Smoking article

Patent metadata

Field	Value
Publication number	US-11528933-B2
Application number	US-201716465063-A
Country	US
Kind code	B2
Filing date	Nov 29, 2017
Priority date	Nov 30, 2016
Publication date	Dec 20, 2022
Grant date	Dec 20, 2022

Abstract

In one aspect an aerosol-generating device comprising a smoking article and a heat source is described. The smoking article includes a smokable material and a cooling agent, the smokable material including a tobacco component. The heat source is disposed to heat, but not burn the smokable material in use. The cooling agent comprises a compound or a combination of compounds according to either of the following formulae, racemates, enantiomers and salts thereof (I, II).

First claim

The invention claimed is:

1. An aerosol-generating device comprising:
a smoking article comprising a smokable material, a cooling agent and method, wherein the cooling agent is impregnated into the smokable material, and the smokable material comprises a tobacco component; and
a heat source disposed to heat, but not burn the smokable material in use;

wherein the cooling agent comprises:
a compound or a combination of compounds according to formula (I), racemates, enantiomers and salts thereof:

wherein
X is selected from the group consisting of C(═O)R 3 and OR 4 ;
Y is selected from the group consisting of H, and OR a
R 1 is selected from the group consisting of CH 3 and OH;
R 2 is selected from the group consisting of H and CH 3 ;
or R 1 and R 2 together form at least ═CH 2 or ═O;
R 3 is selected from H; optionally substituted C 1-4 alkyl; COR 5 ; CO 2 R 5 ; and NR 6 R 7 ;
wherein
R 4 is selected from the group consisting of optionally substituted C 1-4 alkyl; COR 5 ; CO 2 R 5 ;

or, where Y is OR a , R 4 may be R b and R a and R b together form an optionally substituted C 2-4 alkylene group; or where R 1 is not CH 3 , R 4 may be H;
R 5 is selected from the group consisting of H; (CH 2 ) t O(CH 2 ) u OH where t and u are independently 1 to 4; C 1-4 alkyl optionally substituted with ═O, alkoxy, OH, CO 2 H, CH 3 , CON(R 8 ) 2 ; and an optionally substituted 3-7-membered aliphatic heterocyclyl;
R 6 and R 7 are independently selected from the group consisting of H; C 1-4 alkyl optionally substituted with OH, CO 2 R 8 , or a 5-7-membered heteroaryl; C 3-6 cycloalkyl; 5-7-membered heteroaryl; and phenyl which is optionally substituted with CH 3 , CN, CH 2 CN, CH 2 CONH 2 , OCH 3 , or OH;
R 8 is selected from H and C 1-4 alkyl;
and/or a compound or combination of compounds according to formula (II), racemates, enantiomers and salts thereof:

wherein
R 1 ′ is selected from the group consisting of CH(R 5 ′) 2 and R a ′;
R 2 ′ is selected the group consisting of from CH(R 5 ′) 2 and R b ′, where R a ′ and R b ′ together with the carbon atom to which they are attached form an optionally substituted aliphatic 3-6-membered ring;
R 3 ′ is selected from the group consisting of H, CH(R 5 ′) 2 , and C 1-4 alkyl;
R 4 ′ is selected from C 1-4 alkyl optionally substituted with OH, CO 2 R 6 ′, or a 5-7-membered heteroaryl; CO 2 R 6 ′; C 3-6 cycloalkyl; 5-7-membered heteroaryl; and phenyl which is optionally substituted with CH 3 , CN, CH 2 CN, CH 2 CONH 2 , OCH 3 , or OH;
R 5 ′ is selected from the group consisting of H and C 1-4 alkyl optionally substituted with OH;
R 6 ′ is selected from the group consisting of H and C 1-4 alkyl.

2. An aerosol-generating device according to claim 1 , wherein the cooling agent comprises a compound or a combination of compounds according to formula (Ia), racemates, enantiomers and salts thereof:

wherein
R 2 ′ is selected from CH(R 5 ′) 2 and R b ′, where R a ′ and R b ′ together with the carbon atom to which they are attached form 2-isopropyl-5-methylcyclohexylene;
R 3 ′ is selected from H and CH(R 5 ′) 2 ; and
R 5 ′ is selected from H and CH 3 .

3. An aerosol-generating device according to claim 1 , wherein the cooling agent has a vapor pressure of less than about 106 Pa at 20° C.

4. An aerosol-generating device according to claim 1 , wherein the menthol is disposed in the smokable material.

5. An aerosol-generating device according to claim 1 , further comprising a filter.

6. An aerosol-generating device according to claim 5 , wherein menthol is disposed in the filter.

7. An aerosol-generating device according to claim 5 , wherein menthol is disposed in the smokable material and in the filter.

8. An aerosol-generating device according to claim 1 , wherein the weight ratio of cooling agent to menthol in the smoking article is from about 1:150 to about 1:1.

9. An aerosol-generating device according to claim 1 , wherein the cooling agent is selected from the group consisting of:

or combinations thereof.

10. An aerosol-generating device according to claim 1 , wherein the cooling agent is selected from the group consisting of:
1 N-ethyl-2-isopropyl-5-methylcyclohexane carboxamide;
2-isopropyl-N-[(ethoxycarbonyl)methyl]-5-methylcyclohexanecarboxamide;
2-isopropyl-N-(4-methoxylphenyl)-5-methylcyclohexanecarboxamide;
2-isopropyl-N,2,3-trimethylbutanamide;
or combinations thereof.

11. A smoking article for use in an aerosol generating device, the smoking article comprising a smokable material, a cooling agent and method, wherein the cooling agent is impregnated into the smokable material, and the smokable material comprises a tobacco component; and wherein the cooling agent is as defined in claim 1 .

12. A smoking article according to claim 11 ;
wherein the smokable material comprises a tobacco component in an amount of from 60 to 90% by weight of the smokable material, a filler in an amount of 0 to 20% by weight of the smokable material, and an aerosol generating agent in an amount of from 10 to 20% by weight of the tobacco composition,
wherein the tobacco composition has a nicotine content of from 0.5 to 2.5% by weight of the tobacco composition; and
wherein the tobacco component comprises paper reconstituted tobacco in an amount of from 70 to 100% by weight of the tobacco component.

13. A method of manufacturing a smoking article for use with an aerosol-generating device, the method comprising:
impregnating a cooling agent into a smokable material comprising a tobacco component, wherein the cooling agent is as defined in claim 1 ;
applying menthol to the tobacco component; and
combining the smokable material with a filter to provide a smoking article.

Assignees

• British American Tobacco Investments Ltd
• Nico Ventures Trading Ltd

Inventors

• Ballesteros Gomez Pablo Javier
• Phillips Jeremy
• Forster Mark
• Chadjim Hans-Josef

Classifications

• A24B15/32 Primary

  by acyclic compounds · CPC title

• A24B15/12

  of reconstituted tobacco · CPC title

• A24B15/34

  containing a carbocyclic ring other than a six-membered aromatic ring · CPC title

• A24F40/10

  Devices using liquid inhalable precursors · CPC title

• A24D1/20

  Cigarettes specially adapted for simulated smoking devices · CPC title