EP3576552A2 - Verfahren und systeme zur verbesserung der stabilität von vordampfformulierungen von e-vaping-vorrichtungen - Google Patents
Verfahren und systeme zur verbesserung der stabilität von vordampfformulierungen von e-vaping-vorrichtungenInfo
- Publication number
- EP3576552A2 EP3576552A2 EP18703309.7A EP18703309A EP3576552A2 EP 3576552 A2 EP3576552 A2 EP 3576552A2 EP 18703309 A EP18703309 A EP 18703309A EP 3576552 A2 EP3576552 A2 EP 3576552A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- compound
- vapor formulation
- percent
- equal
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
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- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 2
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 2
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 2
- XXHDAWYDNSXJQM-ONEGZZNKSA-N trans-hex-3-enoic acid Chemical compound CC\C=C\CC(O)=O XXHDAWYDNSXJQM-ONEGZZNKSA-N 0.000 description 2
- 229940005605 valeric acid Drugs 0.000 description 2
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 1
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 229910000881 Cu alloy Inorganic materials 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 240000001238 Gaultheria procumbens Species 0.000 description 1
- 235000007297 Gaultheria procumbens Nutrition 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 description 1
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 1
- MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 239000000788 chromium alloy Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000008369 fruit flavor Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
- 229910001120 nichrome Inorganic materials 0.000 description 1
- 229910000623 nickel–chromium alloy Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229920000867 polyelectrolyte Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/10—Chemical features of tobacco products or tobacco substitutes
- A24B15/16—Chemical features of tobacco products or tobacco substitutes of tobacco substitutes
- A24B15/167—Chemical features of tobacco products or tobacco substitutes of tobacco substitutes in liquid or vaporisable form, e.g. liquid compositions for electronic cigarettes
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24F—SMOKERS' REQUISITES; MATCH BOXES; SIMULATED SMOKING DEVICES
- A24F40/00—Electrically operated smoking devices; Component parts thereof; Manufacture thereof; Maintenance or testing thereof; Charging means specially adapted therefor
- A24F40/10—Devices using liquid inhalable precursors
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24F—SMOKERS' REQUISITES; MATCH BOXES; SIMULATED SMOKING DEVICES
- A24F40/00—Electrically operated smoking devices; Component parts thereof; Manufacture thereof; Maintenance or testing thereof; Charging means specially adapted therefor
- A24F40/40—Constructional details, e.g. connection of cartridges and battery parts
Definitions
- the free (for example, hydroxyl) radicals may react with ingredients of the pre-vapor formulation, resulting in a decrease of the stability of the pre-vapor formulation.
- the free radicals may also mix with the vapor generated by the e-vaping device.
- vapor former describes any suitable known compound or mixture of compounds that, in use, facilitates formation of a vapor and that is substantially resistant to thermal degradation at the operating temperature of the e-vaping device.
- Suitable vapor formers may include various compositions of polyhydric alcohols such as at least one of propylene glycol and glycerin.
- the vapor former is propylene glycol.
- the vapor former is included in a solvent of a pre-vapor formulation.
- control circuitry 1 1 may include a time-period limiter.
- control circuitry 1 1 may include a manually operable switch for an adult vaper to initiate heating.
- the time-period of the electric current supply to the heater may be set or pre-set depending on the amount of pre-vapor formulation desired to be vaporized.
- the sensor 16 may detect a pressure drop and the control circuitry 1 1 may supply power to the heater as long as heater activation conditions are met.
- the power supply (or battery) 12 may be rechargeable and include circuitry configured to enable the battery to be chargeable by an external charging device.
- the circuitry when charged, provides power for a given quantity of instances of vapor being drawn through one or more outlets of the e-vaping device 60, negative pressure being applied to an interior of the e-vaping device through one or more outlets 21 , some combination thereof, or the like, after which the circuitry may have to be re-connected to an external charging device.
- the e-vaping device 60 may include control circuitry 1 1 which can be, for example, on a printed circuit board.
- the control circuitry 1 1 may also include a heater activation light 27 that is configured to glow when the device is activated.
- the heater activation light 27 may include a light emitting diode (LED).
- the heater activation light 27 may be arranged to be visible to an adult vaper during vaping.
- the heater activation light 27 may be utilized for e-vaping system diagnostics or to indicate that recharging is in progress.
- the heater activation light 27 may also be configured such that the adult vaper may activate, deactivate, or activate and deactivate the heater activation light 27 for privacy.
- the heater activation light 27 may be located on the tip end of the e-vaping device 60.
- the heater activation light 27 may be located on a side portion of the outer housing of the e-vaping device 60.
- the reservoir 14 of a cartridge 70 that itself may be included in an e-vaping device 60, is configured to hold one or more pre-vapor formulations.
- the polyol compound when the solution compound includes a polyol compound, may be included in the pre-vapor formulation at a concentration that is equal to or greater than about 0.2 percent and equal to or less than about 10 percent by weight based on the weight of the pre-vapor formulation. In some example embodiments, when the solution compound includes a polyol compound, the polyol compound may be included in the pre-vapor formulation at a concentration that is equal to or greater than about 0.2 percent and equal to or less than about 2 percent by weight based on the weight of the pre-vapor formulation.
- the polyol compound when the solution compound includes a polyol compound, may be included in the pre-vapor formulation at a concentration that is equal to or greater than about 8 percent and equal to or less than about 10 percent by weight based on the weight of the pre-vapor formulation.
- the solution compound may include a salt solution.
- the salt solution may include at least one of, for example, sodium chloride, sodium citrate, sodium tartrate, sodium succinate, sodium sulfate, calcium chloride, magnesium chloride, magnesium sulfate, and potassium sulfate.
- the solution compound may include at least one of nicotine, one or more flavorants, one or more organic acids (for example, organic acid compounds), water, and the like.
- the solution compound may adjust the osmolarity of the pre-vapor formulation to be between about 200 milliosmoles per litre to about 500 milliosmoles per litre. In some example embodiments, the solution compound may adjust the osmolarity of the pre-vapor formulation to be between about 280 milliosmoles per litre to about 300 milliosmoles per litre. In some example embodiments, the solution compound may adjust the osmolarity of the pre-vapor formulation to be between about 290 milliosmoles per litre to about 310 milliosmoles per litre.
- the one or more fluids may, in some example embodiments, include a fluid having an osmolarity between about 290 milliosmoles per litre to about 310 milliosmoles per litre, an osmolality between about 290 milliosmoles per kilogram to about 310 milliosmoles per kilogram, or both, such that the pre-vapor formulation may include one or more solution compounds that adjust tonicity of the pre-vapor formulation with regard to the one or more fluids.
- ion exchange agents may include soluble polyelectrolyte polymers with a functional group, such as carboxylic acid groups, sulfonic acid groups such as sulphonated polystyrene, quaternary amino groups such as trimethyl ammonium, and other amino groups.
- a functional group such as carboxylic acid groups, sulfonic acid groups such as sulphonated polystyrene, quaternary amino groups such as trimethyl ammonium, and other amino groups.
- acids may protonate molecular nicotine in the pre-vapor formulation, so that upon heating of the pre-vapor formulation by a heater in the cartridge of the e-vaping device, a vapor having a majority amount of protonated nicotine and a minority amount of unprotonated nicotine may be produced, whereby only a minor portion of all the volatilized (vaporized) nicotine may remain in the gas phase of the vapor.
- the pre-vapor formulation may include up to 5 percent of nicotine, the proportion of nicotine in the gas phase of the vapor may be substantially 1 percent or less of the total nicotine delivered.
- a solution compound is soluble in the pre-vapor formulation.
- one or more solution compounds may be soluble in a solvent that includes at least one of water, propylene glycol, and glycerin.
- one or more acids present in a pre-vapor formulation may be configured to transfer into a vapor generated based on heating of the pre-vapor formulation.
- Transfer efficiency of an acid is the ratio of the mass fraction of the acid in the vapor to the mass fraction of the acid in the pre-vapor formulation.
- an acid or combination of acids present in the pre-vapor formulation may have a liquid to vapor transfer efficiency of about 50 percent or greater, and for example about 60 percent or greater.
- the pre-vapor formulation may include one or more of pyruvic acid, tartaric acid and acetic acid that have vapor transfer efficiencies of about 50 percent or greater, respectively.
- one or more acids present in the pre-vapor formulation may include one or more of pyruvic acid, formic acid, oxalic acid, glycolic acid, acetic acid, isovaleric acid, valeric acid, propionic acid, octanoic acid, lactic acid, sorbic acid, malic acid, tartaric acid, succinic acid, citric acid, benzoic acid, oleic acid, aconitic acid, butyric acid, cinnamic acid, decanoic acid, 3,7-dimethyl-6-octenoic acid, 1-glutamic acid, heptanoic acid, hexanoic acid, 3-hexenoic acid, trans-2-hexenoic acid, isobutyric acid, lauric acid, 2- methylbutyric acid, 2-methylvaleric acid, myristic acid, nonanoic acid, palmitic acid, 4-pentenoic acid, phenylacetic acid, 3-phenyl
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Preparation (AREA)
- Manufacture Of Tobacco Products (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catching Or Destruction (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15/423,699 US20180220697A1 (en) | 2017-02-03 | 2017-02-03 | Methods and systems for improving stability of pre-vapor formulations of e-vaping devices |
| PCT/EP2018/052717 WO2018141941A2 (en) | 2017-02-03 | 2018-02-02 | Methods and systems for improving stability of pre-vapor formulations of e-vaping devices |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP3576552A2 true EP3576552A2 (de) | 2019-12-11 |
Family
ID=61163721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP18703309.7A Pending EP3576552A2 (de) | 2017-02-03 | 2018-02-02 | Verfahren und systeme zur verbesserung der stabilität von vordampfformulierungen von e-vaping-vorrichtungen |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20180220697A1 (de) |
| EP (1) | EP3576552A2 (de) |
| JP (1) | JP7208899B2 (de) |
| KR (1) | KR102649834B1 (de) |
| CN (1) | CN110167365B (de) |
| CA (1) | CA3041189A1 (de) |
| IL (1) | IL268072A (de) |
| MX (1) | MX2019008845A (de) |
| RU (1) | RU2751668C2 (de) |
| WO (1) | WO2018141941A2 (de) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10117463B2 (en) * | 2014-01-03 | 2018-11-06 | Robert P Thomas, Jr. | Vapor delivery device |
| KR102343718B1 (ko) * | 2017-04-24 | 2021-12-24 | 니뽄 다바코 산교 가부시키가이샤 | 에어로졸 생성 장치와, 에어로졸 생성 장치의 제어 방법 및 프로그램 |
| EP3906794A4 (de) * | 2019-01-25 | 2022-10-19 | China Tobacco Hunan Industrial Co., Ltd. | Wasserbasierte flüssigkeit für elektronische zigarette |
| KR20220116469A (ko) * | 2019-12-18 | 2022-08-23 | 필립모리스 프로덕츠 에스.에이. | 에어로졸 발생 시스템용 제형 |
| BR112022011593A2 (pt) * | 2019-12-18 | 2022-08-30 | Philip Morris Products Sa | Formulação para uso em um sistema gerador de aerossol |
| WO2023058750A1 (ja) * | 2021-10-08 | 2023-04-13 | 日本たばこ産業株式会社 | 霧化用液体およびその製造方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102349699B (zh) * | 2011-07-04 | 2013-07-03 | 郑俊祥 | 一种电子烟液的制备方法 |
| US9854839B2 (en) | 2012-01-31 | 2018-01-02 | Altria Client Services Llc | Electronic vaping device and method |
| CN103404969A (zh) * | 2012-10-05 | 2013-11-27 | 佛山市新芯微电子有限公司 | 电子烟装置 |
| MY179801A (en) | 2013-07-19 | 2020-11-16 | Altria Client Services Llc | Liquid aerosol formulation of an electronic smoking article |
| US9877511B2 (en) * | 2013-07-24 | 2018-01-30 | Altria Client Services Llc | Electronic smoking article |
| US10265292B2 (en) | 2013-09-18 | 2019-04-23 | The Werc Shop, LLC | Terpene-based compositions, processes methodologies |
| CN103622161A (zh) * | 2013-11-28 | 2014-03-12 | 刘秋明 | 一种电子烟烟液溶剂及电子烟烟液 |
| CN103598672A (zh) * | 2013-11-28 | 2014-02-26 | 刘秋明 | 一种电子烟烟液溶剂及电子烟烟液 |
| EA201692191A1 (ru) | 2014-04-30 | 2017-03-31 | Олтриа Клайент Сервисиз Ллк | Жидкая рецептура аэрозоля электронного курительного изделия |
| CN104068470A (zh) | 2014-07-07 | 2014-10-01 | 嘉兴市得百科新材料科技有限公司 | 一种电子烟液溶剂及其制备方法 |
| RU2674853C2 (ru) | 2014-07-11 | 2018-12-13 | Филип Моррис Продактс С.А. | Образующая аэрозоль система, содержащая средства обнаружения картриджа |
| CN104256885B (zh) * | 2014-08-05 | 2015-12-30 | 云南中烟工业有限责任公司 | 一种电子烟烟液溶剂 |
| CN104655778B (zh) * | 2015-02-16 | 2016-06-15 | 国家烟草质量监督检验中心 | 一种用于测定电子烟烟液及气溶胶中18种挥发及半挥发性有机物含量的方法 |
| GB201516729D0 (en) | 2015-09-22 | 2015-11-04 | The Technology Partnership Plc | Liquid nicotine formulation |
| CN106562469A (zh) * | 2015-10-07 | 2017-04-19 | 惠州市吉瑞科技有限公司 | 电子烟烟液 |
| CN105310103B (zh) * | 2015-11-04 | 2017-10-24 | 深圳瀚星翔科技有限公司 | 一种电子烟烟油及其制备方法 |
| CN105341990A (zh) * | 2015-12-16 | 2016-02-24 | 浙江中烟工业有限责任公司 | 一种提升电子烟生理满足感的电子烟烟液 |
| CN106072756B (zh) * | 2016-08-04 | 2017-06-23 | 上海应用技术学院 | 一种含苯乙醇糖苷的电子烟液 |
-
2017
- 2017-02-03 US US15/423,699 patent/US20180220697A1/en not_active Abandoned
-
2018
- 2018-02-02 KR KR1020197019108A patent/KR102649834B1/ko active IP Right Grant
- 2018-02-02 WO PCT/EP2018/052717 patent/WO2018141941A2/en unknown
- 2018-02-02 JP JP2019531215A patent/JP7208899B2/ja active Active
- 2018-02-02 CA CA3041189A patent/CA3041189A1/en not_active Abandoned
- 2018-02-02 EP EP18703309.7A patent/EP3576552A2/de active Pending
- 2018-02-02 RU RU2019127181A patent/RU2751668C2/ru active
- 2018-02-02 CN CN201880006151.4A patent/CN110167365B/zh active Active
- 2018-02-02 MX MX2019008845A patent/MX2019008845A/es unknown
-
2019
- 2019-07-15 IL IL268072A patent/IL268072A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR102649834B1 (ko) | 2024-03-21 |
| WO2018141941A2 (en) | 2018-08-09 |
| CN110167365B (zh) | 2023-01-03 |
| JP2020504999A (ja) | 2020-02-20 |
| US20180220697A1 (en) | 2018-08-09 |
| RU2019127181A (ru) | 2021-03-03 |
| CN110167365A (zh) | 2019-08-23 |
| RU2751668C2 (ru) | 2021-07-15 |
| WO2018141941A3 (en) | 2018-12-20 |
| IL268072A (en) | 2019-09-26 |
| MX2019008845A (es) | 2019-09-11 |
| KR20190114964A (ko) | 2019-10-10 |
| JP7208899B2 (ja) | 2023-01-19 |
| RU2019127181A3 (de) | 2021-05-21 |
| CA3041189A1 (en) | 2018-08-09 |
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