Oral products with cellulosic flavor stabilizers

Abstract

The present disclosure provides a product configured for oral use, the product comprising a mixture of a particulate filler component, a cellulose derivative, water, and one or more flavoring agents, the product exhibiting greater stability over time with respect to flavoring component concentration than a comparative product that does not contain the cellulose derivative.

Description

[Technical field]

[0001] The present disclosure relates to flavored products intended for human consumption. The products are configured for oral use and deliver substances, such as flavorings and / or active ingredients, during use. Such products may include tobacco or tobacco-derived products, or may be tobacco-free alternatives. [Background technology]

[0002] Tobacco can be enjoyed in so-called "smokeless" forms. Particularly common smokeless tobacco products are used by inserting some form of processed tobacco or tobacco-containing formulation into the user's mouth. Traditional forms of such smokeless tobacco products include moist snuff, snus, and chewing tobacco, which are usually formed from nearly completely particulate, granular, or cut tobacco and are either broken up by the user or presented to the user in individual portions such as disposable pouches or sachets. Other traditional forms of smokeless products include compressed or agglomerated forms such as plugs, tablets, or pellets. Alternative product forms such as tobacco-containing gums and mixtures of tobacco with other plant materials are also known.See, for example, U.S. Pat. Nos. 1,376,586 to Schwartz, 4,513,756 to Pittman et al., 4,528,993 to Sensabaugh, Jr. et al., 4,624,269 to Story et al., 4,991,599 to Tibbetts, 4,987,907 to Townsend, and 5,092,352 to Sprinkle, III et al. see, for example, US Patent Application Publication No. 5,387,416 to White et al., US Patent Application No. 6,668,839 to Williams, US Patent Application No. 6,834,654 to Williams, US Patent Application No. 6,953,040 to Atchley et al., US Patent Application No. 7,032,601 to Atchley et al., US Patent Application Publication No. 7,694,686 to Atchley et al., US Patent Application Publication No. 2004 / 0020503 to Williams, US Patent Application No. 6,834,654 to Williams, US Patent Application No. 6,953,040 to Atchley et al., US Patent Application Publication No. 2004 / 0020503 to Williams, US Patent Application No. 6,834,654 to Williams, US Patent Application No. 6,953,040 to Atchley et al., US Patent Application Publication No. 6,032,601 to Atchley et al., US Patent Application Publication No. 6,694,686 to Atchley et al., US Patent Application Publication No. 6,834,654 to Williams, US Patent Application ...834,654 to Williams, US Patent Application No. No. 2005 / 0115580 to Inter et al., No. 2006 / 0191548 to Strickland et al., No. 2007 / 0062549 to Holton, Jr. et al., No. 2007 / 0186941 to Holton, Jr. et al., No. 2007 / 0186942 to Strickland et al., No. 2008 / 0029110 to Dube et al., No. 2008 / 0029110 to Robinson et al. See, for example, US Pat. Nos. 2008 / 0029116 to Robinson et al., 2008 / 0173317 to Neilsen et al., 2008 / 0209586 to Neilsen et al., 2009 / 0065013 to Essen et al., and 2010 / 0282267 to Atchley, and WO 2004 / 095959 to Arnarp et al., each of which is incorporated herein by reference, for the types of smokeless tobacco formulations, ingredients, and processing methods described therein.

[0003] Smokeless tobacco product configurations combining tobacco materials with various binders and fillers have been proposed more recently, with exemplary product forms including lozenges, troches, gels, extruded shapes, etc. See, for example, U.S. Patent Application Publication Nos. 2008 / 0196730 to Engstrom et al., 2008 / 0305216 to Crawford et al., 2009 / 0293889 to Kumar et al., 2010 / 0291245 to Gao et al., 2011 / 0139164 to Mua et al., 2012 / 0037175 to Cantrell et al., 2012 / 0055494 to Hunt et al., 2012 / 0138073 to Cantrell et al., and 2012 / 0139074 to Cantrell et al. See the types of products described in 2012 / 0138074 to Holton, Jr., 2013 / 0074855 to Holton, Jr., 2013 / 0074856 to Holton, Jr., 2013 / 0152953 to Mua et al., 2013 / 0274296 to Jackson et al., 2015 / 0068545 to Moldoveanu et al., 2015 / 0101627 to Marshall et al., and 2015 / 0230515 to Lampe et al., each of which is incorporated herein by reference.

[0004] All-white snus portions are becoming increasingly popular and offer a distinct and aesthetically pleasing alternative to traditional snus. Such modern "white" pouch products may contain bleached tobacco or may be tobacco-free. This type of product may suffer from certain drawbacks such as poor product stability, which may result in product discoloration and / or undesirable organoleptic properties. It is therefore desirable in the art to provide a product configured for oral use with improved stability to provide a more enjoyable experience to the user. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] U.S. Pat. No. 1,376,586 [Patent Document 2] U.S. Pat. No. 4,513,756 [Patent Document 3] U.S. Pat. No. 4,528,993 [Patent Document 4] U.S. Pat. No. 4,624,269 [Patent Document 5] U.S. Pat. No. 4,991,599 [Patent Document 6] U.S. Pat. No. 4,987,907 [Patent Document 7] U.S. Patent No. 5,092,352 [Patent Document 8] U.S. Pat. No. 5,387,416 [Patent Document 9] U.S. Patent No. 6,668,839 [Patent Document 10] U.S. Patent No. 6,834,654 [Patent Document 11] U.S. Patent No. 6,953,040 [Patent Document 12] U.S. Patent No. 7,032,601 [Patent Document 13] U.S. Pat. No. 7,694,686 [Patent Document 14] US Patent Application Publication No. 2004 / 0020503 [Patent Document 15] US Patent Application Publication No. 2005 / 0115580 [Patent Document 16] US Patent Application Publication No. 2006 / 0191548 [Patent Document 17] US Patent Application Publication No. 2007 / 0062549 [Patent Document 18] US Patent Application Publication No. 2007 / 0186941 [Patent Document 19] US Patent Application Publication No. 2007 / 0186942 [Patent Document 20] US Patent Application Publication No. 2008 / 0029110 [Patent Document 21] US Patent Application Publication No. 2008 / 0029116 [Patent Document 22] US Patent Application Publication No. 2008 / 0173317 [Patent Document 23] US Patent Application Publication No. 2008 / 0209586 [Patent Document 24] US Patent Application Publication No. 2009 / 0065013 [Patent Document 25] US Patent Application Publication No. 2010 / 0282267 [Patent Document 26] International Publication No. 2004 / 095959 [Patent Document 27] US Patent Application Publication No. 2008 / 0196730 [Patent Document 28] US Patent Application Publication No. 2008 / 0305216 [Patent Document 29] US Patent Application Publication No. 2009 / 0293889 [Patent Document 30] US Patent Application Publication No. 2010 / 0291245 [Patent Document 31] US Patent Application Publication No. 2011 / 0139164 [Patent Document 32] US Patent Application Publication No. 2012 / 0037175 [Patent Document 33] US Patent Application Publication No. 2012 / 0055494 [Patent Document 34] US Patent Application Publication No. 2012 / 0138073 [Patent Document 35] US Patent Application Publication No. 2012 / 0138074 [Patent Document 36] US Patent Application Publication No. 2013 / 0074855 [Patent Document 37] US Patent Application Publication No. 2013 / 0074856 [Patent Document 38] US Patent Application Publication No. 2013 / 0152953 [Patent Document 39] US Patent Application Publication No. 2013 / 0274296 [Patent Document 40] US Patent Application Publication No. 2015 / 0068545 [Patent Document 41] US Patent Application Publication No. 2015 / 0101627 [Patent Document 42] US Patent Application Publication No. 2015 / 0230515 Summary of the Invention [Means for solving the problem]

[0006] The present disclosure generally provides a product configured for oral use, and further provides a method for stabilizing flavor components present in the product. The product is intended to impart taste and deliver a substance, such as nicotine, to the consumer when used orally. The product and method rely on the surprising finding that including a cellulose derivative in the product improves the retention of certain volatile flavor components compared to a comparable product that does not include the cellulose derivative. Thus, in one aspect, the present disclosure provides a product configured for oral use, the product comprising a mixture comprising a particulate filler component, a cellulose derivative, water in an amount of at least about 5% by weight, and one or more flavoring agents.

[0007] In some embodiments, the product comprises at least about 0.5% by weight of the cellulose derivative based on the total weight of the mixture. In some embodiments, the product comprises at least about 1% by weight of the cellulose derivative based on the total weight of the mixture. In some embodiments, the product comprises from about 1% to about 5% by weight of the cellulose derivative based on the total weight of the mixture.

[0008] In some embodiments, the cellulose derivative is a cellulose ether. In some embodiments, the cellulose derivative is one or more of methylcellulose, hydroxyethylcellulose, hydroxypropylcellulose (HPC), hydroxypropylmethylcellulose (HPMC) or carboxymethylcellulose (CMC). In some embodiments, the cellulose derivative is HPC.

[0009] In some embodiments, the particulate filler component comprises a cellulosic material, a starch, or both, hi some embodiments, the particulate filler component comprises microcrystalline cellulose.

[0010] In some embodiments, the one or more flavoring agents include compounds having a carbon-carbon double bond, a carbon-oxygen double bond, a carbon-oxygen single bond, or combinations thereof. In some embodiments, the one or more flavoring agents include one or more aldehydes, ketones, esters, terpenes, terpenoids, or combinations thereof. In some embodiments, the one or more flavoring agents include one or more esters. In some embodiments, the one or more esters are alkyl esters comprising C1-C8 alkanols and C2-C8 alkane carboxylic acids. In some embodiments, the one or more esters include isoamyl acetate, ethyl hexanoate, ethyl heptanoate, allyl hexanoate, or combinations thereof.

[0011] In some embodiments, the product comprises about 1 to about 3 wt. % HPC, about 10 to about 60 wt. % microcrystalline cellulose, and about 1 to about 60 wt. % water, based on the total weight of the mixture.

[0012] In some embodiments, the mixture further comprises one or more salts, one or more organic acids, one or more sweeteners, one or more binders, one or more humectants, one or more gums, one or more active ingredients, tobacco materials, or combinations thereof. In some embodiments, the mixture further comprises one or more active ingredients selected from the group consisting of a nicotine component, a botanical drug, a stimulant, an amino acid, a vitamin, and a cannabinoid. In some embodiments, the mixture further comprises about 0.001 to about 10% by weight of a nicotine component, calculated as the free base, based on the total weight of the mixture.

[0013] In some embodiments, the mixture comprises about 7.5% or less of an alkali metal salt, based on the total weight of the mixture. In some embodiments, the mixture further comprises about 0.1 to about 0.5% by weight of one or more organic acids, based on the total weight of the mixture. In some embodiments, the one or more organic acids are alkyl carboxylic acids, aryl carboxylic acids, or combinations thereof. In some embodiments, the one or more organic acids are citric acid, malic acid, tartaric acid, octanoic acid, benzoic acid, tolueneic acid, salicylic acid, or combinations thereof. In some embodiments, the one or more organic acids are citric acid.

[0014] In some embodiments, the mixture further comprises a tobacco material. In some embodiments, the mixture comprises about 10% or less by weight of tobacco material, excluding any nicotine components present, based on the total weight of the mixture. In some embodiments, the tobacco material is bleached tobacco.

[0015] In some embodiments, the mixture is enclosed in a pouch to form a pouch product, hi some embodiments, the mixture enclosed in the pouch is in the form of free-flowing particulates.

[0016] In some embodiments, the product has a concentration of one or more flavoring agents present therein that is higher than the concentration of the same one or more flavoring agents present in a control product that does not contain a cellulose derivative, as determined by semi-quantitative gas chromatography mass spectrometry, when measured at a period of one day after preparation. In some embodiments, the period is one or more of two days, one week, two weeks, three weeks, or one month after preparation.

[0017] In another aspect, there is provided a method of stabilizing a product configured for oral use as disclosed herein, comprising: i) mixing one or more flavoring agents with a cellulose derivative to form a first mixture; and ii) mixing the first mixture with a particulate filler component and water to form the product.

[0018] In some embodiments, the cellulose derivative is a cellulose ether. In some embodiments, the cellulose derivative is one or more of methylcellulose, hydroxyethylcellulose, hydroxypropylcellulose (HPC), hydroxypropylmethylcellulose (HPMC) or carboxymethylcellulose (CMC). In some embodiments, the cellulose derivative is HPC.

[0019] In some embodiments, the particulate filler component comprises a cellulosic material, a starch, or both, hi some embodiments, the particulate filler component comprises microcrystalline cellulose.

[0020] In some embodiments, the one or more flavoring agents include one or more aldehydes, ketones, esters, terpenes, terpenoids, or combinations thereof. In some embodiments, the one or more flavoring agents include one or more esters. In some embodiments, the one or more esters are alkyl esters comprising a C1-C8 alkanol and a C2-C8 alkyl carboxylic acid. In some embodiments, the one or more esters include isoamyl acetate, ethyl hexanoate, ethyl heptanoate, allyl hexanoate, or combinations thereof.

[0021] In some embodiments, mixing the first mixture with the particulate filler component further comprises adding one or more salts, one or more sweeteners, one or more binders, one or more humectants, one or more gums, one or more active ingredients, tobacco materials, or combinations thereof to the mixture of step ii). In some embodiments, the method further comprises adding one or more active ingredients selected from the group consisting of a nicotine component, a botanical drug, a stimulant, an amino acid, a vitamin, and a cannabinoid. In some embodiments, mixing the first mixture with the particulate filler component further comprises adding about 0.001 to about 10% by weight of a nicotine component, calculated as a free base, based on the total weight of the product. In some embodiments, the method further comprises adding about 0.1 to about 0.5% by weight of one or more organic acids, based on the total weight of the product. In some embodiments, the one or more organic acids are alkyl carboxylic acids, aryl carboxylic acids, or combinations thereof. In some embodiments, the one or more organic acids are citric acid, malic acid, tartaric acid, octanoic acid, benzoic acid, tolueneic acid, salicylic acid, or combinations thereof. In some embodiments, the one or more organic acids is citric acid.

[0022] In some embodiments, the method further comprises enclosing the product in a pouch to form a pouch product, the product optionally being in the form of free-flowing particulates.

[0023] In some embodiments, the product has a concentration of one or more flavoring agents present therein that is higher than the concentration of one or more of the same flavoring agents present in a control product that does not contain a cellulose derivative, as determined by semi-quantitative gas chromatography-mass spectrometry, when measured at a period of one day after preparation. In some embodiments, the period is one or more of two days, one week, two weeks, three weeks, or one month after preparation.

[0024] In another aspect, there is provided a product adapted for oral use, the product being prepared by the methods disclosed herein.

[0025] In another aspect, there is provided a flavor-stabilized product configured for oral use, the product comprising a mixture comprising a particulate filler component, a cellulose derivative, water in an amount of at least about 5% by weight based on the total weight of the mixture, and one or more flavoring agents, wherein the flavor is stabilized by the cellulose derivative.

[0026] The present disclosure includes, but is not limited to, the following embodiments.

[0027] Embodiment 1. A product configured for oral use, comprising a mixture comprising a particulate filler component, a cellulose derivative, water in an amount of at least about 5% by weight based on the total weight of the mixture, and one or more flavoring agents.

[0028] Embodiment 2. The product of embodiment 1, comprising at least about 0.5% by weight of a cellulose derivative, based on the total weight of the mixture.

[0029] Embodiment 3. The product of embodiment 1 or 2, comprising at least about 1% by weight of a cellulose derivative, based on the total weight of the mixture.

[0030] Embodiment 4. The product of any one of embodiments 1 to 3, comprising about 1% to about 5% by weight of a cellulose derivative, based on the total weight of the mixture.

[0031] Embodiment 5. The product of any one of embodiments 1 to 4, wherein the cellulose derivative is a cellulose ether.

[0032] Embodiment 6. The product of any one of embodiments 1 to 5, wherein the cellulose derivative is one or more of methylcellulose, hydroxyethylcellulose, hydroxypropylcellulose (HPC), hydroxypropylmethylcellulose (HPMC) or carboxymethylcellulose (CMC).

[0033] Embodiment 7. The product of any one of embodiments 1 to 6, wherein the cellulose derivative is hydroxypropyl cellulose (HPC).

[0034] Embodiment 8. The product of any one of embodiments 1-7, wherein the particulate filler component comprises a cellulosic material, a starch, or both.

[0035] Embodiment 9. The product of any one of embodiments 1-8, wherein the particulate filler component comprises microcrystalline cellulose.

[0036] Embodiment 10. The product of any one of embodiments 1-9, wherein the one or more flavoring agents comprises a compound having a carbon-carbon double bond, a carbon-oxygen double bond, a carbon-oxygen single bond, or a combination thereof.

[0037] Embodiment 11. The product of any one of embodiments 1-10, wherein the one or more flavoring agents comprise one or more aldehydes, ketones, esters, terpenes, terpenoids, or combinations thereof.

[0038] Embodiment 12. The product of any one of embodiments 1-11, wherein the one or more flavoring agents comprise one or more esters.

[0039] Embodiment 13. The product of any one of embodiments 1 to 12, wherein the one or more esters are alkyl esters comprising a C1 to C8 alkanol and a C2 to C8 alkane carboxylic acid.

[0040] Embodiment 14. The product of any one of embodiments 1-13, wherein the one or more esters comprise isoamyl acetate, ethyl hexanoate, ethyl heptanoate, allyl hexanoate, or combinations thereof.

[0041] Embodiment 15. The product of any one of embodiments 1 to 14, comprising about 1 to about 3% by weight of hydroxypropyl cellulose (HPC), about 10 to about 60% by weight of microcrystalline cellulose, and about 1 to about 60% by weight of water, based on the total weight of the mixture.

[0042] Embodiment 16. The product of any one of embodiments 1-15, wherein the mixture further comprises one or more salts, one or more organic acids, one or more sweeteners, one or more binders, one or more humectants, one or more gums, one or more active ingredients, tobacco materials, or a combination thereof.

[0043] Embodiment 17. The product of any one of embodiments 1 to 16, wherein the mixture further comprises one or more active ingredients selected from the group consisting of nicotine components, botanical derived drugs, stimulants, amino acids, vitamins and cannabinoids.

[0044] Embodiment 18. The product of any one of embodiments 1 to 17, wherein the mixture further comprises from about 0.001 to about 10% by weight of a nicotine component, calculated as the free base, based on the total weight of the mixture.

[0045] Embodiment 19. The product of any one of embodiments 1 to 18, wherein the mixture further comprises about 0.1 to about 0.5 wt. % of one or more organic acids, based on the total weight of the mixture.

[0046] Embodiment 20. The product of any one of embodiments 1-19, wherein the one or more organic acids are alkyl carboxylic acids, aryl carboxylic acids, or combinations thereof.

[0047] Embodiment 21. The product of any one of embodiments 1-20, wherein the one or more organic acids are citric acid, malic acid, tartaric acid, octanoic acid, benzoic acid, tolueneic acid, salicylic acid, or combinations thereof.

[0048] Embodiment 22. The product of any one of embodiments 1 to 21, wherein the one or more organic acids is citric acid.

[0049] Embodiment 23. The product of any one of embodiments 1 to 22, wherein the mixture further comprises tobacco materials.

[0050] Embodiment 24. The product of any one of embodiments 1-23, wherein the mixture comprises no more than about 10% by weight of tobacco material, excluding any nicotine components present, based on the total weight of the mixture.

[0051] Embodiment 25. The product of any one of embodiments 1 to 24, wherein the tobacco material is bleached tobacco.

[0052] Embodiment 26. The product of any one of embodiments 1 to 25, wherein the mixture comprises about 7.5% or less of an alkali metal salt, based on the total weight of the mixture.

[0053] Embodiment 27. The product of any one of embodiments 1 to 26, wherein the mixture is enclosed in a pouch to form a pouch product, and the mixture is optionally in the form of free-flowing particulates.

[0054] Embodiment 28. The product of any one of embodiments 1 to 27, wherein when measured over a period of one day after preparation, the product has a concentration of one or more flavoring agents present therein that is greater than the concentration of the same one or more flavoring agents present in a control product that does not contain the cellulose derivative, as determined by semi-quantitative gas chromatography-mass spectrometry.

[0055] Embodiment 29. The product of any one of embodiments 1 to 28, wherein the period is one or more of 2 days, 1 week, 2 weeks, 3 weeks, or 1 month after preparation.

[0056] Embodiment 30. A method of stabilizing a product configured for oral use, comprising mixing one or more flavoring agents with a cellulose derivative to form a first mixture, and mixing the first mixture with a particulate filler component and water to form the product.

[0057] Embodiment 31. The method of embodiment 30, wherein the cellulose derivative is a cellulose ether.

[0058] Embodiment 32. The method of embodiment 30 or 31, wherein the cellulose derivative is one or more of methylcellulose, hydroxyethylcellulose, hydroxypropylcellulose (HPC), hydroxypropylmethylcellulose (HPMC) or carboxymethylcellulose (CMC).

[0059] Embodiment 33. The method of any one of embodiments 30 to 32, wherein the cellulose derivative is HPC.

[0060] Embodiment 34. The method of any one of embodiments 30-33, wherein the particulate filler component comprises a cellulosic material, a starch, or both.

[0061] Embodiment 35. The method of any one of embodiments 30-34, wherein the particulate filler component comprises microcrystalline cellulose.

[0062] Embodiment 36. The method of any one of embodiments 30-35, wherein the one or more flavoring agents comprise one or more aldehydes, ketones, esters, terpenes, terpenoids, or combinations thereof.

[0063] Embodiment 37. The method of any one of embodiments 30-36, wherein the one or more flavoring agents comprise one or more esters.

[0064] Embodiment 38. The method of any one of embodiments 30-37, wherein the one or more esters is an alkyl ester comprising a C1 to C8 alkanol and a C2 to C8 alkyl carboxylic acid.

[0065] Embodiment 39. The method of any one of embodiments 30-38, wherein the one or more esters comprise isoamyl acetate, ethyl hexanoate, ethyl heptanoate, allyl hexanoate, or a combination thereof.

[0066] Embodiment 40. The method of any one of embodiments 30-39, wherein combining the first mixture with the particulate filler component further comprises adding one or more salts, one or more sweeteners, one or more binders, one or more humectants, one or more gums, one or more active ingredients, tobacco materials, or combinations thereof.

[0067] Embodiment 41. The method of any one of embodiments 30-40, wherein combining the first mixture with the particulate filler component further comprises adding one or more active ingredients selected from the group consisting of a nicotine component, a botanical-derived drug, a stimulant, an amino acid, a vitamin, and a cannabinoid.

[0068] Embodiment 42. The method of any one of embodiments 30-41, further comprising adding about 0.001 to about 10% by weight of a nicotine component, calculated as the free base and based on the total weight of the product.

[0069] Embodiment 43. The method of any one of embodiments 30-42, further comprising adding about 0.1 to about 0.5 wt. % of one or more organic acids, based on the total weight of the product.

[0070] Embodiment 44. The method of any one of embodiments 30-43, wherein the one or more organic acids are alkyl carboxylic acids, aryl carboxylic acids, or combinations thereof.

[0071] Embodiment 45. The method of any one of embodiments 30-44, wherein the one or more organic acids are citric acid, malic acid, tartaric acid, octanoic acid, benzoic acid, tolueneic acid, salicylic acid, or a combination thereof.

[0072] Embodiment 46. The method of any one of embodiments 30-45, wherein the one or more organic acids is citric acid.

[0073] Embodiment 47. The method of any one of embodiments 30-46, further comprising encapsulating the product in a pouch to form a pouch product, the product optionally being in the form of free-flowing particulates.

[0074] Embodiment 48. The method of any one of embodiments 30 to 47, wherein the product has a concentration of one or more flavoring agents present therein that is greater than the concentration of the same one or more flavoring agents present in a control product that does not contain the cellulose derivative, as determined by semi-quantitative gas chromatography-mass spectrometry, when measured over a period of one day after preparation.

[0075] Embodiment 49. The method of any one of embodiments 30-48, wherein the period of time is one or more of 2 days, 1 week, 2 weeks, 3 weeks, or 1 month after preparation.

[0076] Embodiment 50. A product adapted for oral use prepared by the method according to any one of embodiments 30 to 50.

[0077] Embodiment 51. A flavor stabilized product configured for oral use, comprising one or more flavoring agents stabilized by a cellulose derivative, the cellulose derivative optionally being selected from the group consisting of methylcellulose, hydroxyethylcellulose, hydroxypropylcellulose (HPC), hydroxypropylmethylcellulose (HPMC), or carboxymethylcellulose (CMC).

[0078] These and other features, aspects and advantages of the present disclosure will become apparent from a reading of the following detailed description in conjunction with the accompanying drawings, which are briefly described below. The present invention includes any combination of two, three, four or more of the above-described embodiments, as well as any combination of two, three, four or more features or elements described in this disclosure, whether or not such features or elements are explicitly combined in the description of a particular embodiment herein. The present disclosure, in any of its various aspects and embodiments, is intended to be read as a whole such that any separable features or elements of the disclosed invention are intended to be combinable unless the context clearly dictates otherwise.

[0079] Having thus described aspects of the present disclosure in the preceding general terms, reference is now made to the accompanying drawings, which are not necessarily drawn to scale, and which are illustrative only and are not to be construed as limiting the disclosure. [Brief description of the drawings]

[0080] [Figure 1] FIG. 2 is a cross-sectional view of an embodiment of a pouch product taken across the width of the product showing the outer pouch filled with a mixture of the present disclosure. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0081] The present disclosure provides products that exhibit enhanced flavor stability, and methods for stabilizing flavor components in such products. It is desirable to provide products that are suitable for oral use that retain certain initial characteristics, such as initial flavor profile, for customer satisfaction. Surprisingly, according to the present disclosure, in certain embodiments, products that include a particulate filler component, a cellulose derivative, water in an amount of at least about 5% by weight, and one or more flavoring agents are found to enhance the retention of some volatile flavor components present, compared to a control product that does not include a cellulose derivative.

[0082] The present disclosure will now be described more fully hereinafter with reference to exemplary embodiments thereof. These exemplary embodiments are described so that the disclosure will be thorough and complete, and will fully convey the scope of the disclosure to those skilled in the art. Indeed, the present disclosure may be embodied in many different forms, and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that the disclosure will satisfy applicable legal requirements. As used in this specification and claims, the singular forms "a," "an," and "the" include plural referents unless the context clearly dictates otherwise. References to "dry weight %" or "dry weight basis" refer to weight based on dry ingredients (i.e., all ingredients except water). References to "wet weight" refer to the weight of the composition, including water. Unless otherwise indicated, references to "weight %" of a composition reflect the total wet weight of the composition (i.e., including water).

[0083] The products described herein comprise a mixture comprising a cellulose derivative, a particulate filler component, water and one or more flavoring agents. In some embodiments, the mixture further comprises one or more salts, one or more sweeteners, one or more binders, one or more humectants, one or more gums, one or more active ingredients, tobacco materials, tobacco-derived materials, or combinations thereof. The relative amounts of the various components in the mixture may vary and are typically selected to impart the desired sensory and performance characteristics to the oral product. Exemplary individual components of the mixture are described herein below.

[0084] Particulate filler component The mixtures described herein typically include a particulate filler component. Such particulate filler components can perform multiple functions, such as improving certain organoleptic properties, such as texture and mouthfeel, and improving the cohesiveness or compressibility of the product. In general, the filler component is a porous particulate material and is cellulosic. For example, a suitable filler component is any non-tobacco plant material or derivative thereof, including cellulosic materials derived from such sources. Examples of cellulosic non-tobacco plant materials include cereals (e.g., corn, oats, barley, rye, buckwheat, etc.), sugar beet (e.g., FIBREX® brand filler available from International Fiber Corporation), bran fiber, and mixtures thereof. Non-limiting examples of derivatives of non-tobacco plant materials include starch (e.g., from potato, wheat, rice, corn), natural cellulose, and modified cellulose materials. Further examples of possible filler components include maltodextrin, dextrose, calcium carbonate, calcium phosphate, lactose, mannitol, xylitol, and sorbitol. Combinations of fillers can also be used, hi some embodiments, the particulate filler component comprises starch, cellulosic material, or both.

[0085] As used herein, "starch" may refer to pure starch, modified starch, or starch derivatives from any source. Starch is typically present in granular form in almost all green plants and in tissues and organs of various types of plants (e.g., seeds, leaves, rhizomes, roots, tubers, shoots, fruits, grains, and stems). Starch may vary in composition and granular shape and size. Often, starches from different sources have different chemical and physical properties. A particular starch may be selected for inclusion in the mixture based on the starch material's ability to impart specific organoleptic properties to the composition. Starches from various sources may be used. For example, major sources of starch include cereals (e.g., rice, wheat, and corn) and root vegetables (e.g., potato and cassava). Other examples of sources of starch include acorns, kudzu, peanuts, bananas, barley, beans (e.g., favas, lentils, mung beans, peas, chickpeas), breadfruit, buckwheat, canna, chestnut, caracas, katakuri, kudzu, malanga, millet, oats, oca, Polynesian arrowroot, sago, sorghum, sweet potato, quinoa, rye, tapioca, taro, tobacco, water chestnuts, and yams. Certain starches are modified starches. Modified starches frequently have undergone one or more structural modifications designed to alter their high thermal properties. Some starches have been developed by genetic modification and are considered to be "modified" starches. Other starches are obtained and subsequently modified.For example, modified starches can be starches that have been subjected to chemical reactions such as esterification, etherification, oxidation, depolymerization (thinning) by acid catalysis or oxidation in the presence of base, bleaching, transglycosylation and depolymerization (e.g., dextrinization in the presence of a catalyst), crosslinking, enzymatic treatment, acetylation, hydroxypropylation, and / or partial hydrolysis. Other starches are modified by heat treatment, e.g., pregelatinization, dextrinization, and / or cold water swelling processes. Specific modified starches include monostarch phosphate, didarch glycerol, didarch phosphate esterified with sodium trimetaphosphate, didarch phosphate phosphate, acetylated didarch phosphate, starch acetate esterified with acetic anhydride, starch acetate esterified with vinyl acetate, acetylated didarch adipate, acetylated didarch glycerol, hydroxypropyl starch, hydroxypropyl didarch glycerol, starch sodium octenyl succinate.

[0086] In some embodiments, the particulate filler component comprises a cellulose material. One non-limiting example of a cellulose material suitable for use in the products described herein is microcrystalline cellulose ("mcc"). mcc may be synthetic or semi-synthetic, or may be derived entirely from natural cellulose. mcc may be selected from the group consisting of AVICEL® grades PH-100, PH-102, PH-103, PH-105, PH-112, PH-113, PH-200, PH-300, PH-302, VIVACEL® grades 101, 102, 12, 20, and EMOCEL® grades 50M and 90M, and the like, and mixtures thereof. In some embodiments, the particulate filler component comprises mcc. In some embodiments, the filler component is mcc.

[0087] The amount of particulate filler component (e.g., mcc) present in the mixtures described herein can vary according to the desired properties, but is typically up to about 97% by dry weight, with certain embodiments characterized by a filler content of up to about 10% by dry weight. The amount of filler component on a wet weight basis can vary, but is typically up to about 75% of the total composition by weight. A typical range of filler component in the mixture can be about 10 to about 75% of the total weight of the composition, for example, about 10, about 15, about 20, about 25, or about 30 to about 35, about 40, about 45, about 50, about 55, about 60, about 65, about 70, or about 75% by weight (e.g., about 15 to about 60% by weight, or about 25 to about 45% by weight) on a wet weight basis. In certain embodiments, the amount of particulate filler component is at least about 10% by weight, based on the total weight of the mixture, e.g., at least about 20%, or at least about 25%, or at least about 30%, or at least about 35%, or at least about 40%.

[0088] Cellulose Derivatives The mixtures described herein include cellulose derivatives. "Cellulose derivative" refers to a cellulosic material that has been chemically modified by reaction of one or more hydroxyl groups of the cellulose polymer structure with, for example, an esterifying agent or an alkylating agent. Cellulose derivatives include any derivative of cellulose, such as, but not limited to, cellulose esters and cellulose ethers. "Cellulose ester" refers to a cellulose structure in which the hydrogen of one or more hydroxyl groups in the cellulose polymer structure is replaced with, for example, an acyl, nitro, or sulfate group. The cellulose ester can be an organic ester (e.g., cellulose acetate, cellulose triacetate, cellulose propionate, cellulose acetate propionate (CAP), cellulose acetate butyrate (CAB)) or an inorganic ester (e.g., nitrocellulose (cellulose nitrate) and cellulose sulfate). "Cellulose ether" refers to a cellulose structure in which the hydrogen of one or more hydroxyl groups in the cellulose polymer structure is replaced with an alkyl, hydroxyalkyl, or aryl group. Cellulose ethers include, for example, alkyl ethers (e.g., methyl cellulose, ethyl cellulose), hydroxyalkyl ethers (e.g., hydroxyethyl cellulose, hydroxypropyl cellulose (HPC), hydroxyethyl methyl cellulose, hydroxypropyl methyl cellulose (HMPC), ethyl hydroxyethyl cellulose), and carboxyalkyl ethers (e.g., carboxymethyl cellulose (CMC)).

[0089] The amount of cellulose derivative present in the mixture can vary. In some embodiments, the mixture comprises a cellulose derivative in an amount of at least about 0.5% by weight of the cellulose derivative, based on the total weight of the mixture. In some embodiments, the mixture comprises a cellulose derivative in an amount of at least about 1% by weight of the cellulose derivative, based on the total weight of the composition. In some embodiments, the mixture comprises a cellulose derivative in an amount of about 0.5 to about 10% by weight, based on the total weight of the composition. In some embodiments, the mixture comprises a cellulose derivative in an amount of about 1 to about 5% by weight of the cellulose derivative, for example, about 1, about 1.5, about 2, about 2.5, or about 3 to about 3.5, about 4, about 4.5, or about 5% by weight. In some embodiments, the mixture comprises a cellulose derivative in an amount of about 1 to about 3% by weight, based on the total weight of the mixture.

[0090] In some embodiments, the cellulose derivative is a cellulose ether. In some embodiments, the cellulose ether is an alkyl ether or a hydroxyalkyl ether. In one embodiment, the cellulose ether comprises one or more of methylcellulose, HPC, HPMC, hydroxyethylcellulose, or CMC. In one embodiment, the cellulose ether is HPC. In certain embodiments, the mixture comprises about 1 to about 3 wt.% HPC, based on the total weight of the mixture.

[0091] water The water content of the mixture may vary according to the desired properties prior to consumer use of the product. Typically, the mixture, when present in the product prior to insertion into the user's mouth, is less than about 60% by weight of water, generally about 1 to about 60% by weight of water, for example, about 5 to about 55, about 10 to about 50, about 20 to about 45, or about 25 to about 40% by weight of water, based on the total weight of the mixture. In some embodiments, the mixture is at least about 5% water, for example, about 5 to about 60% by weight of water, based on the total weight of the mixture. In certain embodiments, the mixture comprises about 1 to about 3% by weight of HPC, about 10 to about 60% by weight of microcrystalline cellulose, and about 1 to about 60% by weight of water.

[0092] Flavoring Agent The mixtures disclosed herein include one or more flavoring agents. As used herein, a "flavoring agent" or "flavoring agent" is any flavorful or aromatic substance that can change the sensory properties associated with a smokeless tobacco composition. Examples of sensory properties that can be modified by a flavoring agent can include taste, mouthfeel, moistness, coolness / heat, and / or aroma / aroma. Flavoring agents can be natural or synthetic, and the flavor characteristics imparted thereby can be described as, but are not limited to, fresh, sweet, herbal, confectionery, floral, fruity, or spicy. Specific types of flavors include, but are not limited to, vanilla, coffee, chocolate / cocoa, cream, mint, spearmint, menthol, peppermint, wintergreen, eucalyptus, lavender, cardamom, nutmeg, cinnamon, clove, cascarilla, sandalwood, honey, jasmine, ginger, anise, sage, licorice, lemon, orange, apple, peach, lime, cherry, strawberry, and any combination thereof. See also Leffingwell et al., Tobacco Flavoring for Smoking Products, R. J. Reynolds Tobacco Company (1972), the disclosure of which is incorporated herein by reference in its entirety. Flavorings may also include ingredients that are considered humectants, coolants, or smoothing agents, such as eucalyptus. These flavorings may be provided neat (i.e., alone) or in complexes, and may be used as concentrates or flavoring packages (e.g., spearmint and menthol, orange and cinnamon, lime, tropical, etc.). Representative types of components are also described in U.S. Patent No. 5,387,416 to White et al., U.S. Patent Application Publication No. 2005 / 0244521 to Strickland et al., and PCT Application WO 05 / 041699 to Quinter et al., each of which is incorporated herein by reference. In some cases, the flavoring agent may be provided in a spray-dried or liquid form.

[0093] Flavoring agents generally include at least one volatile flavor ingredient. As used herein, "volatile" refers to a chemical that readily forms vapor at ambient temperature (i.e., has a high vapor pressure at a given temperature compared to non-volatile substances). Typically, volatile flavor ingredients have a molecular weight of less than about 400 and often contain at least one carbon-carbon double bond, carbon-oxygen double bond, carbon-oxygen single bond, or combinations thereof. In one embodiment, the at least one volatile flavor ingredient includes one or more alcohols, aldehydes, aromatic hydrocarbons, ketones, esters, terpenes, terpenoids, or combinations thereof. Non-limiting examples of aldehydes include vanillin, ethyl vanillin, p-anisaldehyde, hexanal, furfural, isovaleraldehyde, cuminaldehyde, benzaldehyde, and citronellal. Non-limiting examples of ketones include 1-hydroxy-2-propanone and 2-hydroxy-3-methyl-2-cyclopentenone-1-one. Non-limiting examples of terpenes include sabinene, limonene, gamma-terpinene, beta-farnesene, nerolidol, thujone, myrcene, geraniol, nerol, citronellol, linalool, and eucalyptol.

[0094] In some embodiments, the at least one volatile flavor ingredient comprises one or more esters. As used herein, the term "ester" refers to a compound derived from a carboxylic acid and an alcohol, in which the -OH of the carboxyl (CO2H) group is replaced with an -O-alkyl (alkoxy) group of the alcohol. In some embodiments, the one or more esters are alkyl esters comprising a C1-C8 alkanol and a C2-C8 alkyl carboxylic acid.

[0095] "C1-C8 alkanol" means any straight or branched chain hydrocarbon alcohol having 1 to 8 carbons. The alkanol is saturated (i.e., all sp 3As used herein, the term "unsaturated" refers to a group that is either carbon-carbon, sp , or unsaturated (i.e., has at least one site of unsaturation) at one or more positions in the hydrocarbon chain of the alkanol. 2 It refers to the presence of a double bond. Unsaturated alkanols can be monounsaturated or polyunsaturated. Representative straight chain alkanols include, but are not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, and n-hexyl. Unsaturated alkanols include, but are not limited to, allyl, butenyl, and the like. Branched chain alkanols include, but are not limited to, isopropyl, sec-butyl, isobutyl, tert-butyl, isopentyl, and 2-methylbutyl.

[0096] "C2-C8 alkyl carboxylic acid" means any straight or branched chain hydrocarbon carboxylic acid having from 2 to 8 carbons. As with the alkanols defined above, the alkyl group of the C2-C8 alkyl carboxylic acid can be branched or straight chain, saturated or unsaturated. Non-limiting examples of alkyl carboxylic acids include formic acid, acetic acid, propionic acid, butyric acid, pentanoic acid, hexanoic acid, heptanoic acid, and octanoic acid.

[0097] Non-limiting examples of alkyl esters include allyl hexanoate, ethyl heptanoate, ethyl hexanoate, isoamyl acetate, and 3-methylbutyl acetate. In one embodiment, the one or more esters present in the at least one volatile flavor ingredient include isoamyl acetate, ethyl hexanoate, ethyl heptanoate, allyl hexanoate, or combinations thereof.

[0098] The amount of flavoring utilized in the mixture can vary, but is typically up to about 10% by weight, with certain embodiments characterized by a flavoring content of at least about 0.5% by weight, e.g., from about 0.5 to about 10% by weight, from about 1 to about 6% by weight, or from about 2 to about 5% by weight.

[0099] The amount of flavoring agent (e.g., volatile component) present in the mixture may change over a period of time (e.g., during storage period after preparation of the composition). For example, certain volatile components such as esters, ketones, etc. present in the mixture (e.g., introduced in the form of flavor packages such as lime, tropical, cinnamon, etc.) may evaporate or undergo chemical transformation, resulting in a decrease in the concentration of one or more of the volatile flavor components. In one embodiment, the concentration of one or more of the at least one volatile flavor components present is higher than the concentration of the same one or more volatile flavor components present in a control mixture that does not contain a cellulose derivative.

[0100] organic acid As used herein, the term "organic acid" refers to an organic (i.e., carbon-based) compound characterized by acidic properties. Typically, organic acids are relatively weak acids (i.e., they do not completely dissociate in the presence of water), such as carboxylic acids (-CO2H) or sulfonic acids (-SO2OH). As used herein, reference to an organic acid refers to an organic acid that is intentionally added. In this regard, an organic acid may be intentionally added as a particular composition component, as opposed to being present essentially merely as a component of another composition component (e.g., a small amount of an organic acid that may be inherently present in a composition component, such as a tobacco material). In some embodiments, one or more organic acids are added neat (i.e., in their free acid, solid or liquid form in nature) or as a solution, for example, in water. In some embodiments, one or more organic acids are added in the form of a salt, as described herein below.

[0101] Suitable organic acids typically have a range of lipophilicity (i.e., polarity that provides an appropriate balance of water and organic solubility). Lipophilicity is conveniently measured in terms of logP, which is the partition coefficient of a molecule between an aqueous phase and a lipophilic phase, usually water and octanol, respectively. In some embodiments, the organic acid has a logP value of about 1.5 to about 5.0, e.g., about 1.5, about 2.0, about 2.5, or about 3.0 to about 3.5, about 4.0, about 4.5, or about 5.0.

[0102] In some embodiments, the organic acid is a carboxylic acid or a sulfonic acid. The functional group of the carboxylic acid or sulfonic acid may, for example, be a carboxylic acid having from 1 to 20 carbon atoms (C1-C 20 In some embodiments, the organic acid is an alkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl carboxylic or sulfonic acid.

[0103] As used herein, "alkyl" refers to any straight or branched chain hydrocarbon. The alkyl group may be saturated (i.e., all sp 3 As used herein, the term "unsaturated" refers to an alkyl group that is carbon-carbon, sp 2 It refers to the presence of a double bond. Unsaturated alkyl groups can be monounsaturated or polyunsaturated. Representative straight chain alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, and n-hexyl. Branched chain alkyl groups include, but are not limited to, isopropyl, sec-butyl, isobutyl, tert-butyl, isopentyl, and 2-methylbutyl. Representative unsaturated alkyl groups include, but are not limited to, ethylene or vinyl, allyl, 1-butenyl, 2-butenyl, isobutylenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 2-methyl-2-butenyl, 2,3-dimethyl-2-butenyl, and the like. Alkyl groups can be unsubstituted or substituted.

[0104] As used herein, "cycloalkyl" refers to a carbocyclic group that may be monocyclic or bicyclic. Cycloalkyl groups include rings having 3 to 7 carbon atoms as a monocycle, or rings having 7 to 12 carbon atoms as a bicycle. Examples of monocyclic cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Cycloalkyl groups may be unsubstituted or substituted and may contain one or more sites of unsaturation (e.g., cyclopentenyl or cyclohexenyl).

[0105] The term "aryl" as used herein refers to a carbocyclic aromatic group. Examples of aryl groups include, but are not limited to, phenyl and naphthyl. Aryl groups can be unsubstituted or substituted.

[0106] "Heteroaryl" and "heterocycloalkyl" as used herein refer to an aromatic or non-aromatic ring system in which one or more ring atoms are heteroatoms, such as nitrogen, oxygen, and sulfur, respectively. A heteroaryl or heterocycloalkyl group contains up to 20 carbon atoms and 1-3 heteroatoms selected from N, O, and S. A heteroaryl or heterocycloalkyl can be a monocyclic ring having 3-7 ring members (e.g., 2-6 carbon atoms and 1-3 heteroatoms selected from N, O, and S) or a bicyclic ring having 7-10 ring members (e.g., 4-9 carbon atoms and 1-3 heteroatoms selected from N, O, and S), such as a bicyclo[4,5], [5,5], [5,6], or [6,6] system. Examples of heteroaryl groups include pyridyl, thiazolyl, tetrahydrothiophenyl, pyrimidinyl, furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, tetrazolyl, benzofuranyl, thianaphthalenyl, indolyl, indolenyl, quinolinyl, isoquinolinyl, benzimidazolyl, isoxazolyl, pyrazinyl, pyridazinyl, indolizinyl, isoindolyl, 3H-indolyl, 1H-indazolyl, purinyl, 4H-quinolizinyl, phthalazinyl, naphthalenyl, and the like. Examples include, but are not limited to, phthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, pteridinyl, 4aH-carbazolyl, carbazolyl, phenanthridinyl, acridinyl, pyrimidinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, furazanyl, phenoxazinyl, isochromanyl, chromanyl, imidazolidinyl, imidazolinyl, pyrazolidinyl, pyrazolinyl, benzotriazolyl, benzisoxazolyl, and isotinoyl. Examples of heterocycloalkyl include, by way of example and not limitation, dihydropyridyl, tetrahydropyridyl (piperidyl), tetrahydrothiophenyl, piperidinyl, 4-piperidonyl, pyrrolidinyl, 2-pyrrolidinyl, tetrahydrofuranyl, tetrahydropyranyl, bis-tetrahydropyranyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, decahydroquinolinyl, octahydroisoquinolinyl, piperazinyl, quinuclidinyl, and morpholinyl.The heteroaryl and heterocycloalkyl groups can be unsubstituted or substituted.

[0107] As used herein, and as applied to any of the above alkyl, aryl, cycloalkyl, heteroaryl or heterocyclyl groups, "substituted" means that one or more hydrogen atoms are each independently replaced with a substituent. Exemplary substituents include, but are not limited to, -Cl, Br, F, alkyl, -OH, -OCH3, NH2, -NHCH3, -N(CH3)2, -CN, -NC(=O)CH3, -C(=O)-, -C(=O)NH2 and -C(=O)N(CH3)2. Whenever a group is described as "optionally substituted," the group can be substituted with one or more of the above substituents, independently selected in each instance. In some embodiments, the substituents can be one or more methyl groups or one or more hydroxyl groups.

[0108] In some embodiments, the organic acid is an alkyl carboxylic acid. Non-limiting examples of alkyl carboxylic acids include formic acid, acetic acid, propionic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, and the like. In some embodiments, the organic acid is an alkyl sulfonic acid. Non-limiting examples of alkyl sulfonic acids include propane sulfonic acid and octane sulfonic acid.

[0109] In some embodiments, the alkyl carboxylic or sulfonic acids are substituted with one or more hydroxyl groups. Non-limiting examples include glycolic acid, 4-hydroxybutyric acid, and lactic acid.

[0110] In some embodiments, the organic acid may contain more than one carboxylic acid group or more than one sulfonic acid group (e.g., 2, 3, or 4 or more carboxylic acid groups). Non-limiting examples include oxalic acid, fumaric acid, maleic acid, and glutaric acid. In organic acids containing multiple carboxylic acids (e.g., 2-4 carboxylic acid groups), one or more of the carboxylic acid groups may be esterified. Non-limiting examples include succinic acid monoethyl ester, monomethyl fumarate, monomethyl citrate, or dimethyl citrate, etc.

[0111] In some embodiments, the organic acid may contain more than one carboxylic acid group and one or more hydroxyl groups. Non-limiting examples of such acids include tartaric acid, citric acid, and the like.

[0112] In some embodiments, the organic acid is an aryl carboxylic acid or aryl sulfonic acid. Non-limiting examples of aryl carboxylic and sulfonic acids include benzoic acid, toluene acid, salicylic acid, benzenesulfonic acid, and p-toluenesulfonic acid.

[0113] Further non-limiting examples of suitable organic acids include 2,2-dichloroacetic acid, 2-hydroxyethanesulfonic acid, 2-oxoglutaric acid, 4-acetamidobenzoic acid, 4-aminosalicylic acid, acetic acid, adipic acid, ascorbic acid (L), aspartic acid (L), camphoric acid (+), camphor-10-sulfonic acid (+), capric acid, caproic acid, caprylic acid, cinnamic acid, cyclamic acid, decanoic acid, dodecyl sulfuric acid, ethane-1,2-disulfonic ... These include: Tanesulfonic Acid, Formic Acid, Fumaric Acid, Galactaric Acid, Gentisic Acid, Glucoheptonic Acid, Gluconic Acid, Glucuronic Acid, Glutamic Acid, Glycerophosphoric Acid, Glycolic Acid, Hippuric Acid, Isobutyric Acid, Lactovaric Acid, Lauric Acid, Malonic Acid, Mandelic Acid, Methanesulfonic Acid, Naphthalene-1,5-disulfonic Acid, Naphthalene-2-sulfonic Acid, Oleic Acid, Palmitic Acid, Pamoic Acid, Pyroglutamic Acid, Sebacic Acid, Stearic Acid, and Undecylenic Acid.

[0114] In some embodiments, the one or more organic acids is a single organic acid, hi some embodiments, the one or more organic acids is a combination of several acids, such as two, three, or more organic acids.

[0115] In some embodiments, the organic acid is citric acid, malic acid, tartaric acid, octanoic acid, benzoic acid, toluene acid, salicylic acid, or a combination thereof. In some embodiments, the organic acid is benzoic acid. In some embodiments, the organic acid is citric acid.

[0116] In alternative embodiments, some or even all of the organic acid may be added in the form of a salt with an alkaline component, which may include, but is not limited to, nicotine. Non-limiting examples of suitable salts, for example with nicotine, include formate, acetate, propionate, isobutyrate, butyric acid, alpha methyl butyrate, isovaleric acid, beta methyl valerate, capronate, 2-furoate, phenylacetate, heptanoate, octanoate, nonanoate, oxalate, malonate, glycolate, benzoate, tartrate, levulinic acid, ascorbate, fumarate, citrate, malate, lactate, aspartic acid, salicylate, tosylate, succinate, pyruvic acid, and the like. In some embodiments, the organic acid or a portion thereof may be added in the form of a salt with an alkali metal, such as sodium, potassium, and the like. For organic acids with more than one acid group (such as di- or tri-carboxylic acids), in some cases, one or more of these acid groups may be in such a salt form. Suitable non-limiting examples include monosodium citrate, disodium citrate, etc. In some embodiments, the organic acid is a salt of citric acid, malic acid, tartaric acid, octanoic acid, benzoic acid, toluene acid, salicylic acid, or combinations thereof. In some embodiments, the organic acid is a dicarboxylic acid monoester or tricarboxylic acid diester, respectively, such as the monomethyl ester of citric acid, malic acid, or tartaric acid, or the dimethyl ester of citric acid.

[0117] The amount of organic acid present in the mixture may vary. Generally, when present in the mixture, the organic acid comprises about 0.1 to about 10% by weight of the mixture, which may be present as one or more organic acids. In some embodiments, the mixture is substantially free of organic acid. By "substantially free" of organic acid, it is meant that there is no intentionally added organic acid (e.g., less than 0.1%, less than 0.05%, or 0%). In some embodiments, the mixture comprises about 0.1%, about 0.2%, about 0.3%, about 0.4%, about 0.5%, about 0.6%, about 0.7%, about 0.8%, about 0.9%, about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9%, or about 10% by weight of organic acid. In some embodiments, the mixture comprises about 0.1 to about 0.5 wt. % of the organic acid, e.g., about 0.1, about 0.15, about 0.2, about 0.25, about 0.3, about 0.35, about 0.4, about 0.45, or about 0.5 wt. %. In some embodiments, the mixture comprises about 0.25 to about 0.35 wt. %, e.g., about 0.25, about 0.26, about 0.27, about 0.28, about 0.29, or about 0.3 to about 0.31, about 0.32, about 0.33, about 0.34, or about 0.35 wt. % of the organic acid, based on the total weight of the composition. When a salt of an organic acid is added, the weight % is calculated based on the weight of the free acid, without any counter ion that may be present.

[0118] If present, the amount of acid in the mixture will vary based on the acidity and basicity of other components (e.g., nicotine, salts, buffers, etc.) that may be present in the mixture. Thus, in some embodiments where an organic acid is present, the organic acid is provided in an amount sufficient to provide a pH of the mixture of 7.0 or less (typically about 6.8 or less, about 6.6 or less, or about 6.5 or less). In certain embodiments, the acid content is sufficient to provide a pH of the mixture of about 4.0 to about 7.0, e.g., about 4.5, about 5.0, about 5.5, or about 6.0 to about 6.5, or about 7.0. In some embodiments, the organic acid is provided in an amount sufficient to provide a pH of the mixture of about 5.5 to about 6.5, e.g., about 5.5, about 5.6, about 5.7, about 5.8, about 5.9, or about 6.0 to about 6.1, about 6.2, about 6.3, about 6.4, or about 6.5.

[0119] salt In some embodiments, the mixture may further comprise a salt (e.g., an alkali metal salt), typically used in an amount sufficient to impart the desired sensory properties to the composition. Non-limiting examples of suitable salts include sodium chloride, potassium chloride, ammonium chloride, flour salt, and the like. When present, representative amounts of salt are about 0.5% by weight or more, about 1.0% by weight or more, or about 1.5% by weight or more, but typically comprise about 10% by weight or less, or about 7.5% by weight or less, or about 5% by weight or less (e.g., about 0.5 to about 5% by weight) of the total weight of the composition.

[0120] sweetener The mixture typically further comprises one or more sweeteners. The sweetener can be any sweetener or combination of sweeteners, in natural or artificial form, or as a combination of natural and artificial sweeteners. Examples of natural sweeteners include fructose, sucrose, glucose, maltose, mannose, galactose, lactose, stevia, etc. Examples of artificial sweeteners include sucralose, isomaltulose, maltodextrin, saccharin, aspartame, acesulfame K, neotame, etc. In some embodiments, the sweetener comprises a sugar alcohol. The sugar alcohol is a polyol derived from a monosaccharide or disaccharide, which has a partially or fully hydrogenated form. Sugar alcohols, for example, have from about 4 to about 20 carbon atoms and include erythritol, arabitol, ribitol, isomalt, maltitol, dulcitol, iditol, mannitol, xylitol, lactitol, sorbitol, and combinations thereof (e.g., hydrogenated starch hydrolysates).When present, a representative amount of sweetener may comprise from about 0.1 to about 20% or more of the mixture by weight, for example, from about 0.1 to about 1%, from about 1 to about 5%, from about 5 to about 10%, or from about 10 to about 20% of the composition by weight.

[0121] Binder The binder (or combination of binders) may be used in certain embodiments in an amount sufficient to impart the desired physical attributes and physical integrity to the mixture. Typical binders may be organic or inorganic, or combinations thereof. Representative binders include povidone, sodium alginate, starch-based binders, pectin, carrageenan, pullulan, zein, and the like, and combinations thereof. The amount of binder utilized in the mixture may vary, but is typically up to about 30% by weight, with certain embodiments characterized by a binder content of at least about 0.1% by weight, e.g., from about 1 to about 30% by weight, or from about 5 to about 10% by weight, based on the total weight of the mixture.

[0122] In certain embodiments, the binder comprises a gum, such as a natural gum. As used herein, natural gum refers to a polysaccharide material of natural origin that is useful as a thickening or gelling agent. Representative natural gums derived from plants that are typically water-soluble to some extent include xanthan gum, guar gum, gum arabic, gum ghatti, gum tragacanth, gum karaya, locust bean gum, gellan gum, and combinations thereof. When present, the natural gum binding material is typically present in an amount of up to about 5% by weight, such as about 0.1, about 0.2, about 0.3, about 0.4, about 0.5, about 0.6, about 0.7, about 0.8, about 0.9, or about 1% to about 2, about 3, about 4, or about 5% by weight, based on the total weight of the mixture.

[0123] Moisturizer In certain embodiments, one or more humectants can be used in the mixture. Examples of humectants include, but are not limited to, glycerin, propylene glycol, and the like. If included, the humectant is typically provided in an amount sufficient to impart the desired moisture attributes to the mixture. Additionally, in some examples, the humectant may impart desirable flow characteristics to the mixture for deposition into a mold. If present, the humectant typically comprises about 5% or less of the weight of the mixture (e.g., about 0.5 to about 5%). If present, a representative amount of humectant is about 0.1% to about 1% by weight, or about 1% to about 5% by weight, based on the total weight of the mixture.

[0124] Buffer In certain embodiments, the mixture of the present disclosure may include a pH adjusting agent or buffering agent. Examples of pH adjusting agents and buffering agents that may be used include, but are not limited to, metal hydroxides (e.g., alkali metal hydroxides such as sodium hydroxide and potassium hydroxide), and other alkali metal buffers such as metal carbamates (e.g., potassium carbamate or sodium carbamate), or metal bicarbamates such as sodium bicarbamate. When present, the buffering agent is typically present in an amount of less than about 5% based on the weight of the formulation, for example, about 0.5% to about 5% based on the total weight of the mixture, for example, about 0.75% to about 4%, about 0.75% to about 3%, or about 1% to about 2% by weight. Non-limiting examples of suitable buffering agents include alkali metal acetates, glycine acetates, phosphates, glycerophosphates, citrates, carbamates, carbonate carbamates, borocarbamates, or mixtures thereof.

[0125] Coloring agent Colorants may be used in an amount sufficient to impart desired physical attributes to the mixture. Examples of colorants include various dyes and pigments, such as caramel coloring and titanium dioxide. The amount of colorant utilized in the mixture may vary, but when present, is typically up to about 3% by dry weight, such as about 0.1%, about 0.5%, or about 1% to about 3% by weight, based on the total weight of the mixture.

[0126] Active ingredients The mixture may additionally or alternatively contain active ingredients including, but not limited to, nicotine, botanicals (e.g., lavender, peppermint, chamomile, basil, rosemary, ginger, cannabis, ginseng, maca, and tisanes), stimulants (e.g., caffeine and guarana), amino acids (e.g., taurine, theanine, phenylalanine, tyrosine, and tryptophan), and / or pharmaceutical, nutraceutical, and medical ingredients (e.g., vitamins such as B6, B12, and C, and / or cannabinoids such as tetrahydrocannabinol (THC) and cannabidiol (CBD)). The particular proportions and selection of ingredients will vary depending on the flavor, texture, and other characteristics desired.

[0127] In certain embodiments, a nicotine component may be included in the mixture. By "nicotine component" is meant any suitable form of nicotine (e.g., free base or salt) to provide oral absorption of at least a portion of the nicotine present. Typically, the nicotine component is selected from the group consisting of nicotine free base and nicotine salt. In some embodiments, nicotine is in its free base form and can be readily adsorbed, for example, to microcrystalline cellulose material to form a microcrystalline cellulose-nicotine carrier complex. See, for example, the discussion of nicotine in free base form in US Patent Application Publication No. 2004 / 0191322 by Hansson, which is incorporated herein by reference.

[0128] In some embodiments, at least a portion of the nicotine may be used in the form of a salt. The salt of nicotine may be provided using the types of ingredients and techniques described in U.S. Patent No. 2,033,909 to Cox et al. and Perfetti, Beitrage Tabakforschung Int., 12:43-54 (1983), which are incorporated herein by reference. Additionally, salts of nicotine are available from sources such as Pfaltz and Bauer, Inc. and K&K Laboratories, Division of ICN Biochemicals, Inc. Typically, the nicotine component is selected from the group consisting of nicotine free base, nicotine salts, such as hydrochloride, dihydrochloride, monotartrate, bitartrate, sulfate, salicylate, and nicotine zinc chloride. In some embodiments, the nicotine component or a portion thereof is a nicotine salt having at least a portion of one or more organic acids disclosed herein above.

[0129] In some embodiments, at least a portion of the nicotine may be in the form of a resin complex of nicotine, where the nicotine is bound to an ion exchange resin such as nicotine polacrilex, which is nicotine bound to polymethacrylic acid, such as Amberlite IRP64, Purolite C115HMR, or Doshion P551. See, for example, U.S. Patent No. 3,901,248 to Lichtneckert et al., which is incorporated herein by reference. Another example is a nicotine-polyacryl carbomer complex, including Carbopol 974P. In some embodiments, the nicotine may be present in the form of a nicotine polyacryl complex.

[0130] Typically, the nicotine component (calculated as the free base), if present, is at least about 0.001% by weight of the mixture, e.g., at a concentration ranging from about 0.001% to about 10%. In some embodiments, the nicotine component, calculated as the free base, is present in a concentration of about 0.1% w / w to about 10% by weight, e.g., about 0.1% w / w, about 0.2%, about 0.3%, about 0.4%, about 0.5%, about 0.6%, about 0.7%, about 0.8%, or about 0.9% to about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9%, or about 10% by weight, based on the total weight of the mixture. In some embodiments, the nicotine component is present in a concentration of about 0.1% w / w to about 3% by weight, calculated as the free base, based on the total weight of the mixture, e.g., about 0.1% w / w to about 2.5%, about 0.1% to about 2.0%, about 0.1% to about 1.5%, or about 0.1% to about 1% by weight. These ranges may also apply to other active ingredients described herein.

[0131] Tobacco Materials In some embodiments, the mixture may include tobacco material. The tobacco material may vary in species, variety, and form. Generally, the tobacco material is obtained from harvested plants of the Nicotiana species. Examples of Nicotiana species include N. tabacum, N. rustica, N. alata, N. arentsii, N. excelsior, N. forgetiana, N. glauca, N. glutinosa, N. gossei, N. knigte, N. nigricans ... N. knightiana, N. langsdorffi, N. otophora, N. setchelli, N. sylvestris, N. tomentosa, N. tomentosiformis, N. undulata, N. × sanderae sanderae, N. africana, N. amplexicaulis, N. benavidesii, N. bonariensis, N. debneyi, N. longiflora, N. maritina, N. megalosiphon, N. occidentalis, N. paniculata, N. plumbaginifolia .plumbaginifolia, N. raimondii, N. rosulata, N. simulans, N. stocktonii, N. suaveolens, N. umbratica, N. velutina, N. wigandioides, N. acaulis, N. acuminata, N. attenuata, N.N. benthamiana, N. cavicola, N. clevelandii, N. cordifolia, N. corymbosa, N. fragrans, N. goodspeedii, N. linearis, N. miersii, N. nudicaulis, N. obtusifolia, N. occidentalis subsp. hesperis subsp. Hersperis, N. pauciflora, N. petunioides, N. quadrivalvis, N. repanda, N. rotundifolia, N. solanifolia, and N. spegazzinii. Various representative other types of plants from the Nicotiana species are described in Goodspeed, The Genus Nicotiana, (Chonica Botanica) (1954), U.S. Patent Nos. 4,660,577 to Sensabaugh, Jr. et al., 5,387,416 to White et al., 7,025,066 to Lawson et al., 7,798,153 to Lawrence, Jr. et al., and 8,186,360 to Marshall et al., each of which is incorporated herein by reference. A description of various types of tobacco, growing practices, and harvesting practices is provided in Tobacco Production, Chemistry and Technology, Davis et al. (Eds.) (1999), which is incorporated herein by reference.

[0132] Nicotiana species from which suitable tobacco material can be derived can be derived using genetic modification or breeding techniques (e.g., tobacco plants can be genetically engineered or bred to increase or decrease the production of a component, characteristic or trait). See, for example, the types of genetic modifications of plants described in U.S. Pat. No. 5,539,093 to Fitzmaurice et al., U.S. Pat. No. 5,668,295 to Wahab et al., U.S. Pat. No. 5,705,624 to Fitzmaurice et al., U.S. Pat. No. 5,844,119 to Weigl et al., U.S. Pat. No. 6,730,832 to Dominguez et al., U.S. Pat. No. 7,173,170 to Liu et al., U.S. Pat. No. 7,208,659 to Colliver et al., U.S. Pat. No. 7,230,160 to Benning et al., U.S. Pat. Appl. Pub. No. 2006 / 0236434 to Conkling et al., and WO 2008 / 103935 to Nielsen et al. See also the types of genetic modifications of plants described in U.S. Patent Nos. 4,660,577 to Sensabaugh, Jr. et al., 5,387,416 to White et al., and 6,730,832 to Dominguez et al., each of which is incorporated herein by reference.

[0133] Nicotiana species can be selected in some embodiments for the content of various compounds present therein. For example, plants can be selected based on the fact that they produce relatively large amounts of one or more of the compounds desired to be isolated therefrom. In certain embodiments, plants of Nicotiana species (e.g., Galpao commun tobacco) are specifically grown for their abundance of leaf surface compounds. Tobacco plants can be grown in greenhouses, growth chambers, or outdoor fields, or grown hydroponically.

[0134] Various parts of the Nicotiana species plant may be included within the mixtures disclosed herein. For example, substantially the entire plant (e.g., the whole plant) may be harvested and used as is. Alternatively, various parts or pieces of the plant may be harvested or separated for further use after harvesting. For example, flowers, leaves, stems, stalks, roots, seeds, and various combinations thereof may be isolated for further use or processing. In some embodiments, the tobacco material comprises tobacco leaves (lamina). The mixtures disclosed herein may include processed tobacco parts or pieces, cured and aged tobacco in essentially natural lamina and / or stem form, tobacco extracts, extracted tobacco pulp (e.g., using water as a solvent), or mixtures of the foregoing (e.g., a mixture combining extracted tobacco pulp with granulated aged natural tobacco lamina).

[0135] In certain embodiments, the tobacco material comprises a solid tobacco material selected from the group consisting of lamina and stems. The tobacco used in the mixture most preferably comprises tobacco lamina or a mixture of tobacco lamina and stems, at least a portion of which is smoke treated. The tobacco portion in the mixture may have a processed form, such as processed tobacco stems (e.g., cut rolled stems, cut rolled expanded stems, or cut puffed stems) or volume expanded tobacco (e.g., puffed tobacco such as dry ice expanded tobacco (DIET)). See, for example, the tobacco growth processes described in U.S. Patent Nos. 4,340,073 to de la Burde et al., 5,259,403 to Guy et al., and 5,908,032 to Poindexter et al. and 7,556,047 to Poindexter et al., all of which are incorporated by reference. Additionally, the mixture may optionally incorporate fermented tobacco. See also the types of tobacco processing techniques described in Atchley et al., WO 2005 / 063060, which is incorporated herein by reference.

[0136] Tobacco materials are typically used in a form that can be described as particulate (i.e., fragmented, ground, granulated, or powdered). The manner in which the tobacco material is provided in finely divided or powdered form can vary. Preferably, the plant parts or pieces are comminuted, ground, or micronized using equipment and techniques for micronization, milling, and the like. Most preferably, the plant material is in a form that is relatively dry during grinding or milling, using equipment such as hammer mills, cutter heads, air control mills, and the like. For example, tobacco parts or pieces may be ground or milled when their moisture content is less than about 15% by weight, or less than about 5% by weight. Most preferably, the tobacco material is used in the form of parts or pieces having an average particle size of 1.4 millimeters to 250 microns. In some instances, the tobacco particles can be sized to pass through a screen mesh to obtain the required particle size range. If desired, air classifiers can be used to ensure collection of small tobacco particles of the desired size or range of sizes. If desired, granular tobacco pieces of different sizes may be mixed together.

[0137] The manner in which tobacco is provided in finely divided or powdered form can vary. Preferably, tobacco parts or pieces are comminuted, ground or micronized into a powder-type form using equipment and techniques for micronization, milling, and the like. Most preferably, the tobacco is in a relatively dry form during grinding or milling, using equipment such as hammer mills, cutter heads, air control mills, and the like. For example, tobacco parts or pieces may be ground or milled when their moisture content is less than about 15% to less than about 5% by weight. For example, tobacco plants or parts thereof can be separated into individual parts or pieces (e.g., leaves can be removed from the stems, and / or stems and leaves can be removed from the stems). Harvested plants or individual parts or pieces can be further subdivided into parts or pieces (e.g., leaves can be fragmented, cut, comminuted, micronized, milled, or ground into pieces or pieces that can be characterized as filler type pieces, granules, particulates, or fines). The plant or parts thereof can be subjected to an external force or pressure (e.g., by being subjected to a pressing or rolling process). When such treatment conditions are practiced, the plant or part thereof can have a moisture content that is close to its natural moisture content (e.g., moisture content immediately after harvest), a moisture content achieved by adding moisture to the plant or part thereof, or a moisture content resulting from drying the plant or part thereof. For example, powdered, micronized, crushed or milled pieces of the plant or part thereof can have a moisture content of less than about 25% by weight, often less than about 20% by weight, and frequently less than about 15% by weight.

[0138] For the preparation of oral products, harvested plants of Nicotiana species are typically subjected to a curing process. The tobacco materials incorporated into the mixture for inclusion in the pouch products disclosed herein are appropriately cured and / or aged. Descriptions of different types of curing processes for different types of tobacco are found in Tobacco Production, Chemistry and Technology, Davis et al. (Eds.) (1999). Examples of techniques and conditions for curing fully cured tobacco are found in Nestor et al., Beitrage Tabakforsch. Int., 20, 467-475 (2003), and U.S. Patent No. 6,895,974 to Peele, which are incorporated herein by reference. Exemplary techniques and conditions for air curing tobacco are described in U.S. Patent No. 7,650,892 by Groves et al., Roton et al., Beitrage Tabakforsch. Int., 21, 305-320 (2005), and Staaf et al., Beitrage Tabakforsch. Int., 21, 321-330 (2005), which are incorporated herein by reference. Certain types of tobacco can be subjected to alternative types of curing processes, such as fire curing or sun curing.

[0139] In certain embodiments, tobacco materials that may be used include fully cured or Virginia (e.g., K326), Burley, sun cured (e.g., Indian Kurnool and Oriental tobaccos, including Katerini, Prelip, Komotini, Xanthi and Yambol tobaccos), Maryland, dark, dark burnt, dark air cured (e.g., Madole, Passanda, Cubano, Jatin and Bezuki tobaccos), light air cured (e.g., North Wisconsin and Galpao tobaccos), Indian air cured, Red Russian and Rustica tobaccos, as well as various other rare or specialty tobaccos and various blends of any of the foregoing tobaccos.

[0140] The tobacco material may also be in the form of a so-called "blend". For example, the tobacco material may include a mixture of parts or pieces of fully cured, burley (e.g., Malawian burley) and Oriental tobacco (e.g., tobacco composed of or derived from tobacco lamina, or as a mixture of tobacco lamina and tobacco stem). For example, a representative blend may incorporate about 30 to about 70 parts burley tobacco (e.g., lamina, or lamina and stem) and about 30 to about 70 parts fully cured tobacco (e.g., stem, lamina, or lamina and stem) on a dry weight basis. Other exemplary tobacco blends incorporate about 75 parts fully cured tobacco, about 15 parts burley tobacco and about 10 parts Oriental tobacco, or about 65 parts fully cured tobacco, about 25 parts burley tobacco and about 10 parts Oriental tobacco, or about 65 parts fully cured tobacco, about 10 parts burley tobacco and about 25 parts Oriental tobacco, on a dry weight basis. Another exemplary tobacco blend incorporates from about 20 to about 30 parts Oriental tobacco and from about 70 to about 80 parts fully cured tobacco.

[0141] The tobacco material used in the present disclosure can be subjected to, for example, fermentation, bleaching, etc. If desired, the tobacco material can be subjected to, for example, irradiation, pasteurization, or otherwise controlled heat treatment. Such treatment processes are detailed, for example, in U.S. Patent No. 8,061,362 to Mua et al., which is incorporated herein by reference. In certain embodiments, the tobacco material can be treated with water and an additive that can inhibit the reaction of asparagine to form acrylamide upon heating of the tobacco material (e.g., an additive selected from the group consisting of lysine, glycine, histidine, alanine, methionine, cysteine, glutamic acid, aspartic acid, proline, phenylalanine, valine, arginine, compositions incorporating divalent and trivalent cations, asparaginase, certain non-reducing sugars, certain reducing agents, phenolic compounds, certain compounds having at least one free thiol group or functional group, oxidizing agents, oxidation catalysts, natural plant extracts (e.g., rosemary extracts), and combinations thereof). See, for example, the types of treatment processes described in U.S. Patent Nos. 8,434,496, 8,944,072, and 8,991,403 to Chen et al., all of which are incorporated herein by reference. In certain embodiments, this type of treatment is useful when the original tobacco material is exposed to heat in the aforementioned processes.

[0142] In some embodiments, the type of tobacco material is selected to be initially visually lighter in color (e.g., whitened or bleached) than other tobacco materials to some extent. The tobacco pulp can be whitened in certain embodiments according to any means known in the art, for example, bleached tobacco materials produced by various whitening methods using various bleaching or oxidizing agents and oxidation catalysts. Examples of oxidizing agents include peroxides (e.g., hydrogen peroxide), chlorites, chlorates, perchlorates, hypochlorites, ozone, ammonia, and combinations thereof. Examples of oxidation catalysts are titanium dioxide, manganese dioxide, and combinations thereof. Methods of treating tobacco with bleaching agents are described, for example, in U.S. Pat. No. 787,611 to Daniels, Jr., U.S. Pat. No. 1,086,306 to Oelenheinz, U.S. Pat. No. 1,437,095 to Delling, U.S. Pat. No. 1,757,477 to Rosenhoch, U.S. Pat. No. 2,122,421 to Hawkinson, U.S. Pat. No. 2,148,147 to Baier, U.S. Pat. No. 2,170,107 to Baier, U.S. Pat. No. 2,274,649 to Baier, U.S. Pat. No. 2,770,239 to Pratz et al., and U.S. Pat. No. 3,612,065 to Rosen. Nos. 3,851,653 to Rosen, 3,889,689 to Rosen, 3,943,945 to Rosen, 4,143,666 to Rainer, 4,194,514 to Campbell, 4,366,823, 4,366,824 and 4,388,933 to Rainer et al., 4,641,667 to Schmekel et al., 5,713,376 to Berger and PCT Publication WO 96 / 31255 to Giolvas, all of which are incorporated herein by reference. Other whitening methods using reagents such as ozone and potassium permanganate can also be used. See, for example, U.S. Patent No. 3,943,940 to Minami, which is incorporated herein by reference.

[0143] In some embodiments, the whitened tobacco material can have an ISO brightness of at least about 50%, at least about 60%, at least about 65%, at least about 70%, at least about 75%, or at least about 80%. In some embodiments, the whitened tobacco material can have an ISO brightness ranging from about 50% to about 90%, from about 55% to about 75%, or from about 60% to about 70%. ISO brightness can be measured according to ISO 3688:1999 or ISO 2470-1:2016.

[0144] In some embodiments, whitened tobacco materials can be characterized as being lighter in color (e.g., "whitened") compared to untreated tobacco materials. White is frequently defined with reference to the Commission Internationale de l'Eclairage (CIE) chromaticity diagram. Whitened tobacco materials can, in certain embodiments, be characterized as being closer to pure white on the chromaticity diagram than untreated tobacco materials.

[0145] In various embodiments, the tobacco material can be treated to extract soluble components of the tobacco material therefrom. As used herein, "tobacco extract" refers to an isolated component of the tobacco material that is extracted from solid tobacco pulp by a solvent that is contacted with the tobacco material in an extraction process. Various extraction techniques for tobacco material can be used to provide tobacco extracts and tobacco solid materials. See, for example, the extraction process described in U.S. Patent Application Publication No. 2011 / 0247640 to Beeson et al., which is incorporated herein by reference. Other exemplary techniques for extracting tobacco components are described in Fiore, Fiore, Osborne, Jr. et al., Osborne, Jr. et al., Reid, Wildman et al., Brummer et al., Brummer et al., Poulose et al., Niven, Jr. ...Nos. 4,727,889 to Bernasek et al., 4,887,618 to Clapp et al., 4,941,484 to Clapp et al., 4,967,771 to Fagg et al., 4,986,286 to Roberts et al., 5,005,593 to Fagg et al., 5,018,540 to Grubbs et al., and 5,060,660 to White et al. No. 9, 5,065,775 to Fagg, 5,074,319 to White et al., 5,099,862 to White et al., 5,121,757 to White et al., 5,131,414 to Fagg, 5,131,415 to Munoz et al., 5,148,819 to Fagg, 5,197,4 No. 94, No. 5,230,354 to Smith et al., No. 5,234,008 to Fagg, No. 5,243,999 to Smith, No. 5,301,694 to Raymond et al., No. 5,318,050 to Gonzalez-Parra et al., No. 5,343,879 to Teague, No. 5,360,022 to Newton, No. 5,370,022 to Cla Nos. 5,435,325 to pp et al., 5,445,169 to Brinkley et al., 6,131,584 to Lauterbach, 6,298,859 to Kierulff et al., 6,772,767 to Mua et al., and 7,337,782 to Thompson, all of which are incorporated herein by reference.

[0146] Typical inclusion ranges of tobacco materials may vary depending on the nature and type of tobacco material and the intended effect on the final composition, with exemplary ranges being up to about 30% by weight (e.g., from about 0.1 to about 15% by weight) based on the total weight of the mixture. In some embodiments, products of the present disclosure can be characterized as being completely free or substantially free of tobacco materials (other than purified nicotine as an active ingredient). For example, certain embodiments can be characterized as having less than 1% by weight, or less than 0.5% by weight, or less than 0.1% by weight, or 0% by weight of tobacco materials. In some embodiments, the mixture includes tobacco. In some embodiments, the mixture includes up to about 5% tobacco, e.g., from about 0.1 to about 1%, or from about 1% to about 5% by weight, based on the total weight of the mixture. In some embodiments, the mixture includes traditional tobacco or white tobacco. In some embodiments, the tobacco is white tobacco.

[0147] Other Additives Other additives can be included in the disclosed mixtures. For example, the mixtures can be processed, blended, compounded, combined and / or mixed with other materials or ingredients. The additives can be artificial or can be obtained or derived from herbal or biological sources. Examples of types of additives include gelling agents (e.g., fish gelatin), emulsifiers, oral care additives (e.g., thyme oil, eucalyptus oil, and zinc), preservatives (e.g., potassium sorbate, etc.), antioxidants, disintegration aids, or combinations thereof. For example, representative ingredients, ingredient combinations, relative amounts of the ingredients, and techniques and methods for using the ingredients, see U.S. Pat. No. 9,237,769 to Mua et al., U.S. Pat. No. 7,861,728 to Holton, Jr. et al., U.S. Pat. App. Pub. No. 2010 / 0291245 to Gao et al., and U.S. Pat. App. Pub. No. 2007 / 0062549 to Holton, Jr. et al. Each of which is incorporated herein by reference. These and other exemplary types of additives may include, for example, those previously incorporated herein by reference. Typical content ranges of such additional additives may vary depending on the nature and function of the additive and its intended effect on the final composition, with exemplary ranges of up to about 10% by weight (e.g., from about 0.1 to about 5% by weight) based on the total weight of the mixture.

[0148] The aforementioned additives can be used together (e.g., as an additive blend) or separately (e.g., individual additive components can be added at different stages involved in the preparation of the final mixture). Additionally, additives of the aforementioned types may be encapsulated so as to be provided in the final product or mixture. Exemplary encapsulated additives are described, for example, in WO 2010 / 132444 A2 to Atchley, previously incorporated herein by reference.

[0149] In some embodiments, any one or more of the filler components, tobacco materials, and overall oral products described herein can be described as particulate materials. As used herein, the term "particulate" refers to material in the form of a plurality of individual particles, some of which may be in the form of agglomerates of a plurality of particles, the particles having an average length to width ratio of less than 2:1, such as less than 1.5:1, for example about 1:1. In various embodiments, the particles of particulate materials can be described as substantially spherical or granular.

[0150] The particle size of particulate matter can be measured by sieve analysis. As those skilled in the art will readily appreciate, sieve analysis (otherwise known as gradient testing) is a method used to measure the particle size distribution of particulate materials. Typically, sieve analysis involves a nested column of sieves, preferably including screens in the form of wire mesh fabric. A pre-weighed sample can be introduced into the top or uppermost sieve in the column, which has the largest sieve opening or mesh size (i.e., the largest pore size of the sieve). Each lower sieve in the column has a progressively smaller screen opening or mesh size than the upper sieve. Typically, at the base of the column of sieves, there is a receiver section for collecting any particles having a particle size smaller than the sieve opening size or mesh size of the bottom or lowest sieve in the column (which has the smallest screen opening or mesh size).

[0151] In some embodiments, the column of sieves can be placed on or in a mechanical agitator. The agitator causes vibration of each sieve in the column. The mechanical agitator may be activated for a predetermined period of time to ensure that all particles are collected on the correct sieve. In some embodiments, the column of sieves is agitated for a period of 0.5 minutes to 10 minutes, for example 1 minute to 10 minutes, for example 1 minute to 5 minutes, for example about 3 minutes. Once the agitation of the sieves in the column is complete, the material collected on each sieve is weighed. The weight of each sample on each sieve can then be divided by the total weight to obtain the percentage of mass retained on each sieve. As will be readily understood by one of skill in the art, the sieve opening size or mesh size of each sieve in the column used for sieve analysis can be selected based on the particle size of the sample to be analyzed or the known maximum / minimum particle size. In some embodiments, a column of sieves can be used for sieve analysis, the column comprising 2 to 20 sieves, for example 5 to 15 sieves. In some embodiments, a column of sieves may be used in the sieve analysis, the column comprising 10 sieves. In some embodiments, the maximum sieve opening or mesh size of the sieve used in the sieve analysis may be 1000 μm, such as 500 μm, such as 400 μm, such as 300 μm.

[0152] In some embodiments, any particulate material referred to herein (e.g., filler components, tobacco materials, and overall oral products) can be characterized as having at least 50% by weight of particles having a particle size as measured by sieve analysis of about 1000 μm or less, such as about 500 μm or less, such as about 400 μm or less, such as about 350 μm or less, such as about 300 μm or less. In some embodiments, at least 60% by weight of the particles of any particulate material referred to herein have a particle size as measured by sieve analysis of about 1000 μm or less, such as about 500 μm or less, such as about 400 μm or less, such as about 350 μm or less, such as about 300 μm or less. In some embodiments, at least 70% by weight of the particles of any particulate material referred to herein have a particle size as measured by sieve analysis of about 1000 μm or less, such as about 500 μm or less, such as about 400 μm or less, such as about 350 μm or less, such as about 300 μm or less. In some embodiments, at least 80% by weight of the particles of any particulate material referred to herein have a particle size of about 1000 μm or less, such as about 500 μm or less, such as about 400 μm or less, such as about 350 μm or less, such as about 300 μm or less, as measured by sieve analysis. In some embodiments, at least 90% by weight of the particles of any particulate material referred to herein have a particle size of about 1000 μm or less, such as about 500 μm or less, such as about 400 μm or less, such as about 350 μm or less, such as about 300 μm or less, as measured by sieve analysis. In some embodiments, at least 95% by weight of the particles of any particulate material referred to herein have a particle size of about 1000 μm or less, such as about 500 μm or less, such as about 400 μm or less, such as about 350 μm or less, such as about 300 μm or less, as measured by sieve analysis. In some embodiments, at least 99% by weight of the particles of any particulate material referred to herein have a particle size of about 1000 μm or less, such as about 500 μm or less, for example about 400 μm or less, such as about 350 μm or less, for example about 300 μm or less, as measured by sieve analysis.In some embodiments, about 100% by weight of the particles of any particulate material referred to herein have a particle size of about 1000 μm or less, such as about 500 μm or less, for example about 400 μm or less, such as about 350 μm or less, for example about 300 μm or less, as measured by sieve analysis.

[0153] In some embodiments, at least 50% by weight, such as at least 60% by weight, for example at least 70% by weight, such as at least 80% by weight, for example at least 90% by weight, such as at least 95% by weight, for example at least 99% by weight, of the particles of any particulate material referred to herein have a particle size of from about 0.01 μm to about 1000 μm, such as from about 0.05 μm to about 750 μm, for example from about 0.1 μm to about 500 μm, such as from about 0.25 μm to about 500 μm, as measured by sieve analysis. In some embodiments, at least 50% by weight, such as at least 60% by weight, for example at least 70% by weight, such as at least 80% by weight, for example at least 90% by weight, such as at least 95% by weight, for example at least 99% by weight, of the particles of any particulate material referred to herein have a particle size of from about 10 μm to about 400 μm, such as from about 50 μm to about 350 μm, for example from about 100 μm to about 350 μm, such as from about 200 μm to about 300 μm, as measured by sieve analysis.

[0154] Preparation of mixtures The method of combining the various components of the mixture may vary. Thus, the overall mixture of the various components with, for example, powdered mixture components may be relatively homogenous in nature. The above components, which may be in liquid or dry solid form, may be mixed in a pre-treatment step before mixing with any remaining components of the mixture, or may simply be mixed with all other liquid or dry components. The various components of the mixture may be contacted, combined, or mixed together using any mixing technique or device known in the art. Any mixing method that brings the components of the mixture into intimate contact may be used, such as a mixing device characterized by an impeller or other structure capable of stirring. Examples of mixing devices include casing drums, conditioning cylinders or drums, liquid spraying devices, cone-type blenders, ribbon blenders, mixers available from Littleford Day, Inc. as FKM130, FKM600, FKM1200, FKM2000, and FKM3000, Plough Share type mixer cylinders, Hobart mixers, and the like. See, for example, the types of methods described in U.S. Patent No. 4,148,325 to Solomon et al., U.S. Patent No. 6,510,855 to Korte et al., and U.S. Patent No. 6,834,654 to Williams et al., each of which is incorporated herein by reference. In some embodiments, the ingredients forming the mixture are prepared so that the mixture can be used in a starch molding process to form the mixture. Techniques and methods for blending the mixture will be apparent to those skilled in the art. See, for example, the types of methods described in U.S. Patent No. 4,148,325 to Solomon et al., U.S. Patent No. 6,510,855 to Korte et al., and U.S. Patent No. 6,834,654 to Williams, U.S. Patent No. 4,725,440 to Ridgway et al., and U.S. Patent No. 6,077,524 to Bolder et al., each of which is incorporated herein by reference.

[0155] In certain embodiments, the products of the present disclosure are prepared by i) mixing one or more flavoring agents with a cellulose derivative to form a first mixture, and ii) mixing the first mixture with a particulate filler component and water to form a second mixture. Without wishing to be bound by any particular theory, it is believed that certain volatile components in the flavoring agents (e.g., esters, terpenes, etc.) can interact or in some way complex with the cellulose derivative, which helps to stabilize the resulting second mixture with respect to the retention of the referenced volatile components.

[0156] Oral Formulation Provided herein are products configured for oral use. As used herein, the term "configured for oral use" means that the product is provided in such a form that during use, saliva in the user's mouth passes one or more of the components of the mixture (e.g., flavoring agent and / or nicotine) into the user's mouth. In certain embodiments, the product is adapted to deliver an ingredient to the user through the mucous membrane of the user's mouth, and in some cases, the ingredient is an active ingredient (e.g., including but not limited to nicotine) that can be absorbed through the mucous membrane of the mouth when the product is used. In some embodiments, the ingredient is a taste substance (i.e., a volatile flavor ingredient).

[0157] The products configured for oral use described herein can take a variety of forms, including gels, troches, gums, lozenges, powders, and pouches. Gels can be soft or hard. Particular products configured for oral use are in the form of troches. As used herein, the term "lozenges" refers to a dissolvable oral product made by solidifying a liquid or gel composition such that the final product is a somewhat hardened solid gel. The stiffness of gels is highly variable. Particular products of the present disclosure are in solid form. Particular products can exhibit, for example, one or more of the following characteristics: crispy, granular, chewy, syrupy, pasty, fluffy, smooth, and / or creamy. In certain embodiments, the desired texture properties can be selected from the group consisting of adhesiveness, cohesiveness, density, dryness, friability, granularity, rubberiness, hardness, weight, hygroscopicity, moisture release, mouth coating, roughness, slipperiness, smoothness, viscosity, wetness, and combinations thereof.

[0158] A product comprising the mixture of the present disclosure may be dissolvable. As used herein, the terms "dissolve", "dissolving" and "dissolvable" refer to a composition having water-soluble components that interact with moisture in the oral cavity to go into solution, thereby causing gradual consumption of the product. According to one aspect, a dissolvable product can last in the user's mouth for a given period of time until it completely dissolves. The dissolution rate may vary over a wide range, from about 1 minute or less to about 60 minutes. For example, a fast-release composition typically dissolves and / or releases the active agent in about 2 minutes or less, often about 1 minute or less (e.g., about 50 seconds or less, about 40 seconds or less, about 30 seconds or less, or about 20 seconds or less). Dissolution may occur by any means, such as melting, mechanical disruption (e.g., chewing), enzymatic or other chemical degradation, or by disruption of interactions between the components of the mixture. In some embodiments, the product may be dissolvable, for example, as discussed in U.S. Patent Application Publication No. 20120037175 to Cantrell et al. In other embodiments, the product does not dissolve while the product is in the user's mouth.

[0159] In one embodiment, the product containing the mixture of the present disclosure is in the form of a mixture placed in a moisture-permeable container (e.g., a water-permeable pouch). Such mixtures in the form of water-permeable pouches are typically used by placing one pouch containing the mixture in the mouth of a human subject / user. Generally, the pouch is placed somewhere in the user's oral cavity, for example under the lips, similar to how moist snuff is commonly used. The pouch is preferably not chewed or swallowed. Then, upon exposure to saliva, some of the ingredients of the mixture therein (e.g., flavorings and / or nicotine) pass through, for example, the water-permeable pouch, providing flavor and satisfaction to the user without the user having to expel any part of the mixture. After about 10 to about 60 minutes, typically about 15 to about 45 minutes, of use / enjoyment, a substantial amount of the mixture is ingested by the human subject and the pouch can be removed from the human subject's mouth for disposal.

[0160] Thus, in certain embodiments, the mixture disclosed herein and any other components described above are combined in a moisture-permeable packet or pouch that serves as a container for the use of the mixture to provide a pouch product configured for oral use. Certain embodiments of the present disclosure are described with reference to FIG. 1 of the accompanying drawings, and these described embodiments include a snus-type product having an outer pouch and containing the mixture described herein. As will be described in more detail below, such embodiments are provided by way of example only, and the pouch product of the present disclosure can include other forms of the mixture. The composition / structure of such a packet or pouch, such as the container pouch 102 in the embodiment shown in FIG. 1, can vary. Referring to FIG. 1, a first embodiment of a pouch product 100 is shown. The pouch product 100 includes a moisture-permeable container in the form of a pouch 102 that includes a material 104 that includes the mixture described herein.

[0161] Suitable packets, pouches or containers of the type used in the manufacture of smokeless tobacco products are available under the trade names CatchDry, Ettan, General, Granit, Goteborgs Rape, Grovsnus White, Metropol Kaktus, Mocca Anis, Mocca Mint, Mocca Wintergreen, Kicks, Probe, Prince, Skruf and TreAnkrare. The mixture may be contained and packaged in the pouch in the manner of and using the types of components used in the manufacture of traditional snus-type products. The pouch comprises a liquid-permeable container of a type that may be considered similar in characteristics to the mesh-type materials used in the construction of tea bags. The ingredients of the mixture easily diffuse through the pouch into the mouth of the user.

[0162] Non-limiting examples of suitable types of pouches are described, for example, in U.S. Patent No. 5,167,244 to Kjerstad, which is incorporated herein by reference. The pouches can be provided as individual pouches, or multiple pouches (e.g., 2, 4, 5, 10, 12, 15, 20, 25 or 30 pouches) can be connected or linked together (e.g., in an end-to-end manner) such that single pouches or individual portions can be easily removed from a one-piece strand or matrix of pouches for use.

[0163] Exemplary pouches can be manufactured from materials in such a way that the pouch undergoes controlled dispensing or dissolution during use by the user. Such pouch materials can have the form of mesh, screen, perforated paper, permeable fabric, and the like. For example, a pouch material manufactured from rice paper in a mesh-like form or perforated rice paper can dissolve in the user's mouth. As a result, the pouch and the mixture can each completely disperse in the user's mouth during normal use conditions, and thus both the pouch and the mixture can be ingested by the user. Other examples of pouch materials can be manufactured using materials in combination with materials such as water-dispersible film-forming materials (e.g., binders such as alginates, carboxymethylcellulose, xanthan gum, pullulan, and the like), as well as comminuted cellulose (e.g., fine particle size wood pulp). Preferred pouch materials are water-dispersible or soluble, but may be designed and manufactured such that under normal use conditions, a significant amount of the mixture contents will permeate the pouch material before the pouch loses its physical integrity. If desired, flavor ingredients, disintegration aids, and other desired ingredients may be incorporated into or applied to the pouch material.

[0164] The amount of material contained within each product unit, e.g., pouch, may vary. In some embodiments, the dry weight of the mixture within each pouch is at least about 50 mg, e.g., about 50 mg to about 1 g, about 100 to about 800 mg, or about 200 to about 700 mg. In some smaller embodiments, the dry weight of the mixture within each pouch may be about 100 to about 300 mg. In larger embodiments, the dry weight of the material within each pouch may be about 300 mg to about 700 mg. Other ingredients may be contained within each pouch as desired. For example, at least one strip, piece, or sheet of flavored water-dispersible or water-soluble material (e.g., a fresh edible film-type material) may be placed within each pouch, with or without at least one capsule. Such strips or sheets may be folded or wrinkled to facilitate incorporation within the pouch. See, for example, the types of materials and techniques described in U.S. Patent No. 6,887,307 to Scott et al., and U.S. Patent No. 6,923,981 to Leung et al., and The EFSA Journal (2004) 85, 1-32, which are incorporated herein by reference.

[0165] The pouch products described herein can be packaged within any suitable inner packaging material and / or outer container, see, for example, U.S. Patent No. 7,014,039 to Henson et al., U.S. Patent No. 7,537,110 to Kutsch et al., U.S. Patent No. 7,584,843 to Kutsch et al., U.S. Patent No. 8,397,945 to Gelardi et al., U.S. Patent Application Publication No. D592,956 to Thiellier, U.S. Patent Application Publication No. D594,154 to Patel et al., and U.S. Patent Application Publication No. D625,178 to Bailey et al., U.S. Patent Application Publication No. 2008 / 0173317 to Robinson et al., U.S. Patent Application Publication No. 2009 / 0014343 to Clark et al., U.S. Patent Application Publication No. 2009 / 0014450 to Bjorkholm ... See also various types of containers for smokeless type products described in 2009 / 0250360 to Bellamah et al., 2009 / 0266837 to Gelardi et al., 2009 / 0223989 to Gelardi, 2009 / 0230003 to Thiellier, 2010 / 0084424 to Gelardi, and 2010 / 0133140 to Bailey et al., 2010 / 0264157 to Bailey et al., and 2011 / 0168712 to Bailey et al., which are incorporated herein by reference.

[0166] Storage period The disclosed products configured for oral use may be packaged and stored in any suitable packaging in much the same way that conventional types of smokeless tobacco products are packaged and stored. For example, multiple packets or pouches may be contained in a cylindrical container. The shelf life of the product after preparation may vary. As used herein, "shelf life" refers to the period after preparation of the disclosed product. In some embodiments, one or more of the product characteristics (e.g., retention of volatile flavor components) disclosed herein are exhibited over some or all of the shelf life. In some embodiments, the shelf life (i.e., the period after preparation) is at least 1 day. In some embodiments, the shelf life is about 1 day, about 2 days, or about 3 days to about 1 week, or about 1 week to about 2 weeks, about 2 weeks to about 1 month, or about 1 month to about 2 months, about 2 months to about 3 months, about 3 months to about 4 months, or about 4 months to about 5 months. In some embodiments, the shelf life is any number of days from about 1 to about 150 days. In certain embodiments, the storage period may be greater than 5 months, such as about 6 months, about 7 months, about 8 months, about 9 months, about 10 months, about 11 months, or about 12 months.

[0167] In some embodiments, the products disclosed herein have one or more concentrations of at least one volatile flavor component present that are greater than the concentration of the same one or more volatile flavor components present in a control product that does not contain a cellulose derivative, as determined by semi-quantitative gas chromatography-mass spectrometry, when measured at time points over the disclosed storage period.

[0168] Method for stabilizing a product adapted for oral use - Patents.com In another aspect, a method of stabilizing a product configured for oral use is provided, the stabilized product comprising a mixture disclosed herein, the method comprising: i) mixing one or more flavoring agents, including at least one volatile flavor component, with a cellulose derivative to form a first mixture, and ii) mixing the first mixture with a filler component and water to form a second mixture.

[0169] In some embodiments, the method further comprises adding one or more salts, one or more sweeteners, one or more binders, one or more humectants, one or more gums, one or more active ingredients, tobacco materials, or combinations thereof to the mixture of step ii). In some embodiments, the method further comprises adding one or more active ingredients selected from the group consisting of a nicotine component, a botanical drug, a stimulant, an amino acid, a vitamin, and a cannabinoid. In some embodiments, the method further comprises adding about 0.001 to about 10% by weight of a nicotine component. In some embodiments, the method further comprises adding about 0.1 to about 0.5% by weight of one or more organic acids.

[0170] In some embodiments, the method further comprises providing the mixture in a pouch.

[0171] In some embodiments, the products prepared according to the disclosed methods have a higher concentration of at least one volatile flavor component present when measured over a period of one day after preparation than the concentration of the same one or more volatile flavor components present in a control product that does not contain the first filler component, as determined by semi-quantitative gas chromatography mass spectrometry, in some embodiments, the period is one or more of two days, one week, two weeks, three weeks, or one month after preparation.

[0172] In some embodiments, the concentration is greater than the concentration of the same one or more volatile flavor components present in the product 2 days, 3 days, 1 week, 2 weeks, 1 month, 2 months, 3 months, 4 months, or 5 months after preparation, In some embodiments, the concentration is greater than the concentration of the same one or more volatile flavor components present in a control product 6 months, 7 months, 8 months, 9 months, 10 months, 11 months, or 12 months after preparation.

[0173] Many modifications and other embodiments of the invention will come to mind to one skilled in the art to which the invention pertains having the benefit of the teachings presented in the foregoing description. It is to be understood, therefore, that the invention is not to be limited to the specific embodiments disclosed herein, and that modifications and other embodiments are intended to be included within the scope of the appended claims. Although specific terms are employed herein, they are used in a generic and descriptive sense only and not for purposes of limitation.

[0174] experiment Aspects of the present invention are more fully described by the following examples, which are set forth to illustrate certain aspects of the invention and are not to be construed as limitations thereof.

[0175] General analysis method Methanol (MeOH) was purchased from Sigma-Aldrich (St. Louis, MO, USA). Flavor standards were obtained from RJ Reynolds Flavor Laboratory.

[0176] Semi-quantitative flavor The relative amounts of the various flavors were quantitatively evaluated using gas chromatography / mass spectrometry (GC-MS) with single ion monitoring (SIM) chromatograms against a calibration curve. The instrument used for quantification was an Agilent (Wilmington, Delaware, USA) 6890N / 5973 GC-MS. Analysis of the data was performed using MassHunter Quantitative Analysis 8.07.00. The detailed parameters are listed in Table 1.

[0177] Each sample was accurately weighed into a scintillation vial on an analytical balance for a target weight of 0.5 grams. Each sample was then diluted with 5 mL of isopropanol (5. 9μ d in g / mL 7-quinoline) and placed on an orbital shaker at 200 RPM for 3 hours. After shaking, each sample was filtered through a 0.45 μm PVDF filter and transferred to a GC sample vial for analysis. Each sample was prepared in duplicate and analyzed by GC-MS.

[0178] The amount of internal standard divided by the internal standard peak area is the conversion factor (compound peak area x μ gInternal standard / internal standard area μ Each compound was semi-quantified as a function of the concentration of each compound (g compound). Note that relative extraction efficiencies and relative response factors were not considered.

[0179] [Table 1] EXAMPLES

[0180] [Example 1] Tropical flavor embodiment (for comparison) Comparative control pouch products were prepared, each containing a base formulation of 43% microcrystalline cellulose (mcc) and 41% water, by weight of the mixture, and the additional ingredients described herein (salt, binder, sweetener, humectant, tropical flavor package, and 4 mg nicotine). To prepare the mixtures, a portion of the water was added to the mcc and the other ingredients were mixed and added to the mcc solution.

[0181] [Example 2] Tropical Flavor Embodiment (Invention) A pouch product according to one embodiment was prepared containing a base formulation as in Example 1, but replacing a portion of the mcc (3% HPC, 40% mcc and 41% water, each by weight of the mixture) with 3% by weight of hydroxypropyl cellulose (HPC). To prepare the mixture, a portion of the water was added to the mcc. Separately, a tropical flavor package was added to the HPC. The remaining ingredients were added to the mcc solution and mixed, and finally the flavor / HPC mixture was added.

[0182] [Example 3] Tropical Flavor Embodiment (Invention) A pouch product according to one embodiment was prepared containing a base formulation as in Example 1, but replacing a portion of the mcc (2% HPC, 41% mcc and 41% water, each by weight of the mixture) with 2% by weight of HPC. To prepare the mixture, a portion of the water was added to the mcc. Separately, a tropical flavor package was added to the HPC. The remaining ingredients were added to the mcc solution and mixed, and finally the flavor / HPC mixture was added.

[0183] [Example 4] Semi-quantitative tropical flavor components, 0 to 3% HPC Samples of the products prepared in Examples 1 and 2 were semi-quantitatively evaluated for various flavor components present in the tropical flavor package one day after preparation. The results are shown in Table 2. These results demonstrate the surprising finding that certain volatile flavor components are better retained in formulations containing HPC compared to those containing only mcc filler.

[0184] [Table 2]

[0185] [Example 5] Semi-quantitative tropical flavor component, 2% HPC Samples of the product prepared in Example 3 were semi-quantitatively evaluated for various flavor components present in the tropical flavor package at various times after preparation (1 day, 1 week, 2 weeks, 3 weeks, and 4 weeks, T1-T5, respectively). The results are shown in Table 3. Referring to Table 3, the mixture of Example 3 containing 2% HPC in the base retained readily detectable amounts of ethyl hexanoate, ethyl heptanoate, and allyl hexanoate over the test period.

[0186] [Table 3]

[0187] [Example 6] Semi-quantitative tropical flavor component, 3% HPC Samples of the product prepared in Example 2 were semi-quantitatively evaluated for various flavor components present in the tropical flavor package at various time points after preparation (1 day, 1 week, 2 weeks, 3 weeks, and 4 weeks, T1-T5, respectively). The results are shown in Table 4. Referring to Table 4, the mixture of Example 2 containing 3% HPC in the base had, on average, about 50% higher total flavor component concentration across all time points when compared to the mixture of Example 3 (Table 3) containing 2% HPC in the base.

[0188] [Table 4]

Claims

1. A product adapted for oral use, comprising a mixture comprising: a particulate filler component comprising microcrystalline cellulose; 1% to 5% by weight of a cellulose derivative, based on the total weight of the mixture; Water in an amount of at least 5% by weight, based on the total weight of the mixture; and One or more flavoring agents Contains, contains mixtures of, products.

2. 2. The product of claim 1, wherein the cellulose derivative is a cellulose ether.

3. 2. The product of claim 1, wherein the cellulose derivative is one or more of methyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose (HPC), hydroxypropyl methyl cellulose (HPMC) or carboxymethyl cellulose (CMC).

4. 2. The product of claim 1, wherein the cellulose derivative is hydroxypropyl cellulose (HPC).

5. 10. The product of claim 1, wherein the one or more flavoring agents comprise a compound having a carbon-carbon double bond, a carbon-oxygen double bond, a carbon-oxygen single bond, or a combination thereof.

6. 10. The product of claim 1, wherein the one or more flavoring agents comprise one or more aldehydes, ketones, esters, terpenes, terpenoids, or combinations thereof.

7. 10. The product of claim 1, wherein the one or more flavoring agents comprise one or more esters.

8. The one or more esters may be C １ ~C ８ Alkanols and C ２ ~C ８ 8. The product of claim 7 which is an alkyl ester comprising an alkane carboxylic acid.

9. 8. The product of claim 7, wherein the one or more esters include isoamyl acetate, ethyl hexanoate, ethyl heptanoate, allyl hexanoate, or combinations thereof.

10. 1-3% by weight of hydroxypropyl cellulose (HPC); 10 to 60% by weight of microcrystalline cellulose, and 1 to 60% by weight of water, based on the total weight of the mixture The article of manufacture of claim 1 comprising:

11. 10. The product of claim 1, wherein the mixture further comprises one or more salts, one or more organic acids, one or more sweeteners, one or more binders, one or more humectants, one or more gums, one or more active ingredients, tobacco materials, or combinations thereof.

12. 10. The product of claim 1, wherein the mixture further comprises one or more active ingredients selected from the group consisting of nicotine components, botanical derived drugs, stimulants, amino acids, vitamins and cannabinoids.

13. 10. The product of claim 1, wherein the mixture further comprises 0.001 to 10% by weight of a nicotine component, calculated as the free base, based on the total weight of the mixture.

14. 10. The product of claim 1, wherein the mixture further comprises 0.1 to 0.5 wt. % of one or more organic acids, based on the total weight of the mixture.

15. 15. The product of claim 14, wherein the one or more organic acids are alkyl carboxylic acids, aryl carboxylic acids, or combinations thereof.

16. 15. The product of claim 14, wherein the one or more organic acids are citric acid, malic acid, tartaric acid, octanoic acid, benzoic acid, toluene acid, salicylic acid, or combinations thereof.

17. 15. The product of claim 14, wherein the one or more organic acids is citric acid.

18. 10. The product of claim 1, wherein the mixture further comprises tobacco material.

19. 20. The product of claim 18, wherein the mixture comprises no more than 10% by weight of tobacco material, based on the total weight of the mixture, excluding any nicotine components present therein.

20. 20. The product of claim 18, wherein the tobacco material is bleached tobacco.

21. 10. The product of claim 1, wherein the mixture comprises no more than 7.5% alkali metal salt, based on the total weight of the mixture.

22. The product of claim 1 , wherein the mixture is enclosed in a pouch to form a pouch product.

23. 23. The product of claim 22, wherein the mixture is in the form of free-flowing particulates.

24. 1. A method for stabilizing a product adapted for oral use, comprising: i) mixing one or more flavoring agents with a cellulose derivative to form a first mixture, the cellulose derivative being added such that the product comprises 1% to 5% by weight of the cellulose derivative based on the total weight of the product; and ii) mixing the first mixture with a particulate filler component comprising microcrystalline cellulose and water to form the product; The method includes:

25. 25. The method of claim 24, wherein the cellulose derivative is a cellulose ether.

26. 25. The method of claim 24, wherein the cellulose derivative is one or more of methylcellulose, hydroxyethylcellulose, hydroxypropylcellulose (HPC), hydroxypropylmethylcellulose (HPMC) or carboxymethylcellulose (CMC).

27. 25. The method of claim 24, wherein the cellulose derivative is HPC.

28. 25. The method of claim 24, wherein the one or more flavoring agents comprise one or more aldehydes, ketones, esters, terpenes, terpenoids, or combinations thereof.

29. 25. The method of claim 24, wherein the one or more flavoring agents comprise one or more esters.

30. The one or more esters may be C １ ~C ８ Alkanols and C ２ ~C ８ 30. The method of claim 29, wherein the alkyl ester comprises an alkyl carboxylic acid.

31. 30. The method of claim 29, wherein the one or more esters comprise isoamyl acetate, ethyl hexanoate, ethyl heptanoate, allyl hexanoate, or combinations thereof.

32. 25. The method of claim 24, wherein combining the first mixture with the particulate filler component further comprises adding one or more salts, one or more sweeteners, one or more binders, one or more humectants, one or more gums, one or more active ingredients, tobacco materials, or combinations thereof.

33. 25. The method of claim 24, wherein mixing the first mixture with the particulate filler component further comprises adding one or more active ingredients selected from the group consisting of a nicotine component, a botanical derived drug, a stimulant, an amino acid, a vitamin, and a cannabinoid.

34. 25. The method of claim 24, further comprising adding 0.001 to 10% by weight of a nicotine component, calculated as the free base and based on the total weight of the product.

35. 25. The method of claim 24, further comprising adding 0.1 to 0.5 wt. % of one or more organic acids, based on the total weight of the product.

36. 36. The method of claim 35, wherein the one or more organic acids are alkyl carboxylic acids, aryl carboxylic acids, or combinations thereof.

37. 36. The method of claim 35, wherein the one or more organic acids are citric acid, malic acid, tartaric acid, octanoic acid, benzoic acid, toluene acid, salicylic acid, or combinations thereof.

38. 36. The method of claim 35, wherein the one or more organic acids is citric acid.

39. 25. The method of claim 24, further comprising enclosing the product in a pouch to form a pouch product.

40. 40. The method of claim 39, wherein the product is in the form of free-flowing particulates.

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