WS-3 to the filter material or other parts of the delivery system. Again, the WS-3 may be applied to the wrapper in solution form 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 that faces the filter material in the delivery system.

In some embodiments, in addition to including WS-3 to be delivered in the aerosol that is generated and delivered to the user, the delivery system may include a sensate on at least a portion of its surface to provide an additional sensation to the user during use. For example, the sensate may be provided on a surface of the mouth end of the system localized where the system contacts the user's lips during use. The sensate may be selected to complement the cooling or refreshing sensation provided by the WS-3, as discussed herein.

1 and 2, by way of example and not limitation, a combustible aerosol delivery system 1 according to an exemplary embodiment of the present invention includes a filter 2 and a cylindrical rod 3 of aerosol-generating material. The rod 3 of aerosol-generating material is aligned with the filter 2 such that one end of the rod 3 of aerosol-generating material abuts an end of the filter 2. The filter 2 is a filter material 4 wrapped in a plug wrap 5, and a plug of aerosol-generating material 6, such as tobacco, is surrounded by a paper wrapper 7 to form the rod 3 of aerosol-generating material. The rod 3 of aerosol-generating material is connected to the filter 2 by tipping paper 8 in a conventional manner.

In the embodiment shown in FIG. 1, the plug of aerosol-generating material includes tobacco to which the coolant WS-3 has been applied in accordance with embodiments of the invention described herein.

The embodiment shown in FIG. 2 includes coolant WS-3 provided in the form of a patch 9 at a first location along the length of a wrapper 7 that surrounds a plug of aerosol-generating material to form a 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 during use of the combustible aerosol delivery system, the patch releases the coolant when heated, so that the coolant is delivered only during the last few puffs of the delivery system.

In other embodiments (not shown), the coolant patch may be located at another location along the length of the rod of aerosol-generating material, multiple patches may be provided, or a single patch may extend further along the rod, even the entire length of the rod of aerosol-generating material.

The combustible aerosol delivery system of the present invention can be adapted to any size or dimension known for combustible aerosol delivery systems.

As used herein, the term "tobacco" refers to the material typically found in the tobacco rod of a combustible aerosol delivery system, such as a cigarette, or in tobacco-containing aerosol-generating materials of a non-combustible aerosol delivery system. For example, tobacco includes tobacco bladder, tobacco stem, expanded tobacco, reconstituted tobacco, extruded tobacco, tobacco substitutes, and filler materials.

As used herein, the term "tobacco" includes any part and any associated by-products, such as leaves or stems, of any member of the Nicotiana genus. In some embodiments, the tobacco material is derived from the Nicotiana tabacum species. In some embodiments, the tobacco material is one or more selected from the group consisting of cut stems, cut leaf blades, leaf blades, leaflet blades, stem fibers, short stems, and long stems.

Any type, style and/or variety of tobacco may be used. Examples of tobacco that may be used include, but are not limited to, Virginia, Burley, Orient, Comum, Amarelinho and Maryland tobaccos, as well as blends of any of these types. Those skilled in the art will recognize that working with different types, styles and/or varieties will result in tobaccos with different organoleptic characteristics.

In some embodiments, the delivery system includes a filter. The filter may represent any filter configuration known in the art. Filters for delivery systems typically include one or more of fibrous cellulose acetate, a polypropylene material, a polyethylene material, or a gathered paper material.

In some embodiments, the filter may include an adsorbent material, such as activated carbon. In some embodiments, the filter may include one or more capsules. The capsules may include an aerosol modifier, such as a flavoring, if permitted by local regulations. In some embodiments, the aerosol modifier is not another refrigerant other than WS-3 and/or is not a flavoring that imparts a noticeable odor or taste in addition to the odor or taste of the aerosol-generating material.

As used herein, the terms "flavoring agent" and "flavoring agent" refer to materials that can be used to create a desired taste or odor in products for adult consumers, where local regulations permit. These include extracts (e.g., licorice, hydrangea, magnolia leaf, chamomile, fenugreek, clove, menthol, peppermint, aniseed, cinnamon, herbs, wintergreen, cherry, berry, peach, apple, Drambuie, bourbon, Scotch, whiskey, spearmint, peppermint, lavender, cardamom, celery, cascarilla, nutmeg, sandalwood, bergamot, geranium, honey essence, rose oil, vanilla, lemon oil, orange oil, cassia, caraway, cognac, jasmine, iodine, oleander ... The additives may include, for example, lanthanum, sage, fennel, pepper, ginger, anise, coriander, coffee, or mint oil from any species of the genus Mentha), flavor enhancers, bitter receptor site blockers, sensory receptor site activators or stimulants, sugars and/or sugar substitutes (e.g., sucralose, acesulfame potassium, aspartame, saccharin, cyclamate, lactose, sucrose, glucose, fructose, sorbitol, or mannitol), and other additives such as charcoal, chlorophyll, minerals, botanicals, or breath fresheners. They may be imitation ingredients, synthetic ingredients, natural ingredients, or blends thereof. They may be in any suitable form, such as, for example, oil, liquid, or powder.

Experimental The objective of the experimental work carried out was to demonstrate the distinction between coolants and characterizing flavors, defined as "a noticeable odor or taste other than tobacco odor or taste resulting from an additive or combination of additives."

Test cigarettes were prepared with the following amounts of WS-3 applied in solution form to the aerosol-forming material in the tobacco rod:

WS-3 solutions were prepared using the following solvents (PG is propylene glycol, EtOH is ethanol).

Various cigarettes were prepared and smoked so that (1) menthol flavor intensity, (2) cooling sensation, and (3) tobacco taste intensity could each be rated by testers (N=28) on a scale of 1 to 10.

Where the menthol flavor intensity score is less than 1, the data indicates that WS-3 provides a cooling sensation without menthol flavor. In fact, the ANOVA statistics (shown in Figure 1) indicate that menthol flavor intensity was significantly lower in all coolant-added samples versus menthol-added samples. Notably, WS-3 was not statistically different in menthol flavor attributes relative to both control samples (containing no menthol).

The cooling sensation of the coolant samples was significantly greater than both control products. Statistical PCA analysis confirmed the ANOVA results and showed a clear distinction between both coolant samples (WS-3 and WS-23) and the mentholated products.

Further samples were analysed using "sniffing analysis", a sensory technique applied to characterise the flavour of standardised products by sniffing the tobacco itself, without combustion, using the method described in the international standard ISO 13299. The data are presented in Tables 4 and 5, which show the results of the QDP (Quantitative Descriptive Analysis), giving a score from 0 to 5 for the perception of different tobacco and non-tobacco typical flavour notes.

In Tables 4 and 5, the average critical intensities greater than 1.0 are highlighted in bold. On a categorical scale of 0 to 5, neither the "WS3" nor the "WS23" prototype cigarettes exhibited a critical intensity greater than 1.0 for any non-tobacco typical flavor notes (see Table 5).

Only the mentholated cigarettes were described as having a very strong mint flavor, with a score scale of 4.9. Even the "control" unflavored cigarettes were described as having a very slight mint note, according to the results of the smoking analysis. "WS23" had a non-significant but detectable mint flavor, with a score of 0.7 points (Table 5).

The "typical tobacco flavor notes" are roughly equally detectable in the "control" cigarettes as well as in the prototypes "WS-3" and "WS-23" (see Table 4). This means that tobacco aroma dominates the flavor in all cigarettes except the mentholated cigarettes. These results of the QDP are in very good agreement with the smoking analysis, which also proves the validity of both methods.

From the data it can be concluded that the inclusion of "WS-23" can be identified in both smoke and sniff analyses as a substance that imparts a very slight but detectable mint/menthol flavor. In contrast, the data suggests that the inclusion of "WS-3" coolant provides a cooling sensation without menthol flavor. The data indicates that WS-3 provides minimal non-tobacco flavors and is preferred when an additive is desired that provides a cooling or refreshing sensation without a noticeable or discernible odor or taste other than that of tobacco.

The various embodiments described herein are presented only to aid in understanding and teaching the claimed features. These embodiments are provided only as a representative sample of embodiments and are not exhaustive and/or exclusive. The advantages, embodiments, examples, functions, features, structures, and/or other aspects described herein should not be considered as limitations on the scope of the invention as defined by the claims or limitations on the equivalents of the claims, and it is understood that other embodiments may be utilized and modifications may be made without departing from the scope of the claimed invention. Various embodiments of the present invention may suitably comprise, consist of, or consist essentially of any suitable combination of the disclosed elements, components, features, parts, steps, means, etc., other than those specifically described herein. In addition, the present disclosure may include other inventions not claimed herein but which may be claimed in the future.

Claims (39)

A delivery system comprising an aerosol generating material and a cooling agent WS-3, the cooling agent WS-3 being present in an amount that results in the delivery of an average of at least about 1.5 μg of WS-3 per 35 mL puff. The delivery system of claim 1, wherein the WS-3 is contained in an amount that results in the delivery of an average of about 100 μg or less of WS-3 per 35 mL puff. The delivery system of claim 1 or 2, wherein the delivery system does not contain any additive that imparts a noticeable odor or taste in addition to the odor or taste of the aerosol-forming material. The delivery system of any one of claims 1 to 3, wherein the delivery system does not contain any further coolant in addition to the coolant WS-3. The delivery system of any one of claims 1 to 4, wherein the delivery system is a combustible aerosol delivery system including a rod of aerosol-generating material, and WS-3 is included in an amount that results in the delivery of an average of at least 1.5 μg of WS-3 per puff under ISO smoking techniques. The delivery system of claim 5, wherein the combustible aerosol delivery system comprises WS-3 in an amount that results in the delivery of an average of at least about 25 μg of WS-3 per puff of aerosol generated under ISO smoking techniques. The delivery system of claim 5 or 6, wherein the combustible aerosol delivery system contains WS-3 in an amount that results in the delivery of 100 μg or less of WS-3 in one puff of aerosol generated under ISO smoking techniques. The delivery system according to any one of claims 1 to 4, wherein the delivery system is a non-combustible aerosol delivery system and contains WS-3 in an amount that results in the delivery of an average of at least 1.5 μg of WS-3 per puff under HCI smoking techniques. The delivery system of claim 8, wherein the non-combustible aerosol delivery system comprises WS-3 in an amount that results in the delivery of an average of at least about 2 μg of WS-3 per puff of aerosol generated under HCl smoking. The delivery system of claim 8 or 9, wherein the non-combustible aerosol delivery system contains WS-3 in an amount that results in the delivery of 100 μg or less of WS-3 in one puff of aerosol generated under HCI smoking. The delivery system of any one of claims 1 to 10, wherein the amount of coolant WS-3 contained in the delivery system is at least 0.1 mg or at least 0.3 mg per delivery system. The delivery system of any one of claims 1 to 11, wherein the amount of coolant WS-3 contained in the delivery system is at least 1 mg per delivery system. A delivery system according to any one of claims 1 to 12, wherein the amount of coolant WS-3 contained in said delivery system is equal to or less than 10 mg per delivery system. 14. The delivery system of claim 13, wherein the amount of coolant WS-3 contained in said delivery system is 5 mg or less per delivery system. 14. The delivery system of claim 13, wherein the amount of coolant WS-3 contained in said delivery system is 2.5 mg or less per delivery system. The delivery system of any one of claims 5 to 7, wherein the amount of coolant WS-3 contained in the delivery system is at least 60 μg per mg of tar delivered by the delivery system. 17. A delivery system according to any one of claims 5 to 7 or 16 , wherein the amount of coolant WS-3 contained in the delivery system is no more than 10 mg per mg of tar delivered by the delivery system. 18. The delivery system of claim 17, wherein the delivery system contains no more than 5 mg of coolant WS-3 per mg of tar delivered by the delivery system. 19. The delivery system of claim 1, wherein the delivery system contains at least 0.8 mg of coolant WS-3 per gram of aerosol-forming material. 20. The delivery system of claim 1, wherein the delivery system contains no more than 15 mg of coolant WS-3 per gram of aerosol-forming material. 21. The delivery system of claim 20, wherein the delivery system contains no more than 11 mg of coolant WS-3 per gram of aerosol-forming material. 22. The delivery system of claim 1, wherein the coolant WS-3 is present in the aerosol forming material. 23. The delivery system of claim 22 , wherein the coolant WS-3 is applied to the aerosol-forming material. 24. The delivery system of claim 23, wherein the coolant WS-3 is applied to the aerosol-forming material by spraying a solution of the coolant WS-3 onto the aerosol-forming material or by adding the coolant WS- 3 in solid form to the aerosol-forming material. 23. The delivery system of claim 22 , wherein the coolant WS-3 is added to a wrapper that surrounds the aerosol-forming material. 26. The delivery system of any one of claims 1 to 25 , wherein the delivery system comprises a filter and the coolant WS-3 is present in the filter. 27. The delivery system of claim 26 , wherein the coolant WS-3 is applied to a filter material. 28. The delivery system of claim 27, wherein the coolant WS-3 is applied to the filter material by spraying a solution of the coolant WS-3 onto the filter material or by adding the coolant WS- 3 in solid form to the filter material. 30. The delivery system of claim 24 or 28 , wherein the cooling agent WS-3 in solid form is in powder form. 30. A method of making a delivery system as described in any one of claims 1 to 29 , comprising the step of incorporating the cooling agent WS-3 into the delivery system in an amount that provides a cooling sensation without imparting a noticeable odor or taste in addition to the odor or taste of the aerosol-forming material. 31. The method of claim 30 , comprising applying the coolant WS-3 to the aerosol-forming material. 32. The method of claim 31 , comprising applying the coolant WS-3 to the aerosol-forming material by spraying a solution of the coolant WS-3 onto the aerosol-forming material or by applying the coolant WS- 3 in solid form to the aerosol-forming material. 31. The method of claim 30 , comprising applying the coolant WS-3 to at least a portion of a wrapper surrounding the aerosol-forming material. The method of any one of claims 30 to 33 , comprising incorporating the coolant WS-3 into a filter of the delivery system. 35. The method of claim 34 , comprising applying the coolant WS-3 to a filter material. 36. The method of claim 35, comprising applying the coolant WS-3 to the filter material by spraying a solution of the coolant WS-3 onto the filter material or by applying the coolant WS- 3 in solid form to the filter material. 37. The method of claim 32 or 36 , wherein the solid form of the coolant WS-3 is in powder form. The use of a cooling agent WS-3 to provide a cooling sensation to a user of a delivery system without imparting a characteristic flavor, wherein an average amount of at least about 1.5 μg of WS-3 is delivered in one 35 mL puff. 39. The use of claim 38 , wherein the delivery system does not contain any additives that impart a noticeable odor or taste in addition to the odor or taste of the aerosol-forming material.

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