RU2015123575A - Синтез полиуретановых полимеров посредством катализируемого медью азид-алкинового циклоприсоединения для применений в области покрытий, адгезивов, герметиков и эластомеров - Google Patents
Синтез полиуретановых полимеров посредством катализируемого медью азид-алкинового циклоприсоединения для применений в области покрытий, адгезивов, герметиков и эластомеров Download PDFInfo
- Publication number
- RU2015123575A RU2015123575A RU2015123575A RU2015123575A RU2015123575A RU 2015123575 A RU2015123575 A RU 2015123575A RU 2015123575 A RU2015123575 A RU 2015123575A RU 2015123575 A RU2015123575 A RU 2015123575A RU 2015123575 A RU2015123575 A RU 2015123575A
- Authority
- RU
- Russia
- Prior art keywords
- product
- azide
- interaction
- compound
- reacting
- Prior art date
Links
- 239000000853 adhesive Substances 0.000 title claims 2
- 229920001971 elastomer Polymers 0.000 title claims 2
- 239000000806 elastomer Substances 0.000 title claims 2
- 239000000565 sealant Substances 0.000 title claims 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 229920000642 polymer Polymers 0.000 title 1
- 229920002635 polyurethane Polymers 0.000 title 1
- 239000004814 polyurethane Substances 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- -1 azide compound Chemical class 0.000 claims 14
- 230000003993 interaction Effects 0.000 claims 14
- 239000000047 product Substances 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 5
- 125000000524 functional group Chemical group 0.000 claims 5
- 239000004593 Epoxy Substances 0.000 claims 4
- 150000001540 azides Chemical class 0.000 claims 4
- 239000005056 polyisocyanate Substances 0.000 claims 4
- 229920001228 polyisocyanate Polymers 0.000 claims 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims 2
- 239000002168 alkylating agent Substances 0.000 claims 2
- 229940100198 alkylating agent Drugs 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- 239000011248 coating agent Substances 0.000 claims 2
- 238000000576 coating method Methods 0.000 claims 2
- 239000012948 isocyanate Substances 0.000 claims 2
- 150000002513 isocyanates Chemical class 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 230000000269 nucleophilic effect Effects 0.000 claims 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-UHFFFAOYSA-N 0.000 claims 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims 1
- 238000006736 Huisgen cycloaddition reaction Methods 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 claims 1
- 230000001070 adhesive effect Effects 0.000 claims 1
- 150000001337 aliphatic alkines Chemical class 0.000 claims 1
- 150000001345 alkine derivatives Chemical class 0.000 claims 1
- 125000002355 alkine group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000012634 fragment Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 150000002924 oxiranes Chemical class 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/6745—Acetylenic 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/2845—Monohydroxy epoxy 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
- C09D163/10—Epoxy resins modified by unsaturated compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/08—Polyurethanes from polyethers
-
- 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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
- C09J163/10—Epoxy resins modified by unsaturated compounds
-
- 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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
-
- 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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/08—Polyurethanes from polyethers
-
- E—FIXED CONSTRUCTIONS
- E04—BUILDING
- E04B—GENERAL BUILDING CONSTRUCTIONS; WALLS, e.g. PARTITIONS; ROOFS; FLOORS; CEILINGS; INSULATION OR OTHER PROTECTION OF BUILDINGS
- E04B7/00—Roofs; Roof construction with regard to insulation
-
- E—FIXED CONSTRUCTIONS
- E04—BUILDING
- E04D—ROOF COVERINGS; SKY-LIGHTS; GUTTERS; ROOF-WORKING TOOLS
- E04D7/00—Roof covering exclusively consisting of sealing masses applied in situ; Gravelling of flat roofs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Architecture (AREA)
- Civil Engineering (AREA)
- Structural Engineering (AREA)
- Physics & Mathematics (AREA)
- Electromagnetism (AREA)
- Polyurethanes Or Polyureas (AREA)
- Sealing Material Composition (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13154589 | 2013-02-08 | ||
| EP13154589.9 | 2013-02-08 | ||
| PCT/EP2014/052207 WO2014122153A1 (en) | 2013-02-08 | 2014-02-05 | Synthesis of polyurethane polymers via copper azide-alkyne click chemistry for coatings, adhesives, sealants and elastomer applications |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2015123575A true RU2015123575A (ru) | 2017-03-21 |
Family
ID=47666043
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2015123575A RU2015123575A (ru) | 2013-02-08 | 2014-02-05 | Синтез полиуретановых полимеров посредством катализируемого медью азид-алкинового циклоприсоединения для применений в области покрытий, адгезивов, герметиков и эластомеров |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9790398B2 (enExample) |
| EP (1) | EP2953988B1 (enExample) |
| JP (2) | JP2016513093A (enExample) |
| KR (1) | KR20150115743A (enExample) |
| CN (1) | CN104995229B (enExample) |
| AU (1) | AU2014214024A1 (enExample) |
| RU (1) | RU2015123575A (enExample) |
| WO (1) | WO2014122153A1 (enExample) |
| ZA (1) | ZA201506444B (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20160311973A1 (en) | 2015-04-24 | 2016-10-27 | The Penn State Research Foundation | Clickable waterborne polymers and click-crosslinked waterborne polymers, clickable functional compounds, click functionalized waterborne polymers, and uses thereof |
| CN105542114B (zh) * | 2016-01-29 | 2018-01-02 | 上海益弹新材料有限公司 | 一种软段中含有氰基的热塑性聚氨酯弹性体及其制备方法 |
| CN105693986B (zh) * | 2016-01-29 | 2018-04-17 | 上海益弹新材料有限公司 | 一种耐高温高湿的液压支架密封件 |
| CN105693971B (zh) * | 2016-01-29 | 2017-02-15 | 上海益弹新材料有限公司 | 一种热塑性聚氨酯弹性体及其制备方法 |
| KR101847773B1 (ko) * | 2017-03-20 | 2018-04-11 | 국방과학연구소 | 화학작용제 제거용 다관능화 열가소성 폴리우레탄 및 그 제조방법 |
| US11034805B2 (en) | 2017-05-11 | 2021-06-15 | Chem Link, Inc. | Click chemistry for sealants and adhesives |
| CN107501503B (zh) * | 2017-08-28 | 2020-11-24 | 南京邦鼎生物科技有限公司 | 用于制备抗菌聚氨酯的组合物、抗菌聚氨酯及其制备方法 |
| CN108587544B (zh) * | 2018-03-28 | 2020-11-10 | 西安近代化学研究所 | 一种端叠氮基聚己内酯粘合剂及其合成方法 |
| CN108503795B (zh) * | 2018-04-19 | 2020-10-27 | 西安近代化学研究所 | 三唑啉键交联的聚叠氮缩水甘油醚及其制备方法 |
| CN109161012B (zh) * | 2018-09-13 | 2021-01-05 | 西安近代化学研究所 | 一种含有氨基甲酸酯结构单元的端叠氮基环氧乙烷-四氢呋喃嵌段共聚醚及其合成方法 |
| US11302960B2 (en) * | 2018-11-07 | 2022-04-12 | Factorial Inc. | Polymer solid electrolytes, methods of making, and electrochemical cells comprising the same |
| US11027260B2 (en) | 2019-02-13 | 2021-06-08 | Uchicago Argonne, Llc | Low pressure nanowire membrane for catalytic reactions and methods of making and using the same |
| KR102052653B1 (ko) * | 2019-05-22 | 2019-12-05 | 국방과학연구소 | 혼합형 고체 추진제용 바인더 조성물, 혼합형 고체 추진제용 바인더 및 이의 제조방법 |
| CN110669203B (zh) * | 2019-09-30 | 2021-06-04 | 湖南大学 | 一种分子内多炔基聚氨酯及聚三唑固化体系 |
| CN111004368B (zh) * | 2019-11-08 | 2021-07-23 | 万华化学集团股份有限公司 | 一种低吸湿率的多异氰酸酯组合物及其制备方法 |
| US11292866B2 (en) | 2019-11-25 | 2022-04-05 | Covestro Llc | Low viscosity poly(alkynyl carbamate) polymers |
| US11261344B2 (en) | 2019-11-25 | 2022-03-01 | Covestro Llc | Waterborne azido-alkyne click compositions |
| US11267927B2 (en) | 2019-11-25 | 2022-03-08 | Covestro Llc | Azido-alkyne click and oxysilane hybrid compositions |
| US11352460B2 (en) | 2019-11-25 | 2022-06-07 | Covestro Llc | Waterborne azido-alkyne click compositions |
| US11884770B2 (en) | 2019-11-25 | 2024-01-30 | The University Of Southern Mississippi | Low viscosity poly(alkynyl carbamate) prepolymers |
| US11174334B2 (en) | 2019-11-25 | 2021-11-16 | Covestro Llc | Allophanate carbamate azido-alkyne click compositions |
| US11312817B2 (en) | 2019-11-25 | 2022-04-26 | Covestro Llc | Polyurethane polymers cured via azido-alkyne cycloaddition at ambient or mild curing conditions |
| CN112375516B (zh) * | 2020-11-27 | 2022-04-01 | 惠州市科域新材料科技有限公司 | 一种电子产品专用高粘耐高温压敏胶和制备及其保护膜 |
| KR102549927B1 (ko) * | 2020-12-14 | 2023-06-29 | 숙명여자대학교산학협력단 | 클릭 반응을 이용한 동박 표면 접착층 형성방법 |
| WO2022182492A1 (en) * | 2021-02-25 | 2022-09-01 | Milliken & Company | Liquid applied roofing composite |
| KR102766584B1 (ko) * | 2021-11-25 | 2025-02-12 | 충남대학교산학협력단 | 기계적 물성이 우수한 고관능기를 포함하는 열가소성 폴리우레탄의 제조방법 |
| CN115851347B (zh) * | 2021-12-20 | 2023-12-08 | 中国科学院兰州化学物理研究所 | 一种界面原位润滑体系和润滑添加剂的原位制备方法 |
| CN115572379B (zh) * | 2022-10-17 | 2024-03-12 | 黄山中泽新材料有限公司 | 一种含叠氮聚酯多元醇的制备方法及其在后交联单组分水性聚氨酯中的应用 |
| KR102744393B1 (ko) * | 2024-01-24 | 2024-12-19 | 한국화학연구원 | 아실아자이드 관능성 폴리에테르 및 이의 제조방법 |
| KR102744392B1 (ko) * | 2024-01-24 | 2024-12-19 | 한국화학연구원 | 아실아자이드 관능성 폴리에테르 및 이를 포함하는 경화성 접착제 조성물 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2573561A1 (en) * | 2004-07-22 | 2006-02-02 | The Scripps Research Institute | Polymeric materials via click chemistry |
| US7772358B2 (en) | 2006-09-06 | 2010-08-10 | The Hong Kong University Of Science And Technology | Polytriazoles constructed by 1,3-dipolar cycloaddition |
| EP2009039A1 (en) * | 2007-06-27 | 2008-12-31 | Universiteit Gent | Functionalised polyurethanes |
| US8034396B2 (en) * | 2008-04-01 | 2011-10-11 | Tyco Healthcare Group Lp | Bioadhesive composition formed using click chemistry |
| US8445601B2 (en) * | 2008-11-14 | 2013-05-21 | 3M Innovative Properties Company | Polymeric compositions and method of making and articles thereof |
| WO2011059994A2 (en) * | 2009-11-11 | 2011-05-19 | 3M Innovative Properties Company | Polymeric compositions and method of making and articles thereof |
-
2014
- 2014-02-05 KR KR1020157019920A patent/KR20150115743A/ko not_active Withdrawn
- 2014-02-05 CN CN201480007304.9A patent/CN104995229B/zh not_active Expired - Fee Related
- 2014-02-05 RU RU2015123575A patent/RU2015123575A/ru unknown
- 2014-02-05 JP JP2015556479A patent/JP2016513093A/ja active Pending
- 2014-02-05 EP EP14703572.9A patent/EP2953988B1/en not_active Not-in-force
- 2014-02-05 AU AU2014214024A patent/AU2014214024A1/en not_active Abandoned
- 2014-02-05 WO PCT/EP2014/052207 patent/WO2014122153A1/en not_active Ceased
- 2014-02-05 US US14/766,342 patent/US9790398B2/en not_active Expired - Fee Related
-
2015
- 2015-09-03 ZA ZA2015/06444A patent/ZA201506444B/en unknown
-
2018
- 2018-08-03 JP JP2018146561A patent/JP2018184472A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN104995229A (zh) | 2015-10-21 |
| WO2014122153A1 (en) | 2014-08-14 |
| KR20150115743A (ko) | 2015-10-14 |
| JP2016513093A (ja) | 2016-05-12 |
| CN104995229B (zh) | 2018-04-20 |
| EP2953988B1 (en) | 2018-08-08 |
| EP2953988A1 (en) | 2015-12-16 |
| US20150368530A1 (en) | 2015-12-24 |
| JP2018184472A (ja) | 2018-11-22 |
| ZA201506444B (en) | 2017-03-29 |
| AU2014214024A1 (en) | 2015-07-02 |
| US9790398B2 (en) | 2017-10-17 |
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