KR102626996B1 - 에폭시 접착제를 위한 블로킹된 폴리우레탄 강인화제 - Google Patents

에폭시 접착제를 위한 블로킹된 폴리우레탄 강인화제 Download PDF

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KR102626996B1
KR102626996B1 KR1020187008091A KR20187008091A KR102626996B1 KR 102626996 B1 KR102626996 B1 KR 102626996B1 KR 1020187008091 A KR1020187008091 A KR 1020187008091A KR 20187008091 A KR20187008091 A KR 20187008091A KR 102626996 B1 KR102626996 B1 KR 102626996B1
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composition
toughener
pbd
capping group
mixture
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KR20180052645A (ko
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안드레아스 럿츠
다니엘 슈네이덜
세르지오 그런더
빈두 크리쉬난
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다우 글로벌 테크놀로지스 엘엘씨
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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04Polyurethanes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J163/00Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • 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
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/10Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C08G18/12Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
    • 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
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30Low-molecular-weight compounds
    • C08G18/32Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203Polyhydroxy compounds
    • C08G18/3215Polyhydroxy compounds containing aromatic groups or benzoquinone 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
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/48Polyethers
    • C08G18/4854Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
    • 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
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67Unsaturated compounds having active hydrogen
    • C08G18/69Polymers of conjugated dienes
    • C08G18/698Mixtures with compounds of group C08G18/40
    • 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
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72Polyisocyanates or polyisothiocyanates
    • C08G18/80Masked polyisocyanates
    • C08G18/8061Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/8064Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy compounds
    • 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
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72Polyisocyanates or polyisothiocyanates
    • C08G18/80Masked polyisocyanates
    • C08G18/8061Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/8064Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy compounds
    • C08G18/8067Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy compounds phenolic compounds
    • 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
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72Polyisocyanates or polyisothiocyanates
    • C08G18/80Masked polyisocyanates
    • C08G18/8061Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/807Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
    • C08G18/8077Oximes
    • 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
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72Polyisocyanates or polyisothiocyanates
    • C08G18/80Masked polyisocyanates
    • C08G18/8061Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/807Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
    • C08G18/808Monoamines
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02Non-macromolecular additives
    • C09J11/04Non-macromolecular additives inorganic
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02Non-macromolecular additives
    • C09J11/06Non-macromolecular additives organic

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Inorganic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Epoxy Resins (AREA)
KR1020187008091A 2015-09-10 2016-09-06 에폭시 접착제를 위한 블로킹된 폴리우레탄 강인화제 Active KR102626996B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201562216399P 2015-09-10 2015-09-10
US62/216,399 2015-09-10
PCT/US2016/050342 WO2017044402A1 (en) 2015-09-10 2016-09-06 Blocked polyurethane tougheners for epoxy adhesives

Publications (2)

Publication Number Publication Date
KR20180052645A KR20180052645A (ko) 2018-05-18
KR102626996B1 true KR102626996B1 (ko) 2024-01-19

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KR1020187008091A Active KR102626996B1 (ko) 2015-09-10 2016-09-06 에폭시 접착제를 위한 블로킹된 폴리우레탄 강인화제

Country Status (7)

Country Link
US (2) US20180251633A1 (https=)
EP (1) EP3347391B1 (https=)
JP (1) JP2018532820A (https=)
KR (1) KR102626996B1 (https=)
CN (1) CN107922570B (https=)
BR (1) BR112018003350B1 (https=)
WO (1) WO2017044402A1 (https=)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110892033B (zh) * 2017-06-23 2022-04-15 Ddp特种电子材料美国公司 高温环氧粘合剂配制品
EP3655450B1 (en) * 2017-07-21 2022-08-31 Huntsman Advanced Materials Americas LLC Urea terminated butadiene polymers and butadiene acrylonitrile copolymers
US11820922B2 (en) * 2017-10-18 2023-11-21 Ddp Specialty Electronic Materials Us, Llc Adhesive composition
JP7187347B2 (ja) * 2019-02-26 2022-12-12 株式会社カネカ 硬化性エポキシ樹脂組成物、及びそれを用いた積層体
US20220195267A1 (en) * 2019-06-18 2022-06-23 Ddp Specialty Electronic Materials Us, Llc One-component toughened epoxy adhesives with improved humidity resistance
EP4107203A1 (en) * 2020-02-19 2022-12-28 Covestro LLC Flexibilizing capped prepolymers
EP3892659A1 (de) 2020-04-08 2021-10-13 Covestro Deutschland AG Mit aus cashewnuss-schalenöl erhältlichen phenolen blockierte, niedrigviskose isocyanat-prepolymere, verfahren zur deren herstellung und deren verwendung
JPWO2022034877A1 (https=) * 2020-08-12 2022-02-17
KR102297539B1 (ko) * 2020-08-25 2021-09-02 한국화학연구원 에폭시 접착제 조성물을 위한 트리블록 구조의 폴리우레탄 강인화제
JP2024512348A (ja) * 2021-03-05 2024-03-19 ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェン 衝撃耐性、耐応力性、及び溶接性を備えたエポキシ接着剤
WO2022235802A1 (en) 2021-05-05 2022-11-10 Dow Global Technologies Llc Thermal interface materials
KR102705627B1 (ko) * 2022-01-20 2024-09-11 한국화학연구원 비스페놀-z를 이용한 폴리올과 폴리우레탄합성 및 물성연구
CN116854884B (zh) * 2023-07-13 2025-07-25 中路交科科技股份有限公司 一种路桥高韧环氧用增韧剂、制备方法及其使用方法

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1259897A (en) 1985-04-02 1989-09-26 Madan M. Bagga Bonding process using curable epoxide resin adhesive
JP2003064157A (ja) * 2001-08-24 2003-03-05 Sumitomo Bakelite Co Ltd エポキシ樹脂組成物及び半導体装置
CN1823105B (zh) * 2003-06-04 2010-05-05 克拉通聚合物研究有限公司 由氢化的嵌段共聚物制备的制品
US7557169B2 (en) 2003-07-07 2009-07-07 Dow Global Technologies, Inc. Capping isocyanate prepolymer or polyisocyanate/polyether polyol or polyamine mixture
EP2843022B1 (en) 2003-07-07 2020-12-16 Dow Global Technologies LLC Adhesive epoxy composition and process for applying it
EP1498441A1 (de) * 2003-07-16 2005-01-19 Sika Technology AG Hitzehärtende Zusammensetzungen mit Tieftemperatur-Schlagzähigkeitsmodifikatoren
DE602005020260D1 (de) * 2005-06-02 2010-05-12 Dow Global Technologies Inc Schlagzähmodifizierter Strukturklebstoff auf Epoxid Basis
EP1876194A1 (de) * 2006-06-30 2008-01-09 Sika Technology AG Hitzehärtende Zusammensetzung geeignet zum Verkleben von beschichteten Substraten
US7759435B2 (en) * 2006-09-26 2010-07-20 Loctite (R&D) Limited Adducts and curable compositions using same
EP1916270A1 (de) * 2006-10-24 2008-04-30 Sika Technology AG Hitzehärtende Epoxidharzzusammensetzung mit blockiertem Polyurethanprepolymer
EP1916272A1 (de) 2006-10-24 2008-04-30 Sika Technology AG Hitzehärtende Epoxidharzzusammensetzung enthaltend ein blockiertes und ein epoxidterminiertes Polyurethanprepolymer
DE502007002766D1 (de) * 2007-11-14 2010-03-18 Sika Technology Ag Hitzehärtende Epoxidharzzusammensetzung enthaltend nichtaromatische Harnstoffe als Beschleuniger
WO2009094295A1 (en) * 2008-01-22 2009-07-30 Dow Global Technologies Inc. Structural epoxy resin adhesives containing epoxide-functional, polyphenol-extended elastomeric tougheners
ATE484547T1 (de) 2008-01-30 2010-10-15 Sika Technology Ag Auswaschbeständige hitzehärtende epoxidharzklebstoffe
EP2110397A1 (de) 2008-04-16 2009-10-21 Sika Technology AG Auf amphiphilen Block-Copolymer basierendes Polyurethan-Polymer und dessen Verwendung als Schlagzähigkeitsmodifikator
EP2128182A1 (de) 2008-05-28 2009-12-02 Sika Technology AG Hitzehärtende Epoxidharzzusammensetzung enthaltend einen Beschleuniger mit Heteroatomen
EP2655516B1 (en) * 2010-12-26 2018-12-26 Dow Global Technologies LLC Structural epoxy resin adhesives containing chain-extended elastomeric tougheners capped with phenol, polyphenol or aminophenol compounds
MX2015005866A (es) * 2012-11-08 2016-02-05 Basf Se Eteres de diglicidilo de derivados de 2-fenil-1, 3-propandiol y oligomeros de estos como resinas epoxi curables.
WO2014072515A1 (de) * 2012-11-12 2014-05-15 Sika Technology Ag Neue schlagzähigkeitsmodifikatoren für epoxy-basierte klebstoffe

Also Published As

Publication number Publication date
CN107922570B (zh) 2021-11-30
BR112018003350A2 (https=) 2018-10-02
BR112018003350B1 (pt) 2022-06-14
EP3347391A1 (en) 2018-07-18
EP3347391B1 (en) 2020-10-21
WO2017044402A1 (en) 2017-03-16
US20200181404A1 (en) 2020-06-11
KR20180052645A (ko) 2018-05-18
JP2018532820A (ja) 2018-11-08
US20180251633A1 (en) 2018-09-06
CN107922570A (zh) 2018-04-17

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