EP3749705A4 - Copolymers of ester and ether units, processes for producing same and uses thereof - Google Patents

Copolymers of ester and ether units, processes for producing same and uses thereof Download PDF

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Publication number
EP3749705A4
EP3749705A4 EP19747279.8A EP19747279A EP3749705A4 EP 3749705 A4 EP3749705 A4 EP 3749705A4 EP 19747279 A EP19747279 A EP 19747279A EP 3749705 A4 EP3749705 A4 EP 3749705A4
Authority
EP
European Patent Office
Prior art keywords
copolymers
ester
processes
producing same
ether units
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
EP19747279.8A
Other languages
German (de)
French (fr)
Other versions
EP3749705A1 (en
Inventor
Basile Commarieu
Jean-Christophe Daigle
Pierre-Michel JALBERT
Gilles Lajoie
Catherine Gagnon
Abdelbast Guerfi
Michel Armand
Karim Zaghib
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.)
Hydro Quebec
Original Assignee
Hydro Quebec
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 Hydro Quebec filed Critical Hydro Quebec
Publication of EP3749705A1 publication Critical patent/EP3749705A1/en
Publication of EP3749705A4 publication Critical patent/EP3749705A4/en
Pending legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F299/00Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
    • C08F299/02Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
    • C08F299/04Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyesters
    • C08F299/0485Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyesters from polyesters with side or terminal unsaturations
    • C08F299/0492Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyesters from polyesters with side or terminal unsaturations the unsaturation being in acrylic or methacrylic groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06Polymers provided for in subclass C08G
    • C08F290/061Polyesters; Polycarbonates
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/04Acids; Metal salts or ammonium salts thereof
    • C08F220/06Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/12Esters of monohydric alcohols or phenols
    • C08F220/16Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • 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
    • C08G63/02Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/06Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
    • C08G63/08Lactones or lactides
    • 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
    • C08G63/66Polyesters 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
    • C08G63/00Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/66Polyesters containing oxygen in the form of ether groups
    • C08G63/664Polyesters containing oxygen in the form of ether groups derived from hydroxy carboxylic acids
    • 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
    • C08G63/91Polymers modified by chemical after-treatment
    • C08G63/912Polymers modified by chemical after-treatment derived from hydroxycarboxylic acids
    • 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
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2603Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00Processes of treating or compounding macromolecular substances
    • C08J3/24Crosslinking, e.g. vulcanising, of macromolecules
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L51/00Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L51/08Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/02Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01GCAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES OR LIGHT-SENSITIVE DEVICES, OF THE ELECTROLYTIC TYPE
    • H01G11/00Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
    • H01G11/54Electrolytes
    • H01G11/56Solid electrolytes, e.g. gels; Additives therein
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01MPROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00Secondary cells; Manufacture thereof
    • H01M10/05Accumulators with non-aqueous electrolyte
    • H01M10/052Li-accumulators
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01MPROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00Secondary cells; Manufacture thereof
    • H01M10/05Accumulators with non-aqueous electrolyte
    • H01M10/052Li-accumulators
    • H01M10/0525Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01MPROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00Secondary cells; Manufacture thereof
    • H01M10/05Accumulators with non-aqueous electrolyte
    • H01M10/054Accumulators with insertion or intercalation of metals other than lithium, e.g. with magnesium or aluminium
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01MPROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00Secondary cells; Manufacture thereof
    • H01M10/05Accumulators with non-aqueous electrolyte
    • H01M10/056Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
    • H01M10/0565Polymeric materials, e.g. gel-type or solid-type
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01MPROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00Electrodes
    • H01M4/02Electrodes composed of, or comprising, active material
    • H01M4/13Electrodes for accumulators with non-aqueous electrolyte, e.g. for lithium-accumulators; Processes of manufacture thereof
    • H01M4/137Electrodes based on electro-active polymers
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01MPROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00Electrodes
    • H01M4/02Electrodes composed of, or comprising, active material
    • H01M4/62Selection of inactive substances as ingredients for active masses, e.g. binders, fillers
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01MPROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00Electrodes
    • H01M4/02Electrodes composed of, or comprising, active material
    • H01M4/62Selection of inactive substances as ingredients for active masses, e.g. binders, fillers
    • H01M4/621Binders
    • H01M4/622Binders being polymers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2367/00Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
    • C08J2367/04Polyesters derived from hydroxy carboxylic acids, e.g. lactones
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01MPROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M2300/00Electrolytes
    • H01M2300/0017Non-aqueous electrolytes
    • H01M2300/0065Solid electrolytes
    • H01M2300/0082Organic polymers
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01MPROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M2300/00Electrolytes
    • H01M2300/0088Composites
    • H01M2300/0091Composites in the form of mixtures
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01MPROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00Electrodes
    • H01M4/02Electrodes composed of, or comprising, active material
    • H01M4/62Selection of inactive substances as ingredients for active masses, e.g. binders, fillers
    • H01M4/624Electric conductive fillers
    • H01M4/625Carbon or graphite
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02EREDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10Energy storage using batteries
EP19747279.8A 2018-02-05 2019-02-05 Copolymers of ester and ether units, processes for producing same and uses thereof Pending EP3749705A4 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CA2994005A CA2994005A1 (en) 2018-02-05 2018-02-05 Ester and ether copolymer units, their fabrication process and their uses
PCT/CA2019/050145 WO2019148299A1 (en) 2018-02-05 2019-02-05 Copolymers of ester and ether units, processes for producing same and uses thereof

Publications (2)

Publication Number Publication Date
EP3749705A1 EP3749705A1 (en) 2020-12-16
EP3749705A4 true EP3749705A4 (en) 2022-03-23

Family

ID=67479141

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19747279.8A Pending EP3749705A4 (en) 2018-02-05 2019-02-05 Copolymers of ester and ether units, processes for producing same and uses thereof

Country Status (7)

Country Link
US (1) US20210380745A1 (en)
EP (1) EP3749705A4 (en)
JP (2) JP7366034B2 (en)
KR (1) KR102640042B1 (en)
CN (2) CN111683990B (en)
CA (2) CA2994005A1 (en)
WO (1) WO2019148299A1 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11749805B2 (en) * 2020-01-28 2023-09-05 Ricoh Company, Ltd. Liquid composition for forming electrochemical device, method of manufacturing electrodes, method of manufacturing electrochemical device and electrodes
CN117203813A (en) * 2021-07-29 2023-12-08 株式会社Lg新能源 Gel polymer electrolyte and lithium secondary battery including the same
CN114853621B (en) * 2022-05-05 2023-08-01 华中科技大学 Method for catalyzing primary amine-acrylic ester double-addition reaction and application thereof
CN115572467B (en) * 2022-09-28 2024-01-12 江苏金发科技新材料有限公司 Polyester composition and preparation method and application thereof

Citations (2)

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CA2478659A1 (en) * 2002-03-15 2003-09-25 Japan Science And Technology Agency Electrophoretic buffer
WO2007012979A2 (en) * 2005-04-22 2007-02-01 Universite De Geneve Polylactide compositions and uses thereof

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JP2007188889A (en) * 1995-08-23 2007-07-26 Mitsui Chemicals Inc Solid polymer electrolyte
JP2009070605A (en) * 2007-09-11 2009-04-02 Dai Ichi Kogyo Seiyaku Co Ltd Lithium polymer battery
CA2738835A1 (en) 2008-10-01 2010-04-08 Bayer Materialscience Ag Prepolymer-based polyurethane formulations for producing holographic media
DE102010001470A1 (en) * 2010-02-02 2011-08-04 Henkel AG & Co. KGaA, 40589 Polyether block copolymers and compositions obtainable therefrom
KR101537768B1 (en) * 2012-05-31 2015-07-17 주식회사 엘지화학 Nonaqueous electrolyte and lithium secondary battery using the same

Patent Citations (2)

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Publication number Priority date Publication date Assignee Title
CA2478659A1 (en) * 2002-03-15 2003-09-25 Japan Science And Technology Agency Electrophoretic buffer
WO2007012979A2 (en) * 2005-04-22 2007-02-01 Universite De Geneve Polylactide compositions and uses thereof

Non-Patent Citations (8)

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Title
CHUCK CHRISTOPHER J ET AL: "Air-Stable Titanium Alkoxide Based Metal-Organic Framework as an Initiator for Ring-Opening Polymerization of Cyclic Esters", INORGANIC CHEMISTRY, VOL. 45, ISSUE 17, 22 July 2006 (2006-07-22), pages 6595 - 6597, XP055890833, Retrieved from the Internet <URL:https://pubs.acs.org/doi/pdf/10.1021/ic060969+> [retrieved on 20220211], DOI: 10.1021/ic060969+ *
HUYNH ET AL: "Functionalized injectable hydrogels for controlled insulin delivery", BIOMATERIALS, ELSEVIER, AMSTERDAM, NL, vol. 29, no. 16, 10 March 2008 (2008-03-10), pages 2527 - 2534, XP022559050, ISSN: 0142-9612 *
KWEON H ET AL: "A novel degradable polycaprolactone networks for tissue engineering", BIOMATERIALS, ELSEVIER, AMSTERDAM, NL, vol. 24, no. 5, 1 February 2003 (2003-02-01), pages 801 - 808, XP004398698, ISSN: 0142-9612, DOI: 10.1016/S0142-9612(02)00370-8 *
LI J ET AL: "Preparation and characterization of inclusion complexes formed by biodegradable poly(@e-caprolactone)-poly(tetrahydrofuran)-poly(@e-caprolactone) triblock copolymer and cyclodextrins", POLYMER, ELSEVIER, AMSTERDAM, NL, vol. 45, no. 6, 1 March 2004 (2004-03-01), pages 1777 - 1785, XP004490333, ISSN: 0032-3861, DOI: 10.1016/J.POLYMER.2004.01.021 *
TAN B ET AL: "Crosslinkable surfactants based on linoleic acid-functionalized block copolymers of ethylene oxide and @e-caprolactone for the preparation of stable PMMA latices", POLYMER, ELSEVIER SCIENCE PUBLISHERS B.V, GB, vol. 46, no. 4, 7 February 2005 (2005-02-07), pages 1347 - 1357, XP027728307, ISSN: 0032-3861, [retrieved on 20050207] *
TZENG JY-JIUNN ET AL: "Synthesis, Characterization, and Visible Light Curing Capacity of Polycaprolactone Acrylate", BIOMED RESEARCH INTERNATIONAL, vol. 2018, 1 January 2018 (2018-01-01), pages 1 - 8, XP055890825, ISSN: 2314-6133, Retrieved from the Internet <URL:https://downloads.hindawi.com/journals/bmri/2018/8719624.pdf> DOI: 10.1155/2018/8719624 *
UGUR MUSTAFA HULUSI ET AL: "Synthesis by UV-curing and characterisation of polyurethane acrylate-lithium salts-based polymer electrolytes in lithium batteries", CHEMICK ZVESTI - CHEMICAL PAPERS, VEDA, BRATISLAVA, SK, vol. 68, no. 11, 7 July 2014 (2014-07-07), pages 1561 - 1572, XP035385174, ISSN: 0366-6352, [retrieved on 20140707], DOI: 10.2478/S11696-014-0611-1 *
YOO JE SUN ET AL: "Novel pH and Temperature-Sensitive Block Copolymers: Poly(ethylene glycol)-b-poly([epsilon]-caprolactone)-b- poly([beta]-amino ester)", MACROMOLECULAR RESEARCH, VOL. 14, NR.1, 1 January 2006 (2006-01-01), pages 117 - 120, XP055848622, Retrieved from the Internet <URL:https://link.springer.com/content/pdf/10.1007/BF03219078.pdf> [retrieved on 20211006] *

Also Published As

Publication number Publication date
CA3087944A1 (en) 2019-08-08
KR102640042B1 (en) 2024-02-27
JP7366034B2 (en) 2023-10-20
CN111683990B (en) 2022-11-04
JP2023133421A (en) 2023-09-22
CN115838472A (en) 2023-03-24
CN111683990A (en) 2020-09-18
WO2019148299A1 (en) 2019-08-08
KR20200118470A (en) 2020-10-15
US20210380745A1 (en) 2021-12-09
EP3749705A1 (en) 2020-12-16
CA2994005A1 (en) 2019-08-05
JP2021512200A (en) 2021-05-13

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