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WO2022092080A1 - 重合性組成物、硬化物及び硬化物の製造方法 - Google Patents

重合性組成物、硬化物及び硬化物の製造方法 Download PDF

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Publication number
WO2022092080A1
WO2022092080A1 PCT/JP2021/039474 JP2021039474W WO2022092080A1 WO 2022092080 A1 WO2022092080 A1 WO 2022092080A1 JP 2021039474 W JP2021039474 W JP 2021039474W WO 2022092080 A1 WO2022092080 A1 WO 2022092080A1
Authority
WO
WIPO (PCT)
Prior art keywords
polymerizable composition
carbon atoms
ether
group
polymerization initiator
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.)
Ceased
Application number
PCT/JP2021/039474
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English (en)
French (fr)
Japanese (ja)
Inventor
泰延 大野
剛 遠藤
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.)
Adeka Corp
Original Assignee
Adeka Corp
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
Application filed by Adeka Corp filed Critical Adeka Corp
Priority to CN202180045007.3A priority Critical patent/CN115836100B/zh
Priority to JP2022559154A priority patent/JPWO2022092080A1/ja
Priority to KR1020227041626A priority patent/KR20230096917A/ko
Publication of WO2022092080A1 publication Critical patent/WO2022092080A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C08G59/00Polycondensates 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
    • C08G59/18Macromolecules 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
    • C08G59/68Macromolecules 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 catalysts used
    • 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
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/06Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/16Cyclic ethers having four or more ring atoms
    • C08G65/18Oxetanes

Definitions

  • anion [LX b ] m- of the above general formula examples include perchlorate ion (ClO 4- ) , tetrafluoroborate ion (BF 4- ) , hexafluorophosphate ion (PF 6- ) , and hexa.
  • Inorganic ions such as fluoroantimonate (SbF 6- ) , hexafluoroarsenate (AsF 6- ) and hexachloroantimonate (SbCl 6- ); fluorosulphonate ion (FSO 3- ) , toluene sulfonic acid anion, trinitrobenzene Sulfonic acid ions such as sulfonic acid ion, camphor sulfonic acid ion, nonafluorobutane sulfonic acid ion and hexadecafluorooctane sulfonic acid ion; borate ion such as tetraaryl borate ion and tetrakis (pentafluorophenyl) borate ion; methanecarboxylic acid Carbonate ions such as ions, ethane carboxylic acid ion, propane carboxylic acid ion, butane carboxylic acid
  • the hydrocarbon group having 1 to 20 carbon atoms in the general formula (1) may be a group having 1 to 20 carbon atoms including a carbon atom and a hydrogen atom, and is not particularly limited, but carbon.
  • the cycloalkylalkyl group having 4 to 20 carbon atoms means a group having 4 to 20 carbon atoms in which the hydrogen atom of the alkyl group is replaced with a cycloalkyl group.
  • Examples of the aryl group having 6 to 20 carbon atoms include phenyl, trill, xylyl, ethylphenyl, biphenylyl, naphthyl, anthryl and phenanthrenyl, and the hydrogen atom in these groups is the alkyl group and the alkenyl group.
  • Examples thereof include groups substituted with a carboxyl group or a halogen atom, such as 4-chlorophenyl, 4-carboxyphenyl, 4-vinylphenyl, 4-methylphenyl and 2,4,6-trimethylphenyl.
  • Examples of the monovalent anion represented by X1- in the general formula (1) include a monovalent anion among the anions exemplified as the above-mentioned anion [LX b ] m- .
  • R 1 to R 23 compounds having one or more halogen atoms among R 1 to R 23 are preferable because the obtained polymerizable composition has high curability.
  • a compound in which one or more of R 1 to R 10 is a halogen atom, particularly a fluorine atom is preferable.
  • R 3 or R 8 is a halogen atom because the stability of the compound is high and the curability of the obtained polymerizable composition is high, and both R 3 and R 8 are halogen atoms, especially fluorine. It is preferably an atom.
  • one or more of R 15 to R 18 are halogen atoms, especially chlorine atoms.
  • the thermal cationic polymerization initiator used in the polymerizable composition of the present invention is a compound capable of generating a cationic species or Lewis acid by heating, and any compound may be used, but the above-mentioned photocationic polymerization initiator may be used. Compounds classified as are excluded.
  • thermal cation polymerization initiator examples include salts such as sulfonium salt, iodonium salt, diazonium salt, phosphonium salt, selenium salt, oxonium salt, ammonium salt, thiophenium salt, thiolanium salt, benzylammonium salt, pyridinium salt and hydrazinium salt; Iimide sulfonates such as imide sulfonate and phthalimide sulfonate; polyalkyl polyamines such as diethylenetriamine, triethylenetriamine and tetraethylenepentamine; 1,2-diaminocyclohexane, 1,4-diamino-3,6-diethylcyclohexane and Alicyclic polyamines such as isophoronediamine; aromatic polyamines such as m-xylylene diamine, diaminodiphenylmethane and diaminodiphenylsulfone; the polyamines and
  • acyl group having 2 to 10 carbon atoms in the general formula (2) examples include acetyl, propionyl, isopropionyl, butyryl, isobutyryl, benzoyl, chloroacetyl, dichloroacetyl, trichloroacetyl, trifluoroacetyl, methoxyacetyl and acet. Acetyl and the like can be mentioned.
  • Triglycidyl ether of glycerin Triglycidyl ether of glycerin, triglycidyl ether of trimethylolpropane, tetraglycidyl ether of sorbitol, hexaglycidyl ether of dipentaerythritol, diglycidyl ether of polyethylene glycol and diglycidyl ether of polyhydric alcohols such as diglycidyl ether of polypropylene glycol.
  • Polyglycidyl ether of polyether polyol obtained by adding one or more alkylene oxides to aliphatic polyhydric alcohols such as propylene glycol, trimethylol propane and glycerin; diglycidyl ester of aliphatic long chain dibasic acid etc.
  • Epolite M-1230 Epolite EHDG-L, Epolite 40E, Epolite 100E, Epolite 200E, Epolite 400E, Epolite 70P, Epolite 200P, Epolite 400P, Epolite 1500NP, Epolite 1600, Epolite 80MF, Epolite 100MF, Epolite 100MF , Epolite 3002, Epolite FR-1500 (above, manufactured by Kyoeisha Chemical Co., Ltd.), Santoto ST0000, YD-716, YH-300, PG-202, PG-207, YD-172, YDPN638 (above, manufactured by Nippon Steel Chemical
  • oxetane compound Commercially available products that can be suitably used as the oxetane compound include Aron Oxetane OXT-101, OXT-121, OXT-221, OXT-212, OXT-221 (all manufactured by Toagosei Corporation), Ethanacole EHO, OXBP, and OXTP.
  • OXMA above, manufactured by Ube Kosan Co., Ltd.
  • the content of the oxetane compound is not particularly limited, but is preferably 5 to 90 parts by mass, more preferably 20 to 80 parts by mass, and 30 to 70 parts by mass with respect to 100 parts by mass of the cationically polymerizable compound. Part is particularly preferable.
  • the content of the cationic compound is within the above range, the obtained polymerizable composition is preferable because it has excellent curability.
  • Cyclic lactone compounds such as ⁇ -caprolactone; Thiylan compounds such as ethylene sulfide and thioepicrolhydrin; Thietan compounds such as 1,3-propine sulfide and 3,3-dimethylthietan; Cyclic thioether compounds such as tetrahydrothiophene derivatives; Ethylene Vinyl ether compounds such as glycol divinyl ether, alkyl vinyl ether, 2-chloroethyl vinyl ether, 2-hydroxyethyl vinyl ether, triethylene glycol divinyl ether, 1,4-cyclohexanedimethanol divinyl ether, hydroxybutyl vinyl ether and propenyl ether of propylene glycol; epoxy.
  • Thiylan compounds such as ethylene sulfide and thioepicrolhydrin
  • Thietan compounds such as 1,3-propine sulfide and 3,3-dimethylthietan
  • Cyclic thioether compounds
  • Flame-retardant agents such as melamine phosphate and (poly) piperazine phosphate; hydrocarbon-based, fatty acid-based, aliphatic alcohol-based, aliphatic ester-based, aliphatic amide-based and metal soap-based lubricants; pigments and carbon black, etc.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Resins (AREA)
  • Polyethers (AREA)
  • Polymerisation Methods In General (AREA)
PCT/JP2021/039474 2020-10-30 2021-10-26 重合性組成物、硬化物及び硬化物の製造方法 Ceased WO2022092080A1 (ja)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN202180045007.3A CN115836100B (zh) 2020-10-30 2021-10-26 聚合性组合物、固化物及固化物的制造方法
JP2022559154A JPWO2022092080A1 (zh) 2020-10-30 2021-10-26
KR1020227041626A KR20230096917A (ko) 2020-10-30 2021-10-26 중합성 조성물, 경화물 및 경화물의 제조 방법

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2020182240 2020-10-30
JP2020-182240 2020-10-30

Publications (1)

Publication Number Publication Date
WO2022092080A1 true WO2022092080A1 (ja) 2022-05-05

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PCT/JP2021/039474 Ceased WO2022092080A1 (ja) 2020-10-30 2021-10-26 重合性組成物、硬化物及び硬化物の製造方法

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JP (1) JPWO2022092080A1 (zh)
KR (1) KR20230096917A (zh)
CN (1) CN115836100B (zh)
WO (1) WO2022092080A1 (zh)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2025142521A1 (ja) * 2023-12-27 2025-07-03 日産化学株式会社 カチオン硬化性組成物
JP2025521614A (ja) * 2022-06-29 2025-07-10 レイセオン カンパニー 直接書き込み二重硬化ガスケット

Citations (9)

* Cited by examiner, † Cited by third party
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WO2006085421A1 (ja) * 2005-02-08 2006-08-17 The Yokohama Rubber Co., Ltd. オキセタン化合物およびそれを含む硬化性組成物
JP2006225545A (ja) * 2005-02-18 2006-08-31 Yokohama Rubber Co Ltd:The 硬化性樹脂組成物
JP2009019077A (ja) * 2007-07-10 2009-01-29 Kyocera Chemical Corp 硬化性組成物、表示素子用接着剤及び接着方法
JP2011080044A (ja) * 2009-09-09 2011-04-21 Kyoritsu Kagaku Sangyo Kk 柔軟性にすぐれたカチオン硬化性樹脂組成物
JP2014125507A (ja) * 2012-12-25 2014-07-07 Adeka Corp 光硬化性組成物
WO2018051940A1 (ja) * 2016-09-16 2018-03-22 株式会社Adeka 硬化性組成物及び硬化物
WO2018110297A1 (ja) * 2016-12-12 2018-06-21 株式会社Adeka 組成物
JP2019019286A (ja) * 2017-07-21 2019-02-07 住友電気工業株式会社 接着剤組成物及び光半導体デバイス
WO2019043778A1 (ja) * 2017-08-29 2019-03-07 三菱重工業株式会社 硬化性組成物、硬化性ペースト材、硬化性シート材、硬化性型取り材、硬化方法および硬化物

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CN102471255B (zh) * 2009-10-26 2015-06-03 株式会社艾迪科 芳香族锍盐化合物
JP6367668B2 (ja) * 2014-09-27 2018-08-01 アイカ工業株式会社 熱カチオン硬化性樹脂組成物
KR102696790B1 (ko) * 2015-12-02 2024-08-20 가부시끼가이샤 쓰리본드 양이온 경화성 수지 조성물
KR101900544B1 (ko) * 2015-12-07 2018-09-19 삼성에스디아이 주식회사 이방 도전성 필름용 조성물, 이방 도전성 필름 및 이를 이용한 접속 구조체
CN118325041A (zh) * 2016-06-21 2024-07-12 株式会社Adeka 固化性组合物、固化物的制造方法、及其固化物
CN110114376B (zh) * 2017-03-31 2022-06-14 株式会社Adeka 固化性组合物、固化物的制造方法、其固化物、及使用其的粘接剂
JP2019073574A (ja) 2017-10-12 2019-05-16 住友電気工業株式会社 接着剤組成物及び光半導体デバイス
JP2019183133A (ja) * 2018-04-16 2019-10-24 キヤノン株式会社 硬化性樹脂組成物およびそれを用いた立体物の製造方法
JP7366900B2 (ja) * 2018-07-27 2023-10-23 株式会社Adeka 組成物、硬化物、光学フィルタ及び硬化物の製造方法

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006085421A1 (ja) * 2005-02-08 2006-08-17 The Yokohama Rubber Co., Ltd. オキセタン化合物およびそれを含む硬化性組成物
JP2006225545A (ja) * 2005-02-18 2006-08-31 Yokohama Rubber Co Ltd:The 硬化性樹脂組成物
JP2009019077A (ja) * 2007-07-10 2009-01-29 Kyocera Chemical Corp 硬化性組成物、表示素子用接着剤及び接着方法
JP2011080044A (ja) * 2009-09-09 2011-04-21 Kyoritsu Kagaku Sangyo Kk 柔軟性にすぐれたカチオン硬化性樹脂組成物
JP2014125507A (ja) * 2012-12-25 2014-07-07 Adeka Corp 光硬化性組成物
WO2018051940A1 (ja) * 2016-09-16 2018-03-22 株式会社Adeka 硬化性組成物及び硬化物
WO2018110297A1 (ja) * 2016-12-12 2018-06-21 株式会社Adeka 組成物
JP2019019286A (ja) * 2017-07-21 2019-02-07 住友電気工業株式会社 接着剤組成物及び光半導体デバイス
WO2019043778A1 (ja) * 2017-08-29 2019-03-07 三菱重工業株式会社 硬化性組成物、硬化性ペースト材、硬化性シート材、硬化性型取り材、硬化方法および硬化物

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2025521614A (ja) * 2022-06-29 2025-07-10 レイセオン カンパニー 直接書き込み二重硬化ガスケット
WO2025142521A1 (ja) * 2023-12-27 2025-07-03 日産化学株式会社 カチオン硬化性組成物

Also Published As

Publication number Publication date
CN115836100B (zh) 2024-12-17
JPWO2022092080A1 (zh) 2022-05-05
KR20230096917A (ko) 2023-06-30
TW202223052A (zh) 2022-06-16
CN115836100A (zh) 2023-03-21

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