CA3171439A1 - Thermoplastic polyurethane compositions comprising nitro-substituted polyester diols - Google Patents

Thermoplastic polyurethane compositions comprising nitro-substituted polyester diols Download PDF

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Publication number
CA3171439A1
CA3171439A1 CA3171439A CA3171439A CA3171439A1 CA 3171439 A1 CA3171439 A1 CA 3171439A1 CA 3171439 A CA3171439 A CA 3171439A CA 3171439 A CA3171439 A CA 3171439A CA 3171439 A1 CA3171439 A1 CA 3171439A1
Authority
CA
Canada
Prior art keywords
nitro
composition
acid
dimethyl
substituted
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
Application number
CA3171439A
Other languages
English (en)
French (fr)
Inventor
Katrina Marie Knauer
Jennifer LE ROY
Russell Clayton Pratt
David Samuel Pilsk
Cody James Higginson
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novoloop Inc
Original Assignee
Biocellection Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Biocellection Inc filed Critical Biocellection Inc
Publication of CA3171439A1 publication Critical patent/CA3171439A1/en
Pending legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/42Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/46Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen
    • C08G18/4615Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen containing nitrogen
    • C08G18/463Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen containing nitrogen containing nitro groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/10Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/16Catalysts
    • C08G18/22Catalysts containing metal compounds
    • C08G18/24Catalysts containing metal compounds of tin
    • C08G18/244Catalysts containing metal compounds of tin tin salts of carboxylic acids
    • C08G18/246Catalysts containing metal compounds of tin tin salts of carboxylic acids containing also tin-carbon bonds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/42Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4244Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72Polyisocyanates or polyisothiocyanates
    • C08G18/73Polyisocyanates or polyisothiocyanates acyclic
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72Polyisocyanates or polyisothiocyanates
    • C08G18/74Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/757Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing at least two isocyanate or isothiocyanate groups linked to the cycloaliphatic ring by means of an aliphatic group
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72Polyisocyanates or polyisothiocyanates
    • C08G18/74Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7614Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
    • C08G18/7621Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72Polyisocyanates or polyisothiocyanates
    • C08G18/74Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • C08G18/7671Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72Polyisocyanates or polyisothiocyanates
    • C08G18/74Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7678Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing condensed aromatic rings
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/685Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
    • C08G63/6854Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/6856Dicarboxylic acids and dihydroxy compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/04Oxygen-containing compounds
    • C08K5/05Alcohols; Metal alcoholates
    • C08K5/053Polyhydroxylic alcohols
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/04Oxygen-containing compounds
    • C08K5/13Phenols; Phenolates
    • C08K5/134Phenols containing ester groups
    • C08K5/1345Carboxylic esters of phenolcarboxylic acids
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/16Nitrogen-containing compounds
    • C08K5/17Amines; Quaternary ammonium compounds
    • C08K5/18Amines; Quaternary ammonium compounds with aromatically bound amino groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/16Nitrogen-containing compounds
    • C08K5/22Compounds containing nitrogen bound to another nitrogen atom
    • C08K5/24Derivatives of hydrazine
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/16Nitrogen-containing compounds
    • C08K5/34Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3472Five-membered rings
    • C08K5/3475Five-membered rings condensed with carbocyclic rings
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2110/00Foam properties
    • C08G2110/0083Foam properties prepared using water as the sole blowing agent
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/49Phosphorus-containing compounds
    • C08K5/51Phosphorus bound to oxygen
    • C08K5/52Phosphorus bound to oxygen only
    • C08K5/524Esters of phosphorous acids, e.g. of H3PO3
    • C08K5/526Esters of phosphorous acids, e.g. of H3PO3 with hydroxyaryl compounds

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
CA3171439A 2020-03-13 2021-03-12 Thermoplastic polyurethane compositions comprising nitro-substituted polyester diols Pending CA3171439A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US202062989098P 2020-03-13 2020-03-13
US62/989,098 2020-03-13
US16/985,009 US11028217B1 (en) 2020-03-13 2020-08-04 Thermoplastic polyurethane compositions comprising nitro-substituted polyester diols
US16/985,009 2020-08-04
PCT/US2021/022101 WO2021183883A1 (en) 2020-03-13 2021-03-12 Thermoplastic polyurethane compositions comprising nitro-substituted polyester diols

Publications (1)

Publication Number Publication Date
CA3171439A1 true CA3171439A1 (en) 2021-09-16

Family

ID=76213414

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3171439A Pending CA3171439A1 (en) 2020-03-13 2021-03-12 Thermoplastic polyurethane compositions comprising nitro-substituted polyester diols

Country Status (11)

Country Link
US (1) US11028217B1 (https=)
EP (1) EP4118131A4 (https=)
JP (1) JP2023518213A (https=)
KR (1) KR20230028216A (https=)
CN (1) CN115843302B (https=)
AU (1) AU2021233025B2 (https=)
BR (1) BR112022018257A2 (https=)
CA (1) CA3171439A1 (https=)
IL (1) IL296388B2 (https=)
MX (1) MX2022011369A (https=)
WO (1) WO2021183883A1 (https=)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20230029576A (ko) 2019-12-11 2023-03-03 노보루프, 인크. 폐기물 폴리프로필렌의 분해를 위한 조성물 및 방법
US20230130031A1 (en) * 2020-03-13 2023-04-27 Novoloop, Inc. Thermoplastic Polyurethane Compositions Comprising Nitro-Substituted Polyester Diols
WO2023055374A1 (en) 2021-09-30 2023-04-06 Hewlett-Packard Development Company, L.P. Three-dimensional printing
CN118831656B (zh) * 2024-07-25 2025-11-25 哈尔滨工业大学 一种氮磷硫共掺生物炭的三维电催化氧化催化剂的制备方法及应用

Family Cites Families (28)

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US3692597A (en) * 1955-06-29 1972-09-19 Goodrich Co B F Polyurethane propellant compositions and their preparation
US4099376A (en) * 1955-06-29 1978-07-11 The B.F. Goodrich Company Gas generator and solid propellant with a silicon-oxygen compound as a burning rate modifier, and method for making the same
GB949086A (en) * 1960-04-22 1964-02-12 Bombrini Parodi Delfino Spa Improvements in composite propellants and the like
US3245962A (en) 1963-04-22 1966-04-12 Aerojet General Co Nu-nitro substituted, nitro containing polyurethanes
US3745076A (en) * 1966-02-02 1973-07-10 Us Navy Propellant composition with a nitro containing cross-linked binder
US3475383A (en) * 1967-06-22 1969-10-28 Goodrich Co B F Fuel resistant polyurethanes
CA1074494A (en) 1974-07-10 1980-03-25 Robert Koncos Compositions having good hydrolytic stability and improved strength properties
FR2482606A1 (fr) * 1980-05-14 1981-11-20 Poudres & Explosifs Ste Nale Resines polyurethannes thermoplastiques reticulables comportant des groupements ethyleniques pendants
US4355154A (en) 1981-10-06 1982-10-19 Dow Corning Corporation Method for preparing condensation polymers by emulsion polymerization
US5844165A (en) * 1987-03-26 1998-12-01 Thiokol Corporation Energetic nitro malonate polyester binders
FR2615424B1 (fr) 1987-05-22 1990-02-23 Huettenes Albertus France Compositions pour moule de fonderie contenant du sable, un liant en polyurethane et un compose nitro
US5811506A (en) * 1997-02-03 1998-09-22 Simula Inc. Extrudable thermoplastic elastomeric urea-extended polyurethane
ATE293647T1 (de) * 1996-05-21 2005-05-15 Simula Inc Extrudierbares, thermoplastisches, elastomeres, harnstoff-kettenverlängertes polyurethan
DE19627907A1 (de) * 1996-07-11 1998-01-15 Basf Ag Verfahren zur Herstellung von kompakten oder zelligen Polyurethan-Elastomeren und hierfür geeignete Isocyanatprepolymere
WO1999010400A1 (en) 1997-08-26 1999-03-04 Witco Corporation Polyurethane polymers having excellent hydrolytic stability and solvent resistance
DE10063496A1 (de) 2000-12-20 2002-07-04 Bayer Ag Polyurethanelastomere mit verbesserter Hydrolysestabilität
US20030166823A1 (en) * 2002-03-01 2003-09-04 Thomas Daly Polymers with antimicrobial, bioresistant and fungal resistant properties
CN101050262B (zh) * 2007-05-24 2010-11-24 烟台万华新材料科技有限公司 一种热塑性聚氨酯弹性体生产工艺
US8637584B2 (en) 2007-05-25 2014-01-28 Air Products And Chemicals, Inc. Polyester polyol-containing polyurethane systems having improved hydrolytic stability
CA2714100C (en) * 2008-02-08 2016-03-29 Union Carbide Chemicals & Plastics Technology Llc Flame-retardant polyolefin / thermoplastic polyurethane composition
WO2014088766A2 (en) * 2012-12-06 2014-06-12 Angus Chemical Company Nitrofunctional polyurethane dispersions for binder compositions
EP2746309A1 (de) 2012-12-19 2014-06-25 Basf Se Hydrolysebeständige Polyurethanformkörper aus Polyesterpolyurethan
US9448126B2 (en) 2014-03-06 2016-09-20 Infineon Technologies Ag Single diaphragm transducer structure
US10696786B2 (en) 2014-12-11 2020-06-30 Northrop Grumman Innovation Systems, Inc. Methods of producing energetic polymers, energetic binders, and energetic compositions
CN106674471B (zh) * 2015-11-11 2019-09-03 万华化学集团股份有限公司 一种热塑性聚氨酯弹性体及其制备方法、用途和制品
US10624833B2 (en) * 2016-06-30 2020-04-21 Elementis Specialties, Inc. Crosslinkable coating compositions formulated with dormant carbamate initiator
KR102477958B1 (ko) * 2016-11-25 2022-12-19 코베스트로 도이칠란트 아게 적어도 부분적으로 코팅된 물품을 제조하는 방법
CA3097766A1 (en) * 2018-04-19 2019-10-24 Biocellection Inc. Methods for the decomposition of contaminated plastic waste

Also Published As

Publication number Publication date
MX2022011369A (es) 2023-01-04
IL296388A (en) 2022-11-01
EP4118131A4 (en) 2024-03-06
BR112022018257A2 (pt) 2022-11-22
AU2021233025A1 (en) 2022-10-13
WO2021183883A1 (en) 2021-09-16
CN115843302A (zh) 2023-03-24
JP2023518213A (ja) 2023-04-28
IL296388B2 (en) 2026-04-01
CN115843302B (zh) 2025-12-09
EP4118131A1 (en) 2023-01-18
TW202140598A (zh) 2021-11-01
AU2021233025B2 (en) 2025-02-20
US11028217B1 (en) 2021-06-08
KR20230028216A (ko) 2023-02-28
IL296388B1 (en) 2025-12-01

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