US20140261479A1 - Nicotine-containing products and methods of making - Google Patents

Nicotine-containing products and methods of making Download PDF

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Publication number
US20140261479A1
US20140261479A1 US14/205,723 US201414205723A US2014261479A1 US 20140261479 A1 US20140261479 A1 US 20140261479A1 US 201414205723 A US201414205723 A US 201414205723A US 2014261479 A1 US2014261479 A1 US 2014261479A1
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United States
Prior art keywords
nicotine
anatabine
product
tobacco
containing product
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.)
Abandoned
Application number
US14/205,723
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English (en)
Inventor
Dongmei Xu
James Arthur Strickland
Jeffery Edmiston
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.)
Altria Client Services LLC
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Altria Client Services LLC
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 Altria Client Services LLC filed Critical Altria Client Services LLC
Priority to US14/205,723 priority Critical patent/US20140261479A1/en
Publication of US20140261479A1 publication Critical patent/US20140261479A1/en
Assigned to Altria Client Services Inc. reassignment Altria Client Services Inc. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: EDMISTON, Jeffery, XU, DONGMEI, STRICKLAND, JAMES ARTHUR
Assigned to ALTRIA CLIENT SERVICES LLC reassignment ALTRIA CLIENT SERVICES LLC MERGER AND CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: Altria Client Services Inc., ALTRIA CLIENT SERVICES LLC
Abandoned legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
    • A24B15/36—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring
    • A24B15/38—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only nitrogen as hetero atom
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/10—Chemical features of tobacco products or tobacco substitutes
    • A24B15/16—Chemical features of tobacco products or tobacco substitutes of tobacco substitutes
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
    • A24B15/36—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring
    • A24B15/38—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only nitrogen as hetero atom
    • A24B15/385—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only nitrogen as hetero atom in a five-membered ring

Definitions

  • This disclosure generally relates to nicotine-containing products.
  • Tobacco is a complex mixture of compounds with many different sensorial attributes. Many compounds in tobacco and tobacco smoke play a role in the sensorial aspects of tobacco products.
  • the present disclosure describes nicotine-containing products that also contain anatabine and methods of making such products.
  • a nicotine-containing product comprising anatabine.
  • the ratio of anatabine to nicotine is greater than 5:95. In some embodiments, the ratio of anatabine to nicotine is greater than 10:90. In some embodiments, the ratio of anatabine to nicotine is greater than 15:85.
  • the nicotine is synthetic nicotine. In some embodiments, the nicotine is tobacco-derived nicotine. In some embodiments, the anatabine is synthetic anatabine. In some embodiments, the anatabine is tobacco-derived anatabine.
  • Representative nicotine-containing products include, without limitation, a smokable product and a smokeless product.
  • Representative smokable products include, without limitation, a combustible product and a non-combustible product.
  • Representative combustible products include a cigarette and a cigar.
  • Representative non-combustible products include, without limitation, an e-cigarette, an electronic smoking article, an aerosolized vapor products, and a heated tobacco product.
  • Representative smokeless products include snus, a pouch, a tab, a film, a stick, a woven product, a meltblown product, or a sintered piece.
  • such a product further includes an additive, a sweetener, a flavorant, a polymer, a fiber, filler, a plasticizer, or combinations thereof.
  • a method of making a nicotine-containing product typically includes providing a nicotine-containing product and introducing anatabine into a nicotine-containing product in an amount such that the anatabine to nicotine ratio is greater than 5:95. In some embodiments, the ratio of anatabine to nicotine is greater than 10:90. In some embodiments, the ratio of anatabine to nicotine is greater than 15:85.
  • the nicotine is synthetic nicotine. In some embodiments, the nicotine is tobacco-derived nicotine. In some embodiments, the anatabine is synthetic anatabine. In some embodiments, the anatabine is tobacco-derived anatabine.
  • FIG. 1 shows the pathway by which nicotine and anatabine are produced.
  • Anatabine [2R,(+)]-1,2,3,6-Tetrahydro-2,3′-bipyridine
  • Anatabine has been shown to have affinity for nicotine acetylcholine receptors (Maciuk et al., 2008, J. Pharm. Biomed. Anal., 48:238-46) and has been shown to inhibit monoamine oxidase (U.S. Pat. No. 6,569,470) and the enzyme responsible for nicotine metabolism (Denton et al., 2004, Biochem. Pharmacol., 67:751-6).
  • anatabine may accentuate the nicotine response by binding to the nicotine receptor; anatabine may prolong the increased levels of neurotransmitters in the brain by inhibiting monoamine oxidase; and/or anatabine may extend the time between product use by inhibiting the enzyme responsible for nicotine metabolism.
  • the level of anatabine in dark tobacco is typically less than about 5% of the level of nicotine, but can be as high as 7% in burley tobacco.
  • Ratios of anatabine to nicotine can be greater than that found in cured tobacco leaf; for example, the ratio of anatabine to nicotine can be greater than about 5:95 (e.g., greater than about 6:94, 7:93, 8:92, 9:91, 10:90, 15:85, 20:80, 25:75, 30:70, 35:65, 40:60, 45:55, or 50:50 anatabine-to-nicotine).
  • Nicotine-containing products that include anatabine can take any number of forms, and can include, for example, smokable products (e.g., combustible smokable products, non-combustible vapor-generating products (e.g., electronic e-cigarettes), smokeless products, and liquid aerosol formulations for use in, e.g., an electronic smoking article.
  • Smokeless products also can take many forms including, without limitation, dissolvable or disintegratable products (e.g., tabs, films, sticks), loose and pre-formed moist snuff (e.g., woven products, pouches, snus), and mouth-stable polymer products (e.g., meltblown products and sintered pieces).
  • the nicotine in a nicotine-containing product that also includes anatabine can be tobacco-derived nicotine, synthetic nicotine, or a combination thereof.
  • the anatabine in such a product can be tobacco-derived anatabine, synthetic anatabine, or a combination thereof.
  • Tobacco-derived nicotine and/or tobacco-derived anatabine generally include one or more tobacco organoleptic components in addition to the nicotine and/or anatabine.
  • Tobacco-derived nicotine and/or tobacco-derived anatabine can be extracted from raw tobacco (e.g., green leaf) or processed tobacco.
  • Processed tobacco can include cured tobacco (e.g., dark air-cured, dark fire-cured, flue cured), fermented tobacco, conditioned tobacco and/or pasteurized tobacco (see, for example, U.S. Pat. Nos. 4,528,993; 4,660,577; 4,848,373; and 5,372,149, and U.S. Publication Nos. 2004/0118422 and 2005/0178398).
  • cured tobacco e.g., dark air-cured, dark fire-cured, flue cured
  • fermented tobacco conditioned tobacco and/or pasteurized tobacco
  • conditioned tobacco and/or pasteurized tobacco see, for example, U.S. Pat. Nos. 4,528,993; 4,660,577; 4,848,373; and 5,372,149, and U.S. Publication Nos. 2004/0118422 and 2005/0178398).
  • Tobacco-derived nicotine and/or tobacco-derived anatabine can be obtained by mixing tobacco (i.e., raw or processed) with water or another solvent (e.g., ethanol) and removing the insoluble tobacco material. Nicotine and/or anatabine can be concentrated or purified from a tobacco extract using routine methods. Representative methods of obtaining nicotine and other alkaloids from tobacco are described, for example, in U.S. Pat. Nos. 2,162,738; 3,139,436; 3,396,735; 4,153,063; 4,448,208; 5,487,792; and 5,684,155. In addition, nicotine, anatabine, or a salt thereof, can be produced synthetically. See, for example, U.S. Pat. Nos. 4,442,292; 4,452,984; 6,995,265; 7,112,678; and 8,207,346.
  • a nicotine-containing product that includes anatabine can be substantially free of tobacco plant tissue.
  • tobacco plant tissue refers to processed or non-processed cellulosic parts (e.g., leaves, stems) of a member of the genus Nicotiana , but does not include extracts of tobacco (e.g., tobacco-derived nicotine or tobacco-derived anatabine).
  • a nicotine-containing product that includes anatabine also can include one or more organoleptic components extracted from raw or processed tobacco, yet be substantially free of tobacco plant tissue.
  • a nicotine-containing product that includes anatabine as described herein also can include one or more additives, sweeteners, and/or flavorants, as well as one or more polymers, fibers, fillers, plasticizers, and/or other processing aids to provide a favorable flavor profile and tactile experience.
  • additives sweeteners, and/or flavorants
  • polymers such as polyethylene glycol dimethacrylate, polypropylene glycol dimethacrylate, polysulfate, polysulfate, polysulfate, polyethylene glycol dime, poly(ethylene glycol)-propylene glycol dimethacrylate, poly(ethylene glycol)-propylene glycol dimethacrylate, terpolymer, polymethyl methacrylate, polymethyl methacrylate, polymethyl methacrylate, polymethyl methacrylate, polymethyl methacrylate, polymethyl methacrylate, polymethyl methacrylate, polymethyl methacrylate, polymethyl methacrylate, polymethyl methacrylate, polymethyl meth
  • flavorants can be used in a nicotine-containing product that contains anatabine.
  • the flavorants can be natural or artificial.
  • suitable flavorants include wintergreen, cherry and berry type flavorants, various liqueurs and liquors (such as Dramboui, bourbon, scotch, and whiskey) spearmint, peppermint, lavender, cinnamon, cardamon, apium graveolents, clove, cascarilla, nutmeg, sandalwood, bergamot, geranium, honey essence, rose oil, vanilla, lemon oil, orange oil, Japanese mint, cassia, caraway, cognac, jasmin, chamomile, menthol, ylangylang, sage, fennel, ginger, anise, coriander, coffee, and liquorish.
  • flavorants can be encapsulated.
  • a nicotine-containing product that includes anatabine as described herein can include a polymer.
  • a polymer can be any of a number of different biocompatible and biostable polymers.
  • the polymer is a thermoplastic polymer or a thermoplastic elastomer.
  • Representative polymers include, without limitation, polyurethanes, silicon polymers, polyesters, polyacrylates, polyethylenes, polypropylenes, polyetheramides, polystyrenes (e.g., acrylonitrile butadiene styrene, high impact polystyrenes (HIPS)) polyvinyl alcohols, polyvinyl acetates, polyvinyl chlorides, polybutyl acetates, butyl rubbers (e.g., polyisobutylenes), SEBS, SBS, and mixtures and copolymers thereof.
  • the polymer is a food-grade or medical-grade polymer (e.g., medical-grade polyurethane).
  • a nicotine-containing product containing anatabine also can include fillers such as starch, dicalcium phosphate, lactose, sorbitol, mannitol, and microcrystalline cellulose, calcium carbonate, dicalcium phosphate, calcium sulfate, clays, silica, glass particles, sodium lauryl sulfate (SLS), glyceryl palmitostearate, sodium benzoate, sodium stearyl fumarate, talc, and stearates (e.g., Mg or K), and waxes (e.g., glycerol monostearate, propylene glycol monostearate, and acetylated monoglycerides), stabilizers (e.g., ascorbic acid and monosterol citrate, BHT, or BHA), disintegrating agents (e.g., starch, sodium starch glycolate, cross carmellose, cross linked PVP), pH stabilizers, or preservatives.
  • fillers such as star
  • a nicotine-containing product that includes anatabine also can include one or more plasticizers.
  • Plasticizers can soften the product and thus increase its flexibility. Suitable plasticizers include propylene glycol, glycerin, vegetable oil, and medium chain triglycerides. In some embodiments, the plasticizer can include phthalates. Esters of polycarboxylic acids with linear or branched aliphatic alcohols of moderate chain length can also be used as plasticizers.
  • Methods of making the nicotine-containing products described herein are known in the art. Methods of making such products often utilize automated or semi-automated processes, which can include cutting, pressing, shaping, tableting, rolling, dipping, coating, heating, melting, drying, sintering, melt blowing, needling, pouching, and combinations thereof.
  • automated or semi-automated processes can include cutting, pressing, shaping, tableting, rolling, dipping, coating, heating, melting, drying, sintering, melt blowing, needling, pouching, and combinations thereof.
  • the particular product and the method by which it is made will determine when and in what form (e.g., tobacco-derived or synthetic) the anatabine is introduced.
  • the anatabine can be introduced prior to any processing; in other products and/or processes, the anatabine can be introduced during processing; while yet in other products and/or processes, the anatabine can be introduced after processing is complete but prior to packaging. Depending upon the source of the nicotine and at what point the nicotine is introduced, the anatabine can be introduced together with the nicotine or separately.
  • the nicotine-containing products described herein that include anatabine can be packaged in any type of conventional or non-conventional manner.
  • a plurality of nicotine-containing products that include anatabine can be packaged in a container having a lid.
  • a plurality of nicotine-containing products that include anatabine can be stacked and packaged in a paper, plastic, and/or aluminum foil tube.
  • the packaging can have a child-resistant lid.
US14/205,723 2013-03-15 2014-03-12 Nicotine-containing products and methods of making Abandoned US20140261479A1 (en)

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US201361786344P 2013-03-15 2013-03-15
US14/205,723 US20140261479A1 (en) 2013-03-15 2014-03-12 Nicotine-containing products and methods of making

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WO (1) WO2014150881A1 (fr)

Cited By (23)

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US20180084821A1 (en) * 2016-09-27 2018-03-29 BOND STREET MANUFACTURING LLC (a Florida LLC) Vaporizable Tobacco Wax Compositions
USD825102S1 (en) 2016-07-28 2018-08-07 Juul Labs, Inc. Vaporizer device with cartridge
US10045567B2 (en) 2013-12-23 2018-08-14 Juul Labs, Inc. Vaporization device systems and methods
US10045568B2 (en) 2013-12-23 2018-08-14 Juul Labs, Inc. Vaporization device systems and methods
US10058130B2 (en) 2013-12-23 2018-08-28 Juul Labs, Inc. Cartridge for use with a vaporizer device
US10076139B2 (en) 2013-12-23 2018-09-18 Juul Labs, Inc. Vaporizer apparatus
US10104915B2 (en) 2013-12-23 2018-10-23 Juul Labs, Inc. Securely attaching cartridges for vaporizer devices
US10111470B2 (en) 2013-12-23 2018-10-30 Juul Labs, Inc. Vaporizer apparatus
USD836541S1 (en) 2016-06-23 2018-12-25 Pax Labs, Inc. Charging device
USD842536S1 (en) 2016-07-28 2019-03-05 Juul Labs, Inc. Vaporizer cartridge
US10244793B2 (en) 2005-07-19 2019-04-02 Juul Labs, Inc. Devices for vaporization of a substance
US10279934B2 (en) 2013-03-15 2019-05-07 Juul Labs, Inc. Fillable vaporizer cartridge and method of filling
USD848057S1 (en) 2016-06-23 2019-05-07 Pax Labs, Inc. Lid for a vaporizer
USD849996S1 (en) 2016-06-16 2019-05-28 Pax Labs, Inc. Vaporizer cartridge
USD851830S1 (en) 2016-06-23 2019-06-18 Pax Labs, Inc. Combined vaporizer tamp and pick tool
US10405582B2 (en) 2016-03-10 2019-09-10 Pax Labs, Inc. Vaporization device with lip sensing
US10512282B2 (en) 2014-12-05 2019-12-24 Juul Labs, Inc. Calibrated dose control
US20200035120A1 (en) * 2018-07-27 2020-01-30 Joseph Pandolfino Articles and formulations for smoking products and vaporizers
US10653186B2 (en) 2013-11-12 2020-05-19 VMR Products, LLC Vaporizer, charger and methods of use
USD887632S1 (en) 2017-09-14 2020-06-16 Pax Labs, Inc. Vaporizer cartridge
US10865001B2 (en) 2016-02-11 2020-12-15 Juul Labs, Inc. Fillable vaporizer cartridge and method of filling
GB2595967A (en) * 2020-05-01 2021-12-15 Exhale Tech Ltd Composition and use thereof
US11553734B2 (en) 2018-11-08 2023-01-17 Juul Labs, Inc. Cartridges for vaporizer devices

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NO343402B1 (en) * 2017-04-24 2019-02-25 Swedish Match North Europe Ab A flavoured moist oral pouched nicotine product comprising triglyceride and a method for manufacturing thereof.
WO2019115778A1 (fr) 2017-12-15 2019-06-20 Swedish Match North Europe Ab Produit humide et aromatisé à base de nicotine sous forme de sachet pour administration orale comprenant un triglycéride

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US10244793B2 (en) 2005-07-19 2019-04-02 Juul Labs, Inc. Devices for vaporization of a substance
US10638792B2 (en) 2013-03-15 2020-05-05 Juul Labs, Inc. Securely attaching cartridges for vaporizer devices
US10279934B2 (en) 2013-03-15 2019-05-07 Juul Labs, Inc. Fillable vaporizer cartridge and method of filling
US10653186B2 (en) 2013-11-12 2020-05-19 VMR Products, LLC Vaporizer, charger and methods of use
US10736360B2 (en) 2013-11-12 2020-08-11 Vmr Products Llc Vaporizer, charger and methods of use
US10980273B2 (en) 2013-11-12 2021-04-20 VMR Products, LLC Vaporizer, charger and methods of use
US11134722B2 (en) 2013-11-12 2021-10-05 Vmr Products Llc Vaporizer
US10117466B2 (en) 2013-12-23 2018-11-06 Juul Labs, Inc. Vaporization device systems and methods
US10058129B2 (en) 2013-12-23 2018-08-28 Juul Labs, Inc. Vaporization device systems and methods
US10104915B2 (en) 2013-12-23 2018-10-23 Juul Labs, Inc. Securely attaching cartridges for vaporizer devices
US10111470B2 (en) 2013-12-23 2018-10-30 Juul Labs, Inc. Vaporizer apparatus
US10117465B2 (en) 2013-12-23 2018-11-06 Juul Labs, Inc. Vaporization device systems and methods
US10070669B2 (en) 2013-12-23 2018-09-11 Juul Labs, Inc. Cartridge for use with a vaporizer device
US10058124B2 (en) 2013-12-23 2018-08-28 Juul Labs, Inc. Vaporization device systems and methods
US10159282B2 (en) 2013-12-23 2018-12-25 Juul Labs, Inc. Cartridge for use with a vaporizer device
US10201190B2 (en) 2013-12-23 2019-02-12 Juul Labs, Inc. Cartridge for use with a vaporizer device
US10076139B2 (en) 2013-12-23 2018-09-18 Juul Labs, Inc. Vaporizer apparatus
US10058130B2 (en) 2013-12-23 2018-08-28 Juul Labs, Inc. Cartridge for use with a vaporizer device
US10264823B2 (en) 2013-12-23 2019-04-23 Juul Labs, Inc. Vaporization device systems and methods
US10045568B2 (en) 2013-12-23 2018-08-14 Juul Labs, Inc. Vaporization device systems and methods
US10912331B2 (en) 2013-12-23 2021-02-09 Juul Labs, Inc. Vaporization device systems and methods
US10045567B2 (en) 2013-12-23 2018-08-14 Juul Labs, Inc. Vaporization device systems and methods
US10701975B2 (en) 2013-12-23 2020-07-07 Juul Labs, Inc. Vaporization device systems and methods
US10667560B2 (en) 2013-12-23 2020-06-02 Juul Labs, Inc. Vaporizer apparatus
US11752283B2 (en) 2013-12-23 2023-09-12 Juul Labs, Inc. Vaporization device systems and methods
US10512282B2 (en) 2014-12-05 2019-12-24 Juul Labs, Inc. Calibrated dose control
US10865001B2 (en) 2016-02-11 2020-12-15 Juul Labs, Inc. Fillable vaporizer cartridge and method of filling
US10405582B2 (en) 2016-03-10 2019-09-10 Pax Labs, Inc. Vaporization device with lip sensing
USD913583S1 (en) 2016-06-16 2021-03-16 Pax Labs, Inc. Vaporizer device
USD849996S1 (en) 2016-06-16 2019-05-28 Pax Labs, Inc. Vaporizer cartridge
USD929036S1 (en) 2016-06-16 2021-08-24 Pax Labs, Inc. Vaporizer cartridge and device assembly
USD851830S1 (en) 2016-06-23 2019-06-18 Pax Labs, Inc. Combined vaporizer tamp and pick tool
USD836541S1 (en) 2016-06-23 2018-12-25 Pax Labs, Inc. Charging device
USD848057S1 (en) 2016-06-23 2019-05-07 Pax Labs, Inc. Lid for a vaporizer
USD825102S1 (en) 2016-07-28 2018-08-07 Juul Labs, Inc. Vaporizer device with cartridge
USD842536S1 (en) 2016-07-28 2019-03-05 Juul Labs, Inc. Vaporizer cartridge
US10709165B2 (en) * 2016-09-27 2020-07-14 Bond Street Manufacturing Llc Vaporizable tobacco wax compositions
US20180084821A1 (en) * 2016-09-27 2018-03-29 BOND STREET MANUFACTURING LLC (a Florida LLC) Vaporizable Tobacco Wax Compositions
USD927061S1 (en) 2017-09-14 2021-08-03 Pax Labs, Inc. Vaporizer cartridge
USD887632S1 (en) 2017-09-14 2020-06-16 Pax Labs, Inc. Vaporizer cartridge
US10973255B2 (en) 2018-07-27 2021-04-13 Cabbacis Llc Articles and formulations for smoking products and vaporizers
US10897925B2 (en) * 2018-07-27 2021-01-26 Joseph Pandolfino Articles and formulations for smoking products and vaporizers
US20200035120A1 (en) * 2018-07-27 2020-01-30 Joseph Pandolfino Articles and formulations for smoking products and vaporizers
US11553734B2 (en) 2018-11-08 2023-01-17 Juul Labs, Inc. Cartridges for vaporizer devices
GB2595967A (en) * 2020-05-01 2021-12-15 Exhale Tech Ltd Composition and use thereof

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EP2967121A1 (fr) 2016-01-20
CA2905942A1 (fr) 2014-09-25
WO2014150881A1 (fr) 2014-09-25

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