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    • 专利摘要:
    The present invention relates to the use of a composition comprising a long chain polyol as an electronic cigarette liquid. It also relates to an electronic cigarette liquid composition comprising a long chain polyol, as well as at least one compound selected from nicotine, a nicotine substitute and a flavor. It also relates to an electronic cigarette containing this composition.
    公开号:FR3023453A1
    申请号:FR1456655
    申请日:2014-07-10
    公开日:2016-01-15
    发明作者:Antoine Piccirilli；Vincent Bonnarme
    申请人:Antoine Piccirilli；Vincent Bonnarme；
    IPC主号:
    专利说明:

    [0001] FIELD OF THE INVENTION The present invention relates to the use of a composition comprising a long chain polyol as an electronic cigarette liquid. It also relates to an electronic cigarette liquid composition comprising a long chain polyol, as well as nicotine and / or at least one flavor, and an electronic cigarette or a related device containing this composition. BACKGROUND OF THE INVENTION The e-cigarette market is currently experiencing an important development, since it allows the consumer to maintain the ritual associated with the use of the cigarette without suffering the deleterious effects of the harmful substances that this it contains. The electronic cigarette or e-cigarette runs electricity without burning. It produces a mist of fine particles, commonly called vapor or artificial smoke, visually resembling the smoke produced by burning tobacco. This vapor can be flavored (aroma of tobacco, mint, fruit, chocolate, etc.) and contain or not nicotine. In properly manufactured and used e-cigarettes, the aerosol contains, according to the available data, far fewer deleterious substances to health than tobacco smoke, in particular no solid particles, tar, other carcinogens, or monoxide. of carbon (CO). The e-cigarette comprises three main parts 5 contained in a plastic or metallic envelope: - a battery, - a cartridge or reservoir containing a liquid called "e-liquid", and - an atomizer. The battery is most of the time the largest part of the e-cigarette on disposable products. Reusable cigarettes are "low voltage" batteries (rechargeable batteries), rechargeable by USB cable or charger. In reusable e-cigarettes, the tube housing the battery is screwed onto the cartridge containing the liquid. On some models, a light - usually a red or blue LED - is placed at the other end of the battery tube. The e-liquid storage device may take the form of a cartridge (generally made of silicone, PMMA or stainless metal) or a tank (in particular made of PMMA / polyethylene, borosilicate glass or stainless metal) possibly supplemented with a device for collecting the liquid by capillarity (in particular silica, fiberglass, ceramic metal fabric, nylon thread or borosilicate fibers) in contact with the vaporization system. The atomizer converts the e-liquid to fog simulating smoke. It consists of a spiral or wire mesh that forms a heating resistor. It is more and more often integrated in the refillable cartridge. A micro-valve sensitive to depression caused by inspiration or a manually triggered contactor allows the battery to feed the atomizer. The e-cigarette can be single-use or reusable.
    [0002] The e-liquids used are mainly composed of the following constituents: - synthetic propylene glycol (about 65%) - glycerol (about 25%) - water (5 to 10%) - flavors and dyes (2 to 5%) - nicotine (0 at 20 mg / ml) Some e-liquids may also contain significant amounts of ethanol (> 1%).
    [0003] Some products may be free of synthetic propylene glycol. The objective is in this case to be able to claim products of exclusively vegetable origin. This objective is achieved, however, to the detriment of the longevity of heating resistors, which clog very quickly. In addition, the quality of the emitted smoke is far from adequate in terms of vapor density, and the organoleptic properties of the liquids are strongly modified, because the release of the aromas in the absence of propylene glycol is made less immediate and deeply organoleptically modified. Moreover, the exclusive use of glycerol forces to load the product with water, in order to reduce the viscosity of the e-liquid and thus facilitate the filling of the e-cigarette. But, again, the impact of a high water content radically changes the quality of the vapor emitted and leads to excessive corrosion of the materials as well as rapid and excessive consumption of the e-liquid (faster vaporization). In addition, the presence of water requires the industry to take drastic precautions to avoid any microbiological pollution (eg sterile filtration, adding preservative). Finally, another problem related to the exclusive use of glycerol lies in the fact that this compound is significantly less vaporizable than propylene glycol, so that its vaporization requires a significantly higher heating temperature, which can lead to its degradation and the formation of unwanted by-products such as acrolein. Therefore, the use of synthetic propylene glycol in a larger quantity than glycerol is most often preferred, which does not allow manufacturers to claim a natural origin of their products. In addition, propylene glycol is obtained according to a process that is one of the most energy-intensive in the petrochemical industry and has a strong environmental footprint (Eissen & Co., Angew Chem Int, Ed., 2002, 41, 414-436). results in high energy consumption and high production of volatile organic compounds (VOCs) and waste. In addition, the synthetic propylene glycol is obtained from propylene oxide by a continuous hydration process, according to the following scheme: 0 / ± H20 H2C-CH CH3 + polyglycols The production of propylene glycol is accompanied by the formation of secondary products (di-, and tri- and tetrapropylene glycols) and unconverted propylene oxide (Petrochemical Processes: Major Oxygenated, Chlorinated and Nitrated Derivatives - Alain Chauvel, Gilles Lefebvre - TECHNIP Editions - p26), horn Illustrated below: H 3 C Propylene oxide o C H-13 CH 3 HO-C H 2 CH, OH Propylene glycol -111 CH 2 CH 2 CH 2 CH 2 OH Dipropylene glycol CH 3 CH 3 1 + CH 0 CH HC-CH2 / HO C 'C' OH H3C H2 H2 Dipropylene glycol propylene oxide CH3 CH3 1 I H2 CH 0 C / H / / CC / CH e CH HO H2 H2 i CH3 Tripropylene glycol Therefore, after purification, the minor and recurring organic impurities of propylene glycol are di- and tripropylene glycol, as well as propylene oxide, the residual content of which according to the producers is of the order of 5 to 10 ppm (Propylene Glycol - CIR Expert Panel, June 28-29, 2010 - Draft Report). However, propylene oxide is classified by the North American and European environmental agencies as a carcinogenic and mutagenic compound in animals and as a probable carcinogen in humans. Therefore, it is important to limit exposure to this compound. Also, the Report and Expert Opinion on the eCigarette published by the French Office for Tobacco Prevention (OFT) in May 2013 stresses the need to ensure the absence of carcinogenic contaminants in e-liquids. In fact, it is necessary to avoid the presence of a toxic compound such as propylene oxide and, to a lesser extent, the presence of organic impurities belonging to the family that is strongly criticized from the toxicological point of view of glycol ethers, which alter the quality of e-liquids, like di- and tripropylene glycols. A solution to the aforementioned problems has been proposed in WO 2013/088230. It consists of substituting propylene glycol of plant origin for synthetic propylene glycol, obtained by catalytic hydrogenation of sorbitol, itself derived from corn. Propylene glycol is combined with glycerol of vegetable origin, with nicotine which can be extracted from tobacco leaves and optionally with aromas of natural origin, to obtain an e-liquid of entirely vegetable origin. While this solution effectively overcomes the disadvantages associated with the use of synthetic propylene glycol, it has been demonstrated that the vapor density and the aromatic power produced by these e-liquids of vegetable origin could be improved. replacing propylene glycol with a long chain polyol and this effect was particularly pronounced in the absence of glycerine or in a low glycerine e-liquid composition. By eliminating glycerol, the use of a long chain polyol further helps to protect the heating device of electronic cigarettes by eliminating the rapid fouling phenomenon observed in the presence of glycerin. Another advantage of the absence of glycerin is that the steam produced is freed from the toxic and carcinogenic impurities resulting from the thermal decomposition of glycerol. Another advantage of using a long chain polyol is that it makes it possible to formulate nicotine in the absence of water. It is known that nicotine base in solution in water is converted into protonated nicotine. However, the protonated form is clearly less bioassimilable than nicotine base. Consequently, the use of a long-chain polyol in the absence of water makes it possible to design e-liquids that are more efficient in terms of smoking cessation and more secure because they are less concentrated in nicotine, an alkaloid whose acute toxicity is very high. it has furthermore been observed that a long chain polyol made it possible to obtain e-liquids devoid of nicotine recreating the throat hit (or "throat hit") typically experienced by the user of a conventional cigarette, when the passage of nicotine in the mouth.
    [0004] Until now, this much sought-after effect of e-cigarette users was achieved only by adding a few drops of propylene glycol, glycerin and flavor product to the e-liquid (E-Liquid Flash). ® from FLAVOR ART). However, the latter has all the disadvantages mentioned above, related to the use of propylene glycol and glycerine. The long chain polyols are mainly of synthetic origin but some are of renewable origin, such as 1,4 butanediol, 2,3 butanediol, 1,2 pentanediol. SUMMARY OF THE INVENTION It is therefore an object of the present invention to use a composition comprising a long chain polyol as an electronic cigarette liquid.
    [0005] It also relates to an electronic cigarette liquid composition comprising a long chain polyol, as well as at least one compound selected from nicotine, a nicotine substitute and a flavor.
    [0006] It also relates to an electronic cigarette containing this composition. It finally relates to the use of a long chain polyol in an electronic cigarette liquid containing or not nicotine, to improve the tingling of the throat felt by a user of said liquid and / or the ease of aspiration of the vapor produced by said liquid, or to improve the bioavailability of nicotine. DETAILED DESCRIPTION OF EMBODIMENTS In the present application, the term "electronic cigarette" means all devices equipped with electrical means producing steam and delivering nicotine and / or aroma. This definition therefore includes personal vaporizers (VP), electronic nicotine delivery systems (ENDS for "Electronic Nicotine Delivery System" or ENDD for "Electronic Nicotine Delivery Device"), as well as electronic cigars, electronic pipes and electronic shisha, tobacco-based cigarettes heated or containing tobacco flavor obtained by maceration.
    [0007] By "plant-based" compound is meant a compound comprising at least 95% biobased carbon, as determined by ASTM D6866-12 (Standard Test Methods for Determining the Biobase Content of Solid, Liquid, and Gaseous Samples Using Radiocarbon Analysis). As indicated above, the invention relates to the use of a composition comprising a long chain polyol as an electronic cigarette liquid (hereinafter, "e-liquid"). The long chain polyol may be synthetic or, according to a preferred embodiment of the invention, may be obtained from plant raw materials and referred to herein as "long chain polyol of vegetable origin". In the present invention, the term "long-chain polyol" is understood to mean a compound corresponding to at least one of the following characteristics: a hydrocarbon compound comprising 2, 3 or 4 hydroxyl functional groups, preferably 2; compound comprising 4 to 24 carbon atoms, preferably 4, 5, 6, 7, 8, 9 or 10 carbon atoms; Linear or cyclic compound, preferably linear; - compound of plant or synthetic origin, preferably plant. In a nonlimiting manner, the long chain polyol according to the invention belongs to the group consisting of 1,2-butanediol, 1,3-butanediol, 1,4-butanediol and 2-methyl-1,3-propanediol. 2-methyl-1,3-butanediol, 2-methyl-1,4-butanediol, 2-ethyl-1,3-propanediol, 1,2-pentanediol, 1,3-pentanediol, 1 , 4-pentanediol, 1,5-pentanediol, 1,2-hexanediol, 1,3-hexanediol, 1,4-hexanediol, 1,5-hexanediol, 1,6-hexanediol, 2-hexanediol, methylene-1,3-pentanediol, 2-methyl-1,4-pentanediol, 2-methyl-1,5-pentanediol, 2-ethyl-1,3-butanediol, 2-ethyl-1,4-diol; butanediol, 1,2-octanediol, 1,3-octanediol, 1,4-octanediol, 1,5-octanediol, 1,6-octanediol, 1,7-octanediol, 1,8-octanediol , 2-methyl-1,3-heptanediol, 2-methyl-1,4-heptanediol, 2-methyl-1,5-heptanediol, 2-methyl-1,6-heptanediol, 2-methyl 1,7-heptanediol, 3-methyl-1,2-heptanediol, 3-methyl-1,3-heptanediol, 3-methyl-1,4-heptanediol, 3-methyl-1,5 heptanediol, 3-methyl-1,6-heptanediol, 3-methyl-1,7-heptanediol, 2-ethyl-1,3-hexanediol, 2-ethyl-1,4-hexanediol, ethyl-1,5-hexanediol, 2-ethyl-1,6-hexanediol, 3-ethyl-1,2-hexanediol, 3-ethyl-1,3-hexanediol, 3-ethyl-1,4- hexanediol, 3-ethyl-1,5-hexanediol, 3-ethyl-1,6-hexanediol. Preferably the long chain polyol is 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 1,215 pentanediol, 1,2-hexanediol, 1,2-heptanediol or 1, 2-octanediol. The composition used according to the invention may also contain propylene glycol. The latter may be of synthetic or vegetable origin (that is to say obtained from vegetable raw materials). In the latter case, which is preferred, the propylene glycol may in particular be obtained by hydrogenolysis of sorbitol or vegetable glycerol (New and Future Developments in Catalysis: Catalytic Biomass Chemistry - S. Suib Editor / Elsevier - 2013, pp. 17) or by hydrogenation of vegetable lactic acid (J. Van Haveren & others Bulk Chemicals from Biomass, BioFPR, Nov. 1, 2007. pp. 4157). The biosourced glycerol used to produce the propylene glycol may be of animal or vegetable origin, preferably plant-based. Vegetable glycerol is derived from the hydrolysis (acidic or basic) of vegetable oils or their alcoholysis (transesterification). These oils belong in a non-limiting manner to the group of oils of soya, palm, palm kernel, copra, rapeseed, sunflower, corn germ, cotton, olive, sesame, rice bran, flax, castor oil, avocado, peanut, safflower, grapeseed, or tall oil. It is preferred to use glycerol from non-genetically modified plant varieties, such as palm, rapeseed, sunflower, or copra oils. Sorbitol or biosourced lactic acid used to produce propylene glycol of vegetable origin is generally derived from sugar or starchy plants such as sugar cane, corn, wheat, potato, sugar beet. , rice, or sorghum. Preferably, sorbitol or lactic acid from non-genetically modified plant varieties such as sugar cane or beet is used. More preferably, sorbitol or lactic acid is obtained from non-food lignocellulosic biomasses such as wood, straw, palm bunchees, bagasse, and non-genetically modified maize stalks. It should be noted that the aforementioned methods make it possible to obtain not only propylene glycol, but also 1,3-propanediol (PDO) as a by-product, the proportions of which can be adjusted by appropriately selecting the reaction conditions ( Nur Dyana bt Saar Dissertation submitted in part fulfilling the requirements for the Bachelor of Engineering (Hons) Chemical Engineering, Universiti Teknologi PETRONAS, May 2013). The propylene glycol may represent from 2 to 50% by weight, preferably from 10 to 40% by weight, more preferably from 20 to 30% by weight, relative to the total weight of the composition. According to the invention, it is preferred that the composition used as e-liquid contains no or little glycerin, that is to say it contains from 0 to 40% by weight of glycerine, preferably from 0 to 20% by weight. % by weight, for example from 0 to 5% by weight of glycerin or from 5 to 20% by weight of glycerin, relative to the total weight of the composition. It has indeed been observed, as indicated above, that the absence of glycerin makes it possible to avoid the formation of undesirable by-products when heating the glycerine. It has been found that at the temperature reached by the resistance of an electronic cigarette, glycerol decomposes to acrolein (Cordoba et al Proceedings of COBEM 2011 - 21st Brazilian Conference of Mechanical Engineering, October 24-28, 2011 , Natal, RN, Brazil Brian Metzger, Glycerol Combustion - University of North Carolina Ph.D., August 25, 2007), highly toxic compound at very low concentration (Goniewicz et al., Levels of Selected Carcinogens and Toxicants in Vapor from Electronic Cigarettes - TC Online First, published on March 6, 2013 under 10.1136 / tobaccocontrol-2012-050859). Surprisingly, it has also been noted that the absence of glycerine makes it possible to significantly increase the vapor density and the aromatic power of the electronic cigarette. Advantageously, when it is present, the glycerin is of vegetable origin and obtained according to the methods described above. The composition may also contain synthetic 1,3-propanediol or, according to a preferred embodiment of the invention, it may be obtained from vegetable raw materials and designated here by "1,3-biopropanediol of plant origin ". The 1,3-biopropanediol of vegetable origin can be obtained by fermentation of glucose, in the presence of a native or genetically modified bacterium, chosen in particular from the Klebsiella strains (in particular pneumoniae), Clostridium (in particular butyricum), Citrobacter strains (in particular freundii), Serratia and Escherichia neck, preferably Escherichia neck, and more preferably Escherichia neck K-12. An example of a genetically modified strain is described in US application 2012/258521. The biosourced glucose used to produce 1,3-propanediol is generally derived from sugar or starchy plants such as sugar cane, corn, wheat, potato, sugar beet, rice, or sorghum. Preferably, the glucose is derived from non-genetically modified plant varieties, such as sugar cane or beet. Better still, glucose is derived from non-food lignocellulosic biomasses such as wood, straw, palm bunchees, bagasse, and non-genetically modified maize stalks. The product of the fermentation can be recovered, and the 1,3-biopropanediol purified, by membrane filtration, electrodialysis, concentration or rectification, for example, or by a combination of these techniques. The 1,3-biopropanediol can in particular be purified by distillation, an operation which makes it possible to reach a purity of 99.8%. The impurities present at 0.2% are water and propanol-1 (Chatterjee et al., Glycerol to Propylene Glycol / Department of Chemical & Biomolecular Engineering Senior Design Reports (CBE), University of Pensylvania - April 12, 2011 ), a compound devoid of toxicity. The 1,3-propanediol may represent from 2 to 50% by weight, preferably from 10 to 40% by weight, more preferably from 20 to 30% by weight, relative to the total weight of the composition.
    [0008] Apart from the abovementioned constituents, the composition used according to the invention also contains at least one compound chosen from nicotine, a nicotine substitute (typically a non-addictive molecule but with a sensory effect close to that of nicotine) and a nicotine substitute. aroma. The nicotine can be of synthetic or plant origin and should preferably meet the purity criteria described in the US Pharmacopoeia (USP) and European (PE) in force. It can in particular be extracted from tobacco leaves or obtained by chemical synthesis. The nicotine concentration in the composition according to the invention may range from 0 to 100 mg / ml, preferably from 2 to 25 mg / ml. The flavors can also be flavors of vegetable or synthetic origin such as those approved in the food and / or pharmaceutical fields, in particular those listed in the EU Regulation No. 872/2012 of October 1, 2012 and in the American Pharmacopoeia (USP ) and European (PE) in force. The concentration of flavors can range from 0 to 30% by weight, preferably from 1 to 8% by weight, more preferably from 2 to 5% by weight, relative to the total weight of the composition. The composition used according to the invention may also comprise water and / or an alcohol such as ethanol and / or at least one dye. The water and the alcohol may each represent from 0 to 20% by weight, preferably from 1 to 10% by weight, relative to the total weight of the composition. The dyes may be dyes of vegetable or synthetic origin, such as those approved in the food and / or pharmaceutical fields and in particular those listed in the EU Regulation No. 1331/2008 and in the US and European Pharmacopoeias (USP) ( PE) in force. The concentration of flavors can range from 0 to 30% by weight, preferably from 1 to 8% by weight, more preferably from 2 to 5% by weight, relative to the total weight of the composition.
    [0009] However, it is preferred according to the invention that the composition does not comprise water, with the exception of that possibly contained in the raw materials that the composition contains. Indeed, water can promote the development of pathogenic microorganisms of microbial origin and its use generally requires the use of preservatives or the production of a sterilizing microfiltration. In addition, the addition of water to e-liquids induces a transformation of nicotine base into protonated nicotine. However, it is known to those skilled in the art that the protonated form of nicotine is significantly less bio-assimilable, and in fact less addictive, than nicotine base. Thus, certain long-chain polyols make it possible to formulate very fluid e-liquids, without having to add water, in which the nicotine is present in base form and in its highly bioavailable form, which clearly improves the control of the delivery of nicotine, especially during smoking cessation. The invention also relates to an electronic cigarette containing the composition as described above. This is generally arranged in a cartridge secured to a receptacle housing a power supply system connected to a device for atomizing the composition. It also relates to the use of a long-chain polyol in an electronic cigarette liquid containing or not nicotine, to improve the tingling of the throat felt by a user of said electronic cigarette and / or the ease of aspiration vapor produced by said liquid.
    [0010] Finally, it relates to the use of a long chain polyol in an electronic cigarette liquid containing nicotine to improve the bioavailability of nicotine.
    [0011] The invention will be better understood in the light of the following examples, which are given purely by way of illustration and are not intended to limit the scope of the invention, defined by the appended claims. EXAMPLES Example 1 Preparation and analysis of a composition based on 1,3-butanediol and glycerol In a glass mixer equipped with mechanical stirring, exactly 10.00 kg of 1,3-butanediol, as sold by Kyowa 1,3-butylene glycol, cosmetic grade), 1.00 kg of vegetable glycerin (marketed by Oléon under the reference Glycerine 4810, Pharmacopoeia USP and PE grade), 450.0 g of fruity apple flavor ( sold by the company Safisis under the reference PI 128) and 114.50 g of plant nicotine (marketed by Alchem International under the Nicotine Free Base reference, Pharmaceutical grade Nicotine> 99%). Stirring of the mixture (50 rpm) is maintained for 20 minutes. A sample of 500 g is made for analysis. A measurement of the kinematic viscosity is then carried out at 25 ° C. using a Houillon-m 943 viscometer with a coefficient of 0.35051. Results: The viscosity at 20 ° C. is equal to 65.2 mm 2 / s. Example 2 Preparation and Analysis of a Glycerin-Free Composition The procedure of Example 1 is repeated, but replacing the vegetable glycerin with 1 kg of 1,3-butanediol (supplied by Kyowa) according to the Example 1. The viscosity is then measured under the same conditions as in Example 1. Results: The viscosity at 20 ° C. is equal to 101.2 mm 2 / s. EXAMPLE 3 (Comparative) Evaluation of the Efficacy of Different E-Liquids The procedure of Example 1 is repeated, except that 1,3-butanediol is replaced by synthetic propylene glycol supplied by Dow under the reference Dow® Propylene glycol, grade USP. The viscosity is then measured at 20 ° C. Results: The viscosity at 20 ° C. is 59.2 mm 2 / s. In conclusion, it can be seen that e-liquids based on 1,3-butanediol, which may or may not be associated with glycerin (Examples 1 and 2), can be obtained having viscosities which are entirely comparable to those of a conventional liquid (Example 3). EXAMPLE 4 Evaluation of the Efficacy of Different E-liquids The e-liquid compositions prepared in Examples 1 to 3 are evaluated by a trained panel of 10 persons equipped with a Joytech ™ brand cigarette and an eCab ™ model (December model). 2013). Each tank is filled with an identical amount of e-liquid (1 ml). Also, each panelist blinds a test on the basis of 8 successive puffs spaced 20 seconds and each induced by heating 2 seconds.
    [0012] The evaluation is based on the rating, on a scale of 1 10, of the criteria of vapor density and aromatic power felt. The passage from one product to another is done by each panelist as follows: 5 5 minutes after the last aspiration, the panelist rinses his mouth with 2 glasses of water of 100 ml then quenches with 50 ml of water. A rest period between each assessment is set at 10 minutes. The averaged results obtained are collated in the following table: Product Vapor density Aromatic power (note 1 to 10) (note 1 to 10) Example 1 7.2 ± 1.3 6.7 ± 1.5 Example 2 7, 9 ± 1.2 7.8 ± 1.2 Example 3 6.8 ± 1.1 5.4, ± 1.1 It is clear that 1,3-butanediol associated with vegetable glycerine (Example 1) or not associated with glycerin (Example 2) makes it possible to produce an e-liquid having a vapor density that is quite comparable to, or even greater than that of a conventional e-liquid (Example 3). The 1,3-butanediol-based e-liquids make it possible to obtain an aromatic power greater than that obtained with a conventional e-liquid (Example 3). EXAMPLE 4 Influence of the nature of the solvent on the nicotine base concentration in the e-liquid formulations In a glass mixer equipped with a mechanical stirrer, 5,50 kg of propylene glycol of vegetable origin (rapeseed) are precisely mixed sold by Oléon under the reference Radianol® 4710, Pharmacopoeia USP grade), 4.00 kg of vegetable glycerin (marketed by Oléon under the reference Glycerine 4810, Pharmacopoeia USP and PE grade), 50 g of osmosis water and 162.6 g of vegetable nicotine (marketed by Alchem International under the reference Nicotine Free Base, Pharmaceutical grade Nicotine> 99%).
    [0013] Stirring of the mixture (50 rpm) is maintained for 20 minutes. Product A is then obtained. A sample of 200 g of A is made for analysis. Product A is similarly prepared to prepare product B by replacing propylene glycol and vegetable glycerin with 9,837.4 g of 1,3-butanediol supplied by Kyowa. A sample of 200 g of B is made for analysis. The NMR proton NMR (Nuclear Magnetic Resonance) is taken on an Avance Brucker brand apparatus (500 MHz), products A, B, C, D previously dissolved in D20 (deuterated water). The goal is to measure the percentage of protonated nicotine in the products. This NMR quantification of the proton is carried out on the basis of a calibration curve covering the protonated nicotine concentration range of between 5 and 95%.
    [0014] The results are collated in the following table: Product / Measurement AB Nicotine Concentration 34 81 Protonated,% Clearly, 1,3-butanediol, in allowing the formulation of e-liquids without water, ensures the delivery of nicotine base form (unprotonated) and thus in highly bioavailable form. EXAMPLE 5 Influence of the Nature of the Solvent on the Sensory Properties of the E-liquid and on the Ease of Suction of E-liquid The compositions of e-liquids, Products A and B and C (the latter corresponding to 1, 3 butanediol without added nicotine), prepared in Example 4, are evaluated by a trained panel of 40 persons (male, age 25-49), equipped with a JoytechTM brand cigarette and eCabTM model ( December 2013 model). Each tank is filled with an identical amount of e-liquid (1 ml).
    [0015] Also, each panellist blinds a test on the basis of 8 successive puffs spaced 20 seconds apart and each induced by heating for 2 seconds. The passage from one product to another is carried out by each panelist as follows: 5 minutes after the last aspiration, the panelist rinses his mouth with 2 glasses of 100 ml water and then quenches with 50 ml of water. A rest period between each assessment is set at 10 minutes. The evaluation is based on scoring, on a scale of 1 to 10, the following criteria: 1) the feeling of "throat hit", that is to say the internal tingling effect of the throat conventionally obtained when a smoker inhales a puff of cigarette, which is also felt when an electronic cigarette user sucks a nicotine-rich e-liquid vapor, 2) the ease of e-liquid vapor aspiration. The averaged results obtained are collated in the following table: Product Feeled from the "Throat Hit" Suction Facility (note 1 to 10) (note 1 to 10) Product A 6.4 ± 1.2 6.9 ± 1, 4 Product B 8.9 ± 0.9 6.7 ± 1.1 Product C 8.1 ± 0.8 6.3 ± 1.2 It is clear that 1,3-butanediol associated with nicotine (product B ) induces a much better "hit throat" than a conventional product consisting of glycerine, propylene glycol, water and nicotine (Product A). Finally, it is very interesting to note that 1,3-butanediol alone (product C) induces a very significant "hit throat" in the total absence of nicotine and significantly greater than the product A corresponding to a conventional e-liquid. With respect to the ease of suction of the vapor, e-liquids A, B and C exhibit substantially equivalent performance.
    权利要求:
    Claims (18)
    [0001]
    REVENDICATIONS1. Use of a composition containing a long chain polyol as an electronic cigarette liquid
    [0002]
    2. Use according to claim 1, characterized in that the long-chain polyol is a compound having 4 to 24 carbon atoms, preferably between 4, 5, 6, 7, 8, 9 or 10.
    [0003]
    3. Use according to claim 1 or 2, characterized in that the long-chain polyol is a compound having 2, 3 or 4 hydroxyl functions, preferably 2.
    [0004]
    4. Use according to any one of claims 1 to 3, characterized in that the long chain polyol is a linear or cyclic compound, preferably linear.
    [0005]
    5. Use according to any one of claims 1 to 4, characterized in that the long-chain polyol is a compound of plant or synthetic origin, preferably plant. 25
    [0006]
    6. Use according to any one of claims 1 to 5, characterized in that the long-chain polyol is a compound belonging to the group consisting of 1,2-butanediol, 1,3-butanediol, 1,4-butanediol. butanediol, 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol and mixtures thereof. 10 15 20
    [0007]
    7. Use according to any one of claims 1 to 6, characterized in that the composition contains from 0 to 40% by weight, preferably from 0 to 20% by weight, for example from 0 to 5% by weight or from 5 to 20% by weight of glycerin.
    [0008]
    8. Use according to any one of claims 1 to 7, characterized in that the composition also contains propylene glycol.
    [0009]
    9. Use according to claim 8, characterized in that the propylene glycol is obtained from vegetable raw materials.
    [0010]
    10. Use according to any one of claims 1 to 9, characterized in that the composition also contains 1,3-propanediol, preferably of plant origin.
    [0011]
    11. Use according to any one of claims 1 to 10, characterized in that the composition also contains nicotine and / or a nicotine substitute and / or aroma.
    [0012]
    An electronic cigarette liquid composition comprising a long chain polyol, as well as at least one compound selected from: nicotine, a nicotine substitute and a flavor.
    [0013]
    13. Composition according to claim 12, characterized in that it is free of glycerine.
    [0014]
    14. A composition according to claim 12 or 13, characterized in that it also contains propylene glycol, preferably of plant origin and / or 1,3-propanediol, preferably of plant origin.
    [0015]
    15. Composition according to any one of claims 12 to 14, characterized in that it does not contain water.
    [0016]
    16. Electronic cigarette containing a composition according to any one of claims 12 to 15.
    [0017]
    17. Use of a long chain polyol in an electronic cigarette liquid containing or not nicotine, to improve the tingling of the throat felt by a user of said liquid and / or the ease of aspiration of the steam produced by said liquid.
    [0018]
    18. Use of a long chain polyol in an electronic cigarette liquid containing nicotine to improve the bioavailability of nicotine.
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    JP2022506064A|2022-01-17|Aerosolized formulation
    JP2022506076A|2022-01-17|Aerosolized formulation
    JP2022506068A|2022-01-17|Aerosolizable formulations
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    同族专利:
    公开号 | 公开日
    WO2016005709A1|2016-01-14|
    CN106572694A|2017-04-19|
    EP3166424A1|2017-05-17|
    US20170215470A1|2017-08-03|
    FR3023453B1|2018-08-03|
    EP3166424B1|2019-11-13|
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    法律状态:
    2015-07-31| PLFP| Fee payment|Year of fee payment: 2 |
    2016-01-15| PLSC| Publication of the preliminary search report|Effective date: 20160115 |
    2016-04-08| TP| Transmission of property|Owner name: LABORATOIRES CERES, FR Effective date: 20160307 |
    2016-07-27| PLFP| Fee payment|Year of fee payment: 3 |
    2017-07-19| PLFP| Fee payment|Year of fee payment: 4 |
    2018-07-27| PLFP| Fee payment|Year of fee payment: 5 |
    2019-07-27| PLFP| Fee payment|Year of fee payment: 6 |
    2020-08-29| PLFP| Fee payment|Year of fee payment: 7 |
    2021-07-30| PLFP| Fee payment|Year of fee payment: 8 |
    优先权:
    申请号 | 申请日 | 专利标题
    FR1456655|2014-07-10|
    FR1456655A|FR3023453B1|2014-07-10|2014-07-10|USE OF A COMPOSITION COMPRISING A LONG CHAIN POLYOL AS A BASE OF E-LIQUIDS|FR1456655A| FR3023453B1|2014-07-10|2014-07-10|USE OF A COMPOSITION COMPRISING A LONG CHAIN POLYOL AS A BASE OF E-LIQUIDS|
    US15/323,854| US20170215470A1|2014-07-10|2015-07-10|Use of a composition containing a long-chain polyol as a base for e-liquids|
    CN201580043187.6A| CN106572694A|2014-07-10|2015-07-10|Use of a composition containing a long-chain polyol as a base for e-liquids|
    PCT/FR2015/051919| WO2016005709A1|2014-07-10|2015-07-10|Use of a composition containing a long-chain polyol as a base for e-liquids|
    EP15748285.2A| EP3166424B1|2014-07-10|2015-07-10|Use of a composition containing a long-chain polyol as a base for e-liquids|
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