NICOTINE COMPOSITION, METHOD FOR MAKING AND AEROSOL GENERATING ARTICLES COMPRISING SUCH

Abstract

A nicotine composition is provided, including a non-aqueous solvent; at least 0.2 percent by weight of nicotine based on the weight of the nicotine composition; a first ratio by weight of (β-ionone+β-damascenone) to (phenol) of greater than 0.25; and a second ratio by weight of (furaneol+(2,3-diethyl-5-methylpyrazine)*100)) to (nicotine) of greater than 5×10.sup.−4. A cartridge including the nicotine composition, and a method of preparing the nicotine composition, are also provided.

Claims

1.-15. (canceled)

16. A nicotine composition, comprising: a non-aqueous solvent; at least 0.2 percent by weight of nicotine based on the weight of the nicotine composition; a first ratio by weight of (β-ionone+(3-damascenone) to (phenol) of greater than 0.25; and a second ratio by weight of (furaneol+(2,3-diethyl-5-methylpyrazine)*100)) to (nicotine) of greater than 5×10.sup.−4.

17. The nicotine composition according to claim 16, wherein the first ratio by weight is greater than 0.5.

18. The nicotine composition according to claim 16, wherein the first ratio by weight is greater than 1.

19. The nicotine composition according to claim 16, wherein the first ratio by weight is greater than 1.5.

20. The nicotine composition according to claim 16, wherein the first ratio by weight is greater than 2.

21. The nicotine composition according to claim 16, wherein the first ratio by weight is between 2 and 10 or between 2 and 5.

22. The nicotine composition according to claim 16, wherein the second ratio by weight is between 8×10.sup.−4 and 9×10.sup.−3.

23. The nicotine composition according to claim 16, wherein the nicotine composition comprises between 0.4 percent by weight and 3.6 percent by weight nicotine based on the weight of the nicotine composition.

24. The nicotine composition according to claim 16, further comprising a third ratio by weight of (β-ionone+β-damascenone) to (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone+(R,S)—N-nitrosoanatabine+(R,S)—N-nitrosoanabasine+N-nitrosonornicotine+((2-furanemethanol)/600)), wherein the third ratio by weight is greater than 1.5.

25. The nicotine composition according to claim 16, wherein the nicotine composition is derived from Burley tobacco and Bright tobacco.

26. The nicotine composition according to claim 25, wherein the Bright tobacco is one or more of Oriental tobacco and flue-cured tobacco.

27. The nicotine composition according to claim 16, wherein the non-aqueous solvent is glycerine, propylene glycol, triacetin, 1,3-propanediol, or a mixture thereof.

28. The nicotine composition according to claim 16, further comprising one or more of acetic acid, vanillin, 2-ethyl-3,5-dimethylpyrazine, 2-methylbutanoic acid, 3-methylbutanoic acid, 3-methyl-2,4-nonanedione, 2-methoxyphenol, 2-phenyl ethanol, eugenol, and sotolone.

29. The nicotine composition according to claim 16, wherein the nicotine composition comprises at least 300 micrograms of acetic acid per gram of the nicotine composition.

30. The nicotine composition according to claim 27, further comprising between about 80 percent by weight and about 90 percent by weight of the non-aqueous solvent and between about 10 percent by weight and about 15 percent by weight of water, based on the weight of the nicotine composition.

31. The nicotine composition according to claim 16, wherein the nicotine composition is a liquid nicotine composition.

32. The nicotine composition according to claim 16, wherein the nicotine composition is a gel nicotine composition.

33. A cartridge comprising the nicotine composition of claim 16.

34. A nicotine composition, comprising a non-aqueous solvent, nicotine, a first ratio by weight of (β-ionone+β-damascenone) to (phenol) of greater than 0.25, and a second ratio by weight of (furaneol+(2,3-diethyl-5-methylpyrazine)*100) to (nicotine) of greater than 5×10.sup.−4, prepared by a method comprising the steps of: heating a tobacco starting material at an extraction temperature of between 100 degrees Celsius and 160 degrees Celsius for at least 90 minutes; collecting the volatile compounds released from the tobacco starting material during the heating step; forming a liquid tobacco extract comprising the collected volatile compounds; and forming the nicotine composition from the liquid tobacco extract.

Description

EXAMPLES

Example 1

[0208] A tobacco starting material is prepared from a flue-cured Bright tobacco material. The tobacco material is cut to form tobacco shreds having dimensions of 2.5 millimetres by 2.5 millimetres and the tobacco shreds are loaded into an extraction chamber, without compression. The tobacco starting material is heated within the extraction chamber to a temperature of 130 degrees Celsius for a period of 3 hours. During heating, a flow of nitrogen is passed through the extraction chamber at a flow rate of about 40 litres per minute.

[0209] The volatile compounds released from the tobacco starting material during the heating step are collected by absorption into a liquid solvent formed of propylene glycol at minus 10 degrees Celsius and with agitation of 750 rpm.

[0210] The nicotine composition of Example 1 is a liquid tobacco extract obtained directly from an extraction process at a temperature of 130 degrees Celsius for a period of 3 hours. The nicotine composition provides an optimised level of desirable flavour compounds such as β-damascenone and β-ionone to undesirable compounds such as phenol, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, (R,S)—N-nitrosoanatabine, (R,S)—N-nitrosoanabasine, N-nitrosonornicotine and 2-furanemethanol. The nicotine composition further provides a level of desirable flavour compounds such as furaneol and 2,3-diethyl-5-methylpyrazine to nicotine. In particular, in the nicotine composition the ratio by weight of (β-ionone+β-damascenone) to (phenol) is greater than 0.25, and a ratio by weight of (furaneol+(2,3-diethyl-5-methylpyrazine)*100)) to (nicotine) is greater than 5×10−4.

Example 2

[0211] This example provides two nicotine compositions in accordance with the invention, both of which are concentrated tobacco extracts obtained from an extraction process at a temperature of 130 degrees Celsius for a period of 3 hours, followed by a dessication step to reduce the moisture level of the liquid tobacco extract to approximately 6 percent. The concentrated tobacco extract is then used directly to form the nicotine compositions. In both nicotine compositions, the ratio by weight of (β-ionone+β-damascenone) to (phenol) is greater than 0.25, and a ratio by weight of (furaneol+(2,3-diethyl-5-methylpyrazine)*100)) to (nicotine) is greater than 5×10−4.

Example 2a

[0212] Example 2a relates to a concentrated tobacco extract derived from flue-cured Bright tobacco material. The content of the liquid tobacco extract of Example 2a is as follows: [0213] Nicotine: 0.53% w/w [0214] Propylene Glycol: 91.8% w/w [0215] Water: 6.3% w/w [0216] Balance (including flavourants as detailed in Table 1 below): 1.57% w/w

Example 2b

[0217] Example 2b relates to a concentrated tobacco extract derived from Burley tobacco material. The content of the liquid tobacco extract of Example 2b is as follows: [0218] Nicotine: 1.82% w/w [0219] Propylene Glycol: 89.6% w/w [0220] Water: 5.7% w/w [0221] Balance (including flavourants as detailed in Table 1 below): 2.88% w/w

TABLE-US-00001 TABLE 1 Content of selected flavour compounds in concentrated tobacco extract (all values given in micrograms per kilogram of liquid tobacco extract) Ex- Acetic β- β- 2,3-diethyl-5- 2-ethyl-3,5- 2-methylbutanoic ample acid ionone damascenone furaneol methylpyrazine Vanillin dimethylpyrazine acid 2a 6193580 1352 2995 2420  39 1040  838 14081 2b 3868247  939 1139  154 478  340 1980 16209 Ex- 3-methylbutanoic 3-methyl-2,4- 2- 2- ample acid nonanedione methoxyphenol phenylethanol Eugenol sotolone 2a 20114 273 1649 19875 619 85 2b 36356  69 3169 18196 845 36
The nicotine compositions of Examples 2a and 2b in accordance with the invention contain acceptably low levels of undesirable compounds such as phenol, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, (R,S)—N-nitrosoanatabine, (R,S)—N-nitrosoanabasine, N-nitrosonornicotine and 2-furanemethanol.

Example 3

[0222] This example provides three nicotine compositions in accordance with the invention, each of which is a concentrated tobacco extract obtained from an extraction process at a temperature of 130 degrees Celsius for a period of 3 hours, followed by a dessication step to reduce the moisture level of the liquid tobacco extract to approximately 12.5 percent. The concentrated tobacco extract is then used directly to form the nicotine compositions. In these nicotine compositions, the ratio by weight of (β-ionone+β-damascenone) to (phenol) is greater than 0.25, and a ratio by weight of (furaneol+(2,3-diethyl-5-methylpyrazine)*100)) to (nicotine) is greater than 5×10−4.

Example 3a

[0223] Example 3a relates to a concentrated tobacco extract derived from oriental Bright tobacco material. The content of the concentrated tobacco extract of Example 3a is as follows: [0224] Nicotine: 0.4% w/w [0225] Propylene glycol: 84% w/w [0226] Acetic Acid: 1.0% w/w [0227] Water: 12.5% w/w [0228] Balance (including flavourants): 2.1% w/w

Example 3b

[0229] Example 3b relates to a concentrated tobacco extract derived from flue-cured Bright tobacco material. The content of the concentrated tobacco extract of Example 3b is as follows: [0230] Nicotine: 1.2% w/w [0231] Propylene Glycol: 84% w/w [0232] Acetic acid: 1.0% w/w [0233] Water: 12.5% w/w [0234] Balance (including flavourants): 1.3% w/w

Example 3c

[0235] Example 3c relates to a concentrated tobacco extract derived from Burley tobacco material. The content of the concentrated tobacco extract of Example 3c is as follows: [0236] Nicotine: 2.6% w/w [0237] Propylene Glycol: 84% w/w [0238] Acetic acid: 0.5% w/w [0239] Water: 12.5% w/w [0240] Balance (including flavourants): 0.4% w/w
The nicotine compositions of Example 3 provide an optimised level of desirable flavour compounds such as 3-damascenone and β-ionone to undesirable compounds such as phenol, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, (R,S)—N-nitrosoanatabine, (R,S)—N-nitrosoanabasine, N-nitrosonornicotine and 2-furanemethanol. The nicotine compositions further provide a level of desirable flavour compounds such as furaneol and 2,3-diethyl-5-methylpyrazine to nicotine.

Example 4

[0241] The liquid tobacco extract of Example 1 was concentrated in a desiccation process to reduce the moisture level of the liquid tobacco extract to approximately 15 percent.

[0242] Glycerine was added to the resultant concentrated liquid tobacco extract to form the nicotine composition, such that the nicotine composition contained 20 percent by weight glycerine and 80 percent by weight liquid tobacco extract, based on the weight of the nicotine composition.

Example 5

[0243] Example 5 relates to a nicotine composition in the form of a gel in accordance with the invention. The gel nicotine composition is formed from the liquid tobacco extract of Example 1. The content of the gel nicotine composition is as follows: [0244] Liquid tobacco extract of Example 1: 99.0% w/w [0245] Agar: 1.0% w/w

Example 6

[0246] Three tobacco starting materials in accordance with the present invention are prepared from a flue-cured Bright tobacco material (6A), a Burley tobacco material (6B), and an Oriental tobacco material (6C), respectively.

[0247] Each one of the three tobacco materials is cut to form tobacco shreds having dimensions of 2.5 millimetres by 2.5 millimetres, and the tobacco shreds are loaded into an extraction chamber, without compression.

[0248] Each one of the tobacco starting materials is heated within the extraction chamber to a temperature of 130 degrees Celsius for a period of 120 minutes. During heating, a flow of nitrogen is passed through the extraction chamber at a flow rate of 2 litres per minute.

[0249] The volatile compounds released from each tobacco starting material during the heating step are collected by absorption into a liquid solvent formed of polypropylene glycol at 0 degrees Celsius.

[0250] A liquid tobacco extract is obtained directly from such extraction process. Each liquid extract obtained from each one of the three tobacco starting materials is then concentrated under vacuum (50 mbar) at 55 degrees Celsius until a moisture content of 12 percent±2 percent is reached.

TABLE-US-00002 TABLE 2 Value of selected ratios by weight of desirable to undesirable tobacco compounds within the liquid tobacco extracts (β-ionone + β- damascenone) to (4- (methylnitrosamino)-1-(3- pyridyl)-1-butanone + (furaneol + (R,S)-N-nitrosoanatabine + (2,3-diethyl- (R,S)-N- (β-ionone + β- 5-methylpyr- nitrosoanabasine + N- damascenone) to azine)*100)) nitrosonornicotine + ((2- Example (phenol) to (nicotine) furanemethanol)/600)) 6A 2.27 1.35 × 10.sup.−3 5.25 6B 2.96 1.71 × 10.sup.−3 3.50 6C 4.12 2.75 × 10.sup.−3 7.83

[0251] In all three liquid extracts in accordance with the invention 6A, 6B, and 6C the ratio by weight of (β-ionone+β-damascenone) to (phenol) is consistently and significantly above 2.0. Further, in all three liquid extracts in accordance with the invention 6A, 6B, and 6C the ratio by weight of (furaneol+(2,3-diethyl-5-methylpyrazine)*100)) to (nicotine) is consistently and significantly above 1×10.sup.−3. Additionally, in all three liquid extracts in accordance with the invention 6A, 6B, and 6C the ratio by weight of (β-ionone+β-damascenone) to (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone+(R,S)—N-nitrosoanatabine+(R,S)—N-nitrosoanabasine+N-nitrosonornicotine+((2-furanemethanol)/600)) is consistently and significantly above 3.

COMPARATIVE EXAMPLE

[0252] Two tobacco starting materials are prepared from a flue-cured Bright tobacco material (CE1, CE2). Two further tobacco starting materials are prepared from a Burley tobacco material (CE3, CE4). Each one of the four starting tobacco materials is cut to form tobacco shreds having dimensions of 2.5 millimetres by 2.5 millimetres.

[0253] The tobacco shreds are mixed with an alkaline solution of potassium carbonate in water to achieve a predetermined pH for each tobacco material. One such alkali treatment of a starting tobacco material is described in US 2016/360780.

[0254] In more detail, tobacco starting materials CE1 and CE3 are mixed with an alkaline solution of potassium carbonate in water to achieve a pH of 8, whereas tobacco starting materials CE2 and C4 are mixed with an alkaline solution of potassium carbonate in water to achieve a pH of 9.5.

[0255] Following such alkali treatment, the tobacco shreds of each tobacco starting material are loaded into an extraction chamber, without compression. Each tobacco starting material is heated within the extraction chamber to a temperature of 130 degrees Celsius for a period of 120 minutes. During heating, a flow of nitrogen is passed through the extraction chamber at a flow rate of about 2 litres per minute.

[0256] The volatile compounds released from each tobacco starting material during the heating step are collected by absorption into a liquid solvent formed of polypropylene glycol at 0 degrees Celsius.

[0257] A liquid tobacco extract is obtained directly from such extraction process. Each liquid extract obtained from each one of the four tobacco starting materials is then concentrated under vacuum (50 mbar) at 55 degrees Celsius until a moisture content of 12 percent±2 percent is reached.

TABLE-US-00003 TABLE 3 Value of selected ratios by weight of desirable to undesirable tobacco compounds within the liquid tobacco extracts (β-ionone + β- damascenone) to (4- (methylnitrosamino)-1-(3- pyridyl)-1-butanone + (furaneol + (R,S)-N-nitrosoanatabine + (2,3-diethyl- (R,S)-N- (β-ionone + β- 5-methylpyr- nitrosoanabasine + N- damascenone) to azine)*100)) nitrosonornicotine + ((2- Example (phenol) to (nicotine) furanemethanol)/600)) CE1 0.10 4.53 × 10.sup.−4 0.32 CE2 0.14 2.98 × 10.sup.−4 2.25 CE3 0.12 1.17 × 10.sup.−4 0.39 CE4 0.10 4.30 × 10.sup.−4 0.35

[0258] In all four liquid extracts in accordance with the Comparative Example CE1, CE2, CE3 and CE4 the ratio by weight of (β-ionone+β-damascenone) to (phenol) is consistently and significantly below 0.25. Further, in all four liquid extracts in accordance with the Comparative Example CE1, CE2, CE3 and CE4 the ratio by weight of (furaneol+(2,3-diethyl-5-methylpyrazine)*100)) to (nicotine) is consistently and significantly below 5×10.sup.−4.