RU2019113350A - Полимерная композиция, поглощающая ультрафиолетовое излучение - Google Patents
Полимерная композиция, поглощающая ультрафиолетовое излучение Download PDFInfo
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- RU2019113350A RU2019113350A RU2019113350A RU2019113350A RU2019113350A RU 2019113350 A RU2019113350 A RU 2019113350A RU 2019113350 A RU2019113350 A RU 2019113350A RU 2019113350 A RU2019113350 A RU 2019113350A RU 2019113350 A RU2019113350 A RU 2019113350A
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- Prior art keywords
- esterification
- transesterification
- process according
- carried out
- benzotriazol
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims 4
- 230000005855 radiation Effects 0.000 title claims 2
- 238000000034 method Methods 0.000 claims 16
- 230000032050 esterification Effects 0.000 claims 8
- 238000005886 esterification reaction Methods 0.000 claims 8
- 238000005809 transesterification reaction Methods 0.000 claims 8
- 229920000223 polyglycerol Polymers 0.000 claims 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- OYGYNUPKLMDVHM-UHFFFAOYSA-N 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(N2N=C3C=CC=CC3=N2)=C1O OYGYNUPKLMDVHM-UHFFFAOYSA-N 0.000 claims 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims 2
- 239000012964 benzotriazole Substances 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 229920000570 polyether Polymers 0.000 claims 2
- SLGJCSQBGDYEDI-UHFFFAOYSA-N 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxy-2-methylphenyl]propanoic acid Chemical compound CC1=C(CCC(O)=O)C=C(C(C)(C)C)C(O)=C1N1N=C2C=CC=CC2=N1 SLGJCSQBGDYEDI-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000007932 benzotriazole esters Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- UJRDRFZCRQNLJM-UHFFFAOYSA-N methyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical group CC(C)(C)C1=CC(CCC(=O)OC)=CC(N2N=C3C=CC=CC3=N2)=C1O UJRDRFZCRQNLJM-UHFFFAOYSA-N 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
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- C—CHEMISTRY; METALLURGY
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/48—Polymers modified by chemical after-treatment
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/496—Triazoles or their condensed derivatives, e.g. benzotriazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4993—Derivatives containing from 2 to 10 oxyalkylene groups
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- A—HUMAN NECESSITIES
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- A61K8/00—Cosmetics or similar toiletry preparations
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- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/85—Polyesters
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/86—Polyethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
- C07D249/20—Benzotriazoles with aryl radicals directly attached in position 2
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
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- C08G65/32—Polymers modified by chemical after-treatment
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- C08G65/3314—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group cyclic
- C08G65/3315—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group cyclic aromatic
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- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
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- C08G65/32—Polymers modified by chemical after-treatment
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- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33303—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group
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- C08K5/00—Use of organic ingredients
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- C08K5/0041—Optical brightening agents, organic pigments
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- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
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Claims (20)
1. Способ получения полимерной композиции, поглощающей ультрафиолетовое излучение, содержащей полимерное соединение формулы (3), в этерификации/переэтерификации, причем данный способ включает стадии взаимодействия полиглицериннового интермедиата (2) с бензотриазольным УФ-хромофором (1), содержащим дополнительную функциональную группу для образования полимерного соединения (3) (= простого полиэфира, поглощающего УФ-излучение) в соответствии со следующей схемой реакции:
где
А представляет собой водород или алкил с 1 - 8 атомами углерода, и
k представляет собой число от 1 до 20, и
n и m независимо друг от друга представляют собой число от 0 до 20, причем по меньшей мере одно из m и n составляет ≥1.
2. Способ по п. 1, причем средняя молекулярная масса простого полиэфира формулы (3) составляет > 500, предпочтительно от 500 до 50000, более предпочтительно от 1000 до 20000 и наиболее предпочтительно от 1000 до 10000.
3. Способ по п. 1, причем воду или спирт, который образуется во время реакции, удаляют дистилляцией в процессе реакции этерификации/переэтерификации.
4. Способ по п. 1, причем этерификацию/переэтерификацию проводят при температуре 160 - 270°С, более предпочтительно при температуре 190 - 260°С.
5. Способ по п. 1, причем этерификацию/переэтерификацию проводят без какого-либо дополнительного растворителя.
6. Способ по п. 1, причем этерификацию/переэтерификацию проводят без дополнительных катализаторов этерификации/переэтерификации.
7. Способ по п. 1, причем этерификацию/переэтерификацию проводят в условиях периодического или постоянного вакуума, составляющего менее 250 мбар, более предпочтительно менее 100 мбар.
8. Способ по п. 1, причем этерификацию/переэтерификацию проводят при температуре 190 - 260°С в течение по меньшей мере 16 ч.
9. Способ по п. 1, причем полиглицерин содержит менее 5 % глицерина или линейных и циклических диглицеринов.
10. Способ по п. 1, причем гидроксильное число полиглицерина находится в диапазоне между 700 и 1100, более предпочтительно между 750 и 900.
11. Способ по п. 1, причем бензотриазольная кислота представляет собой 3-(2Н-бензотриазол-2-ил)-5-(1,1-диметилэтил)-4-гидроксибензол-пропановую кислоту (УФ-хромофор).
12. Способ по п. 1, причем бензотриазольный сложный эфир представляет собой сложный метиловый эфир 3-(2H-бензотриазол-2-ил)-5-(1,1-диметилэтил)-4-гидроксибензолпропановой кислоты (УФ-хромофор).
13. Способ по п. 1, причем конечный продукт реакции используют без дополнительной очистки.
14. Способ по любому из пп. 1 - 13, причем 1 часть полиглицерина взаимодействует с 2,8 - 3,2 частями сложного метилового эфира 3-(2H-бензотриазол-2-ил)-5-(1,1-диметилэтил)-4-гидроксибензолпропановой кислоты.
15. Способ по любому из пп. 1 - 13, причем 1 часть полиглицерина взаимодействует с 2,8 - 3,2 частями 3-(2H-бензотриазол-2-ил)-5-(1,1-диметилэтил)-4-гидроксибензолпропановой кислоты.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP16192444.4 | 2016-10-05 | ||
| EP16192444 | 2016-10-05 | ||
| PCT/EP2017/074931 WO2018065341A1 (en) | 2016-10-05 | 2017-10-02 | Ultraviolet radiation absorbing polymer composition |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| RU2019113350A true RU2019113350A (ru) | 2020-11-06 |
| RU2019113350A3 RU2019113350A3 (ru) | 2021-02-05 |
| RU2754980C2 RU2754980C2 (ru) | 2021-09-08 |
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| Application Number | Title | Priority Date | Filing Date |
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| RU2019113350A RU2754980C2 (ru) | 2016-10-05 | 2017-10-02 | Полимерная композиция, поглощающая ультрафиолетовое излучение |
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| Country | Link |
|---|---|
| US (1) | US11046814B2 (ru) |
| EP (1) | EP3523350B1 (ru) |
| JP (1) | JP7114576B2 (ru) |
| KR (1) | KR102505711B1 (ru) |
| CN (1) | CN109790286B (ru) |
| AU (1) | AU2017340812B2 (ru) |
| BR (1) | BR112019006031B1 (ru) |
| CA (1) | CA3038597A1 (ru) |
| ES (1) | ES2939594T3 (ru) |
| RU (1) | RU2754980C2 (ru) |
| WO (1) | WO2018065341A1 (ru) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20200139678A (ko) * | 2018-04-04 | 2020-12-14 | 바스프 에스이 | 비-생물 물질 및 비-케라틴성 물질에 대한 코팅에서의 uv 흡수제로서의 자외 방사선 흡수 중합체 조성물 (uvrap)의 용도 |
| JP7446237B2 (ja) * | 2018-04-04 | 2024-03-08 | ビーエーエスエフ ソシエタス・ヨーロピア | 成形人工ポリマー物品のための光安定剤としての紫外線吸収組成物の使用 |
| WO2022020332A1 (en) | 2020-07-21 | 2022-01-27 | Chembeau LLC | Diester cosmetic formulations and uses thereof |
| KR20220125824A (ko) | 2021-03-03 | 2022-09-15 | 삼성디스플레이 주식회사 | 수지 조성물 및 이를 포함하는 표시 장치 |
| US20240286345A1 (en) * | 2021-06-24 | 2024-08-29 | Hewlett-Packard Development Company, L.P. | Fusing agents with benzotriazole radiation absorbers for three-dimensional printing |
| US20240269922A1 (en) * | 2021-06-24 | 2024-08-15 | Hewlett-Packard Development Company, L.P. | Three-dimensionally printed lens elements |
| WO2022271174A1 (en) * | 2021-06-24 | 2022-12-29 | Hewlett-Packard Development Company, L.P. | Fusing agents with triazine radiation absorbers for three-dimensional printing |
| WO2024253837A1 (en) * | 2023-06-06 | 2024-12-12 | Kenvue Brands Llc | Low penetration sunscreen compositions |
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| DE1165574B (de) | 1960-08-08 | 1964-03-19 | Dehydag Gmbh | Verfahren zur Herstellung von als Emulgiermittel fuer Salbengrundlagen dienenden Mischestern |
| DE2024051C3 (de) | 1970-05-16 | 1986-05-07 | Henkel KGaA, 4000 Düsseldorf | Verwendung der Veresterungsprodukte von Glycerin-Äthylenoxid-Addukten mit Fettsäuren als Rückfettungsmittel in kosmetischen Zubereitungen |
| LU68901A1 (ru) | 1973-11-30 | 1975-08-20 | ||
| JP2004531464A (ja) | 2000-11-06 | 2004-10-14 | ロンザ インコーポレイテッド | 線状のポリグリセロール及びポリグリセロールエステルを調製する方法 |
| GB0028161D0 (en) | 2000-11-17 | 2001-01-03 | Natural Environment Res | Personal care compositions |
| DE10138496A1 (de) | 2001-08-04 | 2003-02-20 | Beiersdorf Ag | Verwendung von Kombinationen von Füllstoffen und Latexpartikeln zur Verstärkung des Lichtschutzfaktors und/oder der UV-A-Schutzleistung kosmetischer oder dermatologischer Formulierungen |
| DE10155200A1 (de) | 2001-11-12 | 2003-05-28 | Skinlab Gmbh | Verwendung von Cholesterin, cholesterinhaltigen Substanzen oder von den Cholesteringehalt erhöhenden Substanzen in kosmetischen und dermatologischen Zubereitungen zum Zwecke der UV-Protektion |
| DE10226352A1 (de) | 2002-06-13 | 2003-12-24 | Beiersdorf Ag | Kosmetische und dermatologische Lichtschutzzubereitungen enthaltend eine synergetische Kombination aus UV-Absorbern und synthetischen organischen Polymeren als Füllstoffe |
| DE10226351A1 (de) | 2002-06-13 | 2003-12-24 | Beiersdorf Ag | Kosmetische und dermatologische Lichtschutzzubereitungen enthaltend eine synergistische Kombination aus UV-Absorbern und in Wasser nicht quellbaren Schichtsilikaten als Füllstoffen |
| DE10226349A1 (de) | 2002-06-13 | 2003-12-24 | Beiersdorf Ag | Kosmetische und dermatologische Lichtschutzzubereitungen enthaltend eine Kombination aus UV-Absorbern und sphärischen Siliziumoxiden |
| DE10229995A1 (de) | 2002-07-03 | 2004-01-15 | Beiersdorf Ag | Kosmetische oder dermatologische Zubereitungen mit einem Gehalt an alpha-Liponsäure |
| EP1892262A1 (en) | 2003-05-26 | 2008-02-27 | Ciba Specialty Chemicals Holding Inc. | Highly compatible and non-migratory polymeric UV-Absorber |
| US7166273B2 (en) | 2003-06-03 | 2007-01-23 | Emd Chemicals, Inc. | Photo stable organic sunscreen compositions |
| WO2007092407A2 (en) | 2006-02-06 | 2007-08-16 | Cargill, Incorporated | Process for preparing polyglycerol and mixed ethers |
| DE102007035567A1 (de) | 2007-07-26 | 2009-01-29 | Basf Se | UV-Filter-Kapsel |
| JP5722312B2 (ja) | 2009-05-29 | 2015-05-20 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | ベンジリデンマロネート類 |
| WO2011003774A2 (en) | 2009-07-07 | 2011-01-13 | Basf Se | Uv filter combinations comprising benzylidene malonates |
| US8227399B2 (en) | 2010-02-12 | 2012-07-24 | Evonik Goldschmidt Gmbh | Polyglycerol esters and their use |
| US9469725B2 (en) * | 2012-06-28 | 2016-10-18 | Johnson & Johnson Consumer Inc. | Ultraviolet radiation absorbing polymers |
| WO2014004474A2 (en) * | 2012-06-28 | 2014-01-03 | Johnson & Johnson Consumer Companies, Inc. | Sunscreen compositions containing an ultraviolet radiation-absorbing polymer |
| US9255180B2 (en) * | 2012-06-28 | 2016-02-09 | Johnson & Johnson Consumer Inc. | Ultraviolet radiation absorbing polyethers |
| US20150164771A1 (en) * | 2013-12-18 | 2015-06-18 | Johnson & Johnson Consumer Companies, Inc. | Sunscreen compositions containing an ultraviolet radiation-absorbing polymer |
| WO2015122770A1 (en) | 2014-02-13 | 2015-08-20 | Clariant International Ltd. | Preparation of polyglycerols |
| US10874603B2 (en) * | 2014-05-12 | 2020-12-29 | Johnson & Johnson Consumer Inc. | Sunscreen compositions containing a UV-absorbing polyglycerol and a non-UV-absorbing polyglycerol |
| EP3471694B1 (en) * | 2016-06-16 | 2025-07-02 | Kenvue Brands LLC | Sunscreen compositions containing a combination of a linear ultraviolet radiation-absorbing polyether and other ultraviolet-screening compounds |
-
2017
- 2017-10-02 BR BR112019006031-6A patent/BR112019006031B1/pt active IP Right Grant
- 2017-10-02 CA CA3038597A patent/CA3038597A1/en active Pending
- 2017-10-02 RU RU2019113350A patent/RU2754980C2/ru active
- 2017-10-02 ES ES17778260T patent/ES2939594T3/es active Active
- 2017-10-02 KR KR1020197009421A patent/KR102505711B1/ko active Active
- 2017-10-02 EP EP17778260.4A patent/EP3523350B1/en active Active
- 2017-10-02 AU AU2017340812A patent/AU2017340812B2/en active Active
- 2017-10-02 CN CN201780061383.5A patent/CN109790286B/zh active Active
- 2017-10-02 JP JP2019518060A patent/JP7114576B2/ja active Active
- 2017-10-02 US US16/338,526 patent/US11046814B2/en active Active
- 2017-10-02 WO PCT/EP2017/074931 patent/WO2018065341A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| KR102505711B1 (ko) | 2023-03-03 |
| JP2019537560A (ja) | 2019-12-26 |
| RU2019113350A3 (ru) | 2021-02-05 |
| US20200299459A1 (en) | 2020-09-24 |
| CN109790286A (zh) | 2019-05-21 |
| BR112019006031A2 (pt) | 2019-06-18 |
| EP3523350B1 (en) | 2022-12-07 |
| CA3038597A1 (en) | 2018-04-12 |
| RU2754980C2 (ru) | 2021-09-08 |
| CN109790286B (zh) | 2022-04-12 |
| KR20190066008A (ko) | 2019-06-12 |
| BR112019006031B1 (pt) | 2022-11-08 |
| ES2939594T3 (es) | 2023-04-25 |
| AU2017340812B2 (en) | 2022-02-10 |
| JP7114576B2 (ja) | 2022-08-08 |
| EP3523350A1 (en) | 2019-08-14 |
| WO2018065341A1 (en) | 2018-04-12 |
| AU2017340812A1 (en) | 2019-04-11 |
| US11046814B2 (en) | 2021-06-29 |
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