EP3215565A1 - Vernetztes polymer basierend auf einem random-copolymer und einem flüchtigen polyaminierten vernetzungsmittel sowie verfahren zur herstellung davon - Google Patents

Vernetztes polymer basierend auf einem random-copolymer und einem flüchtigen polyaminierten vernetzungsmittel sowie verfahren zur herstellung davon

Info

Publication number
EP3215565A1
EP3215565A1 EP15857881.5A EP15857881A EP3215565A1 EP 3215565 A1 EP3215565 A1 EP 3215565A1 EP 15857881 A EP15857881 A EP 15857881A EP 3215565 A1 EP3215565 A1 EP 3215565A1
Authority
EP
European Patent Office
Prior art keywords
mol
random copolymer
polymer
crosslinking agent
unit
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.)
Withdrawn
Application number
EP15857881.5A
Other languages
English (en)
French (fr)
Other versions
EP3215565A4 (de
Inventor
Jean-Christophe Daigle
Serge VERREAULT
Nancy Turcotte
Julie HÂMEL-PAQUET
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-Québec
Original Assignee
Hydro-Québec
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
Priority claimed from CA2870076A external-priority patent/CA2870076A1/fr
Priority claimed from CA2886173A external-priority patent/CA2886173A1/fr
Application filed by Hydro-Québec filed Critical Hydro-Québec
Publication of EP3215565A1 publication Critical patent/EP3215565A1/de
Publication of EP3215565A4 publication Critical patent/EP3215565A4/de
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/16—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings other than six-membered aromatic rings
    • C07C211/18—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings other than six-membered aromatic rings containing at least two amino groups bound to the 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
    • C08F20/00—Homopolymers and copolymers 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
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/12—Esters of monohydric alcohols or phenols
    • C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • 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
    • C08F220/00—Copolymers 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
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C08F220/285—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety
    • C08F220/286—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety and containing polyethylene oxide in the alcohol moiety, e.g. methoxy polyethylene glycol (meth)acrylate
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular 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
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/062—Polyethers
    • 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
    • C08F6/00—Post-polymerisation treatments
    • C08F6/26—Treatment of polymers prepared in bulk also solid polymers or polymer melts
    • C08F6/28—Purification
    • 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
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
    • C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C08G81/024—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G
    • C08G81/025—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G containing polyether sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L55/00—Compositions of homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C08L23/00 - C08L53/00
    • C08L55/005—Homopolymers or copolymers obtained by polymerisation of macromolecular compounds terminated by a carbon-to-carbon double bond
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564—Accumulators 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
    • H01M10/0565—Polymeric materials, e.g. gel-type or solid-type
    • 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
    • C08F220/00—Copolymers 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
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
    • C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
    • 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
    • C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
    • C08F2500/01—High molecular weight, e.g. >800,000 Da.
    • 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
    • C08F2810/20—Chemical modification of a polymer leading to a crosslinking, either explicitly or inherently
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2333/00—Characterised by the use of homopolymers or copolymers 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • C08J2333/04—Characterised by the use of homopolymers or copolymers 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
    • C08J2333/14—Characterised by the use of homopolymers or copolymers 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/052—Li-accumulators
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M2300/00—Electrolytes
    • H01M2300/0085—Immobilising or gelification of electrolyte
    • Y—GENERAL 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10—Energy storage using batteries

Definitions

  • the application relates to the field of polymers and their use in electrochemical applications. More particularly, the technology relates to the field of crosslinked random copolymers.
  • the random copolymer of Formula I or II may be previously formed by the copolymerization of Monomers A and B according to:
  • step (a) includes the addition of a solvent (other than the crosslinking agent)
  • the process may comprise a step of removing this solvent before step (b), which can be carried out by heating at atmospheric pressure, for example, at a temperature between 50 and 100 ° C, preferably between 60 ° C and 90 ° C.
  • the solvent is selected from lower alcohols (such as methanol, ethanol, isopropanol and / or n-propanol), water, and mixtures thereof, preferably a solvent comprising a lower alcohol such as ethanol.
  • Figure 1 shows the reaction profile between the PEGMA-GMA copolymer (39 mol% GMA, 61 mol% PEGMA, molar mass 320,000 g / mol) and the crosslinking agent by DSC.
  • R 1 is a methyl group and R 2 is a hydrogen atom at each occurrence. In another example, R 1 and R 2 are each a methyl group at each occurrence.
  • the random copolymer is of Formula II, defined as follows:
  • the number-average molecular weight of the random copolymer can range from 280,000 to 360,000 g / mol and the unit A represents about 39% by mole of the copolymer composition.
  • the random copolymer of Formula I or II is, for example, previously formed by random copolymerization of the following monomers A and B:
  • the crosslinking agent added to the random copolymer of Formula I or II is a volatile alkyl polyamine compound, for example comprising from 1 to 3 carbon (s), preferably 1 or 2 carbon (s), and at least two amino groups, crosslinking agent preferably having a boiling point of less than 150 ° C.
  • crosslinking agents include ethylene diamine, 1,3-diaminopropane, 1,2-diaminopropane or mixtures thereof, preferably the crosslinking agent is ethylene diamine.
  • the diamine compounds have 4 protons, thus allowing them to crosslink 4 oxirane functions.
  • Example 3 Capacity of the Crosslinked Polymer
  • a battery incorporating an electrolyte membrane formed of the polymer of Example 2 demonstrates a capacity between 130 and 150 mAh / g at 80 ° C.
  • the cathode of the tested cell comprises carbon-coated LiFePO and a PEO-based polymeric binder.
  • the anode of the battery is a lithium film with a thickness of 45 ⁇ .

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Electrochemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Dispersion Chemistry (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Secondary Cells (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Epoxy Resins (AREA)
  • Conductive Materials (AREA)
EP15857881.5A 2014-11-03 2015-11-03 Vernetztes polymer basierend auf einem random-copolymer und einem flüchtigen polyaminierten vernetzungsmittel sowie verfahren zur herstellung davon Withdrawn EP3215565A4 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CA2870076A CA2870076A1 (fr) 2014-11-03 2014-11-03 Agent reticulant polyamine volatile et son utilisation dans la fabrication de polymeres
CA2886173A CA2886173A1 (fr) 2015-03-24 2015-03-24 Polymere reticule a base d'un copolymere aleatoire et d'un agent reticulant polyamine volatil, et ses procedes de fabrication
PCT/CA2015/051127 WO2016070270A1 (fr) 2014-11-03 2015-11-03 Polymere réticule à base d'un copolymère aléatoire et d'un agent réticulant polyamine volatil, et ses procédés de fabrication

Publications (2)

Publication Number Publication Date
EP3215565A1 true EP3215565A1 (de) 2017-09-13
EP3215565A4 EP3215565A4 (de) 2018-06-13

Family

ID=55908305

Family Applications (1)

Application Number Title Priority Date Filing Date
EP15857881.5A Withdrawn EP3215565A4 (de) 2014-11-03 2015-11-03 Vernetztes polymer basierend auf einem random-copolymer und einem flüchtigen polyaminierten vernetzungsmittel sowie verfahren zur herstellung davon

Country Status (7)

Country Link
US (1) US10745526B2 (de)
EP (1) EP3215565A4 (de)
JP (1) JP6685298B2 (de)
KR (1) KR102370277B1 (de)
CN (1) CN107075226B (de)
CA (1) CA2963500C (de)
WO (1) WO2016070270A1 (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20210049114A (ko) * 2018-08-08 2021-05-04 브라이트볼트, 인크. 재충전가능 리튬 배터리들용 고체 중합체 매트릭스 전해질 (pme), 및 그를 사용하여 제조된 배터리들
CN114824451A (zh) * 2021-01-18 2022-07-29 中国科学院宁波材料技术与工程研究所 一种无机复合固体电解质材料及其制备方法
KR20250175068A (ko) * 2024-06-07 2025-12-16 서울대학교산학협력단 이차전지 분리막 코팅용 조성물, 이를 이용한 이차전지 분리막 및 이차전지

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3412657A1 (de) * 1984-04-04 1985-10-17 Hoechst Ag, 6230 Frankfurt Harzartige polymerisate, ihre herstellung und verwendung zur herstellung von formkoerpern
JPH03238704A (ja) * 1990-02-16 1991-10-24 Toyo Ink Mfg Co Ltd 高分子固体電解質
JPH0629043A (ja) * 1992-07-10 1994-02-04 Fuji Photo Film Co Ltd 二次電池
WO2005014698A1 (en) * 2003-08-08 2005-02-17 Mcmaster University Methods for the preparation of cross-linked polymer networks using coacervation and in situ cross-linking
ATE490986T1 (de) * 2005-01-21 2010-12-15 Nippon Soda Co Polymer, vernetztes polymer, zusammensetzung für ein feststoffpolymer-elektrolyt, feststoffpolymer-elektrolyt und klebstoffzusammensetzung
EP1847556B1 (de) * 2005-01-21 2010-12-08 Nippon Soda Co., Ltd. Polymer, vernetztes polymer, zusammensetzung für ein feststoffpolymer-elektrolyt, feststoffpolymer-elektrolyt und klebstoffzusammensetzung

Also Published As

Publication number Publication date
KR102370277B1 (ko) 2022-03-04
CA2963500A1 (fr) 2016-05-12
US10745526B2 (en) 2020-08-18
CA2963500C (fr) 2023-09-05
EP3215565A4 (de) 2018-06-13
WO2016070270A1 (fr) 2016-05-12
US20170327650A1 (en) 2017-11-16
JP2017533323A (ja) 2017-11-09
CN107075226B (zh) 2019-10-18
KR20170078808A (ko) 2017-07-07
JP6685298B2 (ja) 2020-04-22
CN107075226A (zh) 2017-08-18

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