KR102815259B1 - 신규한 아민 작용화 폴리머 및 제조 방법 - Google Patents
신규한 아민 작용화 폴리머 및 제조 방법 Download PDFInfo
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- KR102815259B1 KR102815259B1 KR1020207037061A KR20207037061A KR102815259B1 KR 102815259 B1 KR102815259 B1 KR 102815259B1 KR 1020207037061 A KR1020207037061 A KR 1020207037061A KR 20207037061 A KR20207037061 A KR 20207037061A KR 102815259 B1 KR102815259 B1 KR 102815259B1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/26—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment
- C08L23/36—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment by reaction with nitrogen-containing compounds, e.g. by nitration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/1616—Coordination complexes, e.g. organometallic complexes, immobilised on an inorganic support, e.g. ship-in-a-bottle type catalysts
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/04—Monomers containing three or four carbon atoms
- C08F110/06—Propene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/26—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment
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- 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
- C09D123/00—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers
- C09D123/26—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers modified by chemical after-treatment
-
- 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
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- 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
- C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
- C09J123/26—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers modified by chemical after-treatment
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
- B01J2231/4211—Suzuki-type, i.e. RY + R'B(OR)2, in which R, R' are optionally substituted alkyl, alkenyl, aryl, acyl and Y is the leaving group
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/50—Complexes comprising metals of Group V (VA or VB) as the central metal
- B01J2531/56—Vanadium
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/50—Complexes comprising metals of Group V (VA or VB) as the central metal
- B01J2531/57—Niobium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/50—Complexes comprising metals of Group V (VA or VB) as the central metal
- B01J2531/58—Tantalum
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/824—Palladium
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
- B01J2540/40—Non-coordinating groups comprising nitrogen
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/2243—At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2810/00—Chemical modification of a polymer
- C08F2810/40—Chemical modification of a polymer taking place solely at one end or both ends of the polymer backbone, i.e. not in the side or lateral chains
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Inorganic Chemistry (AREA)
- Plant Pathology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Paints Or Removers (AREA)
- Medicinal Preparation (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862675465P | 2018-05-23 | 2018-05-23 | |
| US62/675,465 | 2018-05-23 | ||
| PCT/CA2019/050704 WO2019222852A1 (en) | 2018-05-23 | 2019-05-23 | Novel amine functionalized polymers and methods of preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20210023879A KR20210023879A (ko) | 2021-03-04 |
| KR102815259B1 true KR102815259B1 (ko) | 2025-06-02 |
Family
ID=68615596
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020207037061A Active KR102815259B1 (ko) | 2018-05-23 | 2019-05-23 | 신규한 아민 작용화 폴리머 및 제조 방법 |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US11795315B2 (https=) |
| EP (1) | EP3797126A4 (https=) |
| JP (2) | JP7448958B2 (https=) |
| KR (1) | KR102815259B1 (https=) |
| CN (1) | CN112585176B (https=) |
| AU (2) | AU2019273133A1 (https=) |
| CA (2) | CA3100853A1 (https=) |
| EA (1) | EA202092823A1 (https=) |
| MX (1) | MX2020012493A (https=) |
| MY (1) | MY207399A (https=) |
| SA (1) | SA520420617B1 (https=) |
| WO (2) | WO2019222834A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA3100853A1 (en) * | 2018-05-23 | 2019-11-28 | The University Of British Columbia | Group 5 metal complexes for producing amine-functionalized polyolefins |
| CA3239579A1 (en) * | 2021-11-24 | 2023-06-01 | The University Of British Columbia | Superhydrophobic coatings, compositions and methods |
| AU2023253730A1 (en) * | 2022-04-13 | 2024-10-31 | The University Of British Columbia | Preparation and methods for the making of amine containing polybutadiene polymers |
| WO2026015747A1 (en) | 2024-07-10 | 2026-01-15 | A2O Advanced Materials, Inc. | Hot melt adhesive polymer blends |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4818588B1 (https=) * | 1969-07-24 | 1973-06-07 | ||
| US4217914A (en) * | 1974-05-16 | 1980-08-19 | L'oreal | Quaternized polymer for use as a cosmetic agent in cosmetic compositions for the hair and skin |
| JP3176386B2 (ja) * | 1991-04-30 | 2001-06-18 | 三菱化学株式会社 | アミノ基含有重合体 |
| JP3718915B2 (ja) * | 1995-10-16 | 2005-11-24 | 味の素株式会社 | 顔料分散剤 |
| US7402642B2 (en) * | 2003-12-23 | 2008-07-22 | Exxonmobil Research And Engineering Company | Linear functional copolymers of ethylene with precise and minimum run length distributions and method of making thereof |
| US20060102895A1 (en) | 2004-11-16 | 2006-05-18 | Hendrix Bryan C | Precursor compositions for forming tantalum-containing films, and tantalum-containing barrier films and copper-metallized semiconductor device structures |
| EP2470575B9 (en) * | 2009-08-28 | 2014-01-15 | The University of Tokyo | Production method of copolymer of allyl monomer containing polar group |
| WO2012040853A1 (en) | 2010-09-28 | 2012-04-05 | The University Of British Columbia | Group 5 metal complexes useful for amine functionalization and synthetic process for manufacture thereof |
| WO2012057884A1 (en) | 2010-10-29 | 2012-05-03 | Applied Materials, Inc. | Nitrogen-containing ligands and their use in atomic layer deposition methods |
| DK2471827T3 (da) * | 2010-12-30 | 2013-11-11 | Universitaetsklinikum Freiburg | Kovalent bundne antimikrobielle polymerer |
| US8669326B2 (en) | 2011-03-25 | 2014-03-11 | Exxonmobil Chemical Patents Inc. | Amine functionalized polyolefin and methods for preparation thereof |
| JP6075020B2 (ja) | 2011-11-16 | 2017-02-08 | 住友化学株式会社 | 重合体、および当該重合体を用いた太陽電池用封止材 |
| FR2999578B1 (fr) | 2012-12-14 | 2015-07-03 | Bostik Sa | Polymeres hydrocarbones a terminaison 2-oxo-1,3-dioxolan-4-yl |
| JP6134619B2 (ja) * | 2013-09-13 | 2017-05-24 | 富士フイルム株式会社 | パターン形成方法、及び、電子デバイスの製造方法 |
| TWI735442B (zh) | 2015-05-28 | 2021-08-11 | 美商陶氏全球科技有限責任公司 | 聚烯烴反應性遙爪預聚合物 |
| CA3064620A1 (en) | 2017-05-26 | 2018-11-29 | The University Of British Columbia | Group 5 metal complexes for catalytic amine functionalization |
| CA3100853A1 (en) | 2018-05-23 | 2019-11-28 | The University Of British Columbia | Group 5 metal complexes for producing amine-functionalized polyolefins |
-
2019
- 2019-01-11 CA CA3100853A patent/CA3100853A1/en active Pending
- 2019-01-11 WO PCT/CA2019/050046 patent/WO2019222834A1/en not_active Ceased
- 2019-01-11 US US17/056,903 patent/US11795315B2/en active Active
- 2019-05-23 US US17/056,529 patent/US11555107B2/en active Active
- 2019-05-23 WO PCT/CA2019/050704 patent/WO2019222852A1/en not_active Ceased
- 2019-05-23 EP EP19806681.3A patent/EP3797126A4/en active Pending
- 2019-05-23 JP JP2020565482A patent/JP7448958B2/ja active Active
- 2019-05-23 CN CN201980048801.6A patent/CN112585176B/zh active Active
- 2019-05-23 EA EA202092823A patent/EA202092823A1/ru unknown
- 2019-05-23 CA CA3103037A patent/CA3103037A1/en active Pending
- 2019-05-23 MX MX2020012493A patent/MX2020012493A/es unknown
- 2019-05-23 KR KR1020207037061A patent/KR102815259B1/ko active Active
- 2019-05-23 MY MYPI2020006148A patent/MY207399A/en unknown
- 2019-05-23 AU AU2019273133A patent/AU2019273133A1/en not_active Abandoned
-
2020
- 2020-11-23 SA SA520420617A patent/SA520420617B1/ar unknown
-
2024
- 2024-01-19 US US18/417,258 patent/US20240247142A1/en active Pending
- 2024-02-22 JP JP2024025476A patent/JP2024075567A/ja active Pending
-
2025
- 2025-04-28 AU AU2025202947A patent/AU2025202947A1/en active Pending
Non-Patent Citations (2)
| Title |
|---|
| M. R. Perry. Catalytic synthesis of amines : from small molecules to nitrogen-containing polymers. University of British Columbia. 2017년 9월. pp.1-336. 1부.* |
| S. Kobayashi et al., Regioselective Ring-Opening Metathesis Polymerization of 3-Substituted Cyclooctenes with Ether Side Chains. Macromolecules. 2016년, 49, pp.2493-2501. 1부.* |
Also Published As
| Publication number | Publication date |
|---|---|
| CN112585176B (zh) | 2023-10-24 |
| SA520420617B1 (ar) | 2025-01-26 |
| AU2019273133A1 (en) | 2021-01-21 |
| US20240247142A1 (en) | 2024-07-25 |
| US11795315B2 (en) | 2023-10-24 |
| BR112020023661A2 (pt) | 2021-02-17 |
| WO2019222834A1 (en) | 2019-11-28 |
| JP2024075567A (ja) | 2024-06-04 |
| AU2025202947A1 (en) | 2025-05-15 |
| EP3797126A4 (en) | 2022-04-13 |
| CN112585176A (zh) | 2021-03-30 |
| KR20210023879A (ko) | 2021-03-04 |
| MY207399A (en) | 2025-02-25 |
| US20220363786A1 (en) | 2022-11-17 |
| CA3103037A1 (en) | 2019-11-28 |
| EA202092823A1 (ru) | 2021-04-21 |
| CA3100853A1 (en) | 2019-11-28 |
| US11555107B2 (en) | 2023-01-17 |
| JP2021525301A (ja) | 2021-09-24 |
| JP7448958B2 (ja) | 2024-03-13 |
| WO2019222852A1 (en) | 2019-11-28 |
| EP3797126A1 (en) | 2021-03-31 |
| MX2020012493A (es) | 2021-03-09 |
| US20210214542A1 (en) | 2021-07-15 |
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