BR112016018532A2 - revestimentos antimicrobianos funcionais de fosfonato para superfícies metálicas. - Google Patents
revestimentos antimicrobianos funcionais de fosfonato para superfícies metálicas.Info
- Publication number
- BR112016018532A2 BR112016018532A2 BR112016018532A BR112016018532A BR112016018532A2 BR 112016018532 A2 BR112016018532 A2 BR 112016018532A2 BR 112016018532 A BR112016018532 A BR 112016018532A BR 112016018532 A BR112016018532 A BR 112016018532A BR 112016018532 A2 BR112016018532 A2 BR 112016018532A2
- Authority
- BR
- Brazil
- Prior art keywords
- metal surfaces
- antimicrobial coatings
- phosphonate functional
- functional antimicrobial
- phosphonate
- Prior art date
Links
- 230000000845 anti-microbial effect Effects 0.000 title 1
- 238000000576 coating method Methods 0.000 title 1
- 239000002184 metal Substances 0.000 title 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 title 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/02—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by baking
- B05D3/0254—After-treatment
- B05D3/0272—After-treatment with ovens
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C07F9/3817—Acids containing the structure (RX)2P(=X)-alk-N...P (X = O, S, Se)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3839—Polyphosphonic acids
- C07F9/3873—Polyphosphonic acids containing nitrogen substituent, e.g. N.....H or N-hydrocarbon group which can be substituted by halogen or nitro(so), N.....O, N.....S, N.....C(=X)- (X =O, S), N.....N, N...C(=X)...N (X =O, S)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
- C07F9/4009—Esters containing the structure (RX)2P(=X)-alk-N...P (X = O, S, Se)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
- C07F9/5728—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/6552—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1606—Antifouling paints; Underwater paints characterised by the anti-fouling agent
- C09D5/1612—Non-macromolecular compounds
- C09D5/1625—Non-macromolecular compounds organic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Materials Engineering (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361766533P | 2013-02-19 | 2013-02-19 | |
| PCT/CA2014/000104 WO2014127451A1 (en) | 2013-02-19 | 2014-02-12 | Phosphorus functional antimicrobial coatings for metal surfaces |
| CAPCT/CA2014/000104 | 2014-02-12 | ||
| PCT/CA2014/050796 WO2015120531A1 (en) | 2013-02-19 | 2014-08-20 | Phosphonate functional antimicrobial coatings for metal surfaces |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR112016018532A2 true BR112016018532A2 (pt) | 2018-05-08 |
| BR112016018532B1 BR112016018532B1 (pt) | 2021-09-14 |
Family
ID=51390427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112016018532-3A BR112016018532B1 (pt) | 2013-02-19 | 2014-08-20 | Composição de revestimento de superfície antimicrobiana, processo para o revestimento de uma superfície, superfície revestida e método de redução do crescimento de microrganismos |
Country Status (9)
| Country | Link |
|---|---|
| US (4) | USRE48510E1 (pt) |
| EP (1) | EP3105237B1 (pt) |
| CN (2) | CN113150592A (pt) |
| AP (1) | AP2015008631A0 (pt) |
| BR (1) | BR112016018532B1 (pt) |
| CA (2) | CA2923610A1 (pt) |
| IL (1) | IL247209A0 (pt) |
| MX (1) | MX2015010720A (pt) |
| WO (2) | WO2014127451A1 (pt) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2884128C (en) | 2012-12-11 | 2016-02-09 | Nano Safe Coatings Incorporated | Uv cured benzophenone terminated quaternary ammonium antimicrobials for surfaces |
| CA2923610A1 (en) | 2013-02-19 | 2014-08-28 | Nano Safe Coatings Incorporated (A Florida Corporation 3 P 14000024914) | Phosphorus functional antimicrobial coatings for metal surfaces |
| US9476754B2 (en) * | 2013-02-28 | 2016-10-25 | Electrolab, Inc. | Method and kit for treatment of components utilized in a crude oil service operation |
| EP3341358B1 (en) | 2015-08-27 | 2023-03-08 | Nano Safe Coatings Incorporated (a Florida Corporation 3 P 14000024914) | Preparation of sulfonamide-containing antimicrobials and substrate treating compositions of sulfonamide-containing antimicrobials |
| CN105887102A (zh) * | 2016-04-25 | 2016-08-24 | 中国科学院兰州化学物理研究所 | 磷酸酯功能化的季铵盐缓蚀剂及其制备方法 |
| US10072032B2 (en) * | 2016-09-19 | 2018-09-11 | Afton Chemical Corporation | AminoBisPhosphonate antiwear additives |
| CN110312507B (zh) | 2016-10-17 | 2021-11-23 | 奥索邦德公司 | 具有低聚或聚合抗微生物剂的表面 |
| US10563042B2 (en) | 2016-12-14 | 2020-02-18 | Ecolab Usa Inc. | Quaternary cationic polymers |
| CN107903286B (zh) * | 2017-10-17 | 2020-08-04 | 山东泰和水处理科技股份有限公司 | 一种阻燃剂环己胺二甲叉膦酸及其制备方法 |
| CN107827926B (zh) * | 2017-10-31 | 2020-05-22 | 中国科学院兰州化学物理研究所 | 小分子功能化的表面活性剂及其制备方法和应用 |
| US11427964B2 (en) | 2018-06-12 | 2022-08-30 | Ecolab Usa Inc. | Quaternary cationic surfactants and polymers for use as release and coating modifying agents in creping and tissue papers |
| EP3898733A2 (en) | 2018-12-19 | 2021-10-27 | 3M Innovative Properties Company | Zwitterionic copolymers, coating compositions, articles, and coating methods |
| EP4140304A1 (en) * | 2019-05-31 | 2023-03-01 | Rolex S.A. | Composition for impregnating a substrate, in particular a watchstrap |
| KR20210031159A (ko) * | 2019-09-11 | 2021-03-19 | 주식회사 엘지화학 | 리튬 이차전지용 비수전해액 및 이를 포함하는 리튬 이차전지 |
| CN113336672A (zh) * | 2021-05-21 | 2021-09-03 | 上海应用技术大学 | 利用威廉姆森成醚反应合成三臂化含端烯/炔烃化合物的方法 |
| CN114405542B (zh) * | 2022-01-28 | 2024-02-27 | 万华化学集团股份有限公司 | 一种负载型磁性纳米金属催化剂及其制备方法和应用 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2774786A (en) | 1953-08-10 | 1956-12-18 | Gen Mills Inc | Phosphono-ammonium surface active agents |
| US3454677A (en) | 1966-03-07 | 1969-07-08 | Eastman Kodak Co | Inner salts of aminophosphonates and preparation thereof |
| US3507937A (en) | 1966-10-04 | 1970-04-21 | Procter & Gamble | Reversed zwitterionic phosphorus compounds |
| US3925453A (en) | 1974-01-25 | 1975-12-09 | Monsanto Co | Quaternary aminoalkylene phosphonic acids and method of preparation |
| US4208401A (en) | 1977-08-19 | 1980-06-17 | Colgate-Palmolive Company | Quaternary ammonium alkylene diphosphonate anti-calculus agents |
| US4420399A (en) | 1978-04-20 | 1983-12-13 | Petrolite Corporation | Quaternary aminomethyl phosphonates as scale inhibitors |
| GB8703606D0 (en) | 1987-02-17 | 1987-03-25 | Ward Blenkinsop & Co Ltd | Benzophenone derivatives |
| US5753634A (en) | 1992-05-29 | 1998-05-19 | The Procter & Gamble Company | Quaternary nitrogen containing phosphonate compounds, pharmaceutical compostions, and methods for treating abnormal calcium and phosphate metabolism |
| GB9801747D0 (en) | 1998-01-27 | 1998-03-25 | Courtaulds Coatings Holdings | Antifouling coatings |
| GB9923577D0 (en) | 1999-10-05 | 1999-12-08 | Glaxo Group Ltd | Chemical constructs |
| US6994890B2 (en) * | 2003-10-31 | 2006-02-07 | Resource Development L.L.C. | Cleaning and multifunctional coating composition containing an organosilane quaternary compound and hydrogen peroxide |
| US7435841B2 (en) * | 2004-03-10 | 2008-10-14 | Rhodia Inc. | Preparation of halohydrocarbyl phosphonic acid diesters |
| FR2878248B1 (fr) * | 2004-11-22 | 2007-01-12 | Surfactis Technologies Soc Par | Composes bisphosphoniques pour empecher ou limiter la fixation de macromolecules, de microorganismes et d'un biofilm sur des surfaces solides, notamment metallique ou minerales |
| EP1991624A2 (en) | 2006-02-23 | 2008-11-19 | E.I. Du Pont De Nemours And Company | Removable antimicrobial coating compositions and methods of use |
| FR2912748B1 (fr) | 2007-02-16 | 2009-11-13 | Centre Nat Rech Scient | Alkyl h-phosphonates de n,n'-dialkylimidazouliums, d'ammoniums quaternaires et leurs utilisations |
| WO2009133696A1 (ja) | 2008-04-30 | 2009-11-05 | 住友ベークライト株式会社 | 糖鎖標識方法 |
| US8361779B2 (en) * | 2010-11-24 | 2013-01-29 | Sachem, Inc. | Buffer compounds |
| WO2012160187A1 (en) * | 2011-05-26 | 2012-11-29 | Jado Technologies Gmbh | Amino- or ammonium-containing sulfonic acid, phosphonic acid and carboxylic acid derivatives and their medical use |
| AU2012351998B2 (en) | 2011-12-14 | 2016-01-14 | Semprus Biosciences Corp. | High ionic strength process for contact lens modification |
| CA2923610A1 (en) | 2013-02-19 | 2014-08-28 | Nano Safe Coatings Incorporated (A Florida Corporation 3 P 14000024914) | Phosphorus functional antimicrobial coatings for metal surfaces |
-
2014
- 2014-02-12 CA CA2923610A patent/CA2923610A1/en not_active Abandoned
- 2014-02-12 MX MX2015010720A patent/MX2015010720A/es unknown
- 2014-02-12 US US15/938,151 patent/USRE48510E1/en active Active
- 2014-02-12 AP AP2015008631A patent/AP2015008631A0/xx unknown
- 2014-02-12 CA CA2900282A patent/CA2900282C/en active Active
- 2014-02-12 WO PCT/CA2014/000104 patent/WO2014127451A1/en active Application Filing
- 2014-02-12 US US14/767,052 patent/US9642369B2/en not_active Ceased
- 2014-08-20 WO PCT/CA2014/050796 patent/WO2015120531A1/en active Application Filing
- 2014-08-20 CN CN202110434783.4A patent/CN113150592A/zh active Pending
- 2014-08-20 EP EP14882515.1A patent/EP3105237B1/en active Active
- 2014-08-20 CN CN201480077909.5A patent/CN106232610A/zh active Pending
- 2014-08-20 BR BR112016018532-3A patent/BR112016018532B1/pt active IP Right Grant
-
2016
- 2016-08-10 IL IL247209A patent/IL247209A0/en unknown
- 2016-08-12 US US15/235,240 patent/US10154668B2/en active Active
-
2018
- 2018-12-11 US US16/215,955 patent/US10327447B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| BR112016018532B1 (pt) | 2021-09-14 |
| IL247209A0 (en) | 2016-09-29 |
| US10154668B2 (en) | 2018-12-18 |
| US20160374345A1 (en) | 2016-12-29 |
| WO2014127451A1 (en) | 2014-08-28 |
| US20160066579A1 (en) | 2016-03-10 |
| AP2015008631A0 (en) | 2015-08-31 |
| US9642369B2 (en) | 2017-05-09 |
| EP3105237A4 (en) | 2017-08-16 |
| MX2015010720A (es) | 2016-07-11 |
| EP3105237A1 (en) | 2016-12-21 |
| WO2015120531A1 (en) | 2015-08-20 |
| EP3105237B1 (en) | 2021-10-06 |
| CA2900282A1 (en) | 2014-08-28 |
| US10327447B2 (en) | 2019-06-25 |
| USRE48510E1 (en) | 2021-04-13 |
| US20190116798A1 (en) | 2019-04-25 |
| CA2923610A1 (en) | 2014-08-28 |
| CN106232610A (zh) | 2016-12-14 |
| CN113150592A (zh) | 2021-07-23 |
| CA2900282C (en) | 2016-07-26 |
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