SMOKING ARTICLE MOUTHPIECE WITH COOLING AGENT INCLUSION COMPLEX

Abstract

A smoking article includes a mouthpiece having an outer surface and a cooling agent inclusion complex disposed on the outer surface.

Claims

1. A smoking article comprising; a mouthpiece having an outer surface; and a cooling agent inclusion complex disposed on the outer surface wherein the cooling agent inclusion complex is a cyclodextrin cooling agent inclusion complex comprising cyclodextrin and a non-volatile cooling agent comprising a carboxamide containing compound.

2. A smoking article according to claim 1 wherein the cooling agent is non-volatile and has a vapour pressure less than about 8.5 Pa.

3. A smoking article according to claim 1 wherein the carboxamide containing compound has the structure (I): ##STR00007## where R is a C1-C12 straight or branched chain alkyl or alkoxy, or arylene or pyridyl.

4. A smoking article according to claim 1 wherein the carboxamide containing compound has the structure (I-B): ##STR00008##

5. A smoking article according to claim 1 wherein the carboxamide containing compound is N-ethyl-p-menthane-3-carboxamide; ethyl 3-(p-menthane-3-carboxamido)acetate; N-(ethoxycarbonylmethyl)-p-menthane-3-carboxamide; N-(4-cyanomethylphenyl)-p-menthane carboxamide; N-(4-aminocarbonylphenyl)-p-menthane; or N-(4-methoxyphenyl)-p-menthanecarboxamide or N-(2-(pyridine-2-yl-)ethyl)-3-p-menthanecarboxamide.

6. A smoking article according to claim 1 wherein the carboxamide containing to compound is N-ethyl-p-menthane-3-carboxamide or ethyl 3-(p-menthane-3-carboxamido)acetate.

7. A smoking article according to claim 1 wherein the carboxamide containing compound has the structure (II): ##STR00009## where R1 is a C1-C6 straight or branched chain alkyl or alkoxy, and each R2 is independently selected from the group consisting of C1-C3 straight or branched chain alkyl.

8. A smoking article according to claim 1 wherein the carboxamide containing compound has the structure (II-C): ##STR00010##

9. A smoking article according to claim 1 wherein the carboxamide containing compound is 2-isopropyl-N,2,3-trimethylbutanamide; N-(2-ethoxyethyl)-2,3-dimethyl-2-isopropylbutanamide; or N-(1-isopropyl-1-methylisobutyl)anisamide; or N-ethyl-2,2-diisopropylbutanamide; or N-(2-hydroxyethyl)-2-isopropyl-2,3-dimethylbutanamide.

10. A smoking article according to claim 1 wherein the carboxamide containing compound is 2-isopropyl-N,2,3-trimethylbutanamide.

11. A smoking article according to claim 1 wherein the carboxamide containing compound is N-ethyl-p-menthane-3-carboxamide.

12. A smoking article comprising; a mouthpiece having an outer surface; and a cooling agent inclusion complex disposed on the outer surface wherein the cooling agent inclusion complex is a cyclodextrin cooling agent inclusion complex comprising cyclodextrin and a non-volatile cooling agent comprising a menthoxy containing compound.

13. A smoking article according to claim 12 wherein the cooling agent is non-volatile and has a vapour pressure less than about 8.5 Pa.

14. A smoking article according to claim 12 wherein the menthoxy containing compound has the structure (III): ##STR00011## where R3 is a C1-C6 straight or branched chain alkyl or alkoxy

15. A smoking article according to claim 12 wherein the carboxamide containing compound has the structure (III-A): ##STR00012##

16. A smoking article according to claim 12 wherein the carboxamide containing to compound has the structure (III-C): ##STR00013##

17. A smoking article according to claim 12 wherein the menthoxy containing compound is menthyl lactate; monomenthyl succinate; monomenthyl glutarate; menthyl pyrrolidin-2-one-5-carboxylate; menthyl ester of 4-(N,N-dimethylamino)-4-oxobutanoic acid; menthyl 3-hydroxybutyrate; 3-l-menthoxypropane-1,2-diol; 2-l-menthoxyethanol; menthone glycerol ketal; p-menthane-3,8-diol; or menthyl methyl ether.

Description

[0030] The disclosure will be further described, by way of example only, with reference to the accompanying drawings, in which:

[0031] FIG. 1 shows a schematic cross section view of a smoking article according to the present disclosure having a cooling agent and cyclodextrin inclusion complex disposed on the outer surface of the mouthpiece.

[0032] The smoking article 10 shown in FIG. 1 includes a tobacco substrate or tobacco rod 12 attached to, and in axial alignment with, a mouthpiece 14, shown here as a filter 14. The mouthpiece or filter 14 includes a filter plug 16 that can be formed of cellulose acetate wrapped in plug wrap 18. Tipping wrapper 19 joins the tobacco rod 12 to the axially aligned mouthpiece or filter 14.

[0033] The cooling agent and cyclodextrin inclusion complex 20 is disposed on the outer surface of the mouthpiece or filter 14. In many embodiments the cooling agent and cyclodextrin inclusion complex 20 is disposed on the tipping wrapper 19 which forms at least a portion of the mouthpiece outer surface.

[0034] As illustrated in FIG. 1, the cooling agent and cyclodextrin inclusion complex 20 does not need a barrier layer or any other layer to prevent migration of the cooling agent and cyclodextrin inclusion complex 20. The cooling agent and cyclodextrin inclusion complex 20 remains stable, active and in place on the tipping paper for an extended period of time without the use of additional layers or coatings.

EXAMPLES

[0035] Sensory studies were performed to determine whether cigarettes having a cooling agent inclusion complex disposed on tipping paper, would provide a more intense cooling sensation, compared to identical cigarettes which had been aged by 6 months.

[0036] Three different groups of cigarettes (1P, 2P, 3P) were prepared and presented to a group of panelists for sensory studies. Each group consisted of a non-aged version of the cigarette and a corresponding version of the cigarette that had been aged by 6 months. In each case, the cigarette had been prepared with an equal amount of cooling agent on its tipping paper.

TABLE-US-00001 TABLE 1 Cigarette Specificaitons Cooling Application Cooling Ageing Products agent method agent form (months) Non-aged 1P N-Ethyl-p- Unprinted Encapsulated 0 Aged 1P menthane-3- basepaper in cyclodextrin 6 Non-aged 2P carboxamide Precoated 0 Aged 2P basepaper with 6 nitrocellulose lacquer Non-aged 3P precoated 0 Aged 3P basepaper with 6 ethylcellulose lacquer

[0037] The panelists were asked to humidify their lips, insert the filter section of a first cigarette into the left side of their mouth, and draw twice on the unlit cigarette, before then removing the cigarette. The panelists were then asked to repeat this process, but with a second cigarette on the right side of their mouth. A few seconds after both cigarettes had been removed, the panelists were then asked to indicate which cigarette provided a more intense cooling sensation. Each cigarette pair was presented to a panelist 7 times in randomized order. Each cigarette pair included one non-aged cigarette and one corresponding aged cigarette as shown in table 1.

[0038] The answers provided by the panelists are shown in table 2 below.

TABLE-US-00002 TABLE 2 Panelist Response Minimum number for significant Number of times the Number of difference Aged Version was Test panelists at 95% CL selected Non-aged 1P vs. Aged 18 14 10 1P Non-aged 2P vs. Aged 19 15 10 2P Non-aged 3P vs. Aged 12 3P

[0039] It was found that there was no significant difference between the non-aged cigarette and the aged cigarette for each test performed. That is, the panelist studies did not overall find that cigarettes having a cooling agent inclusion complex disposed on tipping paper, would provide a more intense cooling sensation, compared to identical cigarettes which had been aged by 6 months.