EP3215565A1 - Polymere réticule à base d'un copolymère aléatoire et d'un agent réticulant polyamine volatil, et ses procédés de fabrication - Google Patents
Polymere réticule à base d'un copolymère aléatoire et d'un agent réticulant polyamine volatil, et ses procédés de fabricationInfo
- 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.)
- Pending
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
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- 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
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- 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)
- Compositions Of Macromolecular Compounds (AREA)
- Secondary Cells (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Epoxy Resins (AREA)
- Conductive Materials (AREA)
Abstract
Description
Claims
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 (fr) | 2017-09-13 |
EP3215565A4 EP3215565A4 (fr) | 2018-06-13 |
Family
ID=55908305
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP15857881.5A Pending EP3215565A4 (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 |
Country Status (7)
Country | Link |
---|---|
US (1) | US10745526B2 (fr) |
EP (1) | EP3215565A4 (fr) |
JP (1) | JP6685298B2 (fr) |
KR (1) | KR102370277B1 (fr) |
CN (1) | CN107075226B (fr) |
CA (1) | CA2963500C (fr) |
WO (1) | WO2016070270A1 (fr) |
Families Citing this family (1)
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 |
Family Cites Families (6)
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 (fr) * | 2003-08-08 | 2005-02-17 | Mcmaster University | Procedes de preparation de reseaux polymeriques reticules par coacervation et reticulation in situ |
JP4685037B2 (ja) * | 2005-01-21 | 2011-05-18 | 日本曹達株式会社 | 高分子、架橋高分子、高分子固体電解質用組成物、高分子固体電解質及び接着性組成物 |
US7645830B2 (en) * | 2005-01-21 | 2010-01-12 | Nippon Soda Co., Ltd. | Polymer, crosslinked polymer, composition for solid polymer electrolyte, solid polymer electrolyte, and adhesive composition |
-
2015
- 2015-11-03 WO PCT/CA2015/051127 patent/WO2016070270A1/fr active Application Filing
- 2015-11-03 CN CN201580059456.8A patent/CN107075226B/zh active Active
- 2015-11-03 KR KR1020177014986A patent/KR102370277B1/ko active IP Right Grant
- 2015-11-03 CA CA2963500A patent/CA2963500C/fr active Active
- 2015-11-03 EP EP15857881.5A patent/EP3215565A4/fr active Pending
- 2015-11-03 US US15/523,875 patent/US10745526B2/en active Active
- 2015-11-03 JP JP2017523470A patent/JP6685298B2/ja active Active
Also Published As
Publication number | Publication date |
---|---|
JP6685298B2 (ja) | 2020-04-22 |
US20170327650A1 (en) | 2017-11-16 |
KR102370277B1 (ko) | 2022-03-04 |
EP3215565A4 (fr) | 2018-06-13 |
CN107075226A (zh) | 2017-08-18 |
CA2963500A1 (fr) | 2016-05-12 |
KR20170078808A (ko) | 2017-07-07 |
US10745526B2 (en) | 2020-08-18 |
CA2963500C (fr) | 2023-09-05 |
CN107075226B (zh) | 2019-10-18 |
WO2016070270A1 (fr) | 2016-05-12 |
JP2017533323A (ja) | 2017-11-09 |
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