WO2025062340A1 - Nicotine extraction from plastic packaging materials - Google Patents

Abstract

The disclosure provides a method of extracting nicotine from waste polymeric packaging materials previously used for storage of nicotine-containing products. The method includes performing solvent extraction of residual nicotine from the waste polymeric packaging materials to provide waste polymeric packaging materials suitable for recycling and having less than 0.25% by weight of residual nicotine.

Description

NICOTINE EXTRACTION FROM PLASTIC PACKAGING MATERIALS

CROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This application claims priority to U.S. Provisional Application No. 63/539,861, filed September 22, 2023, and which is herein incorporated by reference in its entirety.

TECHNICAL FIELD

[0002] The present disclosure relates to methods for decontaminating waste polymeric packaging materials formerly utilized in the storage of tobacco and/or nicotine-containing products, and to waste polymeric packaging materials suitable for recycling.

BACKGROUND

[0003] There are many categories of products intended for oral use and enjoyment. For example, oral tobacco products containing nicotine, which is known to have both stimulant and anxiolytic properties, have been available for many years. Conventional formats for so-called "smokeless" tobacco products include moist snuff, snus, and chewing tobacco, which are typically formed almost entirely of particulate, granular, or shredded tobacco, and which are either portioned by the user or presented to the user in individual portions, such as in single-use pouches. More recent product formats contain purified nicotine, such as pouched products containing a powdered or granular composition, lozenges, pastilles, liquids, gels, emulsions, meltable compositions, and the like. See for example, the types of products set forth in U.S. Pat. Nos. 6,668,839 to Williams; 7,810,507 to Dube et al.; and 8,627,828 to Strickland et al.; as well as US Patent App. Pub. Nos. 2010/0291245 to Gao et al; 2011/0139164 to Mua et al.; 2012/0037175 to Cantrell et al.; 2015/0230515 to Lampe et al., 2021/0330590 to Hutchens et al.; 2022/0160675 to Gerardi et al.; and 2022/0071984 to Poole et al., each of which is incorporated herein by reference.

[0004] Such tobacco or nicotine-containing products are generally stored in polymeric packaging, for example, plastic pouches and/or plastic cans. It is generally desirable to recycle, reuse, or alternatively, safely dispose of such plastic materials once the product has been consumed. Particularly, it is desirable to recycle such polymeric materials to conserve resources and avoid the environmental impact of landfill disposal. However, over time, a portion of the nicotine in the products may migrate from the product and be adsorbed or absorbed onto or into the polymeric material of the packaging. The presence of this residual nicotine may reduce the options available for disposal or recycling of such materials. For example, in certain countries, the residual nicotine content must be less than 0.25% by weight in order for the plastic material to be deemed suitable for recycling. BRIEF SUMMARY

[0005] The present disclosure generally provides methods for extracting nicotine from waste polymeric packaging materials previously used for storage of a product comprising nicotine. To be suitable for recycling, such waste polymeric materials must be substantially free of residual contaminants such as nicotine. While rinsing with an organic solvent is generally adequate to eliminate surface contamination, it has not been proven to efficiently extract contaminants (e.g., nicotine) within the polymer matrix. The method of the present disclosure can also be used as a quality control method to determine if nicotine extraction is necessary. In other words, the nicotine extraction methods noted herein can be applied to a sample of a waste packaging material to determine if large-scale nicotine extraction of the waste material is necessary to meet nicotine content guidelines for recyclability.

[0006] Accordingly, in one aspect is provided a method for extracting nicotine from a waste polymeric packaging material comprising residual nicotine, the method comprising: i) receiving the waste polymeric packaging material comprising residual nicotine at a first nicotine concentration; ii) extracting at least a portion of the residual nicotine from the waste polymeric packaging material, wherein the extracting comprises contacting the waste polymeric packaging material with a solvent at an elevated temperature, forming a decontaminated waste polymeric packaging material having a second nicotine concentration, the second nicotine concentration being lower than the first nicotine concentration; and iii) separating the decontaminated waste polymeric packaging material from the solvent.

[0007] In some embodiments, 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.

[0008] In some embodiments, the waste polymeric packaging material comprises polypropylene, low-density polyethylene, or a combination thereof.

[0009] In some embodiments, the waste polymeric packaging material comprises residual nicotine at a first nicotine concentration in an amount of about 0.01% by weight or higher, such as about 0.1% by weight or higher, such as about 0.3 % by weight to about 1.5% by weight, based on the total weight of the waste polymeric packaging material.

[0010] In some embodiments, the method further comprises dividing the waste polymeric packaging material into smaller pieces prior to the extracting.

[0011] In some embodiments, 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.

[0012] In some embodiments, 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.

[0013] In some embodiments, the solvent is a polar organic solvent or a nonpolar hydrocarbon solvent. [0014] In some embodiments, the solvent is a Cl to C3 alcohol. In some embodiments, the solvent is methanol or ethanol.

[0015] In some embodiments, the elevated temperature is above the boiling point at standard atmospheric pressure of the solvent.

[0016] In some embodiments, the elevated temperature is from about 40°C to about 150°C, or from about 50°C to about 100°C.

[0017] In some embodiments, 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.

[0018] In some embodiments, the heat source is configured to heat the solvent by microwave irradiation.

[0019] In some embodiments, contacting the waste polymeric packaging material with the solvent comprises continuously contacting the waste polymeric packaging material with fresh solvent.

[0020] In some embodiments, the extracting is performed using a Soxhlet apparatus.

[0021] In some embodiments, the extracting is conducted for a period of time, such as from about 30 minutes to about 48 hours.

[0022] In some embodiments, 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.

[0023] In some embodiments, the second nicotine concentration of the decontaminated waste polymeric packaging material is about 0.25% nicotine by weight or less, such as about 0.1% nicotine by weight or less, or about 0.0001% to about 0.01% nicotine by weight.

[0024] In some embodiments, the waste polymeric packaging material is a polymeric packaging material previously used for storage of a product comprising nicotine.

[0025] In another aspect is provided a waste polymeric packaging material suitable for recycling, the waste polymeric packaging material previously used for storage of a product comprising nicotine, the waste polymeric packaging material comprising nicotine in an amount from about 0.0001% to about 0.25% by weight.

[0026] In some embodiments, 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.

[0027] In some embodiments, the waste polymeric packaging material comprises polypropylene, low-density polyethylene, or a combination thereof.

[0028] The disclosure includes, without limitations, the following embodiments.

[0029] Embodiment 1: A method for extracting nicotine from a waste polymeric packaging material comprising residual nicotine, the method comprising: i) receiving the waste polymeric packaging material comprising residual nicotine at a first nicotine concentration; ii) extracting at least a portion of the residual nicotine from the waste polymeric packaging material, wherein the extracting comprises contacting the waste polymeric packaging material with a solvent at an elevated temperature, forming a decontaminated waste polymeric packaging material having a second nicotine concentration, the second nicotine concentration being lower than the first nicotine concentration; and iii) separating the decontaminated waste polymeric packaging material from the solvent.

[0030] Embodiment 2: The method of embodiment 1, wherein 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.

[0031] Embodiment 3 : The method of embodiment 1 or 2, wherein the waste polymeric packaging material comprises polypropylene, low-density polyethylene, or a combination thereof.

[0032] Embodiment 4: The method of any one of embodiments 1-3, wherein the waste polymeric packaging material comprises residual nicotine at a first nicotine concentration in an amount of about 0.01% by weight or higher, such as about 0.1% by weight or higher, such as about 0.3 % by weight to about 1.5% by weight, based on the total weight of the waste polymeric packaging material.

[0033] Embodiment 5: The method of any one of embodiments 1-4, further comprising dividing the waste polymeric packaging material into smaller pieces prior to the extracting.

[0034] 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.

[0035] 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. [0036] Embodiment 8: The method of any one of embodiments 1-7, wherein the solvent is a polar organic solvent or a nonpolar hydrocarbon solvent.

[0037] Embodiment 9: The method of any one of embodiments 1-8, wherein the solvent is methanol or ethanol.

[0038] 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.

[0039] 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.

[0040] Embodiment 12: The method of any one of embodiments 1-11, wherein 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.

[0041] Embodiment 13: The method of embodiment 12, wherein the heat source is configured to heat the solvent by microwave irradiation. [0042] Embodiment 14: The method of any one of embodiments 1-13, wherein contacting the waste polymeric packaging material with the solvent comprises continuously contacting the waste polymeric packaging material with fresh solvent.

[0043] Embodiment 15: The method of embodiment 14, wherein the extracting is performed using a Soxhlet apparatus.

[0044] Embodiment 16: The method of any one of embodiments 1-15, wherein the extracting is conducted for a period of time, such as from about 30 minutes to about 48 hours.

[0045] 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.

[0046] Embodiment 18: The method of any one of embodiments 1-17, wherein the second nicotine concentration of the decontaminated waste polymeric packaging material is about 0.25% nicotine by weight or less, such as about 0.1% nicotine by weight or less, or about 0.0001% to about 0.01% nicotine by weight.

[0047] Embodiment 19: The method of any one of embodiments 1-18, wherein the waste polymeric packaging material is a polymeric packaging material previously used for storage of a product comprising nicotine.

[0048] Embodiment 20: A waste polymeric packaging material suitable for recycling, the waste polymeric packaging material previously used for storage of a product comprising nicotine, the waste polymeric packaging material comprising nicotine in an amount from about 0.0001% to about 0.25% by weight.

[0049] Embodiment 21: The waste polymeric packaging material of embodiment 20, comprising 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.

[0050] Embodiment 22: The waste polymeric packaging material of embodiment 20, comprising polypropylene, low-density polyethylene, or a combination thereof.

[0051] These and other features, aspects, and advantages of the disclosure will be apparent from a reading of the following detailed description together with the accompanying drawing, which is briefly described below. The invention includes any combination of two, three, four, or more of the above-noted embodiments as well as combinations of any two, three, four, or more features or elements set forth in this disclosure, regardless of whether such features or elements are expressly combined in a specific embodiment description herein. This disclosure is intended to be read holistically such that any separable features or elements of the disclosed invention, in any of its various aspects and embodiments, should be viewed as intended to be combinable unless the context clearly dictates otherwise. BRIEF DESCRIPTION OF THE DRAWINGS

[0052] Having thus described aspects of the disclosure in the foregoing general terms, reference will now be made to the accompanying drawings, which are not necessarily drawn to scale. The drawings are exemplary only and should not be construed as limiting the disclosure.

[0053] 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. [0054] 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.

[0055] 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.

[0056] FIG. 4A is a perspective view of a rigid container for holding a nicotine product according to a nonlimiting embodiment of the present disclosure.

[0057] FIG. 4B is an exploded perspective view of the container of FIG. 4A according to a non-limiting embodiment of the present disclosure.

[0058] FIG. 5 is a Soxhlet apparatus according to a non-limiting embodiment of the present disclosure.

[0059] FIG. 6A is a pyrogram of a plastic sample prior to microwave accelerated extraction according to a non-limiting embodiment of the present disclosure.

[0060] FIG.6B is a pyrogram of a plastic sample after microwave accelerated extraction according to a nonlimiting embodiment of the present disclosure.

DETAILED DESCRIPTION

[0061] The present disclosure will now be described more fully hereinafter with reference to example embodiments thereof. These example embodiments are described so that this disclosure will be thorough and complete, and will fully convey the scope of the disclosure to those skilled in the art. Indeed, the disclosure may be embodied in many different forms and should not be construed as limited to the embodiments set forth herein; rather, these embodiments are provided so that this disclosure will satisfy applicable legal requirements.

[0062] As used in this specification and the claims, the singular forms "a," "an," and "the" include plural referents unless the context clearly dictates otherwise.

[0063] The term "about" used throughout this specification is used to describe and account for small fluctuations. For example, 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. [0064] Reference to "dry weight percent" or "dry weight basis" refers to weight on the basis of dry ingredients (i.e., all ingredients except water). Reference to "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).

[0065] The present disclosure provides a method for extracting nicotine from a waste polymeric packaging material, such as a container previously used for storage or dispensing of a product comprising nicotine (e.g., oral nicotine products), said waste polymeric packaging material comprising residual nicotine. The method generally comprises receiving the waste polymeric packaging material; extracting the residual nicotine from the waste polymeric packaging material; and separating the decontaminated waste polymeric packaging material from the solvent. Further provided is a waste polymeric packaging material suitable for recycling, the waste polymeric packaging material previously used for storage of a product comprising nicotine, the waste polymeric packaging material comprising nicotine in an amount from about 0.01% to about 0.25% by weight. The various method steps and waste polymeric packaging materials are further described herein below.

Nicotine Products

[0066] As used herein, the term "nicotine product" denotes any tobacco or nicotine-containing product, including tobacco materials intended for combustion (e.g., cigarette or pipe tobacco), dry snuff intended to be placed in the nasal cavity, and oral nicotine products configured for oral use and intended to be placed in the oral cavity of a user (e.g., between a user's lip or cheek and their gums and/or chewed) for a period of time, during which there is contact between the user's saliva and the product. The term "configured for oral use" as used herein means that the product is provided in a form such that during use, saliva in the mouth of the user causes one or more of the components of the product (e.g., flavoring agents and/or nicotine) to pass into the mouth of the user. In certain embodiments, the product is adapted to deliver components to a user through mucous membranes in the user's mouth and, in some instances, said component is an active ingredient (including, but not limited to, for example, nicotine) that can be absorbed through the mucous membranes in the mouth when the product is used. In some embodiments, the component is a taste substance (i.e., a volatile flavor component).

[0067] Conventional formats for oral nicotine products commonly referred to as “smokeless tobacco” include, for example, moist snuff, snus, and chewing tobacco, which are typically formed almost entirely of particulate, granular, or shredded tobacco, and which are either portioned by the user or presented to the user in individual portions, such as in single-use pouches or sachets.

[0068] Example loose form tobacco products may include tobacco formulations associated with, for example, commercially available GRIZZLY moist tobacco products and KODIAK moist tobacco products that are marketed by American Snuff Company, LLC. Other representative smokeless tobacco products that have been marketed include those referred to as CAMEL Orbs, CAMEL Strips and CAMEL Sticks by R. J. Reynolds Tobacco Company; LEVI GARRETT loose tobacco and TAYLOR'S PRIDE loose tobacco by American Snuff Company, LLC; KAYAK moist snuff and CHATTANOOGA CHEW chewing tobacco by Swisher International, Inc. ; REDMAN chewing tobacco by Pinkerton Tobacco Co. LP; COPENHAGEN moist tobacco and RED SEAL long cut by U.S. Smokeless Tobacco Company; and Taboka by Philip Morris USA.

[0069] Representative types of snuff products, commonly referred to as "snus," which may comprise pasteurized or heat treated tobacco products, are manufactured in Europe, particularly in Sweden, by or through companies such as Swedish Match AB, Fiedler & Lundgren AB, Gustavus AB, Skandinavisk Tobakskompagni A/S, and Rocker Production AB. Snus products available in the U.S.A, have been marketed under the trade names such as CAMEL Snus Frost, CAMEL Snus Original, and CAMEL Snus Spice by R. J. Reynolds Tobacco Company. Snus products, such as CAMEL Snus Original, are commonly supplied in small teabag-like pouches. The pouches are typically a nonwoven fleece material and contain about 0.4 to 1.5 grams of pasteurized tobacco. These products typically remain in a user's mouth for about 10-30 minutes. Unlike certain other smokeless tobacco products, snus products typically do not require expectoration by the user. Other pouch types of smokeless tobacco products include those marketed as COPENHAGEN Pouches (U.S. Smokeless Tobacco), SKOAL Bandits and Pouches (U.S. Smokeless Tobacco), VELO (British American Tobacco); and MARLBORO Snus (Philip Morris USA).

[0070] Example tobacco products may further include pelletized tobacco products (e.g., compressed or molded pellets produced from powdered or processed tobacco, such as those formed into the general shape of a coin, cylinder, bean, pellet, sphere, orb, strip, obloid, cube, bead, or the like), extruded or cast pieces of tobacco (e.g., as strips, films or sheets, including multilayered films formed into a desired shape), products incorporating tobacco carried by a solid substrate (e.g., where substrate materials range from edible grains to inedible cellulosic sticks), extruded or formed tobacco-containing rods or sticks, tobacco-containing capsulelike materials having an outer shell region and an inner core region, straw-like (e.g., hollow formed) tobaccocontaining shapes, sachets or packets containing tobacco (e.g., snus-like products), pieces of tobaccocontaining gum, and the like.

[0071] In addition, traditional tobacco materials and non-tobacco materials have been combined with other ingredients to form product formats distinct from traditional smokeless products, with example formats including lozenges, pastilles, gels, and the like. For example, smokeless tobacco compositions often include such ingredients as tobacco (typically in particulate form), sweeteners, binders, colorants, pH adjusters, fillers, flavoring agents, disintegration aids, antioxidants, oral care additives, and preservatives. For example, oral products which are tobacco-free, including pouched products, chews, melts, pastilles, and the like are known. Such products generally comprise a nicotine component, a fdler such as a cellulosic material (microcrystalline cellulose and/or cellulose ethers), and various combinations of sugar alcohols, gums, non-tobacco botanical materials, humectants, sweeteners, binders, organic acids, and flavoring agents.

[0072] Smokeless tobacco products and pouched, tobacco-free nicotine-containing products include, but are not limited to, products set forth and described generally in U.S. Patent Pub. Nos. 2012/0193265 to Patel et al. and 2013/0206153 to Beeson et al.; U.S. Patent No. 7,861,728 to Holton et al., U.S. Patent Pub No. 2012/0024301 to Carroll et al., US Patent App. Pub. Nos. 2008/0196730 to Engstrom et al.; 2008/0305216 to Crawford et al.; 2009/0293889 to Kumar et al.; 2010/0291245 to Gao et al; 2011/0139164 to Mua et al.; 2012/0037175 to Cantrell et al.; 2012/0055494 to Hunt et al.; 2012/0138073 to Cantrell et al.; 2012/0138074 to Cantrell et al.; 2013/0074855 to Holton, Jr.; 2013/0074856 to Holton, Jr.; 2013/0152953 to Mua et al.; 2013/0274296 to Jackson et al.; 2015/0068545 to Moldoveanu et al.; 2015/0101627 to Marshall et al.; and 2015/0230515 to Lampe et al., U.S. Pat. Nos. 1,376,586 to Schwartz; 3,368,567 to Speer; 4,513,756 to Pittman et al.; 4,606,357 to Dusek et al; 4,821,749 to Toft et al.; 5,167,244 to Kjerstad; 5,387,416 to White; 6,668,839 to Williams; 7,810,507 to Dube et al.; 7,819,124 to Strickland et al.; U.S. Patent Pub. Nos. 2005/0244521 to Strickland et al.; 2006/0191548 to Strickland et al.; 2008/0029116 to Robinson et al.; U.S. Pat. Nos. 4,624,269 to Story et al.; 4,975,270 to Kehoe; and 4,802,498 to Ogren; US Pat. Nos. 6,668,839 to Williams; 6,834,654 to Williams; 6,953,040 to Atchley et al.; 7,032,601 to Atchley et al.; and 7,694,686 to Atchley et al.; 7,810,507 to Dube et al.; 7,819,124 to Strickland et al.; 7,861,728 to Holton, Jr. et al.; 7,901,512 to Quinter et al.; 8,627,828 to Strickland et al.; and 11,246,334 to Atchley, each of which is incorporated herein by reference. Tobacco-free oral products including nicotine are described in, for example, US Patent App. Pub. Nos. 2021/0169889 and 2021/0068446 to Keller et al., and 2022/0071984 to Poole et al.

[0073] In some embodiments, the oral nicotine product is disposed within a moisture-permeable container (e.g., a water-permeable pouch) to form a pouched oral product. Accordingly, in certain embodiments, the product is disposed within a moisture-permeable packet or pouch that acts as a container for use of the product to provide a pouched product configured for oral use. Certain embodiments of the disclosure will be described with reference to FIG. 1 of the accompanying drawings, and these described embodiments involve snus-type products having an outer pouch and containing a composition comprising purified nicotine or tobacco. The composition/construction of such packets or pouches, such as the pouch 102 in the embodiment illustrated in FIG. 1, may be varied. Referring to FIG. 1, there is shown one embodiment of a pouched product 10. The pouched product 10 includes a moisture-permeable container in the form of a pouch 12, which contains a material 14 comprising a composition comprising purified nicotine or tobacco.

[0074] 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.

[0075] 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.

[0076] The amount of material contained within each product unit, for example, a pouch, may vary. In some embodiments, 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. In some smaller embodiments, the dry weight of the composition within each pouch may be from about 100 to about 300 mg. For a larger embodiment, the dry weight of the material within each pouch may be from about 300 mg to about 700 mg.

Packaging for Nicotine Products

[0077] 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.). For example, 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. Particularly, 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.

[0078] FIGS. 2A, 2B, and 2C are schematic side and front views of a multi-compartment flexible sachet container according to some example implementations; FIGS. 2A, 2B, and 2C depict three different views of a container 100 for storing smokeless tobacco or other oral product and having multiple compartments.

[0079] FIG. 2A is a side view of the container 100 without any material stored within the compartments 112, 114. The container 100 is generally shown having a flat, planar configuration when empty; however, there is a certain amount of empty space within the compartments and/or the materials are flexible to accommodate any product stored therein.

[0080] 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. Typically, 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.).

[0081] 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.

[0082] 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. In some implementations, 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.

[0083] The second functional layer 300c is a barrier layer for maintaining product integrity and may be a 12 pm metalized polyester (MPET) film. The second functional layer 300c may be configured to provide a high moisture barrier, i.e., configured to be substantially fluid-impervious so as to prevent the flow of fluids from the internal compartments to the ambient environment. However, in some implementations, the second functional layer may include a material configured to allow for oxygen (or other gas) to diffuse into or out of the compartments while substantially resisting moisture loss therethrough.

[0084] The third functional layer 300e is a sealing layer, which also helps maintain product integrity. In some implementations, the third functional layer 300e may comprise a polyethylene material having a thickness in a range of about 55 pm to about 80 pm. In a particular implementation, 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. In various implementations, the materials used to manufacture the container render the container totally recyclable.

[0085] As an alternative to pouch storage, 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. For example, 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. Patent Pub. No. 2010/0065077 to Lofgreen-Ohm et al.; U.S. Patent Pub. No. 2012/0024301 to Carroll et al., and U.S. Patent Pub. No. 2012/0193265 to Patel et al., each of which is incorporated by reference herein. 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. 2008/0202956 to Welk et al., 2010/0012534 to Hoffman, 2010/0018883 to Patel et al., and 2014/0197054 to Pipes et al.; as well as the various types of containers referenced in U.S. Patent Pub. No. 2013/0206153 to Beeson et al., each of which is incorporated by reference herein. Further, U.S. Pat. No. 8,567,597 to Gibson et al. discloses a compartment container for snus and is incorporated herein by reference in its entirety.

[0086] 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.

[0087] The shape of the outer surface of the container can vary. Container shape may be characterized in relation to a shape of a horizontal cross-section of the container. Typically, such cross-sectional shape may be substantially round or defining a circle. Other cross-sectional shapes are also encompassed, however, including oval, elliptical, triangular, square, rectangle, parallelogram, pentagon, hexagon, heptagon, octagon, and other geometric shapes.

[0088] A non-limiting example of a suitable rigid container 400 is provided in FIGS. 4A and 4B. As shown in FIG. 4A, 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. In some implementations, 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 labels 410 may be made from paper, a film, vinyl or a lamination of materials and may include indicia printed or otherwise deposited thereon including, for example, a logo, product information, or similar. With continued reference to FIG. 4A, the base portion 402 includes a cut-out or recess 406 that provides access to the lower edge 408 of the cover sidewall 418 to assist in removing or otherwise disengaging the cover 404 from the body portion 402, for example, by applying an upward force (F) to the lower edge 408 of the cover Referring to FIG. 4A and FIG. 4B, with the label 410 attached to the container 400, the tabs 412 extend over the outer sidewall 420 of the cover 404 and the secondary wall 416 of the body portion 402, thereby spanning an interface between the body portion and the cover (e.g., where the lower edge 408 of the outer wall 420 of the cover proximately abuts the upper edge of the secondary wall 416 of the body portion). Such containers are described in, for example, U.S. Patent Application Serial No. 18/297,912 to Patel, incorporated herein by reference.

[0089] See also, for example, the various types of containers for nicotine products that are set forth in US Pat. Nos. 7,014,039 to Henson et al.; 7,537,110 to Kutsch et al.; 7,584,843 to Kutsch et al.; 8,397,945 to Gelardi et al., D592,956 to Thiellier; D594,154 to Patel et al.; and D625,178 to Bailey et al.; US Pat. Pub. Nos. 2008/0173317 to Robinson et al.; 2009/0014343 to Clark et al.; 2009/0014450 to Bjorkholm; 2009/0250360 to Bellamah et al.; 2009/0266837 to Gelardi et al.; 2009/0223989 to Gelardi; 2009/0230003 to Thiellier; 2010/0084424 to Gelardi; and 2010/0133140 to Bailey et al; 2010/0264157 to Bailey et al.; 2011/0168712 to Bailey et al. ; and 2022/0297893 to Patel, each of which are incorporated herein by reference. [0090] As discussed further herein below, suitable containers can be produced from polymeric materials such as polypropylene, polyethylene, polystyrene, polyamide, and the like by extrusion and/or molding into desired shapes. Various portions of the container may comprise different types of materials and/or materials having different hardnesses (e.g., some portions may be more flexible than other portions to, for example, provide for expansion, enhanced grip, ease of opening, etc.).

Nicotine Component

[0091] As described herein above, the polymeric packaging materials as described herein have generally been previously utilized in the storage and/or dispensing of a product comprising nicotine or a nicotine component. By "nicotine component" is meant any suitable form of nicotine (e.g., free base or salt) for providing oral absorption of at least a portion of the nicotine present. The source of the nicotine may vary and may be natural or synthetic. Nicotine may be tobacco-derived (e.g., a tobacco extract) or non-tobacco derived (e.g., synthetic or otherwise obtained). Most preferably, the nicotine is naturally occurring and obtained as an extract from a Nicotiana species (e.g., tobacco). The nicotine can have the enantiomeric form S(-)-nicotine, R(+)-nicotine, or a mixture of .S'(-)-nicotinc and R{+) -nicotine. Most preferably, the nicotine is in the form of .S'(-)-nicotinc (e.g., in a form that is virtually all .S'(-)-nicotinc) or a racemic mixture composed primarily or predominantly of .S'(-)-nicotinc (e.g., a mixture composed of about 95 weight parts .S'(-)-nicotinc and about 5 weight parts R(+)-nicotine). Most preferably, the nicotine is employed in virtually pure form or in an essentially pure form. Highly preferred nicotine that is employed has a purity of greater than about 95 percent, more preferably greater than about 98 percent, and most preferably greater than about 99 percent, on a weight basis.

[0092] Typically, the nicotine component is selected from the group consisting of nicotine free base and a nicotine salt. In some embodiments, the nicotine component is nicotine in its free base form, which easily can be adsorbed in for example, a microcrystalline cellulose material to form a microcrystalline cellulose-nicotine carrier complex. See, for example, the discussion of nicotine in free base form in US Pat. Pub. No. 2004/0191322 to Hansson, which is incorporated herein by reference. [0093] In some embodiments, at least a portion of the nicotine component can be employed in the form of a salt. Salts of nicotine can be provided using the types of ingredients and techniques set forth in US Pat. No. 2,033,909 to Cox et al. and Perfetti, Beitrage Tabakforschung Int., 12: 43-54 (1983), which are incorporated herein by reference. Additionally, salts of nicotine are available from sources such as Pfaltz and Bauer, Inc. and K&K Laboratories, Division of ICN Biochemicals, Inc. Typically, the nicotine component is selected from the group consisting of nicotine free base, a nicotine salt such as hydrochloride, dihydrochloride, monotartrate, bitartrate, benzoate, sulfate, salicylate, and nicotine zinc chloride. In some embodiments, the nicotine component is nicotine bitartrate.

[0094] In some embodiments, at least a portion of the nicotine can be in the form of a resin complex of nicotine, where nicotine is bound in an ion-exchange resin, such as nicotine polacrilex, which is nicotine bound to, for example, a polymethacrylic acid, suchas Amberlite IRP64, Purolite C115HMR, orDoshionP551. See, for example, US Pat. No. 3,901,248 to Lichtneckert et al., which is incorporated herein by reference. Another example is a nicotine-polyacrylic carbomer complex, such as with Carbopol 974P. In some embodiments, nicotine may be present in the form of a nicotine polyacrylic complex.

[0095] Typically, the nicotine component (calculated as the free base) is in a concentration of at least about 0.001% by weight of the composition, such as in a range from about 0.001% to about 10%. In some embodiments, the nicotine component is present in a concentration from about 0.1% w/w to about 10% by weight, such as, e.g., from about 0.1% w/w, about 0.2%, about 0.3%, about 0.4%, about 0.5% about 0.6%, about 0.7%, about 0.8%, or about 0.9%, to about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9%, or about 10% by weight, calculated as the free base and based on the total weight of the composition. In some embodiments, the nicotine component is present in a concentration from about 0.1% w/w to about 3% by weight, such as, e.g., from about 0.1% w/w to about 2.5%, from about 0.1% to about 2.0%, from about 0.1% to about 1.5%, or from about 0.1% to about 1% by weight, calculated as the free base and based on the total weight of the composition.

[0096] It has been found according to the present disclosure that nicotine-containing products such as those described herein, when stored within polymeric packaging materials as described herein, may, over time, adsorb or adsorb some portion of the nicotine present in the product e.g., by evaporation, sublimation, direct contact, or any other process of migration. Accordingly, waste polymeric materials used for the storage and/or dispensing of nicotine-containing products may comprise residual nicotine. The amount of residual nicotine may vary based on, for example the duration of exposure of the material to the nicotine containing product, the nature of the material, and the nicotine content of the product stored therein. In some embodiments, the waste polymeric packaging material comprises residual nicotine in an amount greater than about 0.01% by weight, such as from about 0.01% to about 1% by weight. In some embodiments, the polymeric packaging material comprises residual nicotine in an amount from about 0.01%, about 0.05%, or about 0.1%, to about 0.25%, about 0.5%, or about 1% by weight. Determination of the residual nicotine may be performed by, for example, pyrolysis coupled with gas chromatography -mass spectrometry. Unless otherwise indicated, residual nicotine values disclosed herein are obtained by this method, further described in Example 1.

[0097] As described herein above, certain regulatory bodies require a residual nicotine content of polymeric packaging materials of 0.25% or less in order for such material to be safely recycled or to be disposed of as non-hazardous waste. Accordingly, to take advantage of the environmental benefits of recycling, it is desirable to reduce levels of residual nicotine to levels at or below the regulated limits to enable recycling. As further described herein below, the methods disclosed herein efficiently extract residual nicotine, providing waste materials well below the regulatory threshold of 0.25% by weight.

[0098] Although the focus of the disclosure is on nicotine extraction, the same extraction techniques could be applied to other active ingredients or flavorants that leach into the packaging material from the product contained therein. Additional active ingredients include cannabinoids or cannabimimetics, such as tetrahydrocannabinol (THC) and cannabidiol (CBD), terpenes, botanicals, and the like.

Method for extracting nicotine

[0099] The method for extracting nicotine as disclosed herein comprises receiving a waste (e.g., spent or used) polymeric packaging material. By "receiving a waste polymeric packaging material" is meant that the waste polymeric packaging material, such as a container which has been previously used for storage of a product comprising nicotine (e.g., oral nicotine products), said waste polymeric packaging material comprising residual nicotine, is obtained, provided, delivered, or the like, in a form suitable for performing the method. For example, the waste polymeric packaging material is empty with respect to any previously contained product and may have been subject to initial processing. This initial processing may include, but is not limited to, physical removal of product, washing, e.g., with water, detergent, solvent, or combinations thereof.

[0100] Prior to or following the receiving, 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.

[0101] In certain embodiments, the waste polymeric packaging material is subdivided by cutting or shredding into smaller pieces, such as pieces having a length in a range from about 0.5 cm to about 2 cm and a width from about 0.5 cm to about 2 cm. Alternatively, the waste polymeric packaging material is subdivided by grinding the packaging material into a particulate material, such as a particulate material having an average particle size in the range from about 1000 microns to about 5000 microns. In certain embodiments, the waste packaging material is subjected to cryogenic grinding. Although not bound by any theory of operation, it is believed that subdividing the packaging material prior to extraction improves the efficiency of the extraction due to increased surface area available for interaction with the solvent.

[0102] 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. [0103] 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. In some embodiments, the waste polymeric packaging material comprises a plastic of a type appropriate for recycling. Currently, 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. In some embodiments, 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. In some embodiments, 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.

[0104] In some embodiments, 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. In some embodiments, the metallic layer is aluminum.

[0105] In some embodiments, the method further comprises removing the metallic layer prior to the extracting. In some embodiments, removing the metallic layer comprises contacting the sachet with an acid, dissolving the metallic layer.

[0106] The disclosed method generally comprises extracting the residual nicotine from the waste polymeric packaging material. The manner in which the extraction is performed may vary based on the type of polymeric material, the amount of residual nicotine present, the physical form of the polymeric material, the quantity of material to be processed, and the volume of material to be processed per unit of time. Generally, extracting comprises providing a solvent at an elevated temperature; and contacting the waste polymeric packaging material with the solvent at the elevated temperature for a period of time sufficient to remove substantially all residual nicotine from the waste polymeric packaging material. As disclosed herein in the Examples, the efficiency of nicotine extraction, and the time required to extract a suitable portion of the residual nicotine, vary depending on the specific material, the solvent temperature, the degree of physical contact with the solvent, and the like. Generally, increasing solvent temperature and providing conditions which promote diffusion of the residual nicotine into the solvent enhance efficiency of extraction and/or decrease the amount of time necessary to render the waste polymeric material suitable for recycling (i.e., forming a decontaminated waste polymeric packaging material having a residual nicotine content below a pre-determined threshold, such as less than 0.25% by weight).

[0107] 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. In some embodiments, 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. In some embodiments, the solvent has boiling point at standard atmospheric pressure in a range from about 60°C to about 90°C.

[0108] In some embodiments, the solvent is a polar organic solvent (e.g., a Cl to C3 alcohol, such as methanol, ethanol, n-propanol, or isopropanol). In some embodiments, the solvent is methanol. In some embodiments, the solvent is ethanol. In other embodiments, 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.

[0109] In some embodiments, 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. In some embodiments, 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.

[0110] 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.

[oni] In some embodiments, contacting the waste polymeric packaging material with the solvent comprises continuously contacting the waste polymeric packaging material with fresh heated solvent. In a non-limiting embodiment, the extracting may be performed in a Soxhlet apparatus 500 as illustrated in FIG. 5. With reference to 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. By this mechanism, nicotine in the polymeric material is extracted into the solvent and concentrated in the flask 502. [0112] In other embodiments, contacting the waste polymeric packaging material with the solvent may be conducted in a sealed environment, under pressure, with microwave heating. In a non-limiting embodiment, the extracting may be performed in a standard microwave device using a sealed tube to house the solvent and polymeric material. Although not bound by any particular theory of operation, it is believed that performing extraction on a material within a sealed container can improve extraction efficiency due to increased pressure within the sealed container during extraction. As used herein, reference to 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.

[0113] As described above, 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).

[0114] Following the extracting, the method generally comprises separating the decontaminated waste polymeric packaging material from the solvent, the solvent having been enriched with respect to nicotine relative to the waste polymeric material. The separating may comprise any means of physical removing the solvent from contact with the waste polymeric material. In some embodiments, the waste polymeric material is removed from the solvent. In some embodiments, the solvent is removed from contact with the decontaminated waste polymeric packaging material by e.g., draining away the solvent through appropriate valves, pipes, filters, and the like.

[0115] In some embodiments, the method further comprises removing any residual solvent from the decontaminated waste polymeric packaging material. Removal of residual solvent may be achieved by washing the decontaminated waste polymeric packaging material with water, by drying in air at ambient or elevated temperature, or a combination thereof.

[0116] Following the separating and optional removal of residual solvent, 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%.

[0117] The extent of nicotine extraction (i.e., the extraction efficiency) can be determined by GC pyrolysis as set forth in Example 1 herein. For example, a portion of an unextracted sample of waste packaging material can by subjected to GC pyrolysis and a portion of an extracted sample of the same waste packaging material can be subjected to GC pyrolysis. The relative difference in nicotine peaks of the resulting pyrographs (see, e.g., the pyrographs of FIGS. 6A and 6B) can be used to calculate a percentage of nicotine reduction resulting from the extraction. [0118] The quantitative amount of nicotine extracted from a waste packaging material can be determined by small-scale extraction of the packaging material to measure nicotine extracted into the solvent. 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. By combining the GC pyrolysis technique noted above with the chromatography analysis of the extraction solvent, the amount of nicotine within the waste packaging prior to extraction can be estimated.

[0119] In an alternative method of the disclosure, rather than solvent extraction, 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. In certain embodiments, 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.

[0120] 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. For example, a stripping column containing activated carbon or another porous adsorbent can be used.

[0121] Many modifications and other embodiments of the invention will come to mind to one skilled in the art to which this invention pertains having the benefit of the teachings presented in the foregoing description. Therefore, it is to be understood that the invention is not to be limited to the specific embodiments disclosed and that modifications and other embodiments are intended to be included within the scope of the appended claims. Although specific terms are employed herein, they are used in a generic and descriptive sense only and not for purposes of limitation.

EXAMPLES

[0122] Aspects of the present invention are more fully illustrated by the following examples, which are set forth to illustrate certain aspects of the present invention and are not to be construed as limiting thereof.

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.

Table 1. Parameters for GC/MS on-line analysis of pyrolysates

Example 2. General procedure for Soxhlet extraction of nicotine from plastic samples

[0124] A sample of plastic material is placed into a Soxhlet apparatus for nicotine extraction. For sachet samples, 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. For container samples, an entire VELO™ 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.

Example 3. General procedure for determination of nicotine content in extract by LCMS

[0125] 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. Quantitation was done with an external calibration curve of pure nicotine standards with seven different calibration points (12.50, 6.25, 3.13, 1.56, 0.78, 0.39, and 0.19 gg/mL). Higher calibration standards can be used along with LC ultraviolet (UV) detection and 254 nm. This will allow for fewer dilutions since the UV can quantitate with higher concentrations of nicotine. Samples are injected in triplicate and the standard deviation accounted for analytical and sample variation.

Table 2, Mobile phase parameters

Example 4. General procedure for determination of alkaloid content (including nicotine) in extract by GCMS

[0126] 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.

Table 3, Parameters for GC/MS analysis of extract

Example 5. Determination of nicotine content in sachet packaging

[0127] A sample of VELO™ polypropylene sachet packaging having contained VELO™ 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.

Example 6. Determination of nicotine content in can packaging

[0128] A sample of Velo can packaging having contained VELO™ 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 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

[0129] Samples of VELO™ Eco-can packaging (polypropylene/cellulose fiber mix) having contained VELO™ pouches (4, 6, 10, or 10.9 mg nicotine content in product) were analyzed by GCMS/pyrolysis (Example 1) before and after Soxhlet extraction (Example 2). Analysis of the methanol extract was also performed according to Example 4. The pyrolysis-GCMS analysis data are provided in Table 4, which demonstrated that there was an 89% decrease in nicotine content after the 48-hour extraction period. The data also demonstrated that following the 48-hour Soxhlet extraction, all samples were below 0.25% by weight of nicotine. A correction factor was applied to account for irreversibly bound nicotine using the extraction efficiency. Since Soxhlet extraction efficiency was 89% based on GC pyrolysis, the estimated residual nicotine in the original unextracted packaging is provided below. Table 4, Nicotine content of samples by pyrolysis-GCMS

Example 8. Determination of nicotine content in formulation packaging

[0130] Samples of low-density polyethylene bags used to store stability samples of powdered product formulations were analyzed for residual nicotine content by pyrolysis-GCMS (Example 1) before and after Soxhlet extraction (Example 2). Prior to analysis, the LDPE bag samples were cleaned of any excess powdered product with nitrogen gas and by wiping with a dry paper towel. Each of the four LDPE bags were cut into pieces and deposited into separate Soxhlet apparatus. Approximately 100 mL of methanol was used for each of the extractions. The initial pyrolysis-GCMS data indicated that the bag samples contained from 0.35 to 1.08% by weight of residual nicotine before extraction. In each case, the Soxhlet extraction resulted in 99.7% efficiency of nicotine extraction according to the final pyrolysis-GCMS analysis.

Example 9. Comparative extraction efficiencies of various solvent extraction methods

[0131] Samples of oral nicotine product polypropylene packaging were subjected to various residual nicotine extraction methods to determine the extraction efficiencies. Pyrolysis-GCMS (Example 1) was performed before and after the various extraction methods. Allowing the sample to sit in a volume of methanol at room temperature for 7 days provided a 5% extraction efficiency. Performing the same extraction but subjecting the sample to orbital shaking increased efficiency to 10%. Soxhlet extraction according to Example 2 for 1 day provided 68% efficiency, and after 2 days (48 hours) provided 89% extraction efficiency.

[0132] In contrast, use of microwave accelerated extraction provided 94% extraction efficiency with a 45- minute active extraction period. Specifically, a VELO™ 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).

Example 10. Extraction of residual nicotine from a laminated sachet sample

[0133] 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.

Claims

CLAIMS What is claimed is:

1. A method for extracting nicotine from a waste polymeric packaging material comprising residual nicotine, the method comprising: i) receiving the waste polymeric packaging material comprising residual nicotine at a first nicotine concentration; ii) extracting at least a portion of the residual nicotine from the waste polymeric packaging material, wherein the extracting comprises contacting the waste polymeric packaging material with a solvent at an elevated temperature, forming a decontaminated waste polymeric packaging material having a second nicotine concentration, the second nicotine concentration being lower than the first nicotine concentration; and

Hi) separating the decontaminated waste polymeric packaging material from the solvent.

2. The method of claim 1, wherein 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.

3. The method of claim 1, wherein the waste polymeric packaging material comprises polypropylene, low-density polyethylene, or a combination thereof.

4. The method of claim 1, wherein the waste polymeric packaging material comprises residual nicotine at a first nicotine concentration in an amount of about 0.01% by weight or higher, such as about 0.1% by weight or higher, such as about 0.3 % by weight to about 1.5% by weight, based on the total weight of the waste polymeric packaging material.

5. The method of claim 1, further comprising dividing the waste polymeric packaging material into smaller pieces prior to the extracting.

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.

7. The method of claim 1, 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.

8. The method of claim 1, wherein the solvent is a polar organic solvent or a nonpolar hydrocarbon solvent.

9. The method of claim 1, wherein the solvent is methanol or ethanol.

10. The method of claim 1, wherein the elevated temperature is above the boiling point at standard atmospheric pressure of the solvent.

11. The method of claim 1, wherein the elevated temperature is from about 40°C to about 150°C, or from about 50°C to about 100°C.

12. The method of claim 1, wherein 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.

13. The method of claim 12, wherein the heat source is configured to heat the solvent by microwave irradiation.

14. The method of claim 1, wherein contacting the waste polymeric packaging material with the solvent comprises continuously contacting the waste polymeric packaging material with fresh solvent.

15. The method of claim 14, wherein the extracting is performed using a Soxhlet apparatus.

16. The method of claim 1, wherein the extracting is conducted for a period of time, such as from about 30 minutes to about 48 hours.

17. The method of claim 1, 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.

18. The method of claim 1, wherein the second nicotine concentration of the decontaminated waste polymeric packaging material is about 0.25% nicotine by weight or less, such as about 0.1% nicotine by weight or less, or about 0.0001% to about 0.01% nicotine by weight.

19. The method of claim 1, wherein the waste polymeric packaging material is a polymeric packaging material previously used for storage of a product comprising nicotine.

20. A waste polymeric packaging material suitable for recycling, the waste polymeric packaging material previously used for storage of a product comprising nicotine, the waste polymeric packaging material comprising nicotine in an amount from about 0.0001% to about 0.25% by weight.

21. The waste polymeric packaging material of claim 20, comprising 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.

22. The waste polymeric packaging material of claim 20, comprising polypropylene, low-density polyethylene, or a combination thereof.