E-liquid Composition Comprising 1,3-Propanediol Below 50% by Weight of the Composition
20230000136 · 2023-01-05
Assignee
Inventors
Cpc classification
A24B15/302
HUMAN NECESSITIES
A24B15/167
HUMAN NECESSITIES
International classification
A24B15/167
HUMAN NECESSITIES
Abstract
A solvent for aerosol-generating material includes predominantly 1, 3-Propanediol and glycerol, wherein the 1, 3-Propanediol is less than 50% by weight based on the total weight of the solvent. In particular, it is shown also herein that when the ratio of 1, 3-Propanediol to glycerol is 3:7, the solvent significantly improves for example thermal stability as well as decreases inhaled flavours concentrations.
Claims
1-15. (canceled)
16. A solvent for aerosol-generating material, wherein the solvent comprises 1, 3-Propanediol and glycerol, wherein the 1, 3-Propanediol is less than 50% by weight based on a total weight of the solvent.
17. The solvent according to claim 16, wherein a ratio of the 1, 3-Propanediol to the glycerol is between 3:7 and 1:1.
18. The solvent according to claim 16, wherein a ratio of the 1, 3-Propanediol to the glycerol is 3:7 or 1:1.
19. A liquid composition comprising the solvent according to claim 16 and at least one of nicotine, flavourant, or water.
20. The liquid composition according to claim 19, wherein the solvent forms between 52.24 and 99.25% by weight of the composition.
21. The liquid composition according to claim 19, wherein, the composition further comprises between 0.04% and 7.76% by weight of one or a mixture of carboxylic acids based on a total weight of the composition.
22. The liquid composition according to claim 21, wherein the carboxylic acids include at least one acid selected from the group of Benzoic acid, Levulinic acid, D/L-Tartaric acid, Capric acid, Pyruvic acid, Citric acid, Fumaric acid, D/L-Lactic acid, D/L-Malic acid, Sorbic acid, Adipic acid, L-Aspartic acid, L-Glutamic acid, Succinic acid, Gluconic acid, Linoleic acid, Saccharic acid, 3,7 dimethyl-6-octenoic acid, 2-methyl pentanoic acid, trans-2-Hexenoic acid, Caprylic acid, Lauric acid, Stearic acid, Butyric acid, Linolenic acid, Malonic acid, Myristic acid, Oleic acid, Palmitic acid, Phenylacetic acid, Propionic acid, Valeric acid, Decanoic acid, Hexanoic acid, and Octanoic acid.
23. The liquid composition according to claim 21, wherein the liquid composition has a pH value in a range from 6.3 to 6.5.
24. The liquid composition according to claim 19, wherein the liquid composition has a pH value in a range from 5 to 9 and the composition contains no acid.
25. The liquid composition according to claim 19, wherein the liquid composition has a pH value in a range from 5.1 to 8.8 and the composition contains no acid.
26. The liquid composition according to claim 19, wherein the liquid composition has a pH value in a range from 8.8 to 9.8 and the composition contains no acid.
27. The liquid composition according to claim 19, wherein the composition is a gel, a foam, or a semi-solid matrix.
28. An aerosol generating article comprising the liquid composition according to claim 19.
29. A liquid composition comprising the solvent according to claim 16 and nicotine, wherein the nicotine forms at most 10% by weight based on a total weight of the composition.
30. A liquid composition comprising the solvent according to claim 16 and nicotine, wherein the nicotine forms at most 5% by weight based on a total weight of the composition.
31. A liquid composition comprising the solvent according to claim 16 and flavourant, wherein the flavourant forms between 0.7% and 20% by weight based on a total weight of the composition.
32. A liquid composition comprising the solvent according to claim 16 and flavourant, wherein the flavourant forms between 15 and 20% by weight based on a total weight of the composition.
33. An aerosol generating article comprising the solvent according to claim 16.
34. The aerosol generating article according to claim 33, wherein the article is any of an electronic cigarette, an electronic cigarette cartridge, or an e-cigarette liquid.
35. The aerosol-generating article according to claim 33, wherein the article is a heat-not-burn consumable product.
Description
BRIEF DESCRIPTION OF THE DRAWINGS
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DETAILED DESCRIPTION OF THE INVENTION
[0052] The inventors of the present invention have demonstrated that a solvent that comprises 1, 3-Propanediol and glycerol (i.e. Propane-1, 2, 3-triol or also known as glycerine), wherein the 1, 3-Propanediol is less than 50% by weight based on the total weight of the solvent, has a number of advantages compared to the solvent made up of 1, 2-Propanediol and glycerol. These advantages are for instance less stimulating effect on eyes and skin.
[0053] Glycols have been used widely in cosmetics and personal care products to impart beneficial properties such as humectancy, solvency, moisturization and emulsification. Propylene glycol (PG) and 1, 3-Propanediol (PDO) are two examples of glycol. PG, or also known as 1, 2-Propanediol, is chemically different to PDO although they have similar structures and physicochemical properties.
[0054] Due to its lower boiling point and viscosity, and different solvent properties, propylene glycol (PG) is often mixed with glycerine in liquid blends intended for inhalation. However, in relation to glycerine, the safety profile of propylene glycol is less well established in particular at high concentrations.
[0055] Another compound, 1, 3-Propanediol (PDO), which can be manufactured either by a chemical process using petroleum feedstock or by a fermentation (bio-based) process using corn sugar, has been found to be particularly suitable for use in electronic cigarette liquid solutions.
[0056] In this connection, the inventors of the present invention found out that PDO is a good alternative for PG in the solvent for use in e-liquid when less than half of the total weight of the solvent comprises the PDO.
[0057] Moreover, when the solvent comprises over 90%, over 95% or over 98% by weight of 1, 3-Propanediol and glycerol, it is discovered that in terms of fresh-keeping ability, the required concentration of 1, 3-Propanediol is much lower than that of 1,2-propanediol.
[0058] To this end, it is furthermore disclosed herein that apart from the surprising technical effects of the new formulation of solvent for e-cigarettes disclosed herein, the inventors of the present invention further found out that when the solvent comprises predominantly of PDO and glycerol (e.g. over 50%, over 90%, over 95% or over 98% by weight based on total weight), thermal stability of the solvent is improved significantly, with or without nicotine contained therein.
[0059] For instance, thermal stability of formulations of nicotine in PG-VG (1, 2-Propanediol and glycerol) and in PDO-VG (1, 3-Propanediol and glycerol) were compared by differential thermal analysis. It was observed that a significant exothermic peak at around 250° C. corresponding to a vaporisation residue of 3 wt. % is characteristic of PG-VG and corresponds to an energy release of 37-38 J/g indicating chemical interactions between PG and VG at high temperature. To the contrary, the PDO-VG formulation has no exothermic peak. This observation leads to indicate the absence of any chemical interaction between PDO and VG.
[0060] Moreover, the inventors of the invention further discovers that the thermal behaviour of nicotine-PDO formulation unexpectedly demonstrating a co-vaporization process of nicotine and PDO, confirming the absence of chemical interaction between nicotine and PDO. This result suggests that PDO is particularly adapted to ensure a constant delivery of nicotine during vaping process.
[0061] More surprisingly, when the ratio between the PDO and glycerol is provided to be exactly at 3:7, as demonstrated by the experimental data, a number of positive e-cigarette attributes have been observed (i.e. higher mean scores for positive attributes and lower mean scores for negative attributes) compared to the samples where PG and glycerol were provided at the same ratio. These positive results were not observed in other ratios, such as 7:3 and 1:1 of PDO and glycerol.
[0062] The most common attributes of e-cigarettes used included those that are flavoured, contain nicotine, and are of tank style. It has been proposed that attributes that warrant further research include characterizing flavours and product features that allow user customization (i.e. mixing different e-liquids and adjusting voltage or temperature settings).
[0063] For this reason, the inventors of the present invention have looked into one perspective of the e-cigarette attributes, namely the “flavour” and the results are disclosed herein.
[0064] Several solvents according to the present invention having different percentage of combination of the composition have been prepared and tested. The samples were prepared for example as shown in Table 1 below.
TABLE-US-00001 TABLE 1 Solvents prepared according to several combinations. Combined PDO and glycerol Examples (3:7) Nicotine Acid Water Flavour Total 1 79.95 wt. % 0.05 wt. % 0.00 wt. % 0.00 wt. % 20.0 wt. % 100 wt. % 2 70.00 wt. % 10.0 wt. % 0.00 wt. % 0.00 wt. % 20.0 wt. % 100 wt. % 3 79.91 wt. % 0.05 wt. % 0.04 wt. % 0.00 wt. % 20.0 wt. % 100 wt. % 4 62.24 wt. % 10.0 wt. % 7.76 wt. % 0.00 wt. % 20.0 wt. % 100 wt. % 5 77.45 wt. % 0.05 wt. % 0.00 wt. % 2.50 wt. % 20.0 wt. % 100 wt. % 6 67.50 wt. % 10.0 wt. % 0.00 wt. % 2.50 wt. % 20.0 wt. % 100 wt. % 7 77.41 wt. % 0.05 wt. % 0.04 wt. % 2.50 wt. % 20.0 wt. % 100 wt. % 8 59.74 wt. % 10.00 wt. % 7.76 wt. % 2.50 wt. % 20.0 wt. % 100 wt. %
Examples
[0065] The experimental results which will be discussed below is based on the solvent provided according to the Example 5 (for experimental data shown in
[0066] For each flavour, a “p” value has been calculated for each attribute. The “p” value is a probability value indicating the statistically significance of the test comparing two samples or formulations for a given attribute. The lower the “p” value, the better is the confidence of the difference observed in the results. In other words, it means that the interval of confidence of the difference between both samples or formulations is high. A “p” value less than 0.1 means that the two samples which are under testing are different at 90%, while a “p” value less than 0.05 means that the two samples are different at 95%. A “p” value less than 0.01 means that the two samples are different at 99%, while a “p” value less than 0.001 means that the two samples are different at 99.9%,
[0067] Definitions of the attributes respect to each flavour used for characterizing the liquid formulation.
TABLE-US-00002 TABLE 2 Different attributes in the tobacco flavour. Tobacco Flavour Attribute Definition First Impact Measure the feeling you get in the back of your throat and chest when you inhale vapour for the first vape. Vapor Volume Measure the amount of vapour perceived in the mouth per puff when inhaling and exhaling, from low, which is low volume to high which is high volume. Overall Flavour Measure of an overall perception of the flavour intensity (of any kind). Sweet Measure of a sweet flavour associated with confectionary. Tobacco Measure of flavour associated with Tobacco Leaf. Bitter Measure of a bitter taste from low to strong. Caramel Measure of the flavor associated with cooked sugar/honey/syrup with milk. Toffee-like. Chocolate/Cocoa Measure of the flavor associated with cocoa powder. Coffee Measure of the flavor of freshly ground coffee. Toasted Measure of the caramelized, brown notes developed through direct cooking of some foods i.e: bread, nuts . . . etc. Smoky Smoky burnt, BBQ like taste. Off-Taste Any kind of unwanted, bad taste perceived. Natural/Authentic Measure the perceived authenticity and naturalness of the flavor, from Low which is chemical/medicinal/artificial to high which is natural. Mouth/Nose/Throat Measure of a prickling, scratching sensation perceived on the Irritation lips, tongue our back of the throat. Perceived Nicotine Perceived level of nicotine in the product. Strength Overall Flavour Measure of an overall perception of the flavour intensity of any kind. Aftertaste Dryness Lack of salivation perceived in the mouth (dry-out of tongue). Overall Liking How much did you enjoy this product?
TABLE-US-00003 TABLE 3 Different attributes in menthol flavour. Menthol Flavour Attribute Definition First Impact Measure the feeling you get in the back of your throat and chest when you inhale vapour for the first vape. Vapor Volume Measure the amount of vapour perceived in the mouth per puff when inhaling and exhaling, from low, which is low volume to high which is high volume. Overall Flavour Measure of an overall perception of the flavour intensity (of any kind). Sweet Measure of a sweet flavour associated with confectionary. Bitter Measure of a bitter taste from low to strong. Menthol Measure of menthol flavour associated with menthol crystals Peppermint Measure of a peppermint flavour associated with peppermint essence flavour Spearmint Measure of a spearmint flavour associated with spearmint essence flavour Eucalyptus Measure of flavour associated with eucalyptus oil Vanilla Measure of the flavour of Vanillin Creaminess The amount of creaminess perceived in the mouth Citrus Measure of the flavour of citrus like yellow lemon, green lemon or lime Smoky Smoky burnt, BBQ like or fireplace taste Woody Measure of the aromatics of various woods. E.g: oak, cedar wood, sandalwood, cedrene Coffee Measure of the flavor of freshly ground coffee Roasted Measure of the caramelized, brown notes developed through direct cooking of some foods Off-Taste Any kind of unwanted, bad taste perceived. Natural/Authentic Measure the perceived authenticity and naturalness of the flavor, from Low which is chemical/medicinal/artificial to high which is natural. Cooling Degree of cool feeling in mouth when inhaling and exhaling, from low to high Mouth/Nose/Throat Measure of a prickling, scratching sensation perceived on the lips, Irritation tongue our back of the throat. Impact Measure the feeling you get in the back of your throat and chest when you inhale vapour after a while Overall Flavour Measure of an overall perception of the flavour intensity of any kind. Aftertaste Sweet Aftertaste The amount of sweet taste that remains in the mouth Mint Aftertaste The amount of spearmint/peppermint taste that remains in the mouth Cooling Aftertaste Degree of cool feeling in mouth when breathing in and out, from low to high Coating Amount of fatty film perceived covering mouth and palate. Measure of a fatty film sensation on the tongue and the inside of the mouth Dryness Lack of salivation perceived in the mouth (dry-out of tongue). Overall Liking How much did you enjoy this product?
TABLE-US-00004 TABLE 4 Different attributes in fruit flavour. Fruit Flavour Attributes Definition First Impact Measure the feeling you get in the back of your throat and chest when you inhale vapour for the first vape. Vapor Volume Measure the amount of vapour perceived in the mouth per puff when inhaling and exhaling, from low, which is low volume to high which is high volume. Overall Flavour Measure of an overall perception of the flavour intensity (of any kind). Sweet Measure of a sweet flavour associated with confectionary. Tobacco Measure of flavour associated with tobacco leaf Mint/Menthol Measure of flavour and nose clearing effects of mint/menthol Bitter Measure of a bitter taste from low to strong. Apple Measure of apple flavour perceived Pear Measure of pear flavour perceived Pineapple Measure of pineapple flavour perceived Coconut Measure of coconut flavour perceived Raspberry Measure of the raspberry flavour perceived, reminiscent of raspberry. Fruity and floral, violet like Strawberry Measure of the strawberry flavour perceived, reminiscent of strawberry candy Mixed Berries Measure of a mixed berries aftertaste reminiscent of a confectionary mixed berries taste remaining Smoky Smoky burnt, BBQ like or fireplace taste Woody Measure of the aromatics of various woods. E.g: oak, cedar wood, sandalwood, cedrene Coffee Measure of the flavor of freshly ground coffee Roasted Measure of the caramelized, brown notes developed through direct cooking of some foods Off-Taste Any kind of unwanted, bad taste perceived. Natural/Authentic Measure the perceived authenticity and naturalness of the flavor, from Low which is chemical/medicinal/artificial to high which is natural. Cooling Degree of cool feeling in mouth when inhaling and exhaling, from low to high Mouth/Nose/Throat Measure of a prickling, scratching sensation perceived on the Irritation lips, tongue our back of the throat. Impact Measure the feeling you get in the back of your throat and chest when you inhale vapour after a while Overall Flavour Measure of an overall perception of the flavour intensity of any Aftertaste kind. Sweet Aftertaste The amount of sweet taste that remains in the mouth Mint Aftertaste The amount of spearmint/peppermint taste that remains in the mouth Cooling Aftertaste Degree of cool feeling in mouth when breathing in and out, from low to high Coating Amount of fatty film perceived covering mouth and palate. Measure of a fatty film sensation on the tongue and the inside of the mouth Dryness Lack of salivation perceived in the mouth (dry-out of tongue). Overall Liking How much did you enjoy this product?
[0068] To confirm that a given attribute has been improved when PDO is used compared to when PG is used, the perception of that given attribute with PDO should be higher (for positive attributes driving liking) or lower (for negative attributes driving disliking) than the one with PG and the “p” value of that given attribute is within <0.001 to <0.1. In brief, both requirements need to be fulfilled.
[0069] Drivers of liking for formulations are for instance vapour volume, overall flavour intensity, sweet taste, tobacco taste, caramel taste, menthol taste, fruit taste while drivers of disliking are for example Bitter, Off-taste, Mouth/Nose/throat scratching, Drying.
[0070]
[0071] As shown in
TABLE-US-00005 TABLE 5 P value of pairwise comparison of different attributes in the PDO:VG in the ratio of 30:70. Tobacco flavour (PDO/VG 30/70 and PG/VG 30/70) Attribute P value First Impact 0.78 Vapor Volume 0.68 Overall Flavour * 0.050 Sweet 0.75 Tobacco 0.28 Bitter 0.99 Caramel * 0.021 Chocolate/Cocoa 0.34 Coffee 0.63 Toasted 0.33 Smoky 0.29 Off-Taste 0.93 Natural/Authentic 0.94 Mouth/Nose/Throat Irritation 0.96 Perceived Nicotine Strength 0.75 Overall Flavour Aftertaste * 0.039 Dryness 0.40 Overall Liking * 0.081
[0072]
[0073] As shown in
TABLE-US-00006 TABLE 6 P value of pairwise comparison of different attributes in the PDO:VG in the ratio of 30:70. Menthol flavour (PDO/VG 30/70 and PG/VG 30/70) First Impact 0.97 Vapor Volume † 0.080 Overall Flavour * 0.023 Sweet 0.41 Bitter 0.75 Menthol ** 0.006 Peppermint 0.73 Spearmint 0.62 Eucalyptus 0.42 Vanilla 0.79 Creaminess 0.95 Citrus 0.98 Smoky 0.27 Woody 0.29 Coffee 0.35 Roasted 0.81 Off-Taste 0.27 Natural/Authentic 0.61 Cooling 0.12 Mouth/Nose/Throat Irritation 0.68 Impact 0.92 Overall Flavour Aftertaste 0.16 Sweet Aftertaste 0.38 Mint Aftertaste 0.36 Cooling Aftertaste 0.33 Coating 0.83 Dryness 0.29 Overall Liking 0.75
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[0075] As shown in
TABLE-US-00007 TABLE 7 P value of pairwise comparison of different attributes in the PDO:VG in the ratio of 30:70. Fruit flavour - berry (PDO/VG 30/70 and PG/VG 30/70) First Impact 0.54 Vapor Volume 0.85 Overall Flavour 0.59 Sweet † 0.069 Tobacco 0.11 Mint/Menthol 0.32 Bitter 0.96 Apple 0.75 Pear 0.86 Pineapple 0.99 Coconut 0.30 Raspberry 0.28 Strawberry 0.84 Mixed Berries 0.75 Smoky 0.15 Woody 0.37 Coffee 0.23 Roasted 0.93 Off-Taste 0.31 Natural/Authentic 0.63 Cooling 0.95 Mouth/Nose/Throat Irritation 0.91 Impact 0.33 Overall Flavour Aftertaste 0.97 Sweet Aftertaste † 0.10 Mint Aftertaste 0.46 Cooling Aftertaste 0.32 Coating 0.18 Dryness 0.76 Overall Liking 0.25
[0076] Overall, it can be seen that with the PG/VG in the solvent, some attributes are not well perceived like with PDO in the solvent at the same ratio 30/70 as significant lower mean scores is showed in comparison to the sample comprising PDO and glycerol in the same ratio. In addition, the “p” values reported in the tables for those specific attributes show that there is well recognized difference between both samples of solvent.
[0077] Noteworthy, the inventors of the present invention also found out that the solvent comprising PDO as claimed presently is not only stable upon heating (e.g. less than 250° C.) and have better thermal behaviour showing less thermal decomposition by-products compared to PG, PDO also seems to give nicotine a more basic environment ensuring a complete free base nicotine form.
[0078] Furthermore, when the ratio of PDO to glycerol is 3:7, the solvent gives surprisingly better flavouring properties than PG and glycerol. This special effect has not been observed in another ratio, for instance 2:3, 3:2, or 1:4.
[0079] The 1, 3-Propanediol (PDO) used in the present invention is commercially available provided from companies such as Laboratoires Xeres and Naturacig under the product name of “vegetol”. It is therefore foreseen that the PDOs provided by other companies can also be treated as equivalent.
[0080] The liquid composition as used herein contains solvent as described herein, wherein the solvent is glycerol-based (i.e. over 50% by weight). The liquid composition may further include elements such as nicotine, water, flavour, additives, acid, etc. For instance, the weight distribution of these elements can be for instance 0.05-10 wt. % of nicotine, 0-7.76% of acid, 0-10 wt. % of water, 0.7-20 wt. % of flavour, 50-90 wt. % of glycerol.
[0081] As an example, the combined amount of PDO and glycerol according to the present invention may be provided up to 79.95 wt. % based on the total weight of the solvent, the rest being made up of for instance 0.05 wt. % of nicotine and 20 wt. % of flavourant. In a second example, the combined amount of PDO and glycerol may be provided at 70 wt. % while the rest are made up with 10 wt. % nicotine and 20 wt. % flavourant.
[0082] It is furthermore disclosed herein that in embodiments where the composition of the present invention disclosed in
[0083] If the composition comprises acid (e.g. benzoic acid) with 5% of nicotine and flavourant (e.g. American tobacco or American menthol), 1:1 equimolar acid and nicotine, the pH is 5.1 (American tobacco) and 5.2 (American menthol) is used.
[0084]
[0085] For instance, across the three different attributes where the inventors looked into, namely “caramel flavour” (
[0086]
[0087] In more detail, as can be seen in the
[0088]
[0089] When the ratio of PDO and glycerol was provided at 3:7, the mean score for “sweet/strawberry” increased significantly, as can be seen in the
[0090] Noteworthy, the inventors of the present invention also found out that the solvent comprising PDO as claimed presently is not only stable upon heating (e.g. less than 250° C.) and have better thermal behaviour showing less thermal decomposition by-products compared to PG, PDO also seems to give nicotine a more basic environment ensuring a complete free base nicotine form.
[0091] Furthermore, when the ratio of PDO to glycerol is 3:7, the solvent gives surprisingly better flavouring properties than PG and glycerol. This special effect has not been observed in another ratio, for instance 2:3, 3:2, or 1:4.
[0092] The 1, 3-Propanediol (PDO) used in the present invention is commercially available provided from companies such as Laboratoires Xeres and Naturacig under the product name of “vegetol”. It is therefore foreseen that the PDOs provided by other companies can also be treated as equivalent.
[0093] The liquid composition as used herein contains solvent as described herein, wherein the solvent is glycerol-based (i.e. over 50% by weight). The liquid composition may further include elements such as nicotine, water, flavour, additives, acid and etc. For instance, the weight distribution of these elements can be for instance 0.05-10 wt. % of nicotine, 0-7.76% of acid, 0-10 wt. % of water, 0.7-20 wt. % of flavour, 50-90 wt. % of glycerol.
[0094] As an example, the combined amount of PDO and glycerol according to the present invention may be provided up to 79.95 wt. % based on the total weight of the solvent, the rest being made up of for instance 0.05 wt. % of nicotine and 20 wt. % of flavourant. In a second example, the combined amount of PDO and glycerol may be provided at 70 wt. % while the rest are made up with 10 wt. % nicotine and 20 wt. % flavourant.
[0095] It is furthermore disclosed herein that in embodiments where the composition of the present invention does not comprise acid but comprise 5% of nicotine and flavourant (e.g. American tobacco or American menthol), the pH is 8.8 (American tobacco) and 9.8 (American menthol).
[0096] If the composition comprises acid (e.g. benzoic acid) with 5% of nicotine and flavourant (e.g. American tobacco or American menthol), 1:1 equimolar acid and nicotine, the pH is 5.1 (American tobacco) and 5.2 (American menthol) is used.