WO2015117243A1 - Liquid formulation for e-cigarettes - Google Patents

Liquid formulation for 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
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Application number
PCT/CA2015/050088
Other languages
French (fr)
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
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Publication of WO2015117243A1 publication Critical patent/WO2015117243A1/en

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Classifications

    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24BMANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/10Chemical features of tobacco products or tobacco substitutes
    • A24B15/16Chemical features of tobacco products or tobacco substitutes of tobacco substitutes
    • AHUMAN NECESSITIES
    • A24TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24BMANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/10Chemical features of tobacco products or tobacco substitutes
    • A24B15/16Chemical features of tobacco products or tobacco substitutes of tobacco substitutes
    • A24B15/167Chemical 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

Abstract

The present invention provides a vaporizable liquid formulation for refilling cartridges in e-cigarettes or for using directly on atomizers or other controlled temperature vaporizers. Particularly, the liquid formulation is devoid of polyethylene glycol (PEG) and/or propylene glycol as solvent and instead comprises dipropylene glycol or other higher molecular weight linear polyesterdiols.

Description

LIQUID FORMULATION FOR E-CIGARETTES
Field of the invention
[0001] 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. More particularly, 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. Background of the invention
[0002] Combustion of organic materials such as tobacco is known to produce tar and other potentially harmful materials. Electronic cigarettes (or "e-cigarettes") have been developed as an alternative to traditional cigarettes as a means for volatizing active components (US 6041789), such as nicotine, for inhalation without combustion, while at the same time providing the user with an oral experience similar to that of traditional cigarette smoking. US 7,832,410 describes an e-cigarette having a liquid supply bottle in communication with an atomizer for volatizing a nicotine-containing solution. US 7,726,320 discloses a smoking article having an electrically powered aerosol-generating device which heats tobacco contained within the device to generate an aerosol which is described as being similar to tobacco smoke (US 2007/0267031). Other systems provide alternatives for controlled release flavoring (i.e. US
2005/0172976).
[0003] Currently e-cigarettes generally use a liquid containing nicotine, a toxic and addictive substance, as the sole active component (US 2012/0325228; US
2013/0008457), whereas others use caffeine that is also addictive (CN 101926505). It would be especially desirable to develop an alternative formulation that more effectively and safely achieves the pleasure-enhancing attributes of traditional cigarette smoking, which in turn may assist smokers in quitting traditional cigarette-smoking.
[0004] 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. In more recent art, 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.
[0005] Indeed, 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. In fact, propylene glycol, monoglycerol and polyethylene glycol are all accepted as safe for human consumption (food grade), and can be used solely or in
combination, but this does not take into consideration the fact that they are heated to high temperatures which are often variable prior to being inhaled. In the case of unevenly dispersed molecular size PEG 400 (polyethylene glycol 400), which is currently popular in liquid formulations from China, the result is also uneven and contaminants are bound to be created as the liquid heats up sometimes over boiling point in certain hotter spots on the vaporizing coil.
[0006] In addition, the previous art clearly lack concern for the healthy delivery of flavors and/or ingredients for functional medicinal and therapeutic use as oxidizing monoglycols readily react with alkaloid, protein, amine or acid ingredients used in flavoring or as an active component. The delivery technology is not improved, and furthermore, users now choose from a larger variety of electronic cigarettes with a variety of power settings. Many models are imprecise and users often intentionally increase the temperature of the coil to achieve a thicker smoke, causing an accidental burning or polymerisation of the solvents that creates contaminants like formaldehyde and acrolein (as exemplified in recent analysis of some devices, the contaminants are present sometimes in concentrations that are undetectable to the taste and smell but still are harmful to the user). This is due to overheating of the vaporization coil, or wick malfunction which results in a less than optimal flow of liquid to cool the coil ; this can happen as the coil becomes used or in certain "hot spots". For these two reasons, the previous art fails to really improve on the former electronic vapor liquid formulations, which are basically a copy of sublingual or aerosol formulations (Buccal, sublingual and mucosally absorbed herbal compositions for relieving nicotine withdrawal symptoms and craving for nicotine and nicotine containing substances US
2004/0013752 A*\). Recent analysis also shows that uneven burning might be due to the liquid distribution becoming uneven because of frequent temperature changes in the device that cause side-reactions in the formulation. This can in turn induce solvent dehydration or polymerization over time, causing opportunity for a myriad of side reactions like esterifications and oxidations that create even more contaminants. Polyethylene glycol seems even more susceptible to this effect because of the apparent tendency of its larger particles to agglomerate and osmotically steal water from the small chain glycols contained in the solution. The current formulations can thus change behavior as they are being used up.
[0007] Other patent references abound on trying to copy the basic idea of vaporizing herbal or artificial medicinal components but they all fall short of the common sense idea that random conditions give random results. Not only does the occasional burning of liquid may cause undesirable taste and side-effects, it can also cancel out the medicinal effects of many natural compounds and cause side reactions with the active constituents. Resulting compounds could prove toxic and have hazardous health effects.
[0008] There is also the understated fact that others in the art fail to realize: some flavor components do react and burn if the excipients are not calibrated to buffer this particular flavoring to the variety of heating temperatures and materials users will inevitably use. Some units now offer a degree of control over heating temperatures so it is even more important at this time that the art adopt a new approach to the liquid formulation so that flavors can be enjoyed in a manner that does not endanger the health of the end-user. The present invention aims to improve both safety and homogeneity of the art by providing solvents with a much higher temperature resistance and greater/more uniform water holding capacity that prevents virtually all side reactions.
Summary of the invention
[0009] 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.
[0010] More particularly, the liquid formulation is devoid of propylene glycol, polyethylene glycol (PEG or polyethylene oxide) and vegetable glycerin (or
monoglycerol) as solvents (such as in the prior art) and instead comprises purified linear polyester diols and polyglycerols that, due to their higher molecular weight and high temperature proven safety profile, allow a safer delivery of active principle contained therein. [0011] In a further ideal aspect of the invention, there is provided an ecological and biodegradable liquid base improvement which is composed of only naturally derived or naturally occurring ingredients.
[0012] 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.
[0013] In one aspect, 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.
Examples for such 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.
[0014] In another aspect, 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, such as for example: dipentylene glycol or dilimonene glycol.; and (ii) instructions for filling the liquid formulation into the receptacle of an e-cigarette or atomizer. [0015] In another aspect, 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. [0016] In yet another aspect, 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. [0017] 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. [0018] In one aspect, 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.
[0019] In a further aspect, there is provided a bottle comprising a liquid as defined herein.
[0020] In a further aspect, there is provided an e-cigarette comprising a liquid as defined herein. [0021] In a further aspect, there is provided an e-vaporizing product comprising a liquid for vaporizing as defined herein.
Detailed description of the invention
Description of the figures
[0022] FIG. 1. is a schematic illustration of one example of an e-cigarette configuration.
Abbreviations and Definitions
Definitions
[0023] The term "monoglycerol" is used herein interchangeably with the terms "vegetable glycerin" or "glycerol". [0024] The term "polyethylene glycol" refers to a synthetic polydispersed mixture of ethylene oxide glycols used herein interchangeably with "PEG" or "polyethylene oxide".
Detailed description of particular embodiments
Solvent
[0025] Particularly, with respect to the ideal solvent of the invention, 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.
[0026] Particularly, 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; 2) a 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 tetra-, penta-, hexa-, hepta-, octa-, nona- and decaethylene glycols and other derivatives thereof such as acid or sugar conjugates, and esters or ether or alcohol derivatives.
[0027] Particularly, 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-i0 glycol; (terpentylene)2-i0 glycol; (nonylene)2-i0 glycol; (linalylene)2-io glycol;
(isoamylene)2-io glycol; (isobutylene)2-i0 glycol; (geranylene)2-i0 glycol; (bornylene)2-i0 glycol; (benzylene)2-i0 glycol; (allylene)2-i0 glycol; and (caprylylene)2-i0 glycol; acid or sugar conjugates thereof, and ester or ether or alcohol derivatives thereof.
[0028] More particularly, the solvent is selected from the group consisting of: dimethylene glycol (2,3-butanediol); trimethylene glycol (1 ,3-propanediol);
tetramethyleneglycol, pentamethylenglycol, hexamethyleneglycol,
heptamethyleneglycol, octamethyleneglycol, nonamethylenglycol; decamethylene glycol; triethylene glycol; tetraethyleneglycol, pentaethylenglycol, hexaethyleneglycol, heptaethyleneglycol, octaethyleneglycol, nonaethylenglycol; decaethylene glycol;
dipropylene glycol; tripropylene glycol; tetrapropylene glycol, pentapropylene glycol, hexapropylene glycol, heptapropylene glycol, octapropylene glycol, nonapropylene glycol; decapropylene glycol; dibutylene glycol, tributylene glycol; tetrabutylene glycol, pentabutylene glycol, hexabutylene glycol, heptabutylene glycol, octabutylene glycol, nonabutylene glycol, decabutylene glycol and diisobutylene glycol. 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). [0029] Even more particularly, 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.
[0030] Most particularly, 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.
[0031] The above 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. [0032] Some commercial buildings and airplanes now keep their air clean by injecting a vapor of these glycols (produced much in the same manner as electronic cigarettes) inside the air circulation system. All the information in the field seem to agree they are the less toxic inhalation hazards of the glycol family; for example repeated exposure to rats by triethylene glycol vapor caused no toxic effects and the NOEL (no observable effect level) was 1800mg/cubic meter which is dozens of times higher than the levels achieved with personal atomizers. Neither high dosage acute nor repeated exposures to triethylene glycol produced hepatorenal injury characteristic of that caused by the lower glycol homologues. They are also known to be rapidly metabolized in-vivo to harmless compounds of the krebs cycle such as lactic and pyruvic acids.
Co-solvent
[0033] Optionally, 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).
[0034] In particular, 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.
[0035] We are looking away from vegetable glycerin (monoglycerol) because of its tendency to dehydrate under high heat and create toxic substances such as
formaldehyde and acrolein. It also has a tendency to react with organic compounds and flavors, changing the behavior and concentration of the liquids it is mixed therewith. The use of higher molecular weight polyglycerols solves this problem because the molecule is much harder to break and also holds water captive much better than its "mono" counterpart, thereby allowing active cooling of the heating element and smoother less drying vapor. E-cigarette configuration
[0036] The e-cigarette may be of various types of configurations, the details of which form no part of the present invention. In general, 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. One example of an e- cigarette is shown in 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. Other details are described in U.S. Pat. No. 7,832,410, the disclosure of which is hereby incorporated by reference in its entirety.
Other components
[0037] Additional components ingredients may be added to the formulation to improve taste or stability. Such additional components include, but are not limited to, sweeteners, natural flavorants, artificial flavorants, colorants, antioxidants,
preservatives, chelating agents, viscomodulators, tonicifiers, odorants, opacifiers, suspending agents, binders, thickeners, co-solvents and mixtures thereof, 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 acetates or other acid esters such as dimethyl acetate, ethyl acetate, isopropyl acetate, ethylhexyl acetate, butyl acetate, triethyl citrate, dimethyl butyrate and the like. [0038] If desired, 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.
[0039] The following examples are put forth so as to provide those of ordinary skill in the art with a complete disclosure and description of how to make and use the present invention, and are not intended to limit the scope of what the inventor regards as their invention nor are they intended to represent that the experiments below are all or the only experiments performed. Efforts have been made to ensure accuracy with respect to numbers used (e.g. amounts, weights, etc.) but some experimental errors and deviations should be accounted for.
Examples
Example 1 Flavor or active medicinal substance recipes may be prepared by mixing the ingredients listed in Table 1.
TABLE 1
Figure imgf000012_0001
Flavors (mg) 800 mg 1200 mg 1300 mg 1000 mg 1500 mg
Stabilisers /
antioxidants 800 mg 1000 mg 1 100 mg 900 mg 1000 mg (mg)
[0040] While the invention has been described in connection with specific embodiments thereof, it will be understood that it is capable of further modifications and this application is intended to cover any variations, uses, or adaptations of the invention following, in general, the principles of the invention and including such departures from the present disclosure as come within known or customary practice within the art to which the invention pertains and as may be applied to the essential features hereinbefore set forth, and as follows in the scope of the appended claims.
[0041] All patents, patent applications and publications mentioned in this specification are herein incorporated by reference to the same extent as if each independent patent, patent application, or publication was specifically and individually indicated to be incorporated by reference.

Claims

1. A liquid formulation for an e-cigarette and/or other heat-controlled
atomizer/vaporizer devices, comprising a solvent comprising a linear naturally-derived and/or naturally occurring polyesterdiol.
2. A kit for refilling an e-cigarette and/or other heat-controlled vaporizer/atomizer devices, comprising:
(i) a liquid formulation comprising a solvent comprising a linear naturally-derived and/or naturally-occurring polyesterdiol; and
(ii) instructions for filling the liquid formulation into a liquid receptacle of an e- cigarette and/or other heat controlled atomizer/vaporizer device.
3. A method of refilling an e-cigarette and/or other heat-controlled
atomizer/vaporizer devices, comprising the steps of:
(i) providing a liquid formulation comprising a solvent comprising a linear naturally-derived or naturally-occurring polyesterdiol, and
(ii) filling the liquid formulation into a liquid receptacle of an e-cigarette or other heat-controlled atomizer/vaporizer device.
4. A cartridge containing a liquid formulation comprising a solvent comprising a linear naturally-derived or naturally-occurring polyesterdiol.
5. The solvent as defined in any one of claims 1 to 4, wherein the linear polyesterdiol is selected from the group consisting of: (methylene)2-io glycol;
(ethylene)3-10 glycol; (propylene)2-io glycol; (butylene)2-io glycol; (pentylene)2-io glycol; (octylene)2-10 glycol; (terpentylene)2-10 glycol; (nonylene)2-10 glycol; (linalylene)2-10 glycol; (isoamylene)2-10 glycol; (isobutylene)2-10 glycol; (geranylene)2-10 glycol; (bornylene)2-10 glycol; (benzylene)2-10 glycol; (allylene)2-10 glycol; and (caprylylene)2-10 glycol; acid or sugar conjugates thereof, and ester or ether or alcohol derivatives and isomers thereof.
6. The solvent as defined in claim 5, selected from the group consisting of:
dimethylene glycol (2,3-butanediol); trimethylene glycol (1 ,3-propanediol);
tetramethyleneglycol, pentamethylenglycol, hexamethyleneglycol,
heptamethyleneglycol, octamethyleneglycol, nonamethylenglycol; decamethylene glycol; triethylene glycol; tetraethyleneglycol, pentaethylenglycol, hexaethyleneglycol, heptaethyleneglycol, octaethyleneglycol, nonaethylenglycol; decaethylene glycol;
dipropylene glycol; tripropylene glycol; tetrapropylene glycol, pentapropylene glycol, hexapropylene glycol, heptapropylene glycol, octapropylene glycol, nonapropylene glycol; decapropylene glycol; dibutylene glycol, tributylene glycol; tetrabutylene glycol, pentabutylene glycol, hexabutylene glycol, heptabutylene glycol, octabutylene glycol, nonabutylene glycol, decabutylene glycol and other derivatives or isomers such as diisobutylene glycol.
7. The solvent defined in any one of claims 1-6 selected from the group consisting of: trimethylene glycol (1 ,3-propanediol); dimethylene glycol (2,3-butanediol);
dipropylene glycol; tripropylene glycol; triethylene glycol; tetraethylene glycol and pentamethylene glycol including isomers and derivatives thereof.
8. The solvent defined in claim 7 selected from the group consisting of:
dipropylene glycol; tripropylene glycol; triethylene glycol; tetraethylene glycol;
pentamethylene glycol including isomers and derivatives thereof.
9. A liquid formulation for an e-cigarette or other heat-controlled
atomizer/vaporizing devices comprising a polyglycerol of the formula (glycerol)2-io and/or other polyether triols of similar molecular structure.
10. The liquid formulation according to claim 9, wherein said polyglycerol is selected from the group consisting of: diglycerol, triglycerol, tetraglycerol,
pentaglycerol, hexaglycerol, heptaglycerol, octaglycerol, nonaglycerol and decaglycerol and/or other similar polyether triols and isomers or derivatives thereof.
11. The liquid formulation according to claim 10, wherein said polyglycerol is selected from the group consisting of: diglycerol and triglycerol.
12. A kit for refilling an e-cigarette comprising: (i) a liquid formulation as defined in claim 10 or 1 1 ; and
(ii) instructions for filling or using the liquid formulation into a liquid receptacle of an e-cigarette or other atomizer/vaporizer.
13. A method of refilling an e-cigarette or other personal atomizer/vaporizer comprising the steps of:
(i) providing a liquid formulation as defined in claim 10 or 11 ; and
(ii) filling the liquid formulation into a liquid receptacle of an e-cigarette or other atomizer/vaporizer.
14. A cartridge containing a liquid formulation as defined in claim 10 or 1 1.
15. A solvent for e-cigarette filling liquid formulation, said liquid formulation being substantially devoid a solvent selected from the group consisting of: ethylene glycol, polyethylene glycol(PEG), monopropylene glycol, polypropyleneglycol(PPG), monobutylene glycol and monoglycerol.
16. A bottle comprising a liquid as defined in any one of claims 1 to 15.
17. An e-cigarette comprising a liquid as defined in any one of claims 1 to 15.
18. An e-vaporizing product comprising a liquid for vaporizing as defined in any one of claims 1 to 15.
PCT/CA2015/050088 2014-02-07 2015-02-06 Liquid formulation for e-cigarettes WO2015117243A1 (en)

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US10212964B2 (en) 2016-07-07 2019-02-26 Altria Client Services Additive assembly for electronic vaping device
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CN111672431A (en) * 2020-06-04 2020-09-18 云南中烟工业有限责任公司 Reversible phase-change atomized liquid gel containing alkyl-amino-glycosyl three-stage glycosyl gelling agent and preparation method and application thereof
CN111672431B (en) * 2020-06-04 2022-04-08 云南中烟工业有限责任公司 Reversible phase-change atomized liquid gel containing alkyl-amino-glycosyl three-stage glycosyl gelling agent and preparation method and application thereof
CN113876014A (en) * 2021-09-06 2022-01-04 湖北中烟工业有限责任公司 Atomizing agent containing alkylated glycerol and preparation method and application thereof

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