WO2022234776A1 - フェノール樹脂、エポキシ樹脂、硬化性樹脂組成物、硬化物、繊維強化複合材料、及び、繊維強化樹脂成形品 - Google Patents

フェノール樹脂、エポキシ樹脂、硬化性樹脂組成物、硬化物、繊維強化複合材料、及び、繊維強化樹脂成形品 Download PDF

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Publication number
WO2022234776A1
WO2022234776A1 PCT/JP2022/018353 JP2022018353W WO2022234776A1 WO 2022234776 A1 WO2022234776 A1 WO 2022234776A1 JP 2022018353 W JP2022018353 W JP 2022018353W WO 2022234776 A1 WO2022234776 A1 WO 2022234776A1
Authority
WO
WIPO (PCT)
Prior art keywords
resin
epoxy resin
fiber
ortho
represented
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/JP2022/018353
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
真司 恩田
邦裕 森永
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.)
DIC Corp
Original Assignee
DIC Corp
Dainippon Ink and Chemicals Co Ltd
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 DIC Corp, Dainippon Ink and Chemicals Co Ltd filed Critical DIC Corp
Priority to US18/286,285 priority Critical patent/US20240218112A1/en
Priority to JP2022553642A priority patent/JP7188657B1/ja
Priority to EP22798883.9A priority patent/EP4335886A4/en
Priority to JP2022146950A priority patent/JP2022173168A/ja
Publication of WO2022234776A1 publication Critical patent/WO2022234776A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
    • C08J5/0405—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres
    • C08J5/042—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres with carbon fibres
    • 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
    • C08G59/02—Polycondensates containing more than one epoxy group per molecule
    • C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
    • C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
    • 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
    • C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
    • 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
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/02—Fibres or whiskers
    • 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
    • C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
    • C08J2363/04—Epoxynovolacs
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C08L63/04—Epoxynovolacs

Definitions

  • the present invention relates to a fiber-reinforced composite material characterized by containing the curable resin composition and reinforcing fibers.
  • the phenol resin is characterized by being a reaction product of a catechol compound and an ortho-xylylene skeleton-containing compound.
  • the catechol compound is a dihydroxybenzene having hydroxyl groups at the 1- and 2-positions, and the aromatic ring of the catechol compound may have only hydrogen atoms with no substituents, or the hydrogen atoms may be substituted with
  • the group may be a hydrocarbon group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and the substituent may be an alkyl group such as a methyl group or a tert-butyl group. .
  • amide-based compound examples include dicyandiamide, aliphatic dibasic acid, dimer acid, and polyamide resins synthesized from carboxylic acid compounds of fatty acids and amines such as ethylenediamine.
  • curable resin composition Applications for which the curable resin composition is used include printed wiring board materials, resin compositions for flexible wiring boards, interlayer insulating materials for build-up boards, insulating materials for circuit boards such as build-up adhesive films, resin injection Mold materials, adhesives, semiconductor encapsulation materials, semiconductor devices, prepregs, conductive pastes, build-up films, build-up substrates, fiber-reinforced composite materials, molded articles obtained by curing the above composite materials, and the like.
  • printed wiring board materials, insulating materials for circuit boards, and adhesive film applications for build-ups are used for so-called electronic component built-in substrates in which passive components such as capacitors and active components such as IC chips are embedded in the substrate.
  • the curable resin composition is applied on a support film to form a curable resin composition layer for a multilayer printed wiring board A method of manufacturing by using an adhesive film of.
  • the present invention relates to a fiber-reinforced composite material containing the curable resin composition and reinforcing fibers.
  • a method for producing a fiber-reinforced composite material from the curable resin composition each component constituting the curable resin composition is uniformly mixed to prepare a varnish, which is then applied to a reinforcing base material made of reinforcing fibers. It can be produced by polymerizing after impregnation.
  • the epoxy resin of the present invention has a low melt viscosity and is excellent in handleability, so it is suitable for the production of the fiber-reinforced composite material and is preferable.
  • phenol resin (a-1) had a hydroxyl equivalent weight of 87 g/equivalent, a softening point of 76°C, and a melt viscosity of 1.2 dPa ⁇ s at 150°C.
  • the GPC area % of the dimer was 62 area % and the residual catechol was 0.8 area %.
  • a GPC chart is shown in FIG.
  • Examples 5 and 6 use the epoxy resins of Examples 3 and 4 obtained by using the desired phenolic resins of Examples 1 and 2, and thus have high heat resistance. A cured product with high bending properties was obtained.
  • Comparative Example 5 an epoxy resin using a phenolic resin using a compound containing a para-xylylene skeleton instead of an ortho-xylylene skeleton was used. rice field.
  • Comparative Example 6 the epoxy resin of Comparative Example 3, which does not use the ortho-xylylene skeleton-containing compound itself, was used, so the heat resistance was very poor compared to the Examples. Since the liquid epoxy resin was used, the heat resistance and bending properties were not satisfied, and the results were inferior to those of the examples.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Epoxy Resins (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Reinforced Plastic Materials (AREA)
PCT/JP2022/018353 2021-05-06 2022-04-21 フェノール樹脂、エポキシ樹脂、硬化性樹脂組成物、硬化物、繊維強化複合材料、及び、繊維強化樹脂成形品 Ceased WO2022234776A1 (ja)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US18/286,285 US20240218112A1 (en) 2021-05-06 2022-04-21 Phenolic resin, epoxy resin, curable resin composition, cured product, fiber-reinforced composite material, and fiber-reinforced resin molded product
JP2022553642A JP7188657B1 (ja) 2021-05-06 2022-04-21 エポキシ樹脂、硬化性樹脂組成物、硬化物、繊維強化複合材料、及び、繊維強化樹脂成形品
EP22798883.9A EP4335886A4 (en) 2021-05-06 2022-04-21 Phenolic resin, epoxy resin, curable resin composition, cured article, fiber-reinforced composite material and fiber-reinforced resin molded article
JP2022146950A JP2022173168A (ja) 2021-05-06 2022-09-15 フェノール樹脂、エポキシ樹脂、硬化性樹脂組成物、硬化物、繊維強化複合材料、及び、繊維強化樹脂成形品

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2021078718 2021-05-06
JP2021-078718 2021-05-06

Publications (1)

Publication Number Publication Date
WO2022234776A1 true WO2022234776A1 (ja) 2022-11-10

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ID=83932428

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2022/018353 Ceased WO2022234776A1 (ja) 2021-05-06 2022-04-21 フェノール樹脂、エポキシ樹脂、硬化性樹脂組成物、硬化物、繊維強化複合材料、及び、繊維強化樹脂成形品

Country Status (4)

Country Link
US (1) US20240218112A1 (https=)
EP (1) EP4335886A4 (https=)
JP (2) JP7188657B1 (https=)
WO (1) WO2022234776A1 (https=)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023153160A1 (ja) * 2022-02-14 2023-08-17 Dic株式会社 フェノール樹脂、エポキシ樹脂、硬化性樹脂組成物、硬化物、繊維強化複合材料、及び、繊維強化樹脂成形品

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7103499B1 (ja) * 2021-10-27 2022-07-20 Dic株式会社 フェノール樹脂、エポキシ樹脂、硬化性樹脂組成物、硬化物、繊維強化複合材料、及び、繊維強化樹脂成形品

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002226559A (ja) * 2001-02-06 2002-08-14 Akio Negishi ｐＨ変色性ポリマーとその製造法
JP2003201388A (ja) 2002-01-08 2003-07-18 Toray Ind Inc エポキシ樹脂組成物、樹脂硬化物、プリプレグおよび繊維強化複合材料
WO2007007827A1 (ja) * 2005-07-13 2007-01-18 Ube Industries, Ltd. ビフェニレン架橋フェノールノボラック樹脂ならびにその用途
JP2008189708A (ja) * 2007-02-01 2008-08-21 Ube Ind Ltd 低溶融粘度フェノールノボラック樹脂、その製造方法およびそれを用いたエポキシ樹脂硬化物
JP2016190891A (ja) * 2015-03-30 2016-11-10 新日鉄住金化学株式会社 多価ヒドロキシ樹脂、エポキシ樹脂、それらの製造方法、エポキシ樹脂組成物及びその硬化物

Family Cites Families (2)

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US3378518A (en) * 1959-09-28 1968-04-16 Shell Oil Co Polypropylene stabilizer with durylene bis-phenols
CN101233165B (zh) * 2005-08-31 2011-08-31 宇部兴产株式会社 低软化点线型酚醛清漆树脂及其制造方法以及使用其的环氧树脂固化物

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002226559A (ja) * 2001-02-06 2002-08-14 Akio Negishi ｐＨ変色性ポリマーとその製造法
JP2003201388A (ja) 2002-01-08 2003-07-18 Toray Ind Inc エポキシ樹脂組成物、樹脂硬化物、プリプレグおよび繊維強化複合材料
WO2007007827A1 (ja) * 2005-07-13 2007-01-18 Ube Industries, Ltd. ビフェニレン架橋フェノールノボラック樹脂ならびにその用途
JP2008189708A (ja) * 2007-02-01 2008-08-21 Ube Ind Ltd 低溶融粘度フェノールノボラック樹脂、その製造方法およびそれを用いたエポキシ樹脂硬化物
JP2016190891A (ja) * 2015-03-30 2016-11-10 新日鉄住金化学株式会社 多価ヒドロキシ樹脂、エポキシ樹脂、それらの製造方法、エポキシ樹脂組成物及びその硬化物

Non-Patent Citations (1)

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Title
See also references of EP4335886A4

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023153160A1 (ja) * 2022-02-14 2023-08-17 Dic株式会社 フェノール樹脂、エポキシ樹脂、硬化性樹脂組成物、硬化物、繊維強化複合材料、及び、繊維強化樹脂成形品
JPWO2023153160A1 (https=) * 2022-02-14 2023-08-17
JP7444342B2 (ja) 2022-02-14 2024-03-06 Dic株式会社 フェノール樹脂、エポキシ樹脂、硬化性樹脂組成物、硬化物、繊維強化複合材料、及び、繊維強化樹脂成形品
EP4480984A4 (en) * 2022-02-14 2026-04-01 Dainippon Ink & Chemicals Phenolic resin, epoxy resin, hardenable resin composition, hardened product, fiber-reinforced composite material, and fiber-reinforced resin casting

Also Published As

Publication number Publication date
EP4335886A1 (en) 2024-03-13
JPWO2022234776A1 (https=) 2022-11-10
JP7188657B1 (ja) 2022-12-13
US20240218112A1 (en) 2024-07-04
JP2022173168A (ja) 2022-11-17
EP4335886A4 (en) 2025-04-16

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