Title:
GLYCIDYL ETHER GROUP-CONTAINING COMPOUND, CURABLE RESIN COMPOSITION, CURED OBJECT, AND LAMINATE
Document Type and Number:
WIPO Patent Application WO/2023/223924
Kind Code:
A1
Abstract:
Provided is a compound that, although a curable resin, is able to to easily achieve repairability and reformability in a cured object. Also provided is a curable resin composition using the same, and a cured object thereof. The present invention uses a glycidyl ether group-containing compound that is a hydroxy group-containing compound obtained as a result of a structural unit A having at least one glycidyl ether group and a structural unit B different from the structural unit A being connected in A-B-A, and is characterized in that the structural unit A and the structural unit B are bonded by reversible bonds having a dissociation temperature of at least 120°C. The reversible bonds are preferably an adduct structure formed by an anthracene Diels-Alder reaction and a disulfide bond interposed between aromatic rings.
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Inventors:
SUZUKI ETSUKO (JP)
ASANO YUU (JP)
OTSU MASATO (JP)
ARITA KAZUO (JP)
ASANO YUU (JP)
OTSU MASATO (JP)
ARITA KAZUO (JP)
Application Number:
PCT/JP2023/017675
Publication Date:
November 23, 2023
Filing Date:
May 11, 2023
Export Citation:
Assignee:
DAINIPPON INK & CHEMICALS (JP)
International Classes:
C07D303/34; C07D405/14; C08G59/02
Domestic Patent References:
| WO2023038044A1 | 2023-03-16 |
Foreign References:
| CN108641065A | 2018-10-12 | |||
| CN112979925A | 2021-06-18 | |||
| US6211389B1 | 2001-04-03 | |||
| FR1541474A | 1968-10-04 | |||
| US3350423A | 1967-10-31 |
Other References:
FURUTANI MASAHIRO, KAKINUMA AYARU, ARIMITSU KOJI: "A dismantlable photoadhesion system fabricated by an anionic UV curing of epoxy resins with a base amplifier having a disulfide bond", JOURNAL OF POLYMER SCIENCE PART A: POLYMER CHEMISTRY, JOHN WILEY & SONS, INC., US, vol. 56, no. 2, 15 January 2018 (2018-01-15), US , pages 237 - 241, XP093110411, ISSN: 0887-624X, DOI: 10.1002/pola.28898
ZHOU FENGTAO; GUO ZIJIAN; WANG WENYAN; LEI XINGFENG; ZHANG BAOLIANG; ZHANG HEPENG; ZHANG QIUYU: "Preparation of self-healing, recyclable epoxy resins and low-electrical resistance composites based on double-disulfide bond exchange", COMPOSITES SCIENCE AND TECHNOLOGY, ELSEVIER, AMSTERDAM, NL, vol. 167, 29 July 2018 (2018-07-29), AMSTERDAM, NL , pages 79 - 85, XP085504686, ISSN: 0266-3538, DOI: 10.1016/j.compscitech.2018.07.041
HAFEEZULLAH MEMON, YI WEI: "Welding and reprocessing of disulfide-containingthermoset epoxy resin exhibiting behavior reminiscentof a thermoplastic", JOURNAL OF APPLIED POLYMER SCIENCE, JOHN WILEY & SONS, INC., US, vol. 137, no. 47, 15 December 2020 (2020-12-15), US , pages e49541(1 - 10), XP009550578, ISSN: 0021-8995, DOI: 10.1002/app.49541
SI HONGWEI, ZHOU LIN, WU YEPING, SONG LIXIAN, KANG MING, ZHAO XIULI, CHEN MAO: "Rapidly reprocessable, degradable epoxy vitrimer and recyclable carbon fiber reinforced thermoset composites relied on high contents of exchangeable aromatic disulfide crosslinks", COMPOSITES PART B, ELSEVIER, AMSTERDAM, NL, vol. 199, 1 October 2020 (2020-10-01), AMSTERDAM, NL, pages 108278, XP093110419, ISSN: 1359-8368, DOI: 10.1016/j.compositesb.2020.108278
TAKAHASHI AKIRA; OHISHI TOMOYUKI; GOSEKI RAITA; OTSUKA HIDEYUKI: "Degradable epoxy resins prepared from diepoxide monomer with dynamic covalent disulfide linkage", POLYMER, ELSEVIER, AMSTERDAM, NL, vol. 82, 1 January 1900 (1900-01-01), AMSTERDAM, NL, pages 319 - 326, XP029381328, ISSN: 0032-3861, DOI: 10.1016/j.polymer.2015.11.057
TSAI HSING-YING, NAKAMURA YASUYUKI, FUJITA TAKEHIRO, NAITO MASANOBU: "Strengthening epoxy adhesives at elevated temperatures based on dynamic disulfide bonds", MATERIALS ADVANCES, vol. 1, no. 9, 14 December 2020 (2020-12-14), pages 3182 - 3188, XP093110423, ISSN: 2633-5409, DOI: 10.1039/D0MA00714E
KOSSAKOWSKI JERZY, MIROSLAW PERLINSKI: "Synthesis of new N-substituted cyclic imides with potential anxiolytic activity. XXV. Derivatives of halogenodibenzo[e.h]bicyclo[2.2.2]octane-2.3-dicarboximide", ACTA POLONIAE PHARMACEUTICA - DRUG RESEARCH, POLISH PHARMACEUTICAL SOCIETY, WARZSAW., PL, vol. 60, no. 3, 1 January 2003 (2003-01-01), PL , pages 183 - 189, XP093110430, ISSN: 0001-6837
KOSSAKOWSKI JERZY, KRAWIECKA MARIOLA, PERLIŃSKI MIROSŁAW: "Synthesis of new N-substituted cyclic imides with expected anxiolytic activity. XXI. Derivatives of 1,4-dibromo-dibenzo[e.h]bicyclo[2.2.2]octane-2,3-dicarboximide", ACTA POLONIAE PHARMACEUTICA - DRUG RESEARCH, POLISH PHARMACEUTICAL SOCIETY, WARZSAW., PL, vol. 59, no. 1, 1 January 2002 (2002-01-01), PL , pages 37 - 43, XP009550579, ISSN: 0001-6837
ZHOU FENGTAO; GUO ZIJIAN; WANG WENYAN; LEI XINGFENG; ZHANG BAOLIANG; ZHANG HEPENG; ZHANG QIUYU: "Preparation of self-healing, recyclable epoxy resins and low-electrical resistance composites based on double-disulfide bond exchange", COMPOSITES SCIENCE AND TECHNOLOGY, ELSEVIER, AMSTERDAM, NL, vol. 167, 29 July 2018 (2018-07-29), AMSTERDAM, NL , pages 79 - 85, XP085504686, ISSN: 0266-3538, DOI: 10.1016/j.compscitech.2018.07.041
HAFEEZULLAH MEMON, YI WEI: "Welding and reprocessing of disulfide-containingthermoset epoxy resin exhibiting behavior reminiscentof a thermoplastic", JOURNAL OF APPLIED POLYMER SCIENCE, JOHN WILEY & SONS, INC., US, vol. 137, no. 47, 15 December 2020 (2020-12-15), US , pages e49541(1 - 10), XP009550578, ISSN: 0021-8995, DOI: 10.1002/app.49541
SI HONGWEI, ZHOU LIN, WU YEPING, SONG LIXIAN, KANG MING, ZHAO XIULI, CHEN MAO: "Rapidly reprocessable, degradable epoxy vitrimer and recyclable carbon fiber reinforced thermoset composites relied on high contents of exchangeable aromatic disulfide crosslinks", COMPOSITES PART B, ELSEVIER, AMSTERDAM, NL, vol. 199, 1 October 2020 (2020-10-01), AMSTERDAM, NL, pages 108278, XP093110419, ISSN: 1359-8368, DOI: 10.1016/j.compositesb.2020.108278
TAKAHASHI AKIRA; OHISHI TOMOYUKI; GOSEKI RAITA; OTSUKA HIDEYUKI: "Degradable epoxy resins prepared from diepoxide monomer with dynamic covalent disulfide linkage", POLYMER, ELSEVIER, AMSTERDAM, NL, vol. 82, 1 January 1900 (1900-01-01), AMSTERDAM, NL, pages 319 - 326, XP029381328, ISSN: 0032-3861, DOI: 10.1016/j.polymer.2015.11.057
TSAI HSING-YING, NAKAMURA YASUYUKI, FUJITA TAKEHIRO, NAITO MASANOBU: "Strengthening epoxy adhesives at elevated temperatures based on dynamic disulfide bonds", MATERIALS ADVANCES, vol. 1, no. 9, 14 December 2020 (2020-12-14), pages 3182 - 3188, XP093110423, ISSN: 2633-5409, DOI: 10.1039/D0MA00714E
KOSSAKOWSKI JERZY, MIROSLAW PERLINSKI: "Synthesis of new N-substituted cyclic imides with potential anxiolytic activity. XXV. Derivatives of halogenodibenzo[e.h]bicyclo[2.2.2]octane-2.3-dicarboximide", ACTA POLONIAE PHARMACEUTICA - DRUG RESEARCH, POLISH PHARMACEUTICAL SOCIETY, WARZSAW., PL, vol. 60, no. 3, 1 January 2003 (2003-01-01), PL , pages 183 - 189, XP093110430, ISSN: 0001-6837
KOSSAKOWSKI JERZY, KRAWIECKA MARIOLA, PERLIŃSKI MIROSŁAW: "Synthesis of new N-substituted cyclic imides with expected anxiolytic activity. XXI. Derivatives of 1,4-dibromo-dibenzo[e.h]bicyclo[2.2.2]octane-2,3-dicarboximide", ACTA POLONIAE PHARMACEUTICA - DRUG RESEARCH, POLISH PHARMACEUTICAL SOCIETY, WARZSAW., PL, vol. 59, no. 1, 1 January 2002 (2002-01-01), PL , pages 37 - 43, XP009550579, ISSN: 0001-6837
Attorney, Agent or Firm:
ONO Takayuki (JP)
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