JP6715853B2 - 耐寒性シーラント及びその構成成分 - Google Patents
耐寒性シーラント及びその構成成分 Download PDFInfo
- Publication number
- JP6715853B2 JP6715853B2 JP2017542145A JP2017542145A JP6715853B2 JP 6715853 B2 JP6715853 B2 JP 6715853B2 JP 2017542145 A JP2017542145 A JP 2017542145A JP 2017542145 A JP2017542145 A JP 2017542145A JP 6715853 B2 JP6715853 B2 JP 6715853B2
- Authority
- JP
- Japan
- Prior art keywords
- polythioether
- formula
- polymer
- polymer according
- polythioether polymer
- 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.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/12—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/14—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/12—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms
- C07C321/14—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/12—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms
- C07C321/18—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
- C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/12—Polythioether-ethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/02—Polythioethers; Polythioether-ethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J181/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur, with or without nitrogen, oxygen, or carbon only; Adhesives based on polysulfones; Adhesives based on derivatives of such polymers
- C09J181/02—Polythioethers; Polythioether-ethers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Sealing Material Composition (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Epoxy Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2020100997A JP6972238B2 (ja) | 2015-02-13 | 2020-06-10 | 耐寒性シーラント及びその構成成分 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562116019P | 2015-02-13 | 2015-02-13 | |
| US62/116,019 | 2015-02-13 | ||
| PCT/US2016/017347 WO2016130673A1 (en) | 2015-02-13 | 2016-02-10 | Cold-tolerant sealants and components thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020100997A Division JP6972238B2 (ja) | 2015-02-13 | 2020-06-10 | 耐寒性シーラント及びその構成成分 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018506543A JP2018506543A (ja) | 2018-03-08 |
| JP2018506543A5 JP2018506543A5 (enExample) | 2019-03-07 |
| JP6715853B2 true JP6715853B2 (ja) | 2020-07-01 |
Family
ID=55587328
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017542145A Active JP6715853B2 (ja) | 2015-02-13 | 2016-02-10 | 耐寒性シーラント及びその構成成分 |
| JP2020100997A Active JP6972238B2 (ja) | 2015-02-13 | 2020-06-10 | 耐寒性シーラント及びその構成成分 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020100997A Active JP6972238B2 (ja) | 2015-02-13 | 2020-06-10 | 耐寒性シーラント及びその構成成分 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US10287466B2 (enExample) |
| EP (1) | EP3256512B1 (enExample) |
| JP (2) | JP6715853B2 (enExample) |
| KR (1) | KR20170116114A (enExample) |
| CN (1) | CN107207426B (enExample) |
| BR (1) | BR112017017414A2 (enExample) |
| CA (1) | CA2976436A1 (enExample) |
| WO (1) | WO2016130673A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3347406B1 (en) | 2015-09-10 | 2019-07-03 | 3M Innovative Properties Company | Polymerizable compositions, polymerized compositions, and methods of making and using the same |
| CN110050015B (zh) * | 2016-11-04 | 2022-03-08 | Prc-迪索托国际公司 | 含硫的多(烯基)醚、引入含硫的多(烯基)醚的预聚物及其用途 |
| WO2018111637A1 (en) | 2016-12-13 | 2018-06-21 | 3M Innovative Properties Company | Epoxy stabilization using acid-coated nitrogen-containing catalysts, particles, and methods |
| CN110072907B (zh) | 2016-12-13 | 2021-12-14 | 3M创新有限公司 | 使用取代的巴比妥酸实现环氧稳定化 |
| EP3555178A1 (en) | 2016-12-14 | 2019-10-23 | 3M Innovative Properties Company | Sealant tape |
| JP2020535257A (ja) | 2017-09-26 | 2020-12-03 | スリーエム イノベイティブ プロパティズ カンパニー | 硬化性シーラント組成物、シールキャップ、並びにその作製方法及び使用 |
| JP6874226B2 (ja) * | 2017-12-07 | 2021-05-19 | ヌーリオン ケミカルズ インターナショナル ベスローテン フェノーツハップNouryon Chemicals International B.V. | ポリチオエーテルスルフィドを調製する方法 |
| WO2019123260A2 (en) | 2017-12-19 | 2019-06-27 | 3M Innovative Properties Company | Multi-part composition having staged viscosity prior to hardening |
| CN111788246B (zh) | 2018-03-16 | 2022-06-10 | 3M创新有限公司 | 组合物、粘结方法和粘结组件 |
| WO2019175714A1 (en) | 2018-03-16 | 2019-09-19 | 3M Innovative Properties Company | Compositions, method of bonding, and assembly |
| EP3807043A1 (en) | 2018-06-15 | 2021-04-21 | 3M Innovative Properties Company | Assemblies and methods of making a shim |
| WO2020065438A1 (en) | 2018-09-25 | 2020-04-02 | 3M Innovative Properties Company | Polymeric material including uretdione-containing material, polythiol, and acidic stabilizer, two-part compositions, and methods |
| EP3856817A1 (en) | 2018-09-25 | 2021-08-04 | 3M Innovative Properties Company | One-part thermally curable composition |
| US20210388245A1 (en) | 2018-11-09 | 2021-12-16 | 3M Innovative Properties Company | Curable sealant compositions, seal cap, and methods of making and using the same |
| JP7713925B2 (ja) | 2019-07-25 | 2025-07-28 | スリーエム イノベイティブ プロパティズ カンパニー | アセンブリにシムを入れる方法 |
| WO2021094887A1 (en) | 2019-11-15 | 2021-05-20 | 3M Innovative Properties Company | Curable compositions and methods of making and using the same |
| WO2021124033A1 (en) | 2019-12-19 | 2021-06-24 | 3M Innovative Properties Company | Two-part compositions including a uretdione-containing material and inorganic filler, products, and methods |
| JP7613861B2 (ja) | 2020-09-23 | 2025-01-15 | サトーホールディングス株式会社 | Rfidラベル及びrfidラベルの使用方法 |
| CN113913150B (zh) * | 2021-11-18 | 2023-03-14 | 中国航发北京航空材料研究院 | 用于飞机钣金件的贴合面密封剂 |
| EP4496678A1 (en) | 2022-03-21 | 2025-01-29 | 3M Innovative Properties Company | Curable composition, treated backing, coated abrasive articles including the same, and methods of making and using the same |
| CN118900748A (zh) | 2022-03-21 | 2024-11-05 | 3M创新有限公司 | 可固化组合物,含有该可固化组合物的带涂层磨料制品及其制造和使用方法 |
| WO2025200154A1 (en) | 2024-03-29 | 2025-10-02 | 3M Innovative Properties Company | Two-part epoxy composition comprising thiol curative, and catalyst |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2664414A (en) | 1952-03-08 | 1953-12-29 | Shell Dev | Monomers and polymers of unsaturated thioethers |
| GB1276362A (en) * | 1968-05-21 | 1972-06-01 | Aquitaine Petrole | Synthesis of halogenated thioethers |
| CH628074A5 (de) | 1977-03-10 | 1982-02-15 | Ciba Geigy Ag | Haertbare mischungen auf basis von epoxidverbindungen. |
| US4366307A (en) | 1980-12-04 | 1982-12-28 | Products Research & Chemical Corp. | Liquid polythioethers |
| US4609762A (en) | 1984-01-30 | 1986-09-02 | Products Research & Chemical Corp. | Thioethers having a high sulfur content and method therefor |
| JPH0477576A (ja) * | 1990-07-13 | 1992-03-11 | Tatsuta Electric Wire & Cable Co Ltd | 圧電ブザー及びその電極形成用塗料 |
| US5415794A (en) * | 1990-12-28 | 1995-05-16 | Institut Francais Du Petrole | New sulfured compounds, their preparation and their use as additives for lubricating oils |
| FR2671080B1 (fr) | 1990-12-28 | 1994-05-27 | Inst Francais Du Petrole | Nouveaux composes sulfures, leur preparation et leur utilisation comme additifs pour huile lubrifiantes. |
| US5225472A (en) | 1992-05-19 | 1993-07-06 | Courtaulds Aerospace, Inc. | Low viscosity polythiol and method therefor |
| EP0594133B1 (en) | 1992-10-22 | 1998-05-06 | Ajinomoto Co., Inc. | Polythiol epoxy resin composition with extended working life |
| US5464910A (en) | 1993-12-22 | 1995-11-07 | Shikoku Chemicals Corporation | Epoxy resin adduct combined with a borate ester and phenolic compound |
| US5593795A (en) | 1995-05-01 | 1997-01-14 | Minnesota Mining And Manufacturing Company | Polymer electrolyte composition based upon thiol-ene chemistry |
| US6509418B1 (en) * | 1997-02-19 | 2003-01-21 | Prc-Desoto International, Inc. | Sealants and potting formulations including mercapto-terminated polymers produced by the reaction of a polythiol and polyvinyl ether monomer |
| US6372849B2 (en) | 1997-02-19 | 2002-04-16 | Prc-Desoto International, Inc. | Sealants and potting formulations including polymers produced by the reaction of a polythiol and polyvinyl ether monomer |
| US5912319A (en) | 1997-02-19 | 1999-06-15 | Courtaulds Aerospace, Inc. | Compositions and method for producing fuel resistant liquid polythioether polymers with good low temperature flexibility |
| EP0961804B9 (en) * | 1997-02-19 | 2004-03-03 | PRC-Desoto International, Inc. | Composition and method for producing fuel resistant liquid polythioether polymers with good low temperature flexibility |
| US5959071A (en) | 1998-03-31 | 1999-09-28 | Courtaulds Aerospace, Inc. | Composition and method for producing polythioethers having pendent methyl chains |
| JP4704573B2 (ja) | 1999-05-10 | 2011-06-15 | スリーエム イノベイティブ プロパティズ カンパニー | エン−チオールエラストマーを作成するための組成物 |
| CA2402112A1 (en) | 2000-03-09 | 2001-09-13 | Advanced Chemistry And Technology, Inc. | High strength polymers and aerospace sealants therefrom |
| CN1441834A (zh) * | 2000-06-30 | 2003-09-10 | Prc-迪索托国际公司 | 包括由多硫醇和聚乙烯基醚单体的反应而生产的聚合物的密封剂和封装配制剂 |
| US7097883B2 (en) * | 2003-06-05 | 2006-08-29 | Ppg Industries Ohio, Inc. | Low temperature liquid polythioether polymers |
| US7622548B2 (en) | 2003-07-11 | 2009-11-24 | Prc Desoto International, Inc. | Epoxy- or amine/hydroxy-capped polythioethers |
| US20050010003A1 (en) * | 2003-07-11 | 2005-01-13 | Prc-Desoto International, Inc. | Epoxy-capped polythioethers |
| JP4569129B2 (ja) * | 2004-03-04 | 2010-10-27 | 三菱化学株式会社 | リチウム二次電池用非水系電解液及びそれを用いたリチウム二次電池 |
| US7390859B2 (en) | 2005-02-08 | 2008-06-24 | Ppg Industries Ohio, Inc. | Compositions and methods of making compositions exhibiting fuel resistance |
| US8349951B2 (en) | 2005-05-31 | 2013-01-08 | Prc Desoto International, Inc. | Polythioether polymers and curable compositions containing them |
| US20070096396A1 (en) | 2005-10-27 | 2007-05-03 | Sawant Suresh G | Dimercaptan terminated polythioether polymers and methods for making and using the same |
| CN101437875B (zh) | 2006-05-05 | 2011-05-11 | Ppg工业俄亥俄公司 | 硫醚官能的低聚多硫醇以及由其制备的制品 |
| BRPI0809416A2 (pt) * | 2007-03-28 | 2014-09-16 | Contech Entpr Inc | Composto com atividade detentoea e repelente de artrópode estoparasita que se alimenta de sangue, composição, e, método para sintetizar um composto |
| US7879955B2 (en) | 2007-05-01 | 2011-02-01 | Rao Chandra B | Compositions including a polythioether |
| US7875666B2 (en) | 2008-04-24 | 2011-01-25 | Prc-De Soto International, Inc. | Thioethers, methods for their preparation, and compositions including such thioethers |
| CN102227457B (zh) | 2008-11-07 | 2012-10-31 | 横滨橡胶株式会社 | 1液型热固化性环氧树脂组合物 |
| TWI586749B (zh) | 2010-11-19 | 2017-06-11 | 漢高日本股份有限公司 | 單組分環氧樹脂組成物 |
| WO2012093510A1 (ja) | 2011-01-05 | 2012-07-12 | ナミックス株式会社 | 樹脂組成物 |
| US9056949B2 (en) * | 2013-06-21 | 2015-06-16 | Prc-Desoto International, Inc. | Michael addition curing chemistries for sulfur-containing polymer compositions employing bis(sulfonyl)alkanols |
| US9062139B2 (en) * | 2013-03-15 | 2015-06-23 | Prc-Desoto International, Inc. | Sulfone-containing polythioethers, compositions thereof, and methods of synthesis |
| KR20170097754A (ko) * | 2014-12-23 | 2017-08-28 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 이중 경화 폴리티오에테르 |
-
2016
- 2016-02-10 US US15/545,849 patent/US10287466B2/en not_active Expired - Fee Related
- 2016-02-10 CN CN201680009517.4A patent/CN107207426B/zh not_active Expired - Fee Related
- 2016-02-10 JP JP2017542145A patent/JP6715853B2/ja active Active
- 2016-02-10 BR BR112017017414-6A patent/BR112017017414A2/pt not_active Application Discontinuation
- 2016-02-10 KR KR1020177025323A patent/KR20170116114A/ko not_active Withdrawn
- 2016-02-10 WO PCT/US2016/017347 patent/WO2016130673A1/en not_active Ceased
- 2016-02-10 EP EP16711038.6A patent/EP3256512B1/en active Active
- 2016-02-10 CA CA2976436A patent/CA2976436A1/en not_active Abandoned
-
2019
- 2019-05-01 US US16/400,092 patent/US10544339B2/en active Active
-
2020
- 2020-06-10 JP JP2020100997A patent/JP6972238B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP3256512B1 (en) | 2022-07-20 |
| US20180016480A1 (en) | 2018-01-18 |
| CN107207426B (zh) | 2020-02-14 |
| WO2016130673A1 (en) | 2016-08-18 |
| EP3256512A1 (en) | 2017-12-20 |
| US10287466B2 (en) | 2019-05-14 |
| KR20170116114A (ko) | 2017-10-18 |
| JP6972238B2 (ja) | 2021-11-24 |
| JP2018506543A (ja) | 2018-03-08 |
| US10544339B2 (en) | 2020-01-28 |
| JP2020158778A (ja) | 2020-10-01 |
| US20190256752A1 (en) | 2019-08-22 |
| BR112017017414A2 (pt) | 2018-04-03 |
| CA2976436A1 (en) | 2016-08-18 |
| CN107207426A (zh) | 2017-09-26 |
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