WO2015123552A1 - Matériaux composites et polymères de soufre à partir de soufre élémentaire - Google Patents

Matériaux composites et polymères de soufre à partir de soufre élémentaire Download PDF

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Publication number
WO2015123552A1
WO2015123552A1 PCT/US2015/015870 US2015015870W WO2015123552A1 WO 2015123552 A1 WO2015123552 A1 WO 2015123552A1 US 2015015870 W US2015015870 W US 2015015870W WO 2015123552 A1 WO2015123552 A1 WO 2015123552A1
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Prior art keywords
monomers
sulfur
copolymer
level
monomer
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PCT/US2015/015870
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English (en)
Inventor
Dong-Chul Pyun
Richard S. Glass
M. Bonner Denton
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The Arizona Board Of Regents On Behalf Of The University Of Arizona
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Priority to JP2016569566A priority Critical patent/JP2017517603A/ja
Priority to EP15748519.4A priority patent/EP3105280A4/fr
Priority to KR1020167025616A priority patent/KR20160122838A/ko
Publication of WO2015123552A1 publication Critical patent/WO2015123552A1/fr

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    • 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
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/30—Polysulfonamides; Polysulfonimides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
    • C08G59/302—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen containing sulfur
    • 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
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
    • 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
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
    • C08G69/32—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from aromatic diamines and aromatic dicarboxylic acids with both amino and carboxylic groups aromatically bound
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/02—Polyamines
    • C08G73/0246—Polyamines containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
    • C08G73/0253—Polyamines containing sulfur in the main chain
    • 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
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/14—Polysulfides
    • 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
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/20—Polysulfones
    • C08G75/205—Copolymers of sulfur dioxide with unsaturated organic compounds
    • C08G75/22—Copolymers of sulfur dioxide with unsaturated aliphatic compounds
    • 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
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/20—Polysulfones
    • C08G75/23—Polyethersulfones
    • 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
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
    • 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
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • 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
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/20—Manufacture of shaped structures of ion-exchange resins
    • 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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/02—Electrodes composed of, or comprising, active material
    • H01M4/13—Electrodes for accumulators with non-aqueous electrolyte, e.g. for lithium-accumulators; Processes of manufacture thereof
    • H01M4/139—Processes of manufacture
    • H01M4/1399—Processes of manufacture of electrodes based on electro-active polymers
    • 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
    • H01M4/00—Electrodes
    • H01M4/02—Electrodes composed of, or comprising, active material
    • H01M4/13—Electrodes for accumulators with non-aqueous electrolyte, e.g. for lithium-accumulators; Processes of manufacture thereof
    • H01M4/137—Electrodes based on electro-active polymers
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/02—Electrodes composed of, or comprising, active material
    • H01M4/36—Selection of substances as active materials, active masses, active liquids
    • H01M4/38—Selection of substances as active materials, active masses, active liquids of elements or alloys
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/02—Electrodes composed of, or comprising, active material
    • H01M4/36—Selection of substances as active materials, active masses, active liquids
    • H01M4/60—Selection of substances as active materials, active masses, active liquids of organic compounds
    • H01M4/602—Polymers
    • 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

  • FIG. 2 shows lab samples of an elemental sulfur powder, a molten liquid sulfur, and a polymerized sulfur.
  • FIG. 14 shows data from a cycling experiment (C/5) comparing sulfur copolymers and sulfur composite materials as cathodes for electrochemical ceils.
  • FIG. 33 shows typical materials for infrared thermal imaging lens.
  • the copolymer material is a thermoset. In some embodiments, the copolymer material is a thermoplastic. In some embodiments, the copolymer material is self-healing. In some embodiments, when one or more S-S bonds of the sulfur copolymer are broken, the S-S bonds are reconnected by thermal reforming.
  • each B includes the polymerizabie moiety and a 1 -8 atom long linker.
  • Each linker is selected from a group consisting of an alkylene linker and a mono, di- or tri(ethyiene glycol) linker.
  • each B includes an ethyienically unsaturated moiety, an epoxide moiety, a thiirane moiety, or one or more carboxylic anhydrides.

Abstract

La présente invention concerne des matériaux composites et polymères de soufre présentant une teneur élevée en soufre et préparés à partir de soufre élémentaire utilisé comme charge d'alimentation chimique primaire. Les copolymères de soufre sont préparés par polymérisation de soufre élémentaire avec un ou plusieurs monomères amines, thiols, sulfures, monomères alkynyliquement insaturés, nitrones, aldéhydes, cétones, thiiranes, monomères ethyléniquement insaturés, ou époxydes. Les copolymères de soufre peuvent en outre être dispersés avec des composites de métaux ou de céramiques, ou copolymérisés avec du carbone élémentaire, des chromophores organiques photoactifs, ou des fractions réactives et solubilisantes / biocompatibles. Les matériaux composites et polymères de soufre présentent la capacité d'auto-cicatrisation par le biais d'un reformage thermique. Des applications utilisant les matériaux composites et polymères de soufre peuvent comprendre des cellules électrochimiques, des systèmes optiques, des donneurs de H2S et des matériaux antimicrobiens.
PCT/US2015/015870 2014-02-14 2015-02-13 Matériaux composites et polymères de soufre à partir de soufre élémentaire WO2015123552A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2016569566A JP2017517603A (ja) 2014-02-14 2015-02-13 元素状硫黄に由来する硫黄複合材及び重合体材料
EP15748519.4A EP3105280A4 (fr) 2014-02-14 2015-02-13 Matériaux composites et polymères de soufre à partir de soufre élémentaire
KR1020167025616A KR20160122838A (ko) 2014-02-14 2015-02-13 원소 황에서 유래된 황 복합체 및 폴리머 재료

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
US201461940102P 2014-02-14 2014-02-14
US61/940,102 2014-02-14
US201462017750P 2014-06-26 2014-06-26
US62/017,750 2014-06-26
US201462039588P 2014-08-20 2014-08-20
US201462039561P 2014-08-20 2014-08-20
US62/039,561 2014-08-20
US62/039,588 2014-08-20

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WO2015123552A1 true WO2015123552A1 (fr) 2015-08-20

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PCT/US2015/015870 WO2015123552A1 (fr) 2014-02-14 2015-02-13 Matériaux composites et polymères de soufre à partir de soufre élémentaire

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EP (1) EP3105280A4 (fr)
JP (1) JP2017517603A (fr)
KR (1) KR20160122838A (fr)
WO (1) WO2015123552A1 (fr)

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CN108079975A (zh) * 2015-12-18 2018-05-29 宁波高新区夏远科技有限公司 一种空气净化器用复合光触媒滤网材料
WO2018109150A1 (fr) * 2016-12-16 2018-06-21 Universität Osnabrück Matériau d'électrode, procédé de fabrication d'électrodes, lesdites électrodes, ainsi que cellules électrochimiques
CN110040718A (zh) * 2019-04-03 2019-07-23 温州大学 一种硫杂杯芳烃基16核分子簇衍生的多壁碳纳米管的制备方法
CN110582873A (zh) * 2017-05-03 2019-12-17 雷普索尔有限公司 作为电池活性材料的硫族物聚合物-碳复合物
CN110752371A (zh) * 2019-10-31 2020-02-04 哈尔滨工业大学 一种具有自修复功能的锂硫电池正极活性材料及其制备方法
CN110957495A (zh) * 2019-12-19 2020-04-03 南昌大学 一种3D碳纳米球氧还原催化剂HFeSNC的制备方法
US10833330B1 (en) 2011-08-11 2020-11-10 Arizona Board Of Regents On Behalf Of The University Of Arizona Sulfur composites and polymeric materials from elemental sulfur
US10894863B2 (en) 2014-02-14 2021-01-19 Arizona Board Of Regents On Behalf Of The University Of Arizona Cathode materials for Li—S batteries
US10920020B2 (en) 2011-08-11 2021-02-16 Arizona Board Of Regents On Behalf Of The University Of Arizona 3D-printing of ultra-high refractive index polymers
CN112424262A (zh) * 2018-05-11 2021-02-26 艾尼股份公司 具有高硫含量的弹性体三元共聚物及其制备方法
US11015023B2 (en) 2011-08-11 2021-05-25 Arizona Board Of Regents On Behalf Of The University Of Arizona Fire retardant compositions utilizing elemental sulfur
CN113174615A (zh) * 2021-04-30 2021-07-27 中南大学 一种铝电解惰性阳极用金属陶瓷材料及其制备方法
US11078333B2 (en) 2015-07-13 2021-08-03 Arizona Board Of Regents On Behalf Of The University Of Arizona Copolymerization of elemental sulfur to synthesize high sulfur content polymeric materials
WO2022023650A1 (fr) 2020-07-30 2022-02-03 Saint-Gobain Glass France Vitrage de vehicule avec insert et dispositif a camera thermique associe
CN115819768A (zh) * 2023-02-23 2023-03-21 广东工业大学 一种可逆粘合聚多硫化物及其制备方法
US11649548B2 (en) 2016-12-09 2023-05-16 Arizona Board Of Regents On Behalf Of The University Of Arizona Metallopolymers for catalytic generation of hydrogen
CN116162198A (zh) * 2023-03-02 2023-05-26 浦诺菲新材料有限公司 一种自修复氟涂层涂布液的制备方法，以及一种汽车漆面保护膜
US11674005B2 (en) 2017-06-15 2023-06-13 Arizona Board Of Regents On Behalf Of The University Of Arizona Chalcogenide Hybrid Inorganic/organic Polymer (CHIP) materials as improved crosslinking agents for vulcanization
US11795248B2 (en) 2011-08-11 2023-10-24 Arizona Board Of Regents On Behalf Of The University Of Arizona Copolymerization of elemental sulfur and epoxy functional styrenics

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KR102114145B1 (ko) * 2017-02-22 2020-05-22 (주)엘지하우시스 황 함유 고분자 및 황 함유 고분자의 제조방법
CN108872169B (zh) * 2018-05-07 2021-02-05 广西大学 定量测定植物根表皮组织中混合组分CdS/ZnS量子点的方法
EP3824015A1 (fr) * 2018-07-19 2021-05-26 Shell Internationale Research Maatschappij B.V. Procédé de préparation de polymères d'organosilane contenant du soufre
KR102244915B1 (ko) * 2018-09-12 2021-04-26 주식회사 엘지화학 황-탄소 복합체, 이의 제조방법 및 이를 포함하는 리튬 이차전지
KR102094844B1 (ko) * 2018-09-18 2020-04-23 인하대학교 산학협력단 신규 황 고분자 및 그의 용도
KR102013530B1 (ko) * 2018-10-23 2019-08-23 재단법인 하이브리드 인터페이스기반 미래소재 연구단 염료―흑연 리튬이온 배터리용 음극재 및 그 제조방법
KR102306923B1 (ko) * 2020-02-05 2021-09-29 한국화학연구원 초음파를 이용한 상온 재가공 가능한 황 함유 가교 고분자의 제조방법
KR102595613B1 (ko) * 2020-11-13 2023-10-30 한국화학연구원 촉매적 역가황 중합법을 이용한 황 함유 가교 고분자의 제조방법 및 이의 제조방법으로 제조된 황 함유 가교 고분자
KR102625325B1 (ko) * 2021-08-11 2024-01-16 한국생산기술연구원 자가치유 가능한 에폭시접착제

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