EP3917339B1 - An oral nicotine product comprising a ph adjusting agent - Google Patents

An oral nicotine product comprising a ph adjusting agent Download PDF

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Publication number
EP3917339B1
EP3917339B1 EP20703956.1A EP20703956A EP3917339B1 EP 3917339 B1 EP3917339 B1 EP 3917339B1 EP 20703956 A EP20703956 A EP 20703956A EP 3917339 B1 EP3917339 B1 EP 3917339B1
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EP
European Patent Office
Prior art keywords
nicotine
filling material
oral pouched
equal
salt
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Active
Application number
EP20703956.1A
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German (de)
English (en)
French (fr)
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EP3917339C0 (en
EP3917339A1 (en
Inventor
Mårten KINDVALL
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Swedish Match North Europe AB
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Swedish Match North Europe AB
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Publication date
Priority claimed from NO20190141A external-priority patent/NO345073B1/no
Priority claimed from SE1950119A external-priority patent/SE544446C2/en
Application filed by Swedish Match North Europe AB filed Critical Swedish Match North Europe AB
Publication of EP3917339A1 publication Critical patent/EP3917339A1/en
Application granted granted Critical
Publication of EP3917339C0 publication Critical patent/EP3917339C0/en
Publication of EP3917339B1 publication Critical patent/EP3917339B1/en
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    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/10—Chemical features of tobacco products or tobacco substitutes
    • A24B15/16—Chemical features of tobacco products or tobacco substitutes of tobacco substitutes
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B13/00—Tobacco for pipes, for cigars, e.g. cigar inserts, or for cigarettes; Chewing tobacco; Snuff
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
    • A24B15/241—Extraction of specific substances
    • A24B15/243—Nicotine
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/287—Treatment of tobacco products or tobacco substitutes by chemical substances by inorganic substances only
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
    • A24B15/302—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances by natural substances obtained from animals or plants
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
    • A24B15/36—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring
    • A24B15/40—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/42—Treatment of tobacco products or tobacco substitutes by chemical substances by organic and inorganic substances
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24F—SMOKERS' REQUISITES; MATCH BOXES; SIMULATED SMOKING DEVICES
    • A24F23/00—Cases for tobacco, snuff, or chewing tobacco
    • A24F23/02—Tobacco pouches

Definitions

  • the present disclosure relates to an oral pouched nicotine product comprising no tobacco or a small amount of tobacco and use of a pH adjuster for counteracting an increase in pH when said product is stored.
  • oral smokeless tobacco products are used in the oral cavity of a consumer to provide nicotine satisfaction from the tobacco in the product.
  • the oral smokeless tobacco product generally comprises water, salt, pH adjuster(s) and additional ingredients such as flavours and humectants.
  • these products are called snuff.
  • the snuff may be dry or moist, and may be provided in loose form or in pouched form.
  • Moist snuff is divided into two types, namely American snuff and Scandinavian snuff.
  • American moist snuff is commonly produced through a fermentation process of moisturized ground or cut tobacco.
  • Scandinavian-type moist snuff (snus) is commonly produced using a heat-treatment process (pasteurization) instead of fermentation. The heat treatment is carried out in order to degrade, destroy or denature at least a portion of the organisms within the tobacco preparation.
  • Oral pouched nicotine products comprising no tobacco or a small amount of tobacco are now becoming increasingly popular among consumers due to inter alia their appealing appearance, freshness and taste. Moreover, this kind of product allows a user to enjoy nicotine without being exposed to tobacco.
  • US2018/271139 discloses an oral pouched smokeless tobacco product which generally includes a tobacco composition comprising divided (e.g. ground or cut) tobacco material, water, salt (e.g. sodium chloride, potassium chloride, magnesium chloride, calcium chloride or any combinations thereof), pH adjuster (e.g. sodium carbonate, sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate, sodium bicarbonate or magnesium carbonate) and optionally one or more additional ingredients.
  • the salt is added mainly for its effect on taste but it also has a preservative action which contributes to improved shelf life of the product. Salt, such as sodium chloride lowers the water activity of the products, thus preventing micro-organisms from growing.
  • WO 2012/134380 discloses a pouch containing nicotine in free salt form, i.e. an oral pouched nicotine-containing non-tobacco snuff product.
  • the product comprises a powder of at least one free nicotine salt, at least one pH adjusting agent and at least one filler, and a water insoluble pouch, wherein said pouch is permeable for saliva and therein dissolved parts of the powder, wherein said product upon contact with purified water gives a pH of at least 6.
  • EP 3 087 852 discloses an oral pouched product having a rectangular shape.
  • the oral pouched product may be an oral pouched non-tobacco nicotine-containing snuff product.
  • the filling material of the product may be a particulate material comprising nicotine or a salt thereof and one or more fillers, such as polysaccharides and/or microcrystalline cellulose.
  • salt such as sodium chloride, potassium chloride, magnesium chloride, calcium chloride and any combinations thereof, may be added mainly for its effect on taste but it also has a preservative action which contributes to improved shelf life of the product. Salt, such as sodium chloride, lowers the water activity of the products, thus preventing microorganisms from growing.
  • pH is known to contribute to regulating the uptake of nicotine through the mucous membranes in the oral cavity of a consumer, such as a human.
  • a pH adjusting agent is needed to increase the amount of nicotine present in the form of a free base, which may be absorbed through the mucous membranes in the oral cavity of a consumer.
  • an alkaline pH reduces nicotine extraction from the product.
  • a very high pH has a negative effect on the taste of the product and is also detrimental for the oral mucous membranes.
  • an acidic pH improves nicotine mobility and extraction from the product, but diminishes nicotine uptake in the oral cavity and is bad for oral health. Consequently, it is frequently desired to adjust the pH of oral pouched nicotine products to be neutral or slightly alkaline such as from pH 7 to 10. Commonly, this is achieved using pH adjusters comprising sodium carbonate and/or sodium bicarbonate.
  • WO 2009/082331 discloses a tobacco or non-tobacco product comprising magnesium carbonate for conferring pH stability to the product and preventing growth of bacteria and fungi therein.
  • WO 2015/193379 discloses a tobacco or non-tobacco product comprising magnesium carbonate.
  • the composition is enclosed by a wrapping material, which comprises magnesium carbonate.
  • a wrapping material which comprises magnesium carbonate.
  • the oral pH is stabilized during use of said product.
  • Figure 1 shows that the oral pH during use of oral smokeless tobacco products drops during use.
  • WO 2018/233795 discloses a nicotine pouch containing a matrix composition comprising a combination of nicotine and a water-soluble composition.
  • An object of the present disclosure is to alleviate at least one of the problems discussed above, and to provide advantages and aspects not provided by hitherto known technique. Further, it is an object of the present disclosure to prevent, reduce and/or counteract a change in pH such as an increase in pH in an oral pouched nicotine product comprising no tobacco or a small amount of tobacco.
  • the present disclosure provides an oral pouched nicotine product comprising a filling material and a saliva-permeable pouch of a packaging material enclosing the filling material, the filling material comprising or consisting of:
  • the present disclosure also provides a use of a salt of Formula I, or a hydrate of said salt, as described herein for controlling pH in an oral pouched nicotine product comprising a filling material, said filling material comprising:
  • tobacco material is used herein for tobacco extract and/or fibrous material of tobacco leaves or parts of tobacco leaves, such as lamina and stem.
  • the leaves and parts of leaves may be finely divided (disintegrated), such as ground, cut, shredded or threshed, and the parts of leaves may be blended in defined proportions in the tobacco material.
  • tobacco as used herein is meant any part, e.g., leaves, stems, and stalks, of any member of the genus Nicotiana.
  • the tobacco may be whole, shredded, threshed, cut, ground, cured, aged, fermented, or treated otherwise, e.g., granulated or encapsulated.
  • Oral and oral use is in all contexts used herein as a description for use in the oral cavity of a human, such as buccal placement.
  • moisture content refers to the total amount of oven volatile ingredients, such as water and other oven volatiles (e.g. propylene glycol) in the preparation, composition or product referred to.
  • the moisture content is given herein as percent by weight (wt%) of the total weight of the preparation, composition or product referred to.
  • Some fibrous materials may exhibit hygroscopic properties. Hygroscopic materials maintain equilibrium moisture content depending on the ambient moisture and temperature.
  • the moisture content as referred to herein may be determined by using a method based on literature references Federal Register/ vol.74, no.
  • the moisture content is determined gravimetrically by taking 2.5 ⁇ 0.25 g sample and weighing the sample at ambient conditions, herein defined as being at a temperature of 22 °C and a relative humidity (RH) of 60%, before evaporation of moisture and after completion of dehydration.
  • Mettler Toledo's Moisture Analyzer HB43 a balance with halogen heating technology, is used (instead of an oven and a balance as in the mentioned literature references) in the experiments described herein.
  • the sample is heated to 105°C (instead of 99.5 ⁇ 0.5°C as in the mentioned literature references).
  • the measurement is stopped when the weight change is less than 1 mg during a 90 seconds time frame.
  • the moisture content as weight percent of the sample is then calculated automatically by the Moisture Analyzer HB43.
  • “Flavour” or “flavouring agent” is used herein for a substance used to influence the aroma and/or taste of the nicotine product, including, but not limited to, essential oils, single flavour compounds, compounded flavourings, and extracts.
  • % w/w refers to the weight percent of the ingredient referred to of the total weight of the preparation, composition or product referred to.
  • dry weight percent As used herein, reference to "dry weight percent”, “% by weight, based on dry weight” and the like refers to the weight percent of the ingredient referred to on the basis of the total weight of the dry ingredients, i.e. all ingredients of the preparation, composition or product referred to excluding the moisture content.
  • wet weight percent As used herein, reference to "wet weight percent”, “% by weight, based on wet weight” and the like refers to the weight percent of the ingredient referred to on the basis of the total weight of the ingredients, i.e. all ingredients of the preparation, composition or product referred to including the moisture content. Thus, “% by weight, based on total weight” as used herein is the same as “% by weight, based on wet weight”.
  • oral pouched nicotine product refers to a portion of nicotine-containing filling material packed in a saliva-permeable pouch material intended for oral use.
  • oral pouched nicotine products are oral pouched nicotine non-tobacco products and oral pouched low tobacco nicotine products.
  • oral pouched nicotine non-tobacco product refers to a portion of nicotine-containing filling material packed in a saliva-permeable pouch material intended for oral use wherein no tobacco is included in said product.
  • oral pouched low tobacco nicotine product refers to a portion of nicotine-containing filling material packed in a saliva-permeable pouch material intended for oral use wherein an amount of tobacco material within the range of from about 0.1% to about 10% by weight or from about 0.1% to about 5% by weight, based on the total weight of the filling material, is included in said product.
  • non-particulate refers to a component which is not in particulate form.
  • the flavouring agent described herein may be a non-particulate flavouring agent such as a liquid, an oil or a mixture thereof.
  • particle non-tobacco material refers to a non-tobacco material comprising particles.
  • the particles may have an average particle size within the range of from 50 to 500 ⁇ m.
  • the oral pouched nicotine product as disclosed herein is intended for use in the oral cavity, such as by buccal placement (e.g. by placing the pouched product between the upper or lower gum and the lip or cheek), and may therefore be referred to as portion-packed (pouched) product for oral use.
  • the oral pouched nicotine product is sized and configured to fit comfortably and discreetly in a user's mouth between the upper or lower gum and the lip or cheek.
  • the oral pouched nicotine product as disclosed herein may have an oblong shape, such as a substantially rectangular shape (as seen from above when the product is placed on a planar surface).
  • the longitudinal direction of the product corresponds to the length of the substantially rectangular product and the transverse direction of the product corresponds to the width of the substantially rectangular product.
  • the total weight of the oral pouched nicotine product may be within the range of from about 0.3 to about 1.5 g.
  • the filling material of the oral pouched nicotine product described herein may be provided as a powder or granulate.
  • the filling material enclosed by the saliva-permeable pouch of the packaging material may be provided in a non-compressed form.
  • the pouch of the oral pouched nicotine product may be made of any suitable saliva-permeable (and preferably non-dissolvable) packaging material, such as a non-woven material.
  • the packaging material (herein also called pouch material) may be a nonwoven material comprising staple fibres of regenerated cellulose, such as viscose rayon staple fibres, and a binder, such as a polyacrylate.
  • the oral pouched (i.e. portion-packed) nicotine products may be positioned randomly in a container or in a pattern, for instance as described in WO 2012/069505 .
  • each oral pouched nicotine product may be placed in a sachet.
  • the present disclosure provides an oral pouched nicotine product comprising a filling material and a saliva-permeable pouch of a packaging material enclosing the filling material, the filling material comprising or consisting of:
  • n may have the value 1 and m may have the value 2.
  • the anion A n ' of the oral pouched nicotine product described herein may be selected from one or more of the following: chloride, lactate, malate, citrate, ascorbate, acetate, sulphate, nitrate, gluconate, glutamate, guanylate, inosinate, propionate, sorbate, benzoate, formate, pangamate.
  • M 2+ may then be Ca 2+ .
  • anion A n- of the oral pouched nicotine product described herein may be selected from one or more of the following: chloride, lactate, citrate, ascorbate, acetate, sulphate, nitrate, propionate, benzoate, formate, pangamate.
  • M 2+ may then be Mg 2+ .
  • anion A n- of the oral pouched nicotine product described herein may be selected from one or more of the following: chloride, lactate, citrate, acetate, sulphate, nitrate, gluconate, benzoate, formate.
  • M 2+ may then be Mn 2+ .
  • the anion A n- of the oral pouched nicotine product described herein may be selected from one or more of the following: chloride, acetate, sulphate, nitrate, formate.
  • the anion A n- of the oral pouched nicotine product described herein may be selected from one or more of the following: chloride, acetate, sulphate, nitrate, gluconate, propionate, formate.
  • M 2+ may then be Zn 2+ .
  • the anion A n- of the oral pouched nicotine product described herein may be selected from one or more of the following: chloride, acetate, sulphate, nitrate, gluconate, propionate, formate.
  • the anion A n- of the oral pouched nicotine product described herein may be selected from one or more of the following: chloride, lactate, sulphate, nitrate.
  • M 2+ may then be Fe 2+ .
  • the anion A n- of the oral pouched nicotine product described herein may be selected from one or more of the following: chloride, lactate, malate, citrate, ascorbate, tartrate, acetate, gluconate, aspartate, glycinate.
  • M 2+ may then be Ca 2+ .
  • the pH adjusting agent of the oral pouched nicotine product as described herein allows the pH to be within the range of from about 7 to about 10. This pH may be achieved after manufacture of the product, such as immediately after manufacture of the product. Further, this pH is provided upon storage of the product such as upon storage as described herein. As described herein, achieving and/or maintaining a pH within the range of about 7 to about 10, such as from about 7 to about 9.5, such as from about 7 to about 9.2, such as from about 7 to about 9, such as from about 8 to about 9, is a significant advantage since it allows for good nicotine extraction and taste while not impacting oral mucous membranes negatively.
  • the salt of Formula I acts by preventing formation of hydroxide ions from water and the carbonate ions of the pH adjusting agent. Instead, it is believed that the salt of Formula I reacts with the carbonate ions of the pH adjusting agent to form a carbonate salt having low water solubility. For instance, when the salt of Formula I is CaCl 2 a carbonate salt of formula CaCO 3 may be formed. As a result, the pH of or in the oral pouched nicotine product into which the pH adjusting agent is incorporated increases less as compared to a corresponding product lacking the salt of Formula I.
  • the salt of Formula I may have a water solubility equal to or above about 0.04 M, such as above about 0.045 M, such as above about 0.05 M. Additionally or alternatively, the Formula I may have a water solubility equal to or above one or more of the following: about 0.045 M, such as equal to or above about 0.05 M, such as equal to or above about 0.06 M, such as equal to or above about 0.07 M, such as equal to or above about 0.8 M, such as equal to or above about 0.9 M, such as equal to or above about 1.0 M. Further, the salt of Formula I may have a water solubility equal to or less than about 10 M, such as less than about 5 M, such as less than about 3 M.
  • the salt of Formula I may have a water solubility equal to or above about 1 g/L such as equal to or above about 2 g/L, such as equal to or above about 3 g/L, such as equal to or above about 4 g/L, such as equal to or above about 5 g/L, such as equal to or above about 10 g/L, such as equal to or above about 50 g/L, such as equal to or above about 100 g/l, such as equal to or above about 150 g/L, such as equal to or above about 200 g/L, such as equal to or above about 250 g/L, such as equal to or above about 300 g/L, such as equal to or above about 350 g/L such as equal to or above about 400 g/L, such as equal to or above about 450 g/L, such as equal to or above about 500 g/L, such as equal to or above about 600 g/L, such as equal to or above about 700 g/L.
  • a water solubility equal to
  • the salt of Formula I may have a water solubility equal to or less than about 1 kilogram/L, such as about 900 g/L, such as about 800 g/L.
  • g stands for gram(s) and L stands for liter.
  • M stands for molar, i.e. mole per liter (i.e. mole/L or mol/L).
  • the solution may be the solution resulting from mixing such as dissolving the salt of Formula I with the water. Additionally or alternatively, the solution may be measured in g/L, i.e. gram(s) per liter of solution.
  • The may be the solution resulting from dissolving the salt of Formula I with the water. Additionally or alternatively, the solution may be the solution to which the salt of Formula I is added.
  • the water solubility described herein such as the water solubility of the salt of Formula I described herein may be measured at a temperature from about 10 °C to about 40 °C, such as from about 20°C to about 25 °C. Further, the water solubility may be measured at atmospheric pressure such as at a pressure of about 101,325 Pa, i.e. 101,325 Pascal.
  • the oral pouched nicotine product may be free from tobacco, i.e. an oral pouched nicotine non-tobacco product.
  • the oral pouched nicotine product may comprise a low amount of tobacco material thereby providing an oral pouched low tobacco nicotine product.
  • the amount of tobacco material of the oral pouched low tobacco nicotine product may be within the range of from about 0.1 % to about 10% by weight such as from about 0.1 % to about 5% by weight, such as from about 0.1 wt% to about 1 wt%, based on the total weight of the filling material. The presence of this small amount of tobacco will not impact the pH of the product to be substantially different from that exhibited by the oral pouched tobacco free products described herein.
  • the tobacco material may be provided in a form as described herein.
  • the tobacco material may be a purified tobacco material, such as a bleached tobacco material or a tobacco extract.
  • the tobacco material described herein may comprise one, two or more particulate non-tobacco materials.
  • the amount of water of the filling material of the oral pouched nicotine product described herein may be present in an amount within the range of from about 0.5 wt% to about 12 wt% such as from about 0.5 wt% to about 5 wt%, such as from about 0.5 wt% to about 3 wt%, such as about 3 wt%, based on the total weight of the filling material.
  • the amount of water is within the range of from about 0.5 wt % to about 12 wt% or from about 0.5 wt% to about 3 wt% as described herein the oral pouched nicotine product may be considered dry, i.e. a dry oral pouched nicotine product.
  • the water content of the filling material of the oral pouched nicotine product described herein may be within the range of from about 20 wt% to about 50 wt%, such as from 20 wt% to 45 wt%, based on the total weight of the filling material.
  • the amount of water is within the range of from about 20 wt% to about 45 wt% as described herein the oral pouched nicotine product may be considered moist, i.e. a moist oral pouched nicotine product.
  • the pH adjusting agent described herein reduces, prevents and/or counteracts an increase in pH in an oral pouched nicotine product when it is stored.
  • the oral pouched nicotine product may be dry or moist.
  • the storage may be as described herein.
  • the salt of Formula I, or the hydrate of said salt, of the pH adjusting agent described herein may be present in an amount within the range of from about 0.05 wt% to about 10 wt%,such as from about 0.05 wt% to about 7 wt%, such as from about 0.05 wt% to about 5 wt%, such as from about 0.05 wt% to about 3 wt%, such as from about 0.05 wt% to about 2 wt%, such as from about 0.05 wt% to about 1 wt%, based on the total weight of the filling material.
  • the salt of Formula I or hydrate of the salt may be present in an amount within the range of from about 0.05 wt% to about 0.3 wt% or from about 0.1 wt% to about 0.3 wt%, based on the total weight of the filling material.
  • the Na 2 CO 3 , K 2 CO 3 , NaHCO 3 and/or KHCO 3 of the pH adjusting agent described herein may be present in an amount within the range of about 1 wt% to about 10 wt%, such as from about 1.5 wt% to about 4 wt% or from about 4 wt% to about 9 wt%, based on the total weight of the filling material of the oral pouched nicotine product.
  • the divalent metal ion M 2+ of the salt of Formula I may be Ca 2+ or Mg 2+ .
  • the divalent metal ion M 2+ may be Mn 2+ , Zn 2+ or Fe 2+ .
  • the divalent metal ion M 2+ of the salt of Formula may be Mn 2+ .
  • the divalent metal ion M 2+ of the salt of Formula may be Zn 2+ .
  • the divalent metal ion M 2+ of the salt of Formula may be Fe 2+ .
  • the salt of Formula I described herein may comprise or consist of CaCl 2 or a hydrate thereof. Additionally or alternatively, the salt of Formula I described herein may comprise or consist of MgCl 2 and/or ZnCl 2 or a hydrate of any of the aforementioned salts. Further, the salt of Formula I described herein may comprise or consist of MnCl 2 and/or FeCl 2 or a hydrate of the aforementioned salts.
  • the anion A n- of the salt of Formula I described herein may be lactate.
  • a salt of Formula I as described herein which comprises or consists of calcium lactate and/or zinc lactate.
  • the salt of Formula I may comprise or consist of magnesium lactate and/or iron lactate. It will be appreciated that any of the aforementioned salts may be provided in the form of a hydrate.
  • the anion A n- of the salt of Formula I described herein may be acetate.
  • a salt of Formula I as described herein which comprises or consists of calcium acetate and/or zinc acetate.
  • the salt of Formula I may comprise or consist of magnesium acetate and/or iron acetate. It will be appreciated that any of the aforementioned salts may be provided in the form of a hydrate.
  • the pH adjusting agent comprises or consists of Na 2 CO 3 and CaCl 2 . In a further example the pH adjusting agent comprises or consists of Na 2 CO 3 , NaHCO 3 and CaCl 2 . In a further example, the pH adjusting agent comprises or consists of K 2 CO 3 and CaCl 2 . In yet a further example, the pH adjusting agent comprises or consists of NaHCO 3 and CaCl 2 . In still a further example, the pH adjusting agent comprises or consists of KHCO 3 and CaCl 2 .
  • the pH adjusting agent comprises or consists of (i) Na 2 CO 3 and NaHCO 3 and (ii) CaCl 2 or a hydrate thereof.
  • the pH adjusting agent as described herein may be present in an amount from about 4 wt% to about 9 wt% based on the total weight of the filling material of the oral pouched nicotine product.
  • the amount of water may be within the range of from about 0.5 wt% to about 12 wt% or from about 0.5 wt% to about 3 wt%, based on the total weight of the filling material of the oral pouched nicotine product, and/or the amount of filling material may be within the range of from about 60 wt% to about 90 wt% or from about 30 wt% to about 85 wt%, based on the total weight of the filling material of the oral pouched nicotine product.
  • non-particulate non-tobacco material may comprise or consist of maltitol and/or microcrystalline cellulose.
  • the non-particulate non-tobacco material comprises or consists of microcrystalline cellulose and optionally maltitol.
  • the pH adjusting agent described herein may comprise or consist of (i) Na 2 CO 3 and (ii) CaCl 2 or a hydrate thereof.
  • the pH adjusting agent may be present in an amount from about 1.5 wt% to about 4 wt% based on the total weight of the filling material of the oral pouched nicotine product.
  • the amount of water may be within the range of from about 20 wt% to about 45 wt%, based on the total weight of the filling material of the oral pouched nicotine product, and/or the amount of filling material may be within the range of from about 30 wt% to about 90 wt% or from about 30 wt% to about 85 wt%, based on the total weight of the filling material of the oral pouched nicotine product.
  • the non-particulate non-tobacco material may comprise or consist of cellulose and/or microcrystalline cellulose.
  • the oral pouched nicotine product described herein may be free from sodium chloride, i.e. NaCl. Alternatively, it may comprise NaCl in an amount within the range of from about 0.1 wt% to about 5 wt% such as from about 0.1 wt% to about 3 wt%, based on the total weight of the filling material.
  • the oral pouched nicotine product described herein may further comprise MgCO 3 . Additionally or alternatively, the oral pouched nicotine product described herein may comprise CaCO 3 and/or dolomite.
  • the oral pouched nicotine product described herein may comprise no further salt and/or no further pH adjuster.
  • the filling material of the oral pouched nicotine product described herein may comprise particulate non-tobacco material within the range of from about 30 wt% to about 90 wt%, such as from about 30 wt% to about 85 wt%, such as from about 30 wt% to about 80 wt%, such as from about 60 wt% to about 90 wt%, based on the total weight of the filling material.
  • the filling material described herein may be water-insoluble optionally further including water soluble filling material.
  • at least part of the filling material of the oral pouched nicotine product described herein may be water-insoluble such as water-insoluble at room temperature and/or at atmospheric pressure.
  • the particulate non-tobacco material may be water-insoluble, water-soluble or a combination thereof.
  • the particulate non-tobacco material may comprise or consist of a sugar alcohol such as maltitol, and/or of cellulose such as microcrystalline cellulose and/or powdered cellulose.
  • the particulate non-tobacco material may comprise maltitol and/or microcrystalline cellulose.
  • the filling material of the oral pouched nicotine product described herein may comprise one or more water-insoluble fibers selected from the group consisting of maize fibers, oat fibers, tomato fibers, barley fibers, rye fibers, sugar beet fibers, buck wheat fibers, wheat fibers, pea fibers, potato fibers, apple fibers, cocoa fibers, bamboo fibers, citrus fibers, and any combination thereof.
  • the water-insoluble fibers may form part of the non-tobacco particulate material.
  • the filling material may comprise one, two or more nicotine sources.
  • the filling material of the oral pouched nicotine product as described herein may comprise within the range of from about 1.0 % to about 10 % by weight of the nicotine source, based on the total weight of the filling material.
  • the nicotine source may be a nicotine salt and/or nicotine base.
  • the nicotine source such as nicotine base may be bound to an ion exchange resin, such as polacrilex, e.g. via a salt bridge.
  • the ion exchange resin may function as a solid support for the nicotine source such as nicotine base.
  • Nicotine base such as in the form of an oily liquid, may be synthetically produced or extracted from tobacco.
  • the nicotine source described herein may comprise or consist of one or more of the following: nicotine hydrochloride, nicotine dihydrochloride, nicotine monotartrate, nicotine bitartrate, nicotine bitartrate dihydrate, nicotine sulphate, nicotine zinc chloride monohydrate, nicotine salicylate, nicotine polacrilex.
  • the nicotine source may be a nicotine salt such as a nicotine salt selected from the group consisting of nicotine hydrochloride, nicotine dihydrochloride, nicotine monotartrate, nicotine bitartrate, nicotine bitartrate dihydrate, nicotine sulphate, nicotine zinc chloride monohydrate and nicotine salicylate, and any combination thereof.
  • a nicotine salt selected from the group consisting of nicotine hydrochloride, nicotine dihydrochloride, nicotine monotartrate, nicotine bitartrate, nicotine bitartrate dihydrate, nicotine sulphate, nicotine zinc chloride monohydrate and nicotine salicylate, and any combination thereof.
  • the filling material may comprise nicotine bitartrate and/or nicotine bitartrate dihydrate.
  • the amount of nicotine source such as nicotine salt and/or nicotine base per pouched product may be within the range from about 0.1 mg to about 20 mg of nicotine calculated as nicotine base, such as about 0.5 mg, about 1.0 mg, about 1.5 mg, about 2.0 mg, about 2.5 mg, about 3.0 mg, about 3.5 mg, about 4.0 mg, about 4.5 mg, about 5.0 mg, about 6.0 mg, about 7.0 mg, about 8.0 mg, about 9.0 mg, about 10 mg, about 12 mg, about 14 mg, about 16 mg, about 18 mg, or about 20 mg of nicotine.
  • the nicotine salt of the filling material in the oral pouched nicotine product as disclosed herein may be a nicotine salt present in solid form and/or dissolved form.
  • the nicotine source as disclosed herein may be adsorbed or non-adsorbed onto the particulate non-tobacco material as disclosed herein. It will be appreciated that the expression “adsorbed onto” means that the nicotine source adheres to an outer surface of the non-tobacco particulate material. When the nicotine source is adsorbed onto the non-tobacco particulate material it adheres to the outer surface of said non-tobacco particulate material without substantially penetrating into any void(s) of said non-tobacco particulate material.
  • the nicotine source as disclosed herein may be absorbed into and/or adsorbed onto the tobacco material described herein.
  • the filling material of the oral pouched nicotine product described herein may further comprise a flavouring agent.
  • the filling material may comprise one, two or more flavouring agents.
  • the flavouring agent may be a non-encapsulated agent.
  • the flavouring agent may be encapsulated.
  • the non- encapsulated flavouring agent and the encapsulated flavouring agent may be the same or different.
  • an encapsulated flavouring agent is a flavouring agent contained within a capsule. Accordingly, a non-encapsuled flavouring agent is not contained within a capsule.
  • flavouring agent of the filling material in the oral pouched nicotine product as disclosed herein may be a hydrophobic flavouring agent.
  • the flavouring agent of the filling material of the oral pouched nicotine product described herein may be an oil, a liquid, a lyophilized material, a spray-dried material, or a mixture thereof.
  • the flavouring agent(s) is/are an oil and/or a liquid.
  • the filling material of the oral pouched nicotine product described herein may comprise within the range of from about 0.5 % to about 3 % by weight of the flavouring agent, based on the total weight of the filling material.
  • the filling material of the oral pouched nicotine product described may comprise a humectant such as polypropylene glycol.
  • the particulate non-tobacco material, the nicotine source, the water, the pH adjusting agent, optionally the tobacco material, optionally the flavouring agent and optionally the humectant may be homogeneously mixed.
  • Anatabine is one of the minor alkaloids found in plants in the Solanaceae family, which inter alia includes the tobacco plant.
  • the oral pouched nicotine non-tobacco product described herein may be free from tobacco, i.e. may contain no tobacco material, and may then consequently be free from anatabine.
  • the oral pouched nicotine product described herein may contain a small amount of tobacco material, such as from about 0.1% to about 10% by weight as described herein, and may then not comprise any anatabine except for the anatabine present in said tobacco material.
  • the oral pouched nicotine product described herein may be free from glycerides such triglycerides.
  • the oral pouched nicotine product described herein may comprise glycerides such as triglycerides.
  • the filling material of the oral pouched nicotine product as described herein may be manufactured using a method comprising the step(s) of:
  • the filling material of the oral pouched nicotine product as described herein may be manufactured using a method comprising the steps of:
  • the method may further comprise a step of enclosing the filling material in a saliva-permeable pouch of a packaging material.
  • the pH of the oral pouched nicotine product may be within the range of from about 7.0 to about 10.0, such as a pH within the range of from about 7 to about 9, such as from about 7 to about 9.5, such as from about 7 to about 9.2, such as from about 8 to about 9, such as about 8, such as about 8.3, such as about 8.5 or such as about 8.8, when it is dispersed in purified water.
  • these pH values are favourable for nicotine extraction and taste while not negatively affecting oral mucous membranes.
  • the pH may be measured as described herein.
  • the oral pouched nicotine product may exhibit these pH values upon manufacture and/or also upon storage.
  • the pH of the filling material may be measured by adding 100 milliliters (ml) of water such as distilled water to 5.0 grams of filling material to provide a mixture, followed by stirring of said mixture such as stirring at 100 rpm for about 5 minutes and then measuring the pH on at least part of said mixture.
  • the pH of the filling material described herein may be measured at room temperature such as room temperature at atmospheric pressure.
  • a pH meter may be used for the measurement.
  • "rpm" stands for revolutions per minute.
  • room temperature intends a temperature from about 20°C to about 25 °C, such as about 22°C.
  • the atmospheric pressure may be a pressure of about 101,325 Pa, i.e. 101,325 Pascal.
  • an oral pouched nicotine product as described herein, wherein the pH of said product does not exceed about 10, does not exceed about 9.5 or does not exceed about 9 upon storage. Additionally or alternatively, the pH of the oral pouched nicotine product changes by no more than ⁇ 0.5 pH units upon storage.
  • the storage may take place at a relative humidity from about 60% to about 75%, at a temperature from about 22°C to about 30°C and/or for a time of about 15 weeks. In an example, the storage takes place at a relative humidity at about 75%, at a temperature at about 30°C and/or for a time of about 15 weeks. In a further example, the storage takes place at about 30°C and/or for a time of about 15 weeks.
  • the storage described herein may take place in a container such as a packaging and/or consumer container suitable for oral pouched nicotine products.
  • the container described herein may be adapted for being conveniently carried in a consumer pocket or handbag, and/or may also be used for packaging any known type of snuff product such as oral pouched nicotine products as described herein.
  • the container may be made of plastics and/or metal. Further, the container may have any desired shape or geometrical form. For example, the container may have the form of a cylinder.
  • the container may comprise a top and a base defining an interior space.
  • the base may comprise a base surface and surrounding walls extending from said base surface.
  • the top may be in the form of a lid that is detachable from the base of the container, or in the form of a lid that is hinged or otherwise attached to the base of the container.
  • the lid may be attached by to the base by snap-fit.
  • the container may be tamper resistant.
  • the container may be as described in WO 2017/125405 which is incorporated herein in its entirety.
  • the container may be as shown in the Design Registration in Norway No. 085548 .
  • Component (i) of the pH adjusting agent of the oral pouched nicotine product described herein may comprise or consist of one or more of the following: Na 2 CO 3 , K 2 CO 3 , NaHCO 3 , KHCO 3 . Further, the pH adjusting agent of the oral pouched nicotine product described herein may consist of:
  • pH adjusting agent of or in the oral pouched nicotine product as described herein may comprise or consist of:
  • pH adjusting agent as described herein in which:
  • pH adjusting agent as described herein in which:
  • the pH adjusting agent described herein comprises or consists of (i) Na 2 CO 3 and/or NaHCO 3 , and (ii) CaCl 2 .
  • the pH adjusting agent may comprise or consist of (i) K 2 CO 3 and/or KHCO 3 , and (ii) CaCl 2 .
  • the CaCl 2 may be present in the form of a hydrate such as a monohydrate.
  • an oral pouched nicotine product lacking the salt of Formula I increases its pH when it is stored.
  • the salt of Formula I is combined with Na 2 CO 3 , K 2 CO 3 , NaHCO 3 and/or KHCO 3 , such as in amounts as described herein, this results in a pH adjusting agent that allows for:
  • ⁇ 0.5 pH units used herein may intend + 0.5 pH units and/or - 0.5 pH units.
  • a salt of Formula I or a hydrate of said salt, as described herein for controlling pH in or of an oral pouched nicotine product comprising a filling material, said filling material comprising said salt of Formula I, or a hydrate thereof, and
  • the salt of Formula I, or a hydrate thereof may be mixed with the other components of the filling material.
  • the salt of Formula I, or a hydrate thereof may be substantially homogenously mixed with the other components of the filling material.
  • the amount of the filling material components may be as described in this document.
  • the salt of Formula I such as CaCl 2 , Na 2 CO 3 , K 2 CO 3 , NaHCO 3 and/or KHCO 3 may be present in amounts as described herein.
  • the salt of Formula I such as CaCl2, Na 2 CO 3 , K 2 CO 3 , NaHCO 3 and/or KHCO 3 may be present in an amount such as a total amount from 1 wt% to 15 wt%, such as from 1 wt% to 10 wt%, such as from 1 wt% to 9 wt%, such as from 1 to 7 wt% or such as from 1 wt% to 5 wt%, based on the total weight of the filling material of said oral pouched nicotine product.
  • the controlling may comprise or consist of:
  • the storage described herein may take place at a relative humidity from about 60% to about 75%, at a temperature from about 22°C to about 30°C and/or for a time of about 15 weeks. In an example, the storage takes place at a relative humidity at about 75%, at a temperature at about 30°C and/or for a time of about 15 weeks. In a further example, the storage takes place at about 30°C and/or for a time of about 15 weeks.
  • the present disclosure also provides a method for controlling pH in or of an oral pouched nicotine product, such as an oral pouched nicotine product as described herein, when said product is stored.
  • the controlling may be as described herein.
  • the method involves use of a pH adjusting agent as described herein.
  • the method may comprise or consist of preparing an oral pouched nicotine product as described herein followed by storage of said product.
  • the storage may be as described herein.
  • the controlling of pH as described herein may impart an improved storage stability such as improved storage stability of an oral pouched nicotine product as described herein.
  • the storage stability may be improved with respect to a corresponding oral pouched nicotine product lacking the salt of Formula I.
  • the oral pouched nicotine product described herein may be considered a portion packed oral nicotine product.
  • the filling material may be in the form of a particles, granules, beads, a powder such as a dry powder or a moist powder, a dry mixture or a moist mixture.
  • the present disclosure is also directed to the filling material as described herein, i.e. the filling material as such excluding any packaging such as a pouch.
  • Example 1 Substantially dry oral pouched tobacco free nicotine product
  • Table 1A Sample Calcium chloride (w/w%) Nicotine bitartrate dihydrate (w/w%) Sodium bicarbonate (w/w%) Sodium carbonate (w/w%) Fillers (w/w%) Start moisture (w/w%) 1 0 2.51 2.33 1.91 93.25 1.08 2 0.1 2.51 2.33 1.91 93.15 1.02 3 1 2.51 2.33 1.91 92.25 1.38 4 5 2.51 2.33 1.91 88.25 2.00 5 10 2.51 2.33 1.91 83.25 3.86
  • the granulates were packed into portion pouches of 0.4 g each using a water permeable nonwoven pouch material.
  • the pouches were packed into plastic cans suitable for containment of oral pouches.
  • the plastic cans were as described in WO 2017/125405 .
  • the pH was analysed for the fresh samples before storage, using the herein described method.
  • the plastic cans were thereafter transferred to a climate cabinet (VC0100, Vötsch Industrietechnik) for storage.
  • the cabinet conditions were set at 35°C and 75 % RH. Storage was done for 15 weeks. After 2, 4, 6, 8, 10 and 15 weeks cans from each sample were taken out of the climate cabinet and the pH of the pouches was analyzed, using the herein defined method.
  • "g” stands for gram(s)
  • RH stands for relative humidity.
  • snus Two batches of snus (GR One and General One) were prepared in a standard snus production procedure using production scale equipment and the composition disclosed in Table 2. Tobacco, fibre and water were mixed in a blender. The blend was heated to 100°C and the temperature kept between 85-100 °C for 4.5 hours. Before cooling sodium chloride, sodium carbonate, propylene glycol and additional water was added and mixed into the snus blend. After cooling a final addition of flavour and additional sodium chloride were added and mixed into the snus blend. The snus was packed into water permeable nonwoven pouch material and the pouches packed into plastic cans suitable for containment of oral pouches. The plastic cans were as shown in the Design Registration in Norway No. 085548 .
  • the pH was analyzed for the fresh samples before storage, using the herein described method.
  • the plastic cans were thereafter transferred to a climate cabinet for storage.
  • the cabinet conditions were set at 22 °C and 60 % RH. Storage was done for 17 weeks. After 1, 3, 5, 10 and 17 weeks cans from each sample were taken out of the climate cabinet and the pH of the pouches was analyzed, using the herein defined method.
  • Two batches (Ang-124 and Ang-125) of a moist oral nicotine product were prepared in lab scale (500 g per batch) according to the composition in Table 3A. Dry ingredients (nicotine bitartrate, sodium carbonate, calcium chloride (only in Ang-124), cellulose, sodium chloride and sweetener were mixed in a lab mixer (Kenwood) to a homogenous powder blend. Water, glycerol and vegetable oil were added followed by continued mixing. The water was present in an amount of about 30-40 wt% based on the total amount of the composition.
  • the two samples of oral nicotine blend were distributed in plastic cans suitable for oral pouched nicotine products.
  • the plastic cans were thereafter sealed with a side label and transferred to a climate cabinet for storage.
  • the plastic cans were as shown in the Design Registration in Norway No. 085548 .
  • the cabinet conditions were set at 22 °C and 60 % RH. Storage was done for 15 weeks. After 2, 4, 8, 10 and 15 weeks cans from each sample were taken out of the climate cabinet and the pH of the pouches was analyzed, using the herein defined method.
  • the pH of the filling material of the above-mentioned examples was measured by adding 100 ml of distilled water to 5.0 gram of filling material, in a 125 ml beaker, stirring the resulting mixture at room temperature with a magnetic stirrer at 100 rpm for about 5 minutes, and then measuring the pH of an extract obtained therefrom with a calibrated
  • pH meter (according to the manufacturer's instructions) pH meter. For correctness of readings, the sample solutions were analyzed within one hour. In this document, “rpm” stands for revolutions per minute. In this document, room temperature intends a temperature from about 20 °C to about 25 °C, such as about 22 °C.

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EP20703956.1A 2019-02-01 2020-01-31 An oral nicotine product comprising a ph adjusting agent Active EP3917339B1 (en)

Applications Claiming Priority (3)

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NO20190141A NO345073B1 (en) 2019-02-01 2019-02-01 AN ORAL NICOTINE PRODUCT COMPRISING A pH ADJUSTING AGENT
SE1950119A SE544446C2 (en) 2019-02-01 2019-02-01 AN ORAL NICOTINE PRODUCT COMPRISING A pH ADJUSTING AGENT
PCT/EP2020/052437 WO2020157280A1 (en) 2019-02-01 2020-01-31 AN ORAL NICOTINE PRODUCT COMPRISING A pH ADJUSTING AGENT

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US11969502B2 (en) 2019-12-09 2024-04-30 Nicoventures Trading Limited Oral products
US20210169126A1 (en) * 2019-12-09 2021-06-10 Nicoventures Trading Limited Oral composition with salt inclusion
US11872231B2 (en) 2019-12-09 2024-01-16 Nicoventures Trading Limited Moist oral product comprising an active ingredient
US11911375B2 (en) * 2020-11-16 2024-02-27 Fertin Pharma A/S Solid oral nicotine formulation
US20220151292A1 (en) * 2020-11-16 2022-05-19 Ncp Nextgen A/S Nicotine pouch composition
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EP3917339C0 (en) 2023-06-07
US20220095671A1 (en) 2022-03-31
KR20210122776A (ko) 2021-10-12
PH12021551469A1 (en) 2021-12-06
EP3917339A1 (en) 2021-12-08
WO2020157280A1 (en) 2020-08-06
CA3127725A1 (en) 2020-08-06

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