CA3058852A1 - Process for recovery of iodine from aqueous solutions - Google Patents
Process for recovery of iodine from aqueous solutions Download PDFInfo
- Publication number
- CA3058852A1 CA3058852A1 CA3058852A CA3058852A CA3058852A1 CA 3058852 A1 CA3058852 A1 CA 3058852A1 CA 3058852 A CA3058852 A CA 3058852A CA 3058852 A CA3058852 A CA 3058852A CA 3058852 A1 CA3058852 A1 CA 3058852A1
- Authority
- CA
- Canada
- Prior art keywords
- iodine
- process according
- molecular
- solution
- molecular iodine
- 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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 title claims abstract description 186
- 229910052740 iodine Inorganic materials 0.000 title claims abstract description 186
- 239000011630 iodine Substances 0.000 title claims abstract description 184
- 238000000034 method Methods 0.000 title claims abstract description 101
- 238000011084 recovery Methods 0.000 title claims abstract description 39
- 239000007864 aqueous solution Substances 0.000 title claims abstract description 38
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims abstract description 98
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 48
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 51
- 239000000243 solution Substances 0.000 claims description 51
- 150000004694 iodide salts Chemical class 0.000 claims description 44
- -1 iodide ions Chemical class 0.000 claims description 20
- 150000002484 inorganic compounds Chemical class 0.000 claims description 15
- 229910010272 inorganic material Inorganic materials 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 238000000859 sublimation Methods 0.000 claims description 12
- 230000008022 sublimation Effects 0.000 claims description 12
- KBZFDRWPMZESDI-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxylic acid Chemical compound NC1=CC(C(O)=O)=CC(C(O)=O)=C1 KBZFDRWPMZESDI-UHFFFAOYSA-N 0.000 claims description 11
- 239000002872 contrast media Substances 0.000 claims description 11
- 230000026045 iodination Effects 0.000 claims description 10
- 238000006192 iodination reaction Methods 0.000 claims description 10
- 239000000543 intermediate Substances 0.000 claims description 9
- 239000007800 oxidant agent Substances 0.000 claims description 9
- 239000003637 basic solution Substances 0.000 claims description 6
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims description 5
- 229940006461 iodide ion Drugs 0.000 claims description 5
- 230000001590 oxidative effect Effects 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- 230000033558 biomineral tissue development Effects 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 230000020477 pH reduction Effects 0.000 claims description 4
- 230000002745 absorbent Effects 0.000 claims description 3
- 239000002250 absorbent Substances 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000004064 recycling Methods 0.000 abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
- 230000003647 oxidation Effects 0.000 description 26
- 238000007254 oxidation reaction Methods 0.000 description 26
- 229910052799 carbon Inorganic materials 0.000 description 25
- 239000000203 mixture Substances 0.000 description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 21
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 14
- 238000010521 absorption reaction Methods 0.000 description 13
- 238000011282 treatment Methods 0.000 description 13
- 238000003756 stirring Methods 0.000 description 11
- 230000002378 acidificating effect Effects 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- JEZJSNULLBSYHV-UHFFFAOYSA-N 5-amino-2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound NC1=C(I)C(C(O)=O)=C(I)C(C(O)=O)=C1I JEZJSNULLBSYHV-UHFFFAOYSA-N 0.000 description 3
- 101100328886 Caenorhabditis elegans col-2 gene Proteins 0.000 description 3
- 239000003929 acidic solution Substances 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001449 anionic compounds Chemical class 0.000 description 2
- 238000001461 argentometric titration Methods 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 229910001412 inorganic anion Inorganic materials 0.000 description 2
- XQZXYNRDCRIARQ-LURJTMIESA-N iopamidol Chemical compound C[C@H](O)C(=O)NC1=C(I)C(C(=O)NC(CO)CO)=C(I)C(C(=O)NC(CO)CO)=C1I XQZXYNRDCRIARQ-LURJTMIESA-N 0.000 description 2
- 229960004647 iopamidol Drugs 0.000 description 2
- QZUPTXGVPYNUIT-UHFFFAOYSA-N isophthalamide Chemical class NC(=O)C1=CC=CC(C(N)=O)=C1 QZUPTXGVPYNUIT-UHFFFAOYSA-N 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- WGLQHUKCXBXUDV-UHFFFAOYSA-N 3-aminophthalic acid Chemical class NC1=CC=CC(C(O)=O)=C1C(O)=O WGLQHUKCXBXUDV-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000005695 dehalogenation reaction Methods 0.000 description 1
- 238000005831 deiodination reaction Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- NJKDOADNQSYQEV-UHFFFAOYSA-N iomeprol Chemical compound OCC(=O)N(C)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NJKDOADNQSYQEV-UHFFFAOYSA-N 0.000 description 1
- 229960000780 iomeprol Drugs 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical group CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B7/00—Halogens; Halogen acids
- C01B7/13—Iodine; Hydrogen iodide
- C01B7/14—Iodine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B2210/00—Purification or separation of specific gases
- C01B2210/0001—Separation or purification processing
- C01B2210/0003—Chemical processing
- C01B2210/0004—Chemical processing by oxidation
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B2210/00—Purification or separation of specific gases
- C01B2210/0043—Impurity removed
- C01B2210/0068—Organic compounds
- C01B2210/007—Hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP17174675 | 2017-06-07 | ||
| EP17174675.3 | 2017-06-07 | ||
| PCT/EP2018/064981 WO2018224581A1 (en) | 2017-06-07 | 2018-06-07 | A process for the recovery of iodine from aqueous solutions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA3058852A1 true CA3058852A1 (en) | 2018-12-13 |
Family
ID=59070431
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3058852A Pending CA3058852A1 (en) | 2017-06-07 | 2018-06-07 | Process for recovery of iodine from aqueous solutions |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US11691875B2 (enExample) |
| EP (1) | EP3634908B1 (enExample) |
| JP (1) | JP7132252B2 (enExample) |
| KR (1) | KR102562581B1 (enExample) |
| CN (1) | CN110662713B (enExample) |
| AU (1) | AU2018281892B2 (enExample) |
| CA (1) | CA3058852A1 (enExample) |
| ES (1) | ES2981784T3 (enExample) |
| IL (1) | IL271228B2 (enExample) |
| MX (1) | MX2019014608A (enExample) |
| NZ (1) | NZ757793A (enExample) |
| WO (1) | WO2018224581A1 (enExample) |
| ZA (1) | ZA201907151B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20220002121U (ko) | 2021-02-23 | 2022-08-30 | 성기봉 | 공간 토출기 |
| WO2025114248A1 (en) | 2023-11-28 | 2025-06-05 | Bracco Imaging Spa | Process for obtaining iodide from solutions comprising iodine-containing aromatic compound |
| CN118270944A (zh) * | 2024-03-26 | 2024-07-02 | 中国人民解放军陆军特色医学中心 | 碘对比剂剩余废弃物的处理设备及方法 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH608189A5 (enExample) | 1974-12-13 | 1978-12-29 | Savac Ag | |
| DE3108991A1 (de) * | 1981-03-10 | 1982-09-23 | Gesellschaft für Strahlen- und Umweltforschung mbH, 8000 München | Verfahren zum abtrennen und sammeln von jod |
| IT1152493B (it) | 1982-08-09 | 1986-12-31 | Bracco Ind Chimica Spa | Metodo per il recupero dello iodio da acque madri ed effluenti contenenti iodio organico |
| US4853480A (en) * | 1987-08-06 | 1989-08-01 | Eastman Kodak Company | Oxyiodination incorporating an iodine generator for the conversion of methyl iodide to iodine |
| US4976947A (en) * | 1990-02-20 | 1990-12-11 | Eastman Kodak Company | Process for the recovery of elemental iodine from alkyl iodides |
| DE4236724A1 (de) * | 1992-10-30 | 1994-05-05 | Schering Ag | Verfahren zur Rückgewinnung von Jod aus jodierten organischen Verbindungen |
| JPH06144804A (ja) | 1992-11-09 | 1994-05-24 | Godo Shigen Sangyo Kk | 有機沃素化合物を含有する廃液から沃素を回収する方法 |
| US5763650A (en) * | 1995-05-23 | 1998-06-09 | Fructamine S.P.A. | Process for the preparation of a halosubstituted aromatic acid |
| DE19702814A1 (de) * | 1997-01-20 | 1998-08-06 | Schering Ag | Verfahren zur Jodrückgewinnung aus Jodaromaten |
| IT1303796B1 (it) * | 1998-11-27 | 2001-02-23 | Bracco Spa | Processo per il recupero dello iodio da soluzioni acquose contenenticomposti organici iodurati. |
| IT1319670B1 (it) | 2000-12-01 | 2003-10-23 | Bracco Spa | Processo per la preparazione di 5-ammino-n,n'-bis(2-idrossi-1-(idrossimetil)etil))-1,3-benzendicarbossammide (i) e 5-ammino-n,n'- |
| RU2233792C2 (ru) | 2002-04-05 | 2004-08-10 | Некоммерческое партнерство Современные научные технологии "СОНАТЕХ" | Колонна сорбции йода из растворов |
| WO2006118280A1 (ja) * | 2005-05-02 | 2006-11-09 | Nippoh Chemicals Co., Ltd. | ヨウ素の回収方法 |
| DE102005048789A1 (de) * | 2005-10-12 | 2007-04-19 | Technocon Gmbh | Verfahren zur Rückgewinnung von elementarem Jod aus jodorganischen Verbindungen |
| JP5189255B2 (ja) | 2006-07-03 | 2013-04-24 | 合同資源産業株式会社 | 偏光フィルム製造廃液からのヨウ素回収方法 |
| CN101554994B (zh) * | 2009-05-20 | 2010-09-29 | 山西新天源医药化工有限公司 | X-ct系列造影剂生产废液中碘的回收方法 |
| CN103508421A (zh) * | 2013-10-15 | 2014-01-15 | 四川大学 | X-ct系列造影剂生产废液中碘的回收方法 |
| JP6438770B2 (ja) * | 2015-01-07 | 2018-12-19 | 日宝化学株式会社 | ヨウ素の回収方法 |
| CN105439089A (zh) * | 2016-01-11 | 2016-03-30 | 浙江海洲制药有限公司 | 医药生产废水中碘的回收方法 |
| CN105460896B (zh) | 2016-01-11 | 2018-02-06 | 浙江海洲制药有限公司 | X‑ct系列造影剂生产废水中碘的回收方法 |
-
2018
- 2018-06-07 CA CA3058852A patent/CA3058852A1/en active Pending
- 2018-06-07 KR KR1020197032716A patent/KR102562581B1/ko active Active
- 2018-06-07 EP EP18728179.5A patent/EP3634908B1/en active Active
- 2018-06-07 US US16/619,594 patent/US11691875B2/en active Active
- 2018-06-07 CN CN201880033336.4A patent/CN110662713B/zh active Active
- 2018-06-07 MX MX2019014608A patent/MX2019014608A/es unknown
- 2018-06-07 WO PCT/EP2018/064981 patent/WO2018224581A1/en not_active Ceased
- 2018-06-07 ES ES18728179T patent/ES2981784T3/es active Active
- 2018-06-07 NZ NZ757793A patent/NZ757793A/en unknown
- 2018-06-07 AU AU2018281892A patent/AU2018281892B2/en active Active
- 2018-06-07 JP JP2019567625A patent/JP7132252B2/ja active Active
-
2019
- 2019-10-29 ZA ZA2019/07151A patent/ZA201907151B/en unknown
- 2019-12-05 IL IL271228A patent/IL271228B2/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2981784T3 (es) | 2024-10-10 |
| AU2018281892A1 (en) | 2019-10-24 |
| EP3634908A1 (en) | 2020-04-15 |
| JP7132252B2 (ja) | 2022-09-06 |
| CN110662713B (zh) | 2023-11-28 |
| RU2019139859A (ru) | 2021-07-09 |
| NZ757793A (en) | 2022-04-29 |
| KR20200016207A (ko) | 2020-02-14 |
| IL271228B1 (en) | 2023-03-01 |
| JP2020522456A (ja) | 2020-07-30 |
| AU2018281892B2 (en) | 2023-08-24 |
| IL271228B2 (en) | 2023-07-01 |
| US20200131036A1 (en) | 2020-04-30 |
| IL271228A (en) | 2020-01-30 |
| CN110662713A (zh) | 2020-01-07 |
| EP3634908B1 (en) | 2024-03-06 |
| MX2019014608A (es) | 2020-02-07 |
| WO2018224581A1 (en) | 2018-12-13 |
| ZA201907151B (en) | 2021-02-24 |
| KR102562581B1 (ko) | 2023-08-02 |
| US11691875B2 (en) | 2023-07-04 |
| RU2019139859A3 (enExample) | 2021-09-30 |
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