WO2015117243A1 - Composition liquide pour e-cigarettes - Google Patents

Composition liquide pour e-cigarettes Download PDF

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Publication number
WO2015117243A1
WO2015117243A1 PCT/CA2015/050088 CA2015050088W WO2015117243A1 WO 2015117243 A1 WO2015117243 A1 WO 2015117243A1 CA 2015050088 W CA2015050088 W CA 2015050088W WO 2015117243 A1 WO2015117243 A1 WO 2015117243A1
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WO
WIPO (PCT)
Prior art keywords
glycol
liquid formulation
cigarette
liquid
solvent
Prior art date
Application number
PCT/CA2015/050088
Other languages
English (en)
Inventor
Samuel BELLEROSE
Original Assignee
Bellerose Samuel
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 Bellerose Samuel filed Critical Bellerose Samuel
Publication of WO2015117243A1 publication Critical patent/WO2015117243A1/fr

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Classifications

    • 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
    • A24B15/10—Chemical features of tobacco products or tobacco substitutes
    • A24B15/16—Chemical features of tobacco products or tobacco substitutes of tobacco substitutes
    • A24B15/167—Chemical features of tobacco products or tobacco substitutes of tobacco substitutes in liquid or vaporisable form, e.g. liquid compositions for electronic cigarettes

Definitions

  • the present invention relates to a formulation, particularly a liquid formulation, for disposable cartridges or for refilling cartridges in electrical smoking systems (such as e-cigarettes) or to be used with other types of atomizers such as for example: drip atomizers, herbal vaporizers, convection vaporizers etc.
  • the liquid formulation is devoid of propylene glycol and synthetic polymers of ether oxides such as polyethylene glycols (PEGn like polyethylene glycol 400) and vegetable glycerin (or monoglycerol) as seen in the prior art.
  • PEGn polyethylene glycols
  • vegetable glycerin or monoglycerol
  • E-cigarette liquid (or e-cigarette atomizing liquid) is the most popular cigarette substitute product.
  • the formulation usually comprises excipients such as solvents, thickening agents, stabilizing agents, flavoring and/or taste regulators and optionally alkaloids such as nicotine or other pleasure-enhancing compounds.
  • excipients such as solvents, thickening agents, stabilizing agents, flavoring and/or taste regulators and optionally alkaloids such as nicotine or other pleasure-enhancing compounds.
  • others disclose new formulations comprising all sorts of naturally addictive products instead of nicotine but without any improvement in delivery than the regular propylene glycol, PEG (polyethylene glycol) and vegetable glycerin (monoglycerol) solvents.
  • the e-liquid is usually composed of propylene glycol and/or glycerol as solvents.
  • Propylene glycol and glycerol both have the property to vaporize at low temperature (about 60°C) while forming a vapor that gives the impression of cigarette smoke.
  • propylene glycol, monoglycerol and polyethylene glycol are all accepted as safe for human consumption (food grade), and can be used solely or in
  • a first aspect of the invention being to deliver flavor and/or medicinal substances through a heat and oxidation resistant carrier, which is a needed improvement in the art due to health concerns associated with previous formulations, namely degradation (to formaldehyde), dehydration (to acrolein), oxidation, ionization and other side reactions.
  • the liquid formulation is devoid of propylene glycol, polyethylene glycol (PEG or polyethylene oxide) and vegetable glycerin (or
  • Embodiments of the present invention are directed to liquid formulations for e-cigarettes, e-cigarettes, single use devices, drip atomizers, or as a liquid add-on for herbal or other type of controlled temperature vaporizers and/or in refilling cartridges for e-cigarettes containing a new formulation devoid or substantially devoid of short chain diols such as propylene glycol and already disclosed synthetic ether oxide polymers like PEG (polyethyleneglycol)/PPG (polypropyleneglycol) and vegetable glycerin (or monoglycerol) as seen in the prior art and instead comprises linear polyester diols and polyglycerols of even molecular size and dispersion that create better water repartition and protect active ingredients and flavors by increasing their solubility and heat-resistance.
  • a new formulation devoid or substantially devoid of short chain diols such as propylene glycol and already disclosed synthetic ether oxide polymers like PEG (polyethyleneglycol)/PPG (
  • a refilling liquid for an e-cigarette or vaporizing apparatus contains a formulation comprising a solvent selected from the group consisting of long- chain polyesterdiols such as for example di-, tri- or higher molecular weight
  • polyesterdiol but in a linear non-oxidized form that is also even in molecular size.
  • solvent can be selected from the group consisting of: triethylene glycol (triglycol), trimethylene glycol (1 ,3-propanediol); tripropylene glycol, dimethylene glycol (2,3-butanediol); and other linear long chain polyesterdiols such as for example: dipropylene glycol (4-oxa-2,6-heptandiol); dibutylene glycol; pentamethylene glycol and/or including polymers of rarer organic esterdiol groups such as, for example: limonene, pentylene, octylene, terpentylene, nonylene, linalylene, isoamylene, isobutylene, geranylene, bornylene, benzylene, caprylylene, pinene and allylene glycols, such as for example: dipentylene glycol or dilimonene glycol.
  • trimethylene glycol 1,3-propanediol
  • a kit for refilling an e-cigarette or vaporizer apparatus comprises (i) a liquid formulation comprising a solvent selected from the group consisting of polyesterdiols, more particularly: triethylene glycol (triglycol), trimethylene glycol (1 ,3-propanediol); tripropylene glycol, dimethylene glycol (2,3-butanediol); and other linear long chain polyesterdiols such as for example : dipropylene glycol (4-oxa- 2,6-heptandiol); dibutylene glycol; pentamethylene glycol and/or including polymers of rarer organic esterdiol groups such as, for example: limonene, pentylene, octylene, terpentylene, nonylene, linalylene, isoamylene, isobutylene, geranylene, bornylene, benzylene, caprylylene, pinene and allylene glycols,
  • a solvent selected from
  • a method of refilling an e-cigarette includes the steps of (i) providing a liquid formulation comprising a solvent selected from the group consisting of: linear naturally-derived or naturally-occurring polyesterdiols, and (ii) filling the liquid formulation into the receptacle of an e-cigarette or controlled temperature atomizer or vaporizer.
  • an e-cigarette comprises a cartridge containing a liquid formulation comprising a solvent selected from the group consisting of: linear naturally-derived polyesterdiols or naturally-occurring polyesterdiols.
  • the e-cigarette may be of a single-use or disposable type, or may be refillable with the liquid formulation to facilitate reuse.
  • FIG. 1 Further embodiments of the present invention are directed to a liquid formulation for e-cigarettes or other vaporizers, refilling cartridges for e-cigarettes or other vaporizers, e-cigarettes, other vaporizers, all containing a new formulation devoid or substantially devoid of glycerine or monoglycerol (propane-1 ,2,3-triol) for the same aforementioned health concerns and instead uses polyglycerols or other polyether triols.
  • a refilling liquid for an e-cigarette contains a formulation comprising a polyglycerol selected from the group consisting of: diglycerol, triglycerol, tetra-, penta-, hexa-, hepta-, octa-, nona- and decaglycerol and derivatives thereof such as acid or sugar conjugates, ethers or esters and other polyether triols of similar structure.
  • a polyglycerol selected from the group consisting of: diglycerol, triglycerol, tetra-, penta-, hexa-, hepta-, octa-, nona- and decaglycerol and derivatives thereof such as acid or sugar conjugates, ethers or esters and other polyether triols of similar structure.
  • a bottle comprising a liquid as defined herein.
  • an e-cigarette comprising a liquid as defined herein.
  • an e-vaporizing product comprising a liquid for vaporizing as defined herein.
  • FIG. 1. is a schematic illustration of one example of an e-cigarette configuration.
  • polyethylene glycol refers to a synthetic polydispersed mixture of ethylene oxide glycols used herein interchangeably with “PEG” or “polyethylene oxide”.
  • the polyesterdiol is a linear two to ten units polymer (also referred to as (ester) 2- io glycol), that is naturally-produced or naturally-derived from sources such as vegetables, fruits, bacteria, yeast, algae, etc.. and subsequently purified to give a compound free of variable viscosity and dehydration effects.
  • the naturally-derived or naturally-occurring polyesterdiol is 1) a polymethylene glycol such as; dimethylene glycol (2,3-butanediol); trimethylene glycol (1 ,3-propanediol), including tetra-, penta-, hexa-, hepta-, octa-, nona- and
  • decamethylene glycols and other derivatives thereof such as acid esters, sugar conjugates, and ether or alcohol derivatives
  • polypropylene glycol such as:
  • dipropylene glycol tripropylene glycol, including tetra-, penta-, hexa-, hepta-, octa-, nona- and decapropylene glycol and other derivatives thereof; 3) a polybutylene glycol such as: dibutylene glycol, tributylene glycol, including tetra-, penta-, hexa-, hepta-, octa-, nona- and decabutylene glycol, and other derivatives thereof; 4) also including 2- 10 unit polymers of rare organic ester types such as pentylene, octylene, terpentylene, nonylene, linalylene, isoamylene, isobutylene, geranylene, bornylene, benzylene and allylene, caprylylene, such asfor example, polyisobutylene glycol such as diisobutylene glycol; and 5) triethylene glycol, including te
  • the solvent is a linear naturally-derived or naturally-occurring polyesterdiol selected from the group consisting of: (ethylene) 3-10 glycol; (methylene) 2- io glycol; (propylene) 2- io glycol; (butylene) 2- io glycol; (pentylene) 2- io glycol; (octylene) 2- i 0 glycol; (terpentylene) 2- i 0 glycol; (nonylene) 2- i 0 glycol; (linalylene) 2 -io glycol;
  • the solvent is selected from the group consisting of: dimethylene glycol (2,3-butanediol); trimethylene glycol (1 ,3-propanediol);
  • the chemical structure of the invention is clearly defined ranging from the simpler trimethylene glycol to longer forms like 1 ,6-hexanediol (or hexamethylene glycol) to even longer forms like decamethylene glycol or even longer forms which are specially chosen to differ from the commonly used monomers or polydisperse polyesters (like synthetic PEG 400 or PPG).
  • the intended objective of this aspect of the invention is to use a substance with strong and even hygroscopic properties which solves the uneven distribution of water and flavor/active ingredients.
  • These new purified compounds such as produced by Sigma and Dow are also resistant to heat-related dehydration, polymerization and oxidation, effectively solving direct health concerns associated with the prior art formulations (acrolein and formaldehyde).
  • the solvent used for the formulation of the invention comprises : trimethylene glycol (1 ,3-propanediol); dimethylene glycol (2,3-butanediol); pentamethylene glycol; dipropylene glycol; tripropylene glycol; tetraethylene glycol or triethylene glycol due to their recent ecological production methods and proven safety.
  • the formulation's solvent comprises dipropylene glycol and/or tripropylene glycol and/or triethylene glycol and/or tetraethylene glycol and/or pentamethylene glycol due to their temperature and oxidation resistance and proven vapor safety profiles.
  • polyesterdiols are new ingredients on the market that have a remarkable safety profile and better heat and chemical stability than propylene glycol due to their molecular structure. These ingredients are now considered natural eco- glycol because of a new process to produce a very pure form by fermenting corn sugars which is expected to eventually cover all glycols/glycerols of the present invention. They are now labeled ECOCERT and FDA food safe, 100% natural and made through sustainable development. Their unique behavior makes them a perfect replacement for propylene glycol. Not only they are safer and less irritating, but they also have a smoother, sweeter taste and are known anti-bacterial and sanitizers when vaporized.
  • the polyesterdiol such as triethylene glycol or dipropylene glycol can be mixed with a co-solvent ester triol such as polyglycerol of the formula
  • (glycerol) 2- io such as, for example: diglycerol; triglycerol; tetraglycerol, pentaglycerol, hexaglycerol, heptaglycerol, octaglycerol, nonaglycerol or decaglycerol or other polyether triols (trihydric alcohols).
  • diglycerol has shown to have much better heat resistance than its parent monoglycerol. It is also found in food preparations and produced from natural sources.
  • the e-cigarette may be of various types of configurations, the details of which form no part of the present invention.
  • e-cigarettes may be of a single- use or disposable type, or may be refillable with liquid alkaloid compositions and/or cartridges containing liquid compositions to facilitate reuse.
  • FIG. 1 An air inlet 4 is provided on the external wall of a shell 14 which houses LED 1 , cell 2, electronic circuit board 3, normal pressure cavity 5, sensor 6, vapor-liquid separator 7, atomizer 9, liquid-supplying bottle 11 , mouthpiece 15, microswitch 16, gas vent 17, and air passage 18.
  • the electronic circuit board 3 has an electronic switching circuit and a high frequency generator.
  • a negative pressure cavity 8 is provided in the sensor 6 and is separated from the sensor 6 by a ripple film.
  • An atomization cavity 10 is provided in the atomizer 9.
  • a retaining ring 13 is provided for locking the liquid-supplying bottle 11 between one side of the liquid-supplying bottle 11 and the shell 14; and an aerosol passage 12 is provided on the other side of the liquid- supplying bottle.
  • Additional components ingredients may be added to the formulation to improve taste or stability.
  • additional components include, but are not limited to, sweeteners, natural flavorants, artificial flavorants, colorants, antioxidants,
  • preservatives including, but not limited to, xanthum gum, carboxymethylcellulose, carboxyethylcellulose, hydroxypropylcellulose, methylcellulose, microcrystalline cellulose, starches, dextrins, maltodextrins, other polyols (including sugar alcohols, such as sorbitol, lactitol or mannitol), carbohydrates (e.g., lactose), propylene glycol alginate, gellan gum, guar, pectin, tragacanth gum, gum acacia, locust bean gum, gum arabic, mannitol, natural and/or artificial mint flavors, sucralose, silicon dioxide, stearic acid, hydroxypropyl methylcellulose, mono and diglycerides (acyl glycerols), ether and sugar
  • one or more flavorants may be added to the composition, non- limiting examples of which include peppermint, menthol, wintergreen, spearmint, propolis, eucalyptus, cinnamon, tobacco, fruits or the like.
  • the total amount of flavorants typically ranges from about 0.5 to about 15 wt. %, often from about 1 to about 10 wt. %, based on the total weight of the composition.
  • Example 1 Flavor or active medicinal substance recipes may be prepared by mixing the ingredients listed in Table 1.
  • Flavors 800 mg 1200 mg 1300 mg 1000 mg 1500 mg

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Preparation (AREA)

Abstract

La présente invention concerne une composition liquide vaporisable permettant de recharger des cartouches pour e-cigarettes ou destinée à être utilisée directement sur des atomiseurs ou d'autres vaporisateurs à température régulée. Ladite composition liquide ne contient, en particulier, pas de polyéthylène glycol (PEG) et/ou de propylène glycol en tant que solvant, mais, à la place, elle contient du dipropylène glycol ou d'autres polyesterdiols linéaires de poids moléculaire élevé.
PCT/CA2015/050088 2014-02-07 2015-02-06 Composition liquide pour e-cigarettes WO2015117243A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201461937111P 2014-02-07 2014-02-07
US61/937,111 2014-02-07

Publications (1)

Publication Number Publication Date
WO2015117243A1 true WO2015117243A1 (fr) 2015-08-13

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ID=53777102

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CA2015/050088 WO2015117243A1 (fr) 2014-02-07 2015-02-06 Composition liquide pour e-cigarettes

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WO (1) WO2015117243A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018023890A1 (fr) * 2016-08-03 2018-02-08 华健 Liquide à vaporiser pour cigarette électronique combinant plusieurs alcools
WO2018073261A1 (fr) * 2016-10-18 2018-04-26 Philip Morris Products S.A. Procédés et systèmes destinés à améliorer la stabilité de la formulation de pré-vapeur d'un dispositif de vapotage électronique
WO2018152637A1 (fr) * 2017-02-22 2018-08-30 Gene Bernaudo Systèmes de composition d'agent de mélange de cigarettes électroniques
US10212964B2 (en) 2016-07-07 2019-02-26 Altria Client Services Additive assembly for electronic vaping device
CN109788795A (zh) * 2016-10-18 2019-05-21 菲利普莫里斯生产公司 用于增大电子蒸汽烟装置的蒸汽前调配物稳定性的方法和系统
CN111672431A (zh) * 2020-06-04 2020-09-18 云南中烟工业有限责任公司 一种包含烃基-氨基-糖基三段式糖基胶凝剂的可逆相变雾化液凝胶及其制备方法和应用
CN113876014A (zh) * 2021-09-06 2022-01-04 湖北中烟工业有限责任公司 一种含有烷基化甘油的雾化剂及其制备方法和应用
US11992038B2 (en) 2018-12-31 2024-05-28 Philip Morris Products S.A. Liquid nicotine formulation comprising partially water-soluble solvent

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0337504A2 (fr) * 1985-08-26 1989-10-18 R.J. Reynolds Tobacco Company Moyens produisant un aérosol pour un article à fumer et article à fumer avec tels moyens
US20120325228A1 (en) * 2011-06-23 2012-12-27 Williams Jonnie R Alkaloid composition for e-cigarette
CA2766749A1 (fr) * 2011-07-04 2013-01-04 Junxiang Zheng Type de methode de preparation de liquide pour cigarettes electroniques
CN104256885A (zh) * 2014-08-05 2015-01-07 云南中烟工业有限责任公司 一种电子烟烟液溶剂
US20150101606A1 (en) * 2013-10-14 2015-04-16 Jackie L. White Devices for vaporizing and delivering an aerosol agent

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0337504A2 (fr) * 1985-08-26 1989-10-18 R.J. Reynolds Tobacco Company Moyens produisant un aérosol pour un article à fumer et article à fumer avec tels moyens
US20120325228A1 (en) * 2011-06-23 2012-12-27 Williams Jonnie R Alkaloid composition for e-cigarette
CA2766749A1 (fr) * 2011-07-04 2013-01-04 Junxiang Zheng Type de methode de preparation de liquide pour cigarettes electroniques
US20150101606A1 (en) * 2013-10-14 2015-04-16 Jackie L. White Devices for vaporizing and delivering an aerosol agent
CN104256885A (zh) * 2014-08-05 2015-01-07 云南中烟工业有限责任公司 一种电子烟烟液溶剂

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* Cited by examiner, † Cited by third party
Title
ALDRICH HANDBOOK OF FINE CHEMICALS, 2009, pages 1040, 2197, 2584, 2617 *

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10212964B2 (en) 2016-07-07 2019-02-26 Altria Client Services Additive assembly for electronic vaping device
US11317654B2 (en) 2016-07-07 2022-05-03 Altria Client Services Llc Additive assembly for electronic vaping device
US11849768B2 (en) 2016-07-07 2023-12-26 Altria Client Services Llc Additive assembly for electronic vaping device
WO2018023890A1 (fr) * 2016-08-03 2018-02-08 华健 Liquide à vaporiser pour cigarette électronique combinant plusieurs alcools
WO2018073261A1 (fr) * 2016-10-18 2018-04-26 Philip Morris Products S.A. Procédés et systèmes destinés à améliorer la stabilité de la formulation de pré-vapeur d'un dispositif de vapotage électronique
CN109788795A (zh) * 2016-10-18 2019-05-21 菲利普莫里斯生产公司 用于增大电子蒸汽烟装置的蒸汽前调配物稳定性的方法和系统
WO2018152637A1 (fr) * 2017-02-22 2018-08-30 Gene Bernaudo Systèmes de composition d'agent de mélange de cigarettes électroniques
US11992038B2 (en) 2018-12-31 2024-05-28 Philip Morris Products S.A. Liquid nicotine formulation comprising partially water-soluble solvent
CN111672431A (zh) * 2020-06-04 2020-09-18 云南中烟工业有限责任公司 一种包含烃基-氨基-糖基三段式糖基胶凝剂的可逆相变雾化液凝胶及其制备方法和应用
CN111672431B (zh) * 2020-06-04 2022-04-08 云南中烟工业有限责任公司 一种包含烃基-氨基-糖基三段式糖基胶凝剂的可逆相变雾化液凝胶及其制备方法和应用
CN113876014A (zh) * 2021-09-06 2022-01-04 湖北中烟工业有限责任公司 一种含有烷基化甘油的雾化剂及其制备方法和应用

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