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    • 专利摘要:
    The present invention relates to the use of a composition containing 1,3-propanediol as an electronic cigarette liquid. It also relates to an electronic cigarette liquid composition comprising 1,3-propanediol, and 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:FR3015187A1
    申请号:FR1456453
    申请日:2014-07-04
    公开日:2015-06-26
    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 containing 1,3-propanediol as an electronic cigarette liquid. It also relates to an electronic cigarette liquid composition comprising 1,3-propanediol, as well as nicotine and / or at least one aroma, and an electronic cigarette 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.
    [0002] 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, an indicator light - usually a red or blue diode 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.
    [0003] 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%).
    [0004] 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, since the release of the flavors in the absence of propylene glycol is made less immediate. 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). 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 by one of the most energy-intensive processes in petrochemicals and has a strong environmental footprint (Eissen et al., 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 according to a continuous hydration process, according to the following scheme: ## STR2 ## 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 - Editions TECHNIP-p26), as illustrated below: ## STR1 ## wherein: ## STR1 ## CH2 OH Prvierip. Prnpylerie ^ t., OrryW.-e. , Xide. ## STR1 ## Thus, after purification, the organic impurities minor and recurrent propylene glycol are di- and tripropylene glycol, as well as propylene oxide whose residual content 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 e-Cigarette published by the French Office for Smoking 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.
    [0005] A solution to the aforementioned problems has been proposed in the application WO 2013/088230. It consists in substituting synthetic propylene glycol with propylene glycol Pro'Dy ene Oxide of plant origin, obtained by catalytic hydrogenation of sorbitol, itself derived from corn. Propylene glycol is combined with glycerol of plant origin, nicotine that can be extracted from tobacco leaves and possibly 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 now been demonstrated that the vapor density and the aromatic power produced by these e-liquids of vegetable origin could be improved by replacing propylene glycol with 1,3-propanediol (PDO) and that this effect was particularly pronounced in the absence of glycerin or in a low glycerine e-liquid composition. By eliminating glycerol, the use of PDO also contributes to protecting the heating device of electronic cigarettes by eliminating the phenomenon of rapid fouling observed in the presence of glycerin. Another advantage related to the absence of glycerine is that the steam produced is freed from toxic and carcinogenic impurities resulting from the thermal decomposition of glycerol.
    [0006] It has furthermore been observed that PDO makes it possible to obtain e-liquids devoid of nicotine recreating the tingle throat (or "throat hit") typically experienced by the user of a conventional cigarette, during the passage of the nicotine in the mouth. Until now, this effect, much sought after by e-liquid users, was achieved only by adding a few drops of a product based on propylene glycol, glycerin and flavors to the e-liquid (E-Liquid Flash® by FLAVOR ART). However, the latter has all the disadvantages mentioned above, related to the use of propylene glycol and glycerine.
    [0007] PDO of plant origin is today produced industrially by fermentation of glucose. It is currently used as an intermediate resin synthesis, as a solvent, humectant, preservative in the food industry, cosmetics, pharmaceuticals and personal care products, and as a component of hydraulic fluids, antifreezes, brake fluids, coolants, as a component of cleaning liquids, detergents, co-solvent paints, and solvents in the printing ink industry. Also, to the knowledge of the Applicant, the PDO has never been described as constituting e-liquids. SUMMARY OF THE INVENTION The present invention thus relates to the use of a composition containing 1,3-propanediol as an electronic cigarette liquid.
    [0008] It also relates to an electronic cigarette liquid composition comprising 1,3-propanediol, as well as at least one compound selected from nicotine, a nicotine substitute and a flavor.
    [0009] It also relates to an electronic cigarette containing this composition.
    [0010] 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 flavor. This definition therefore includes personal vaporizers (VP), electronic nicotine delivery systems (ENDS for "Electronic Nicotine Delivery System" or ENDD 10 for "Electronic Nicotine Delivery Device"), as well as electronic cigars, electronic pipes and electronic shishas, tobacco-based cigarettes heated or containing a tobacco aroma obtained by maceration. 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 previously indicated, the invention relates to the use of a composition containing PDO as an electronic cigarette liquid (hereinafter, "e-liquid"). The PDO can be synthetic or, according to a preferred embodiment of the invention, it can be obtained from vegetable raw materials and hereinafter referred to as "PDO of plant origin". The PDO of plant origin can be obtained by fermentation of glucose, in the presence of a native or genetically modified bacterium, chosen in particular from the strains of Klebsiella (in particular pneumoniae), Clostridium (in particular butyricum), Citrobacter (in particular freundii), Serratia and Escherichia coli, preferably Escherichia coli, and more preferably Escherichia coli K-12. An example of a genetically modified strain is described in US application 2012/258521. The biosourced glucose used to produce PDO 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 PDO purified, by membrane filtration, electrodialysis, concentration or rectification, for example, or by a combination of these techniques. The PDO 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 PDO may represent from 50 to 99% by weight, preferably from 60 to 95% by weight, more preferably from 70 to 90% by weight, relative to the total weight of the composition. 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 13-17 or by hydrogenation of vegetable lactic acid (J. Van Haveren & others Bulk Chemicals from Biomass, BioFPR, november 1, 2007. pp 41-57). The biosourced glycerol used to produce the propylene glycol may be of animal or vegetable origin, preferably vegetable. 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. The 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. Better yet, sorbitol or lactic acid is obtained from non-food lignocellulosic biomasses such as wood, straw, palm bunchees, bagasse, and non-genetically modified maize stalks.
    [0011] It should be noted that the aforementioned methods make it possible to obtain not only propylene glycol, but also PDO as a co-product, the proportions of which can be adjusted by appropriately selecting the conditions of the reaction (Nur Dyana et al. Bachelor of Engineering (Hons) Chemical Engineering, Universiti Teknologi PETRONAS, May 2013).
    [0012] 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.
    [0013] 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 glycerol, 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. It has indeed been observed, as indicated above, that the absence of glycerine 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 Congress of Mechanical Engineering, 24-28 October 2011, Natal , RN, Brazil Metzger Brian, Glycerol Combustion - Thesis of the University of North Carolina, August 1, 2007), highly toxic compound at very low concentration (Goniewicz & al., Levels of Selected Carcinogens and Toxicants in Vapors from Electronic Cigarettes - TC Online First, published on March 6, 2013 under 10.1136 / tobaccocontrol-2012-050859). Surprisingly, it was also noted that the absence of glycerine significantly increased the vapor density and 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. 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.
    [0014] 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 50 mg / ml, preferably from 2 to 20 mg / ml.
    [0015] 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. 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, 1,3-propanediol makes it possible to formulate very fluid e-liquids, without the addition of osmosis water, in which the nicotine is present in base form and in its highly bioavailable form, which clearly improves the control of delivery of nicotine, especially during smoking cessation.
    [0016] Advantageously, the composition according to the invention has a kinematic viscosity at 20 ° C. of less than 200 mPas / s, preferably less than 100 mPa.s, more preferably less than 75 mPa.s, better still less than 60 mPa.s. said viscosity being greater than 30 mPa.s, preferably greater than 40 mPa.s and more preferably greater than 50 mPa.s. 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.
    [0017] It still relates to the use of 1,3-propanediol 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. Finally, it relates to the use of 1,3-propanediol in an electronic cigarette liquid containing nicotine, to improve the bioavailability of nicotine. The invention will be better understood in the light of the following examples, which are given for illustrative purposes only and are not intended to limit the scope of the invention as defined by the appended claims. EXAMPLES Example 1 (comparative) Preparation and analysis of a composition based on propylene glycol of plant origin In a glass mixer equipped with mechanical stirring, it is precisely mixed with 10.00 kg of propylene glycol of vegetable origin. (Rapeseed) marketed by Oléon under the reference Radianol® 4710, Pharmacopoeia USP grade), 1.00 kg of vegetable glycerin (marketed by Oléon under the reference 20 Glycerine 4810, Pharmacopoeia USP and PE grade), 450.0 g fruity aroma of apple (marketed by Safisis under the reference PT 128) and 114.50 of plant nicotine (marketed by Nicobrand under the reference Nicotine Free Base, Pharmaceutical grade 25 Nicotine> 99%). Stirring of the mixture (50 rpm) is maintained for 20 minutes. A 500g sample is taken for analysis. The mixture is analyzed by gas phase chromatography coupled to mass spectrometry according to the method described in the publication by Cao et al (Cao XL, Corriveau J. An isotope dilution headspace method with gas chromatography-mass spectrometry for determination of propylene oxide Food Addit Contam Part A Chem Anal Control Expo Risk Assessment 2009 Apr; 26 (4): 482-6. In parallel, the analysis is made to determine the biobased carbon content according to ASTM method D6866-12. Results: Under the analytical conditions (sensitivity 0.5 ng / g), no trace of propylene oxide or di- and tripropylene glycols was detected. The biobased carbon content of the mixture is equal to 99.8%. EXAMPLE 2 Preparation and Analysis of a PDO Composition The procedure is the same as in Example 1, but replacing the plant propylene glycol with 1,3-propanediol supplied by DuPont. & Tate & Lyle LLC as Zemea® Propanediol. Results: Under the analysis conditions (sensitivity 0.5 ng / g), no trace of propylene oxide or di- and tripropylene glycols was detected. The biobased carbon content of the mixture is 99.7%.
    [0018] Example 3 (Comparative) Preparation and Analysis of a Composition Based on Synthetic Propylene Glycol The procedure of Example 1 is repeated, but replacing the propylene glycol of plant origin with synthetic propylene glycol supplied by the Dow company under the reference Dow® Propylene glycol, grade USP. Results: Under the conditions of analysis (sensitivity 0.5 ng / g), no trace of di- and tripropylene glycols is detected. On the other hand, the content of free propylene oxide is 2.5 mg / kg. The biobased carbon content of the mixture is 9.2%. These results show that the synthetic propylene glycol contains undesirable impurities which are not contained in the PDO of plant origin, as illustrated in Example 2. Example 4: Preparation and analysis of a glycerin-free composition the same as in Example 1, but replacing the plant-derived propylene glycol and glycerol with PDO of plant origin according to Example 2. Results: Under the conditions of analysis (sensitivity 0.5 ng (g) no trace of propylene oxide or di- and tripropylene glycols is detected. The biobased carbon content of the mixture is equal to 99.8%.
    [0019] Example 5 Evaluation of the Efficacy of Different E-liquids The e-liquid compositions prepared in Examples 1 to 4 are evaluated by a trained panel of 10 people 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. The evaluation is based on the rating, on a scale of 1 to 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 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.
    [0020] 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 5.8 ± 1.3 5.7 ± 1.5 Example 2 7.8 ± 1.2 7.9 ± 1.2 Example 3 5.6, ± 1.4 5.4, ± 1.1 Example 4 9.0 ± 1.3 8.9 ± 1.2 It is clear that the Propylene glycol of plant origin (Example 1) has substantially the same properties as synthetic propylene glycol (Example 3). In contrast, PDO (Example 2) has a significantly higher vapor density and aromatic power, which is further increased in the absence of glycerin (Example 4). Compared with synthetic propylene glycol, it also makes it possible to produce e-liquid compositions having a small environmental footprint and free of undesirable impurities such as propylene oxide and its derivatives, or even acrolein. EXAMPLE 6 Influence of the nature of the solvent on the viscosity and the nicotine concentration base in the e-liquid formulations In a glass mixer equipped with a mechanical stirrer, 6.00 kg of propylene glycol were precisely mixed. vegetable origin (rapeseed) 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) and 16, 26 g of vegetable nicotine (marketed by Nicobrand under the reference Nicotine Free Base, Pharmaceutical grade Nicotine> 99%). Stirring of the mixture (50 rpm) is maintained for 20 minutes. Product A is then obtained. A sample of 200 g of A is taken for analysis. The product A is then similarly carried out to prepare the product B corresponding to a mixture consisting of 5.50 kg of propylene glycol, 4.00 kg of glycerin, 50 g of osmosis water and 162.6 g of nicotine. A sample of 200g of B is made for analysis.
    [0021] Product A is similarly prepared to prepare product C corresponding to a mixture consisting of 9,837.4 g of 1,3-propanediol supplied by DuPont & Tate & Lyle LLC under the reference Zemea® Propanediol and of 162, 6 g of vegetable nicotine (marketed by Nicobrand under the reference Nicotine Free Base, Pharmaceutical grade Nicotine> 99%). A sample of 200g of C is made for analysis. Finally, product D consists solely of 1,315 propanediol supplied by DuPont & Tate & Lyle LLC under the reference Zemea® Propanediol. The kinematic viscosity of the products A, B, C and D is then measured. Moreover, a proton NMR spectrum (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 objective is to measure the percentage of nicotine protonated 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%. The results are collated in the following table: Product / measure ABCD Kinematic viscosity at 20 ° C, mPas / sec 410.3 53.1 52.3 52.6 Nicotine concentration 34 78 16 protonated,% These tests show that that 1,3-propanediol product C, in which no addition of osmosis water has been made, has a very advantageous viscosity (<60 mPa / s), resulting in a fluidity making it easy to fill a electronic cigarette tank. On the other hand, the product A has a very high viscosity, greater than 400 mPa / s. This type of viscous solution is not usable as e-liquid since it can not be poured at room temperature into the tank body of an electronic cigarette. By comparison, thanks to the presence of water, product B has a fluidity comparable to that of products C and D. It also corresponds to currently commercial solutions present on the e-liquid market. Therefore, it is clear that 1,3-propanediol makes it possible very advantageously to prepare very fluid e-liquids without the addition of osmosis water, thus without preservatives or without having to engage a sterilizing microfiltration. In addition, by allowing the formulation of e-liquids without water, 1,3-propanediol ensures the delivery of nicotine in base form (not protonated) and thus in highly bioavailable form.
    [0022] Example 7 Influence of the nature of the solvent on the sensory properties of the e-liquid and the ease of vapor suction The e-liquid compositions B, C and D prepared in Example 6 are evaluated by a trained panel of 40 people (male between 25 and 49 years old), 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). Also, each panelist performs a blind test on the basis of 8 successive puffs spaced 20 seconds and each induced by heating 2 seconds. The passage from one product to another is done by each panelist as follows: 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 evaluation is based on the notation, on a scale of 1 to 10, of the following criteria: 1) the feeling of "throat hit", that is to say the effect of internal tingling of the throat classically 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 average results obtained are collated in the following table: Throat Hit Suction Facility Product (note 1 to 10) (note 1 to 10) Product B 6.2 ± 1.2 6.9 ± 1, 4 Product C 8.9 ± 0.9 7.9 ± 1.1 Product D 8.1 ± 1.1 8.1 ± 1.2 Clearly 1,3-propanediol is associated with nicotine (product C) induces a throat hit superior to a conventional product consisting of glycerine, propylene glycol, water and nicotine (Product B). Finally, it is very interesting to note that 1,3propanediol alone (product D) induces a significant "throat hit" in the absence of nicotine and significantly greater than product B.
    [0023] With regard to the ease of aspiration of the induced vapor, again the e-liquids C and D prove to be superior to the product B.
    权利要求:
    Claims (17)
    [0001]
    REVENDICATIONS1. Use of a composition containing 1,3-propanediol as an electronic cigarette liquid.
    [0002]
    2. Use according to claim 1, 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.
    [0003]
    3. Use according to claim 1 or 2, characterized in that the composition also contains propylene glycol. 15
    [0004]
    4. Use according to claim 3, characterized in that the propylene glycol is obtained from vegetable raw materials.
    [0005]
    5. Use according to claim 4, characterized in that the propylene glycol is obtained by hydrogenolysis of sorbitol or vegetable glycerol or by hydrogenation of vegetable lactic acid.
    [0006]
    6. Use according to any one of claims 1 to 5, characterized in that the composition additionally contains nicotine and / or aroma.
    [0007]
    7. Use according to any one of claims 1 to 6, characterized in that 1,3-propanediol is obtained from vegetable raw materials.
    [0008]
    8. Use according to claim 7, characterized in that 1,3-propanediol is obtained by fermentation of glucose in the presence of a bacterium such as Escherichia coli, preferably Escherichia coli K-12.
    [0009]
    An electronic cigarette liquid composition comprising 1,3-propanediol, as well as at least one compound selected from: nicotine, a nicotine substitute, and a flavor.
    [0010]
    10. Composition according to claim 9, characterized in that it is free of glycerine.
    [0011]
    11. Composition according to claim 9 or 10, characterized in that it also contains propylene glycol, preferably of plant origin. 15
    [0012]
    12. Composition according to any one of claims 9 to 11, characterized in that 1,3-propanediol is obtained from vegetable raw materials. 20
    [0013]
    13. Composition according to any one of claims 9 to 12, characterized in that it does not contain water.
    [0014]
    14. Composition according to any one of claims 9 to 13, characterized in that it has a kinematic viscosity at 20 ° C of less than 200 mPas / s, preferably less than 100 mPa.s, more preferably less than 75 mPa. .s, better, less than 60 mPa.s, said viscosity being greater than 30 mPa.s, preferably greater than 40 mPa.s and more preferably greater than 50 mPa.s.
    [0015]
    15. Electronic cigarette containing a composition according to any one of claims 9 to 14.
    [0016]
    16. Use of 1,3-propanediol 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 .
    [0017]
    17. Use of 1,3-propanediol in an electronic cigarette liquid containing nicotine to improve the bioavailability of nicotine.
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    FR3110347A1|2021-11-26|VAPING COMPOSITIONS
    RU2764269C1|2022-01-17|Aerosol forming composition
    FR2949343A1|2011-03-04|PROCESS FOR OBTAINING PLANT EXTRACT, PLANT EXTRACT OBTAINED BY THE METHOD, AND COSMETIC OR DERMATOLOGICAL COMPOSITION CONTAINING THE EXTRACT
    CN113265299A|2021-08-17|Watermelon essence and electronic atomized liquid containing same
    同族专利:
    公开号 | 公开日
    DE112015000032T5|2015-11-19|
    EP3107409B1|2018-02-14|
    CN106455675A|2017-02-22|
    FR3015186A1|2015-06-26|
    GB201512314D0|2015-08-19|
    EP3107409A1|2016-12-28|
    FR3015187B1|2017-02-17|
    WO2015101760A1|2015-07-09|
    GB2524204A|2015-09-16|
    US20160262443A1|2016-09-15|
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    法律状态:
    2015-07-31| PLFP| Fee payment|Year of fee payment: 2 |
    2015-08-07| TP| Transmission of property|Owner name: LABORATOIRES CERES, FR Effective date: 20150626 |
    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
    FR1451970A|FR3015186A1|2014-03-11|2014-03-11|USE OF A COMPOSITION COMPRISING 1,3-PROPANEDIOL AS E-LIQUID|
    FR1456453A|FR3015187B1|2014-03-11|2014-07-04|USE OF A COMPOSITION COMPRISING 1,3-PROPANEDIOL AS E-LIQUID|FR1456453A| FR3015187B1|2014-03-11|2014-07-04|USE OF A COMPOSITION COMPRISING 1,3-PROPANEDIOL AS E-LIQUID|
    CN201580024929.0A| CN106455675A|2014-03-11|2015-03-10|Use of a composition containing 1,3-propanediol as an e-liquid|
    US14/650,329| US20160262443A1|2014-03-11|2015-03-10|Use of a composition containing 1,3-propanediol as e-liquid|
    PCT/FR2015/050599| WO2015101760A1|2014-03-11|2015-03-10|Use of a composition containing 1,3-propanediol as an e-liquid|
    DE112015000032.1T| DE112015000032T5|2014-03-11|2015-03-10|Use of a composition comprising 1,3-propanediol as e-liquid|
    GB1512314.4A| GB2524204A|2014-03-11|2015-03-10|Use of a composition containing 1,3-propanediol as an e-liquid|
    EP15717542.3A| EP3107409B1|2014-03-11|2015-03-10|Use of a composition containing 1,3-propanediol as an e-liquid|
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