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WO2018159674A1 - Composition de résine thermodurcissable, film durci, substrat présentant un film durci, composant électronique et composition d'encre pour jet d'encre - Google Patents

Composition de résine thermodurcissable, film durci, substrat présentant un film durci, composant électronique et composition d'encre pour jet d'encre Download PDF

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Publication number
WO2018159674A1
WO2018159674A1 PCT/JP2018/007498 JP2018007498W WO2018159674A1 WO 2018159674 A1 WO2018159674 A1 WO 2018159674A1 JP 2018007498 W JP2018007498 W JP 2018007498W WO 2018159674 A1 WO2018159674 A1 WO 2018159674A1
Authority
WO
WIPO (PCT)
Prior art keywords
resin composition
thermosetting resin
weight
composition according
cured film
Prior art date
Application number
PCT/JP2018/007498
Other languages
English (en)
Japanese (ja)
Inventor
敏行 高橋
智嗣 古田
信太 諸越
Original Assignee
Jnc株式会社
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 Jnc株式会社 filed Critical Jnc株式会社
Priority to KR1020197027672A priority Critical patent/KR20190121804A/ko
Priority to CN201880015285.2A priority patent/CN110382588A/zh
Priority to JP2019503060A priority patent/JP6996548B2/ja
Publication of WO2018159674A1 publication Critical patent/WO2018159674A1/fr

Links

Classifications

    • 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
    • C08G59/40—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 curing agents used
    • C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
    • B41J2/00—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed
    • B41J2/005—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by bringing liquid or particles selectively into contact with a printing material
    • B41J2/01—Ink jet
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • 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
    • C08G59/40—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 curing agents used
    • 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
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/04—Carbon
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/062—Copolymers with monomers not covered by C08L33/06
    • C08L33/068—Copolymers with monomers not covered by C08L33/06 containing glycidyl groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/22—Secondary treatment of printed circuits
    • H05K3/28—Applying non-metallic protective coatings

Definitions

  • Patent Document 6 proposes a thermosetting black inkjet ink containing an epoxy resin, an oxetane compound, a copolymer having a specific structure, carbon black, a solvent, and the like.
  • the flux resistance and solder resistance when used as a solder resist have not been studied.
  • Tetracarboxylic dianhydride (a1) The tetracarboxylic dianhydride (a1) is not particularly limited, but specific examples include 3,3 ′, 4,4′-benzophenone tetracarboxylic dianhydride, 2,2 ′, 3,3′-benzophenone tetra Carboxylic dianhydride, 2,3,3 ′, 4′-benzophenone tetracarboxylic dianhydride, 3,3 ′, 4,4′-diphenylsulfone tetracarboxylic dianhydride, 2,2 ′, 3 3′-diphenylsulfonetetracarboxylic dianhydride, 2,3,3 ′, 4′-diphenylsulfonetetracarboxylic dianhydride, 3,3 ′, 4,4′-diphenylethertetracarboxylic dianhydride, 2 , 2 ′, 3,3′-diphenyl ether tetracarboxy
  • ethylene glycol, propylene glycol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol and 1,8-octanediol are preferable, and 1,4- Butanediol, 1,5-pentanediol and 1,6-hexanediol are particularly preferable from the viewpoint of good solubility in the reaction solvent (a5).
  • propylene glycol monomethyl ether acetate diethylene glycol methyl ethyl ether, triethylene glycol dimethyl ether, methyl 3-methoxypropionate and N-methyl-2-pyrrolidone are preferable from the viewpoint of solubility.
  • reaction solvent (a5) When the reaction solvent (a5) is used in an amount of 100 parts by weight or more based on 100 parts by weight of the total of the tetracarboxylic dianhydride (a1), the diamine (a2) and the polyvalent hydroxy compound (a3), the reaction proceeds smoothly. Therefore, it is preferable.
  • the content of the polyester amic acid (A) is excellent in the adhesion to the metal and the solid content of the composition according to an embodiment of the present invention (the composition is obtained) from the viewpoint of obtaining a cured film excellent in chemical resistance.
  • the amount obtained by removing the solvent from the product is preferably 1 to 60 parts by weight, more preferably 5 to 55 parts by weight, and still more preferably 10 to 50 parts by weight per 100 parts by weight.
  • the content of the epoxy compound (B) is preferably 10 to 600 parts by weight, more preferably 20 to 500 parts by weight, still more preferably 30 to 400 parts by weight based on 100 parts by weight of the polyester amide acid (A). Parts by weight.
  • the copolymer (C) is obtained, for example, by radical copolymerization of a monomer having oxiranyl or oxetanyl and another monomer.
  • the production method is not particularly limited, the copolymer (C) can be produced by heating the above-mentioned radical polymerizable compounds in the presence of a radical initiator.
  • a radical initiator organic peroxides, azo compounds and the like can be used.
  • the reaction temperature for radical copolymerization is not particularly limited, but is usually in the range of 50 to 150 ° C.
  • the reaction time is not particularly limited, but is usually in the range of 1 to 48 hours.
  • the reaction can be performed under any pressure of increased pressure, reduced pressure, or atmospheric pressure.
  • the content of the solvent (D) is not limited. However, when the composition is supplied onto the substrate by an ink jet method, the jetting property of the composition is improved, so that the content in 100 parts by weight of the composition
  • the content is preferably 45 to 90 parts by weight, and more preferably 50 to 80 parts by weight. Further, from the same viewpoint, it is preferable to adjust the solvent (D) so that the content of the solvent having a boiling point of 200 ° C. or more in 100 parts by weight of all the solvents contained in the composition is 50 parts by weight or more, It is more preferable to adjust the solvent (D) so as to be 55 parts or more.
  • the colorant (E) contained in the composition according to an embodiment of the present invention can obtain a light shielding property so that, for example, an insulating film for protecting a metal wiring can recognize a wiring pattern and an inspection apparatus.
  • the dye and pigment content is preferably 2 parts by weight or more and more preferably 3 parts by weight or more with respect to 100 parts by weight of the resin solid content excluding the solvent, dye and pigment of the composition.
  • the jetting property of the composition is improved, so that the solid content of the resin excluding the solvent, dye and pigment is 100 parts by weight.
  • the dye and pigment content is preferably 15 parts by weight or less, and more preferably 10 parts by weight or less.
  • the epoxy compound (B) and the copolymer (C) 1 equivalent of a compound having one oxiranyl group is used as the epoxy compound (B) and the copolymer (C), and a compound having one acid anhydride group is used as the epoxy curing agent (F).
  • the amount of the epoxy curing agent (F) is 2 times equivalent to the total amount of the epoxy compound (B) and the copolymer (C).
  • dianhydride a1
  • diamine (a2) polyvalent hydroxy compound
  • a3 monohydric alcohol
  • reaction solvent a5
  • polyhydric acid anhydride (a6) and copolymer
  • the names and abbreviations of the monomer (c1), the polymerization initiator (c2) and the reaction solvent (c3) used in are shown below. This abbreviation is used in the following description.
  • thermosetting resin compositions were prepared in the same manner as in Example 1, except that the types and amounts of each component were changed as shown in Tables 3 and 4.
  • thermosetting resin compositions were prepared in the same manner as in Example 1 except that the types and amounts of each component were changed as shown in Table 4.
  • the cured film formed from the ink according to Example 14 had a residual number of grids of 0 after the flux resistance test (second time). Since the ink of Example 14 contains a large amount of colorant, it is considered that the colorant (E) affected the flux resistance of the cured film. In the cured films formed from the inks of Examples 3 and 10, the remaining number of grids in the flux resistance test (second time) and (third time) was 0. Since the inks according to these examples contain the epoxy compound (B) containing 40% by weight of nanosilica, it is considered that nanosilica affected the flux resistance of the cured film.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Epoxy Resins (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

Afin de conférer une bonne adhérence à un substrat, une bonne résistance au flux, une bonne résistance à la soudure et une bonne résistance aux solvants, cette composition de résine thermodurcissable contient un poly(amide ester d'acide) (A), un composé époxy (B) présentant un poids moléculaire moyen en poids inférieur à 10.000 et un copolymère (C) présentant un radical oxiranyle ou oxétanyle et présentant un poids moléculaire moyen en poids de 10.000 ou plus.
PCT/JP2018/007498 2017-03-02 2018-02-28 Composition de résine thermodurcissable, film durci, substrat présentant un film durci, composant électronique et composition d'encre pour jet d'encre WO2018159674A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
KR1020197027672A KR20190121804A (ko) 2017-03-02 2018-02-28 열경화성 수지 조성물, 경화막, 경화막 부착 기판, 전자 부품 및 잉크젯용 잉크 조성물
CN201880015285.2A CN110382588A (zh) 2017-03-02 2018-02-28 热硬化性树脂组合物、硬化膜、带硬化膜基板、电子部件及喷墨用墨水组合物
JP2019503060A JP6996548B2 (ja) 2017-03-02 2018-02-28 インクジェット用インク組成物、硬化膜、硬化膜付き基板および電子部品

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2017039665 2017-03-02
JP2017-039665 2017-03-02

Publications (1)

Publication Number Publication Date
WO2018159674A1 true WO2018159674A1 (fr) 2018-09-07

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PCT/JP2018/007498 WO2018159674A1 (fr) 2017-03-02 2018-02-28 Composition de résine thermodurcissable, film durci, substrat présentant un film durci, composant électronique et composition d'encre pour jet d'encre

Country Status (5)

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JP (1) JP6996548B2 (fr)
KR (1) KR20190121804A (fr)
CN (1) CN110382588A (fr)
TW (1) TW201842064A (fr)
WO (1) WO2018159674A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021157680A1 (fr) * 2020-02-07 2021-08-12 三菱瓦斯化学株式会社 Composition de résine, préimprégné, carte stratifiée, carte stratifiée revêtue de feuille métallique et carte de circuit imprimé

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI747607B (zh) * 2020-11-12 2021-11-21 大陸商宸鴻科技（廈門）有限公司 形成絕緣層的墨水組成物、方法和觸控面板

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996011239A1 (fr) * 1994-10-05 1996-04-18 Goo Chemical Co., Ltd. Encre resist de photosoudure, carte a circuit imprime et procede de fabrication
JP2014169353A (ja) * 2013-03-01 2014-09-18 Jnc Corp 熱硬化性組成物
JP2015081336A (ja) * 2013-10-24 2015-04-27 Jnc株式会社 熱硬化性樹脂組成物
WO2015068703A1 (fr) * 2013-11-05 2015-05-14 太陽インキ製造株式会社 Composition durcissable, film de revêtement durci utilisant celle-ci, et carte de circuit imprimé
JP2015163685A (ja) * 2014-01-28 2015-09-10 Jnc株式会社 熱硬化性組成物及びそれを用いた硬化物

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60188482A (ja) 1984-03-09 1985-09-25 Hitachi Chem Co Ltd スクリーン印刷用レジストインク
JPS61272A (ja) 1984-06-12 1986-01-06 Taiyo Ink Seizo Kk インキ組成物
TWI288142B (en) 2003-05-09 2007-10-11 Taiyo Ink Mfg Co Ltd Photocuring/thermosetting ink jet composition and printed wiring board using same
JP4994923B2 (ja) 2007-04-06 2012-08-08 太陽ホールディングス株式会社 黒色ソルダーレジスト組成物およびその硬化物
JP5488175B2 (ja) 2010-04-28 2014-05-14 Ｊｎｃ株式会社 インクジェット用インク
WO2016129670A1 (fr) 2015-02-12 2016-08-18 積水化学工業株式会社 Composition durcissable pour jet d'encre, et procédé de fabrication d'un composant électronique

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996011239A1 (fr) * 1994-10-05 1996-04-18 Goo Chemical Co., Ltd. Encre resist de photosoudure, carte a circuit imprime et procede de fabrication
JP2014169353A (ja) * 2013-03-01 2014-09-18 Jnc Corp 熱硬化性組成物
JP2015081336A (ja) * 2013-10-24 2015-04-27 Jnc株式会社 熱硬化性樹脂組成物
WO2015068703A1 (fr) * 2013-11-05 2015-05-14 太陽インキ製造株式会社 Composition durcissable, film de revêtement durci utilisant celle-ci, et carte de circuit imprimé
JP2015163685A (ja) * 2014-01-28 2015-09-10 Jnc株式会社 熱硬化性組成物及びそれを用いた硬化物

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021157680A1 (fr) * 2020-02-07 2021-08-12 三菱瓦斯化学株式会社 Composition de résine, préimprégné, carte stratifiée, carte stratifiée revêtue de feuille métallique et carte de circuit imprimé
JP6986212B1 (ja) * 2020-02-07 2021-12-22 三菱瓦斯化学株式会社 樹脂組成物、プリプレグ、積層板、金属箔張積層板、及びプリント配線板

Also Published As

Publication number Publication date
JPWO2018159674A1 (ja) 2019-12-26
KR20190121804A (ko) 2019-10-28
JP6996548B2 (ja) 2022-01-17
CN110382588A (zh) 2019-10-25
TW201842064A (zh) 2018-12-01

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