[go: up one dir, main page]

WO2025062340A1 - Extraction de nicotine à partir de matériaux d'emballage en plastique - Google Patents

Extraction de nicotine à partir de matériaux d'emballage en plastique Download PDF

Info

Publication number
WO2025062340A1
WO2025062340A1 PCT/IB2024/059111 IB2024059111W WO2025062340A1 WO 2025062340 A1 WO2025062340 A1 WO 2025062340A1 IB 2024059111 W IB2024059111 W IB 2024059111W WO 2025062340 A1 WO2025062340 A1 WO 2025062340A1
Authority
WO
WIPO (PCT)
Prior art keywords
nicotine
packaging material
polymeric packaging
solvent
waste polymeric
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/IB2024/059111
Other languages
English (en)
Inventor
III Robert Owen BUSSEY
Cody O'Neal PERRY
Serban C. Moldoveanu
Christopher Keller
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
RJ Reynolds Tobacco Co
Original Assignee
RJ Reynolds Tobacco Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by RJ Reynolds Tobacco Co filed Critical RJ Reynolds Tobacco Co
Publication of WO2025062340A1 publication Critical patent/WO2025062340A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
    • B29B17/00—Recovery of plastics or other constituents of waste material containing plastics
    • B29B17/02—Separating plastics from other materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J11/00—Recovery or working-up of waste materials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
    • B29B17/00—Recovery of plastics or other constituents of waste material containing plastics
    • B29B2017/001—Pretreating the materials before recovery
    • B29B2017/0021—Dividing in large parts
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
    • B29B17/00—Recovery of plastics or other constituents of waste material containing plastics
    • B29B17/02—Separating plastics from other materials
    • B29B2017/0213—Specific separating techniques
    • B29B2017/0293—Dissolving the materials in gases or liquids
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29L—INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
    • B29L2031/00—Other particular articles
    • B29L2031/712—Containers; Packaging elements or accessories, Packages
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00—Technologies for solid waste management
    • Y02W30/50—Reuse, recycling or recovery technologies
    • Y02W30/62—Plastics recycling; Rubber recycling

Definitions

  • the extracting further comprises heating the waste polymeric packaging material and solvent with a heat source, such as a heat source configured to heat the solvent by radiant heat, convection, or by direct thermal contact.
  • a heat source such as a heat source configured to heat the solvent by radiant heat, convection, or by direct thermal contact.
  • the extracting is performed using a Soxhlet apparatus.
  • the extracting is conducted for a period of time, such as from about 30 minutes to about 48 hours.
  • the method further comprises removing residual solvent from the decontaminated waste polymeric packaging material, such as by washing the decontaminated waste polymeric packaging material with water, drying the decontaminated waste polymeric packaging material, or both.
  • Embodiment 3 The method of embodiment 1 or 2, wherein the waste polymeric packaging material comprises polypropylene, low-density polyethylene, or a combination thereof.
  • Embodiment 6 The method of claim 5, wherein the dividing comprises one or more of cutting or shredding the waste polymer packaging material into smaller pieces or grinding the waste polymer packaging material into particles.
  • Embodiment 7 The method of any one of embodiments 1-6, wherein the solvent has boiling point at standard atmospheric pressure in a range from about 50°C to about 150°C, or from about 60°C to about 90°C.
  • Embodiment 8 The method of any one of embodiments 1-7, wherein the solvent is a polar organic solvent or a nonpolar hydrocarbon solvent.
  • Embodiment 9 The method of any one of embodiments 1-8, wherein the solvent is methanol or ethanol.
  • Embodiment 10 The method of any one of embodiments 1-9, wherein the elevated temperature is above the boiling point at standard atmospheric pressure of the solvent.
  • Embodiment 11 The method of any one of embodiments 1-10, wherein the elevated temperature is from about 40°C to about 150°C, or from about 50°C to about 100°C.
  • Embodiment 15 The method of embodiment 14, wherein the extracting is performed using a Soxhlet apparatus.
  • Embodiment 17 The method of any one of embodiments 1-16, further comprising removing residual solvent from the decontaminated waste polymeric packaging material, such as by washing the decontaminated waste polymeric packaging material with water, drying the decontaminated waste polymeric packaging material, or both.
  • FIG. 1 is a cross-sectional view of a non-limiting pouched smokeless tobacco product embodiment, taken across the width of the product, showing an outer pouch filled with a composition comprising nicotine.
  • FIGS. 2A, 2B, and 2C are schematic side and front views of a multi-compartment flexible sachet for holding a nicotine product according to a non-limiting embodiment of the present disclosure.
  • FIG. 3 is schematic side view of a roll of a panel material for sachets according to a non-limiting embodiment of the present disclosure.
  • FIG. 4A is a perspective view of a rigid container for holding a nicotine product according to a nonlimiting embodiment of the present disclosure.
  • FIG. 4B is an exploded perspective view of the container of FIG. 4A according to a non-limiting embodiment of the present disclosure.
  • FIG. 5 is a Soxhlet apparatus according to a non-limiting embodiment of the present disclosure.
  • FIG. 6A is a pyrogram of a plastic sample prior to microwave accelerated extraction according to a non-limiting embodiment of the present disclosure.
  • FIG.6B is a pyrogram of a plastic sample after microwave accelerated extraction according to a nonlimiting embodiment of the present disclosure.
  • the term "about” used throughout this specification is used to describe and account for small fluctuations.
  • the term “about” can refer to less than or equal to ⁇ 10%, such as less than or equal to ⁇ 5%, less than or equal to ⁇ 2%, less than or equal to ⁇ 1%, less than or equal to ⁇ 0.5%, less than or equal to ⁇ 0.2%, less than or equal to ⁇ 0.1% or less than or equal to ⁇ 0.05%. All numeric values herein are modified by the term “about,” whether or not explicitly indicated. A value modified by the term “about” of course includes the specific value. For instance, "about 5.0" must include 5.0.
  • dry weight percent or “dry weight basis” refers to weight on the basis of dry ingredients (i.e., all ingredients except water).
  • wet weight refers to the weight of the composition including water. Unless otherwise indicated, reference to “weight percent” of a composition reflects the total wet weight of the composition (i.e., including water).
  • Suitable packets, pouches or containers of the type used for the manufacture of smokeless tobacco products are available under the tradenames CATCHDRY (Swedish Match), ETTAN (Swedish Match), GENERAL (Swedish Match), GRANIT (Fiedler & Lundgren), GOTEBORGS RAPE (Swedish Match), GROVSNUS WHITE (Swedish Match), METROPOL KAKTUS (Fiedler & Lundgren), MOCCA (Anis, Mint, Wintergreen; Fiedler & Lundgren), KICKS AND PROBE (Swedish Match), PRINCE (British American Tobacco), SKRUF (Skruf Snus AB), and TRE ANKRARE (Swedish Match).
  • the composition may be contained in pouches and packaged, in a manner and using the types of components used for the manufacture of conventional snus types of products.
  • the pouch provides a liquid-permeable container of a type that may be considered to be similar in character to the mesh-like type of material that is used for the construction of a tea bag. Components of the composition readily diffuse through the pouch and into the mouth of the user.
  • Non-limiting examples of suitable types of pouches are set forth in, for example, US Pat. No. 5,167,244 to Kjerstad, which is incorporated herein by reference.
  • Pouches can be provided as individual pouches, or a plurality of 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 a single pouch or individual portion can be readily removed for use from a one-piece strand or matrix of pouches.
  • the amount of material contained within each product unit may vary.
  • the dry weight of the composition within each pouch is at least about 50 mg, for example, from about 50 mg to about 2 grams, from about 100 to 800 about mg, or from about 200 to about 700 mg.
  • the dry weight of the composition within each pouch may be from about 100 to about 300 mg.
  • the dry weight of the material within each pouch may be from about 300 mg to about 700 mg.
  • Nicotine products as described above are commonly stored in resealable containers or other packaging devices (e.g., cans, packets, pouches, bags, sacks, cases, sachets, etc.).
  • smokeless tobacco products or tobacco intended for smoking may be stored in and dispensed from flexible pouches or sachets.
  • Pouches or sachets are typically made from laminated plastic films that include a closure mechanism, such as one or more of a zipper-type closure, a snap-fit mechanism, an adhesive, or a hook and loop fastener.
  • pouches or sachets may include a Zip-lock® type mechanism as available from SC Johnson.
  • Laminated film pouches or sachets typically include at least three layers, for example, an outer printing layer made of a polyester, a high moisture barrier middle layer made of a metalized polyester, and an inner sealing layer made of a low-density polyethylene.
  • FIG.2B is a front view of the container 100 and depicts the container 100 with a generally rectangular shaped outline; however, size and shape of the container can vary to suit a particular application, e.g., type of product, quantity of product, and size or shape of product.
  • the closure mechanisms 106, 108 may be selected to suit a particular application and may include zipper-type closures (e.g., Ziploc® as available from SC Johnson) or similar snap-fit type closure mechanisms, an adhesive, a hook and loop type fastener (e.g., Velcro® as available from the Velcro Company), and folding.
  • the closure mechanisms 106, 108 are two-part mechanisms, with a first part 106a, 108a disposed on the front panel 102 (e.g., proximate longitudinal end (a)) and a second part 106/?, 108/? disposed on the back panel 104 (e.g., proximate longitudinal end (b)).
  • the two parts are brought into contact with one another to effect sealing (e.g., via a slider or application of a force (i.e., press and seal)).
  • the closure mechanism halves 106a, 106/?. 108a, 108/? may be attached to the panels via any of the manners known to a person of the skill in the art (e.g., sonic welding, adhesive, etc.).
  • FIG. 2C is an opposite side view of the container 100 depicting the container 100 in use, where a fresh product 130 is stored within the first compartment 112 and a waste product 132 (e.g., used chew) is stored within the second compartment 114.
  • a fresh product 130 is stored within the first compartment 112
  • a waste product 132 e.g., used chew
  • FIG. 3 depicts a roll of an exemplary material 300 for use as any of the panels described above and may include a lamination of paper/poly/metal/poly layers.
  • the material 300 shown includes five layers, three basic or functional layers 300a, 300c, 300e, and two adhesive layers 300b, 300d disposed there between.
  • the first functional layer 300a is typically a printing layer for application of, for example, a high-quality decoration, logo, etc.
  • the first layer 300a is a 12 pm polyester (PET) film, however, the material and thickness this or any of the other layers may vary for a particular application.
  • the first layer 300a may be configured for reverse printing making the inks, and by extension, logos, etc. scratch-proof. Additionally, the first layer 300a may have a matte, gloss, or combination finish, a textured surface, a surface varnish or other finishes as known to a person of skill in the art.
  • the third functional layer 300e is a sealing layer, which also helps maintain product integrity.
  • the third functional layer 300e may comprise a polyethylene material having a thickness in a range of about 55 pm to about 80 pm.
  • the third functional layer 300e is a 70 pm low density polyethylene (LDPE) film.
  • the third functional layer is the product contact layer and, depending on the product, may require regulatory approval for direct product contact.
  • the adhesive layers 300b, 300d are provided to form a lamination or film that is used for the various panels as are known to a person of skill in the art.
  • the materials used to manufacture the container render the container totally recyclable.
  • nicotine-containing products may be stored in a rigid container.
  • Various types of rigid containers for storing and dispensing such products are known in the art and are often characterized by a hand-held size that can be easily stored and transported.
  • snus products have been packaged in tins, "pucks" or “pots” that are manufactured from plastics. See, for example, those types of containers generally disclosed in U.S. Pat. No. 4,098,421 to Foster; U.S. Pat. No. 4,190,170 to Boyd; U.S. Pat. No. 8,440,023 to Carroll et al.; U.S. Patent Pub. No. 2010/0065076 to Bergstrom et al.; U.S.
  • Yet other types of containers for smokeless types of tobacco products are set forth in U.S. Pat. No. 8,458,996 to Bried et al.; D574,709 to Crotts et al. and D649,284 to Patel et al.; U.S. Patent Pub. Nos.
  • Suitable containers such as those referenced above generally have a base or body portion and a cover or lid, where the cover, the body portion, or both include structure to provide sealing properties with respect to the products.
  • a desirable feature for certain containers is the protection of the product from environmental effects, particularly those effects that may degrade the product stored in the container. For example, in humid environments, moisture may invade the storage space housing the product, thereby damaging the product or otherwise rendering the product unusable. In other instances, venting within the enclosure formed by the container may be needed for properly storing a product.
  • the containers may also include structure to improve other characteristics of the container and the interface between the body portion and the lid, such as, for example, child-resistant features that make it difficult for a child to separate the cover and the body portion, thereby reducing the risk of children accessing the contents of the container.
  • Such containers may also include a side label to prevent moisture loss from the product. Examples of containers that may incorporate such structures are described in U.S. Patent Publication Nos. 2022/0071280 to Patel et al. and 2022/0104543 to Patel et al., the entire disclosures of which are hereby incorporated by reference herein.
  • FIGS. 4A and 4B A non-limiting example of a suitable rigid container 400 is provided in FIGS. 4A and 4B.
  • the cover 404 and body portion 402 generally abut one another when engaged and their respective outer surfaces are substantially flush with one another, which makes it difficult to separate the parts from their engaged or sealed position.
  • the cover 404 is secured to the body portion 402 via a snap or interference fit, which provides additional resistance to separating the parts.
  • the container may also include one or more labels 410a, 410b (collectively 410) attached to the base 402, the lid 404, or both.
  • the waste polymeric packaging material may be processed, e.g., to subdivide the packaging material into smaller pieces by shredding, grinding, or other suitable operations, using, for example, equipment such as hammer mills, cutter heads, air control mills, or the like.
  • Suitable waste polymeric packaging materials include, but are not limited to, polymeric primary or secondary containers used to store and/or dispense nicotine products, such as smokeless tobacco products. Such packaging materials are further described hereinbelow.
  • the nature of the waste polymeric packaging material for use in the method may vary but is generally of the type referred to as a plastic.
  • the waste polymeric packaging material comprises a plastic of a type appropriate for recycling.
  • plastics materials appropriate for recycling include polyethylene, polyethylene terephthalate, and possibly polypropylene. Additional or fewer plastics may be recycled according to region and available facilities.
  • the waste polymeric packaging material comprises polypropylene, polyethylene, polyvinyl chloride, an ethylene vinyl acetate co-polymer, polyvinylidene dichloride, a polyester terephthalate, an ethylene methacrylic acid co-polymer, or a combination thereof.
  • the waste polymeric packaging material comprises polypropylene, low-density polyethylene, or a combination thereof. Particularly desirable is the recycling of polyethylene-containing plastics, such as low- and high-density polyethylene, due to their ease of recycling and the abundance of these plastics. Accordingly, in some embodiments, the waste polymeric packaging material comprises or is polyethylene, such as low-density polyethylene.
  • the waste polymeric packaging material is a sachet previously used for storage of a nicotine product, the sachet comprising a metallic layer and one or more polymeric layers.
  • the metallic layer is aluminum.
  • the method further comprises removing the metallic layer prior to the extracting.
  • removing the metallic layer comprises contacting the sachet with an acid, dissolving the metallic layer.
  • Suitable extraction solvents include, but are not limited to, solvents in which free base nicotine and/or nicotine salts exhibit good solubility.
  • Suitable solvents have a boiling point at standard pressure below the melting point of the waste polymeric material and are chemically compatible with the waste polymeric material.
  • the solvent has a boiling point at standard atmospheric pressure in a range from about 50°C to about 150°C, such as from about 50°C, about 60°C, about 70°C, about 80°C, about 90°C, or about 100°C, to about 110°C, about 120°C, about 130°C, about 140°C, or about 150°C.
  • the solvent has boiling point at standard atmospheric pressure in a range from about 60°C to about 90°C.
  • the solvent is a polar organic solvent (e.g., a Cl to C3 alcohol, such as methanol, ethanol, n-propanol, or isopropanol).
  • a polar organic solvent e.g., a Cl to C3 alcohol, such as methanol, ethanol, n-propanol, or isopropanol.
  • the solvent is methanol. In some embodiments, the solvent is ethanol.
  • the solvent is a nonpolar hydrocarbon solvent, such as various aliphatic or aromatic hydrocarbon solvents which can be unsubstituted or substituted with alkyl groups or halogens, for example, aromatic hydrocarbon solvents such as benzene, toluene, xylene, monochlorobenzene, dichlorobenzene, chlorotoluene; aliphatic paraffin hydrocarbons, for example, pentane, hexane, heptane, octane, nonane, decane; alicyclic hydrocarbon compounds, for example, cyclohexane, decahydronaphthalene; and halogenated alkanes, for example, dichloroethane and dichlorobutane.
  • aromatic hydrocarbon solvents such as benzene, toluene, xylene, monochlorobenzene, dichlorobenzene, chlorotoluene
  • aliphatic paraffin hydrocarbons
  • the elevated temperature at which the solvent is provided is approximately the same as the boiling point of the solvent at standard atmospheric pressure. In some embodiments, the elevated temperature at which the solvent is provided is below that of the boiling point of the solvent at standard atmospheric pressure. For example, in some embodiments, the solvent is heated to a temperature below the boiling point prior to contacting the polymeric material. In some embodiments, the solvent is heated to a temperature at or above the boiling point, then allowed to condense and cool to a temperature below the boiling point prior to contacting the polymeric material. In some embodiments, the elevated temperature is above the boiling point at standard atmospheric pressure of the solvent. Achievement of temperatures above the normal boiling point may be achieved by providing the heated solvent under pressure.
  • the elevated temperature is from about 40°C to about 150°C, such as from about 45, about 50, about 55, about 60, about 65, about 70, about 75, about 80, about 85, about 90, about 95, or about 100, to about 110, about 120, about 130, about 140, or about 150°C. In some embodiments, the elevated temperature is from about 50°C to about 100°C.
  • the solvent may be heated in various manners, such as exposing the solvent to a conventional (e.g., radiant, convective, or direct contact) thermal source, or by exposure to microwave irradiation.
  • a conventional thermal source e.g., radiant, convective, or direct contact
  • microwave irradiation e.g., microwave irradiation
  • contacting the waste polymeric packaging material with the solvent comprises continuously contacting the waste polymeric packaging material with fresh heated solvent.
  • the extracting may be performed in a Soxhlet apparatus 500 as illustrated in FIG. 5.
  • solvent is placed in a flask 502, which is heated by a heat source such as a heating mantle 504. Vaporized solvent then travels through the Soxhlet extraction body 506 and condenses in a water-cooled condenser 508. The condensed solvent then fills the Soxhlet extraction body 506, which has disposed therein the polymeric material. Once the solvent reaches a predetermined level, gravity and a siphoning effect draw the solvent back into the flask 502.
  • contacting the waste polymeric packaging material with the solvent may be conducted in a sealed environment, under pressure, with microwave heating.
  • the extracting may be performed in a standard microwave device using a sealed tube to house the solvent and polymeric material.
  • a sealed container refers to a container sealed such that there is no gas exchange between the interior of the container and the exterior environment surrounding the container.
  • the length of time for which the waste polymeric packaging material is contacted with the solvent may vary depending on various factors (solvent, temperature, pressure, and the like). In some embodiments, the period of time is from about 30 minutes to about 48 hours, such as about 30 minutes, about 1 hour, about 1.5 hours, about 3 hours, about 6 hours, about 12 hours, about 24 hours, or about 48 hours. Higher temperatures, increased surface area of polymeric material, and enhanced contact with solvent may all reduce the period of time necessary to achieve substantial removal of the residual nicotine (i.e., providing decontaminated waste polymeric packaging material).
  • the waste polymeric packaging material so obtained is suitable for recycling, containing a nicotine in an amount of about 0.25% or less, such as 0.25%, 0.2%, 0.15%, 0.1%, 0.05%, 0.01%, 0.001%, 0.0001%, or even 0%.
  • Detectors used for nicotine solvent analysis are gas chromatography mass spectrometry or liquid chromatography ultraviolet/mass spectrometry as set forth in Examples 3 and 4 herein.
  • the method for extracting nicotine from a waste polymeric packaging material can involve heating the waste polymeric packaging material above the vaporization point for nicotine, which at one atmosphere, is 247 °C, for a time sufficient to drive off a significant amount of nicotine vapor from the waste polymeric packaging material.
  • An example time period is from about 30 minutes to about 48 hours, such as about 30 minutes, about 1 hour, about 1.5 hours, about 3 hours, about 6 hours, about 12 hours, about 24 hours, or about 48 hours. If charring or melting of the waste polymeric material is not desired during the process, the type of polymeric material involved should be taken into consideration when determining the viability of this alternative process.
  • the heating can be accomplished using any known means of heating, including use of heat sources configured to heat the waste polymeric packaging material by radiant heat, convection, or by direct thermal contact.
  • this nicotine extraction process can be combined with melting of the waste polymeric packaging material as part of a recycling process. In other words, the heating required to melt the waste polymeric packaging material will also result in vaporization of nicotine from the material.
  • the above alternative process can be combined with a system for treating the nicotine-rich vapor leaving the waste polymeric packaging material such as through use of a stripper to remove nicotine from the vapor prior to release of the vapor to the atmosphere.
  • a stripping column containing activated carbon or another porous adsorbent can be used.
  • Example 1 General procedure for determination of extraction efficiency of plastic sample by pyrolvsis- gas chromatography [0123] A sample of the appropriate plastic material (2 mg sample weight) is vaporized with a pyrolysis accessory (filament type Pyroprobe Model 5200 with auto sampler; CDS Analytical, CDS, Oxford, PA 19363, USA), and the resulting vapor injected onto an Agilent 7890B/5977B GC/MS with a High Efficiency Source (HES; Agilent; Wilmington, DE 19808, USA) using a DB-1701 type column. The pyrolysis is performed in flash mode in helium at a pyrolysis temperature Teq of 350°C. The total heating time THt is 20 seconds, and the heating rate is 20°C/ms. The GC/MS analysis parameters are listed in Table 1.
  • a sample of plastic material is placed into a Soxhlet apparatus for nicotine extraction.
  • a single sachet is cut into 1 cm pieces, the pieces placed into a cellulose thimble and weighted with glass beads, and the thimble placed into a Soxhlet apparatus.
  • an entire VELOTM can is cut into small pieces and the pieces added directly to the Soxhlet apparatus.
  • the Soxhlet apparatus is equipped with a 150 mL round bottom flask containing 125 ml of methanol. When heated to the boiling point, the condensing methanol in contact with the sample is approximately 45 °C. The extraction is performed for 48 hours.
  • Nicotine content of methanol extracts is determined by LCMS using a UPLC system (Waters) using an XTERRA RP18 3.0 X 50 mm, 5 gm column.
  • the mobile phase is Solvent A: 95:5 Water/Methano 1/0.1% formic acid at pH 9.5.
  • Solvent B is methanol with 0.1% formic acid at pH 9.5. All solvents are adjusted to pH with ammonium hydroxide.
  • the LC gradient is provided in Table 2. Positive mode mass spectrometry is used with single ion monitoring of 163.0 Da at a 15-volt cone voltage. Samples may need to be diluted for analysis with mass spectrometry.
  • An Agilent7890A GCMS system is used to quantitate nicotine and monitor levels of nicotine-related compounds such as beta-nicotyrine, nicotine N'-oxide, myosmine, and cotinine. All samples are injected in triplicate and the standard deviation accounted for analytical and sample variation. Quantitation is done with an external calibration curve of pure nicotine standards with seven different calibration points (31.25, 15.63, 7.81, 3.91, 1.95, 0.98, and 0.49 pg/mL). To report values below the LOQ, the lowest calibration standard of 0.49 pg/mL is converted to % nicotine with the mass of the sample.
  • the GCMS parameters for nicotine quantitation are provided in Table 3.
  • Example 5 Determination of nicotine content in sachet packaging
  • VELOTM polypropylene sachet packaging having contained VELOTM pouches (6 mg nicotine) for approximately 1 year was assayed for residual nicotine content according to the procedures in Examples 1 and 2.
  • GCMS pyrolysis (Example 1) performed on a sample before and after a 48-hour Soxhlet extraction (Example 2) demonstrated a 50% decrease in nicotine concentration.
  • the nicotine concentration in the sample after the Soxhlet extraction was 0.0047% by weight; however, as noted, the extraction efficiency was only 50% based on the comparative pyrolysis data. It is believed the thimble constricted solvent flow which means the sachet pieces had less contact with the solvent. Subsequent experiments with no thimble showed a 90% or greater extraction of nicotine.
  • GCMS pyrolysis (Example 1) performed on a sample before and after a 48-hour Soxhlet extraction (Example 2) demonstrated a 98% decrease in nicotine concentration following the extraction. Specifically, the nicotine concentration in the sample after the Soxhlet extraction was 0.0004% by weight.
  • Example 7 Determination of nicotine content in sachet and can packaging
  • a VELOTM rigid can container previously utilized to store pouches of a nicotine-containing composition (10.9 mg nicotine; stored 14 months) was subjected to cryogrinding to form packaging particles and 100 mg aliquots were sealed in cylindrical vessels with 10 mL of methanol. The vessels were heated in a CEM Mars 6 microwave (final temp: 100 °C; ramp time 25 minutes, hold time: 45 minutes; cool time: 45 minutes). Pyrograms of the sample, obtained according to Example 1, are provided as FIGS. 6A and 6B (before and after extraction, respectively). With reference to FIGS. 6A and 6B, when normalized to sample mass, the extraction efficiency was 94% and the average % residual nicotine was 0.082% (s.d. of 0.001).
  • a laminated sachet is cut into pieces, and the pieces submerged in hydrochloric or sulfuric acid at a concentration suitable to dissolve the aluminum layer.
  • the remaining plastic layers are then subjected to micro wave accelerated nicotine extraction in a CEM Mars 6 micro wave (10 mL of methanol; final temp: 100°C; ramp time 25 minutes, hold time: 45 minutes; cool time: 45 minutes).
  • Extraction efficiency should be equal to or better than the polypropylene microwave extraction due to the lower density plastic.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Sustainable Development (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Environmental & Geological Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Packages (AREA)

Abstract

L'invention concerne un procédé d'extraction de nicotine à partir de matériaux d'emballage polymères usagés utilisés précédemment pour le stockage de produits contenant de la nicotine. Le procédé comprend la réalisation d'une extraction par solvant de nicotine résiduelle à partir des matériaux d'emballage polymères usagés pour fournir des matériaux d'emballage polymères usagés appropriés pour le recyclage et comprenant moins de 0,25% en poids de nicotine résiduelle.
PCT/IB2024/059111 2023-09-22 2024-09-19 Extraction de nicotine à partir de matériaux d'emballage en plastique Pending WO2025062340A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202363539861P 2023-09-22 2023-09-22
US63/539,861 2023-09-22

Publications (1)

Publication Number Publication Date
WO2025062340A1 true WO2025062340A1 (fr) 2025-03-27

Family

ID=93211677

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2024/059111 Pending WO2025062340A1 (fr) 2023-09-22 2024-09-19 Extraction de nicotine à partir de matériaux d'emballage en plastique

Country Status (1)

Country Link
WO (1) WO2025062340A1 (fr)

Citations (84)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1376586A (en) 1918-04-06 1921-05-03 Schwartz Francis Tobacco-tablet
US2033909A (en) 1934-12-19 1936-03-17 Niacet Chemicals Corp Manufacture of calcium levulinate
US3368567A (en) 1965-03-23 1968-02-13 Morton Pharmaceuticals Inc Method of producing a tablet containing a tobacco concentrate
US3901248A (en) 1970-07-22 1975-08-26 Leo Ab Chewable smoking substitute composition
US4098421A (en) 1977-06-24 1978-07-04 J. L. Clark Manufacturing Co. Container for snuff or the like
US4190170A (en) 1979-01-15 1980-02-26 United States Tobacco Company Snuff can and the like
US4513756A (en) 1983-04-28 1985-04-30 The Pinkerton Tobacco Company Process of making tobacco pellets
US4606357A (en) 1984-11-19 1986-08-19 Dusek Russell L Tobacco composition
US4624269A (en) 1984-09-17 1986-11-25 The Pinkerton Tobacco Company Chewable tobacco based product
US4802498A (en) 1987-07-02 1989-02-07 Warren Ogren Resin-based chewing tobacco
US4821749A (en) 1988-01-22 1989-04-18 R. J. Reynolds Tobacco Company Extruded tobacco materials
US4975270A (en) 1987-04-21 1990-12-04 Nabisco Brands, Inc. Elastomer encased active ingredients
US5167244A (en) 1990-01-19 1992-12-01 Kjerstad Randy E Tobacco substitute
US5387416A (en) 1993-07-23 1995-02-07 R. J. Reynolds Tobacco Company Tobacco composition
DE19839147A1 (de) * 1998-08-28 2000-03-02 Marzinkowski Joachim M Verfahren zur Aufbereitung von gebrauchtem Kunststoffmaterial sowie Vorrichtung zur Durchführung dieses Verfahrens
US6668839B2 (en) 2001-05-01 2003-12-30 Jonnie R. Williams Smokeless tobacco product
US20040191322A1 (en) 2002-12-20 2004-09-30 Henri Hansson Physically and chemically stable nicotine-containing particulate material
US6834654B2 (en) 2001-05-01 2004-12-28 Regent Court Technologies, Llc Smokeless tobacco product
US6953040B2 (en) 2001-09-28 2005-10-11 U.S. Smokeless Tobacco Company Tobacco mint plant material product
US20050244521A1 (en) 2003-11-07 2005-11-03 Strickland James A Tobacco compositions
US7014039B2 (en) 2003-06-19 2006-03-21 R.J. Reynolds Tobacco Company Sliding shell package for smoking articles
US7032601B2 (en) 2001-09-28 2006-04-25 U.S. Smokeless Tobacco Company Encapsulated materials
US20060191548A1 (en) 2003-11-07 2006-08-31 Strickland James A Tobacco compositions
US20080029116A1 (en) 2006-08-01 2008-02-07 John Howard Robinson Smokeless tobacco
US20080173317A1 (en) 2006-08-01 2008-07-24 John Howard Robinson Smokeless tobacco
USD574709S1 (en) 2007-08-03 2008-08-12 R.J. Reynolds Tobacco Company Container
US20080196730A1 (en) 2004-07-02 2008-08-21 Radi Medical Systems Ab Smokeless Tobacco Product
US20080202956A1 (en) 2007-02-28 2008-08-28 J.L. Clark, Inc. Lid For Tobacco Can
US20080305216A1 (en) 2007-06-08 2008-12-11 Philip Morris Usa Inc. Capsule clusters for oral consumption
US20090014343A1 (en) 2007-05-07 2009-01-15 Philip Morris Usa Inc. Pocket-size hybrid container for consumer items
US20090014450A1 (en) 2003-08-18 2009-01-15 Gustavus Ab Snuff-box lid
US7537110B2 (en) 2005-06-02 2009-05-26 Philip Morris Usa Inc. Container for consumer article
USD592956S1 (en) 2008-02-08 2009-05-26 Philip Morris Usa Inc. Container
USD594154S1 (en) 2007-11-13 2009-06-09 R.J. Reynolds Tobacco Company Container with bottom compartment
US7584843B2 (en) 2005-07-18 2009-09-08 Philip Morris Usa Inc. Pocket-size hand-held container for consumer items
US20090223989A1 (en) 2008-03-04 2009-09-10 R.J. Reynolds Tobacco Company Dispensing Container
US20090230003A1 (en) 2008-02-08 2009-09-17 Philip Morris Usa Inc. Pocket-sized container
US20090250360A1 (en) 2007-11-30 2009-10-08 Philip Morris Usa Inc. Pocket-size container for consumer items
US20090266837A1 (en) 2008-04-25 2009-10-29 R. J. Reynolds Tobacco Company Dispensing Container
US20090293889A1 (en) 2007-11-28 2009-12-03 Philip Morris Usa Inc. Smokeless compressed tobacco product for oral consumption
US20100012534A1 (en) 2008-07-18 2010-01-21 J.L. Clark, Inc. Lid for tobacco container
US20100018883A1 (en) 2008-07-28 2010-01-28 Pankaj Patel Smokeless tobacco products and processes
US20100065077A1 (en) 2006-11-28 2010-03-18 Caroline Lofgreen-Ohrn Snuff box
US20100084424A1 (en) 2006-12-12 2010-04-08 John Gelardi Container with pivoting cover
US7694686B2 (en) 2003-12-22 2010-04-13 U.S. Smokeless Tobacco Company Conditioning process for tobacco and/or snuff compositions
US20100133140A1 (en) 2008-12-01 2010-06-03 Bailey Ryan A Dual cavity sliding dispenser
USD625178S1 (en) 2009-04-16 2010-10-12 R.J. Reynolds Tobacco Company, Inc. Container with hinged insert
US7810507B2 (en) 2006-02-10 2010-10-12 R. J. Reynolds Tobacco Company Smokeless tobacco composition
US20100264157A1 (en) 2009-04-16 2010-10-21 R.J. Reynolds Tobacco Company Dispensing container for metered dispensing of product
US7819124B2 (en) 2006-01-31 2010-10-26 U.S. Smokeless Tobacco Company Tobacco articles and methods
US20100291245A1 (en) 2008-12-08 2010-11-18 Philip Morris Usa Inc. Soft, chewable and orally dissolvable and/or disintegrable products
US7861728B2 (en) 2006-02-10 2011-01-04 R.J. Reynolds Tobacco Company Smokeless tobacco composition having an outer and inner pouch
US7901512B2 (en) 2003-11-03 2011-03-08 U.S. Smokeless Tobacco Company Flavored smokeless tobacco and methods of making
US20110139164A1 (en) 2009-12-15 2011-06-16 R. J. Reynolds Tobacco Company Tobacco Product And Method For Manufacture
US20110168712A1 (en) 2010-01-12 2011-07-14 R.J. Reynolds Tobacco Company Dispensing container
US20120024301A1 (en) 2010-04-14 2012-02-02 Altria Client Services Inc. Preformed Smokeless Tobacco Product
US20120037175A1 (en) 2010-08-11 2012-02-16 R.J. Reynolds Tobacco Company Meltable smokeless tobacco composition
US20120055494A1 (en) 2010-09-07 2012-03-08 Rj Reynolds Tobacco Company Smokeless Tobacco Product Comprising Effervescent Composition
US20120138074A1 (en) 2010-12-01 2012-06-07 Rj Reynolds Tobacco Company Smokeless tobacco pastille and moulding process for forming smokeless tobacco products
US20120138073A1 (en) 2010-12-01 2012-06-07 Rj Reynolds Tobacco Company Smokeless tobacco pastille and injection molding process for forming smokeless tobacco products
US20120193265A1 (en) 2011-01-31 2012-08-02 American Snuff Company, Llc Container for smokeless tobacco products
US8397945B2 (en) 2010-02-23 2013-03-19 R.J. Reynolds Tobacco Company Dispensing container
US20130074855A1 (en) 2011-09-22 2013-03-28 R.J. Reynolds Tobacco Company Translucent smokeless tobacco product
US20130074856A1 (en) 2011-09-22 2013-03-28 R.J. Reynolds Tobacco Company Translucent smokeless tobacco product
US8440023B2 (en) 2009-10-09 2013-05-14 Philip Morris Usa Inc. Flavored packaging insert for smokeless tobacco
US8458996B2 (en) 2008-03-11 2013-06-11 U.S. Smokeless Tobacco Company Container device for tobacco articles
US20130152953A1 (en) 2011-12-14 2013-06-20 R. J. Reynolds Tobacco Company Smokeless tobacco product comprising effervescent composition
US20130206153A1 (en) 2012-02-13 2013-08-15 R.J. Reynolds Tobacco Company Whitened tobacco composition
US20130274296A1 (en) 2012-04-17 2013-10-17 R.J. Reynolds Tobacco Company Remelted ingestible products
US8567597B2 (en) 2008-12-12 2013-10-29 British American Tobacco (Investments) Limited Compartmented container for snus
US20140197054A1 (en) 2013-01-11 2014-07-17 R.J. Reynolds Tobacco Company Container for smokeless tobacco products and related packaged product assembly and method
US20150068545A1 (en) 2013-09-09 2015-03-12 R.J. Reynolds Tobacco Company Smokeless tobacco composition incorporating a botanical material
US20150101627A1 (en) 2013-10-16 2015-04-16 R.J. Reynolds Tobacco Company Smokeless tobacco pastille
US20150230515A1 (en) 2014-02-14 2015-08-20 R.J. Reynolds Tobacco Company Tobacco-containing gel composition
WO2020221920A1 (fr) * 2019-05-01 2020-11-05 Novochem Green Additives 4 B.V. Composition de recyclage eutectique
US20210068446A1 (en) 2019-09-11 2021-03-11 R. J. Reynolds Tobacco Company Oral product with cellulosic flavor stabilizer
US20210169889A1 (en) 2019-12-09 2021-06-10 Nicoventures Trading Limited Oral products
US20210330590A1 (en) 2019-12-09 2021-10-28 Nicoventures Trading Limited Agents for oral composition
US11246334B2 (en) 2009-05-11 2022-02-15 Altria Client Services Llc Method and device for flavoring smokeless tobacco
US20220071280A1 (en) 2020-09-04 2022-03-10 Nicoventures Trading Limited Child-resistant container for tobacco-containing products
US20220071984A1 (en) 2019-09-11 2022-03-10 Nicoventures Trading Limited Oral product with nicotine and ion pairing agent
US20220104543A1 (en) 2020-09-04 2022-04-07 Nicoventures Trading Limited Child-resistant container for tobacco-containing products
US20220160675A1 (en) 2020-11-25 2022-05-26 Nicoventures Trading Limited Oral cannabinoid product with lipid component
US20220297893A1 (en) 2021-03-18 2022-09-22 Nicoventures Trading Limited Multi-compartment containers

Patent Citations (87)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1376586A (en) 1918-04-06 1921-05-03 Schwartz Francis Tobacco-tablet
US2033909A (en) 1934-12-19 1936-03-17 Niacet Chemicals Corp Manufacture of calcium levulinate
US3368567A (en) 1965-03-23 1968-02-13 Morton Pharmaceuticals Inc Method of producing a tablet containing a tobacco concentrate
US3901248A (en) 1970-07-22 1975-08-26 Leo Ab Chewable smoking substitute composition
US4098421A (en) 1977-06-24 1978-07-04 J. L. Clark Manufacturing Co. Container for snuff or the like
US4190170A (en) 1979-01-15 1980-02-26 United States Tobacco Company Snuff can and the like
US4513756A (en) 1983-04-28 1985-04-30 The Pinkerton Tobacco Company Process of making tobacco pellets
US4624269A (en) 1984-09-17 1986-11-25 The Pinkerton Tobacco Company Chewable tobacco based product
US4606357A (en) 1984-11-19 1986-08-19 Dusek Russell L Tobacco composition
US4975270A (en) 1987-04-21 1990-12-04 Nabisco Brands, Inc. Elastomer encased active ingredients
US4802498A (en) 1987-07-02 1989-02-07 Warren Ogren Resin-based chewing tobacco
US4821749A (en) 1988-01-22 1989-04-18 R. J. Reynolds Tobacco Company Extruded tobacco materials
US5167244A (en) 1990-01-19 1992-12-01 Kjerstad Randy E Tobacco substitute
US5387416A (en) 1993-07-23 1995-02-07 R. J. Reynolds Tobacco Company Tobacco composition
DE19839147A1 (de) * 1998-08-28 2000-03-02 Marzinkowski Joachim M Verfahren zur Aufbereitung von gebrauchtem Kunststoffmaterial sowie Vorrichtung zur Durchführung dieses Verfahrens
US6668839B2 (en) 2001-05-01 2003-12-30 Jonnie R. Williams Smokeless tobacco product
US6834654B2 (en) 2001-05-01 2004-12-28 Regent Court Technologies, Llc Smokeless tobacco product
US7032601B2 (en) 2001-09-28 2006-04-25 U.S. Smokeless Tobacco Company Encapsulated materials
US6953040B2 (en) 2001-09-28 2005-10-11 U.S. Smokeless Tobacco Company Tobacco mint plant material product
US20040191322A1 (en) 2002-12-20 2004-09-30 Henri Hansson Physically and chemically stable nicotine-containing particulate material
US7014039B2 (en) 2003-06-19 2006-03-21 R.J. Reynolds Tobacco Company Sliding shell package for smoking articles
US20090014450A1 (en) 2003-08-18 2009-01-15 Gustavus Ab Snuff-box lid
US7901512B2 (en) 2003-11-03 2011-03-08 U.S. Smokeless Tobacco Company Flavored smokeless tobacco and methods of making
US20050244521A1 (en) 2003-11-07 2005-11-03 Strickland James A Tobacco compositions
US20060191548A1 (en) 2003-11-07 2006-08-31 Strickland James A Tobacco compositions
US8627828B2 (en) 2003-11-07 2014-01-14 U.S. Smokeless Tobacco Company Llc Tobacco compositions
US7694686B2 (en) 2003-12-22 2010-04-13 U.S. Smokeless Tobacco Company Conditioning process for tobacco and/or snuff compositions
US20080196730A1 (en) 2004-07-02 2008-08-21 Radi Medical Systems Ab Smokeless Tobacco Product
US7537110B2 (en) 2005-06-02 2009-05-26 Philip Morris Usa Inc. Container for consumer article
US7584843B2 (en) 2005-07-18 2009-09-08 Philip Morris Usa Inc. Pocket-size hand-held container for consumer items
US7819124B2 (en) 2006-01-31 2010-10-26 U.S. Smokeless Tobacco Company Tobacco articles and methods
US7861728B2 (en) 2006-02-10 2011-01-04 R.J. Reynolds Tobacco Company Smokeless tobacco composition having an outer and inner pouch
US7810507B2 (en) 2006-02-10 2010-10-12 R. J. Reynolds Tobacco Company Smokeless tobacco composition
US20080173317A1 (en) 2006-08-01 2008-07-24 John Howard Robinson Smokeless tobacco
US20080029116A1 (en) 2006-08-01 2008-02-07 John Howard Robinson Smokeless tobacco
US20100065076A1 (en) 2006-11-28 2010-03-18 Niklas Bergstrom Snuff box
US20100065077A1 (en) 2006-11-28 2010-03-18 Caroline Lofgreen-Ohrn Snuff box
US20100084424A1 (en) 2006-12-12 2010-04-08 John Gelardi Container with pivoting cover
US20080202956A1 (en) 2007-02-28 2008-08-28 J.L. Clark, Inc. Lid For Tobacco Can
US20090014343A1 (en) 2007-05-07 2009-01-15 Philip Morris Usa Inc. Pocket-size hybrid container for consumer items
US20080305216A1 (en) 2007-06-08 2008-12-11 Philip Morris Usa Inc. Capsule clusters for oral consumption
USD574709S1 (en) 2007-08-03 2008-08-12 R.J. Reynolds Tobacco Company Container
USD649284S1 (en) 2007-11-13 2011-11-22 R.J. Reynolds Tobacco Company Container with bottom compartment
USD594154S1 (en) 2007-11-13 2009-06-09 R.J. Reynolds Tobacco Company Container with bottom compartment
US20090293889A1 (en) 2007-11-28 2009-12-03 Philip Morris Usa Inc. Smokeless compressed tobacco product for oral consumption
US20090250360A1 (en) 2007-11-30 2009-10-08 Philip Morris Usa Inc. Pocket-size container for consumer items
USD592956S1 (en) 2008-02-08 2009-05-26 Philip Morris Usa Inc. Container
US20090230003A1 (en) 2008-02-08 2009-09-17 Philip Morris Usa Inc. Pocket-sized container
US20090223989A1 (en) 2008-03-04 2009-09-10 R.J. Reynolds Tobacco Company Dispensing Container
US8458996B2 (en) 2008-03-11 2013-06-11 U.S. Smokeless Tobacco Company Container device for tobacco articles
US20090266837A1 (en) 2008-04-25 2009-10-29 R. J. Reynolds Tobacco Company Dispensing Container
US20100012534A1 (en) 2008-07-18 2010-01-21 J.L. Clark, Inc. Lid for tobacco container
US20100018883A1 (en) 2008-07-28 2010-01-28 Pankaj Patel Smokeless tobacco products and processes
US20100133140A1 (en) 2008-12-01 2010-06-03 Bailey Ryan A Dual cavity sliding dispenser
US20100291245A1 (en) 2008-12-08 2010-11-18 Philip Morris Usa Inc. Soft, chewable and orally dissolvable and/or disintegrable products
US8567597B2 (en) 2008-12-12 2013-10-29 British American Tobacco (Investments) Limited Compartmented container for snus
USD625178S1 (en) 2009-04-16 2010-10-12 R.J. Reynolds Tobacco Company, Inc. Container with hinged insert
US20100264157A1 (en) 2009-04-16 2010-10-21 R.J. Reynolds Tobacco Company Dispensing container for metered dispensing of product
US11246334B2 (en) 2009-05-11 2022-02-15 Altria Client Services Llc Method and device for flavoring smokeless tobacco
US8440023B2 (en) 2009-10-09 2013-05-14 Philip Morris Usa Inc. Flavored packaging insert for smokeless tobacco
US20110139164A1 (en) 2009-12-15 2011-06-16 R. J. Reynolds Tobacco Company Tobacco Product And Method For Manufacture
US20110168712A1 (en) 2010-01-12 2011-07-14 R.J. Reynolds Tobacco Company Dispensing container
US8397945B2 (en) 2010-02-23 2013-03-19 R.J. Reynolds Tobacco Company Dispensing container
US20120024301A1 (en) 2010-04-14 2012-02-02 Altria Client Services Inc. Preformed Smokeless Tobacco Product
US20120037175A1 (en) 2010-08-11 2012-02-16 R.J. Reynolds Tobacco Company Meltable smokeless tobacco composition
US20120055494A1 (en) 2010-09-07 2012-03-08 Rj Reynolds Tobacco Company Smokeless Tobacco Product Comprising Effervescent Composition
US20120138074A1 (en) 2010-12-01 2012-06-07 Rj Reynolds Tobacco Company Smokeless tobacco pastille and moulding process for forming smokeless tobacco products
US20120138073A1 (en) 2010-12-01 2012-06-07 Rj Reynolds Tobacco Company Smokeless tobacco pastille and injection molding process for forming smokeless tobacco products
US20120193265A1 (en) 2011-01-31 2012-08-02 American Snuff Company, Llc Container for smokeless tobacco products
US20130074855A1 (en) 2011-09-22 2013-03-28 R.J. Reynolds Tobacco Company Translucent smokeless tobacco product
US20130074856A1 (en) 2011-09-22 2013-03-28 R.J. Reynolds Tobacco Company Translucent smokeless tobacco product
US20130152953A1 (en) 2011-12-14 2013-06-20 R. J. Reynolds Tobacco Company Smokeless tobacco product comprising effervescent composition
US20130206153A1 (en) 2012-02-13 2013-08-15 R.J. Reynolds Tobacco Company Whitened tobacco composition
US20130274296A1 (en) 2012-04-17 2013-10-17 R.J. Reynolds Tobacco Company Remelted ingestible products
US20140197054A1 (en) 2013-01-11 2014-07-17 R.J. Reynolds Tobacco Company Container for smokeless tobacco products and related packaged product assembly and method
US20150068545A1 (en) 2013-09-09 2015-03-12 R.J. Reynolds Tobacco Company Smokeless tobacco composition incorporating a botanical material
US20150101627A1 (en) 2013-10-16 2015-04-16 R.J. Reynolds Tobacco Company Smokeless tobacco pastille
US20150230515A1 (en) 2014-02-14 2015-08-20 R.J. Reynolds Tobacco Company Tobacco-containing gel composition
WO2020221920A1 (fr) * 2019-05-01 2020-11-05 Novochem Green Additives 4 B.V. Composition de recyclage eutectique
US20210068446A1 (en) 2019-09-11 2021-03-11 R. J. Reynolds Tobacco Company Oral product with cellulosic flavor stabilizer
US20220071984A1 (en) 2019-09-11 2022-03-10 Nicoventures Trading Limited Oral product with nicotine and ion pairing agent
US20210330590A1 (en) 2019-12-09 2021-10-28 Nicoventures Trading Limited Agents for oral composition
US20210169889A1 (en) 2019-12-09 2021-06-10 Nicoventures Trading Limited Oral products
US20220071280A1 (en) 2020-09-04 2022-03-10 Nicoventures Trading Limited Child-resistant container for tobacco-containing products
US20220104543A1 (en) 2020-09-04 2022-04-07 Nicoventures Trading Limited Child-resistant container for tobacco-containing products
US20220160675A1 (en) 2020-11-25 2022-05-26 Nicoventures Trading Limited Oral cannabinoid product with lipid component
US20220297893A1 (en) 2021-03-18 2022-09-22 Nicoventures Trading Limited Multi-compartment containers

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BUSSEY OWEN ET AL: "Nicotine Extraction from Polypropylene Modern Oral Packaging", 1 November 2023 (2023-11-01), pages 1 - 1, XP093236027, Retrieved from the Internet <URL:https://www.coresta.org/sites/default/files/abstracts/2023_TSRC76_Bussey.pdf> [retrieved on 20241220] *
PERFETTI, BEITRAGE TABAKFORSCHUNG INT., vol. 12, 1983, pages 43 - 54

Similar Documents

Publication Publication Date Title
JP6845875B2 (ja) 容器
DK2986532T3 (en) CONTAINER WITH SUBSTANCE CARRIER
JP6464207B2 (ja) 無煙タバコ製品用容器
EP2986170B1 (fr) Récipient comprenant une première chambre et une seconde chambre
US20100018883A1 (en) Smokeless tobacco products and processes
US20110303511A1 (en) Smokeless tobacco products and processes
WO2010014506A2 (fr) Produits du tabac sans fumée et procédés
CA2926375A1 (fr) Traitement du tabac
GB2561266A (en) Carrier, apparatus and method
WO2012061192A1 (fr) Produits du tabac sans fumée et processus associés
JP2015013647A (ja) シガレット類包装製品
JP2023120351A (ja) 送達ビヒクル
EP2986171B1 (fr) Récipient
WO2025062340A1 (fr) Extraction de nicotine à partir de matériaux d&#39;emballage en plastique
WO2020208106A1 (fr) Support et son procédé d&#39;utilisation
EP3721722A1 (fr) Procédé de fabrication
HK40015555A (en) Tobacco treatment
HK1222994B (en) Tobacco treatment

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 24793887

Country of ref document: EP

Kind code of ref document: A1