WO2017170883A1 - Composition durcissable, procédé de production d'un produit durci, et son produit durci - Google Patents

Composition durcissable, procédé de production d'un produit durci, et son produit durci Download PDF

Info

Publication number
WO2017170883A1
WO2017170883A1 PCT/JP2017/013288 JP2017013288W WO2017170883A1 WO 2017170883 A1 WO2017170883 A1 WO 2017170883A1 JP 2017013288 W JP2017013288 W JP 2017013288W WO 2017170883 A1 WO2017170883 A1 WO 2017170883A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
mass
parts
carbon atoms
formula
Prior art date
Application number
PCT/JP2017/013288
Other languages
English (en)
Japanese (ja)
Inventor
和彦 松土
智志 渡辺
Original Assignee
株式会社Adeka
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 株式会社Adeka filed Critical 株式会社Adeka
Priority to CN202410291187.9A priority Critical patent/CN118185235A/zh
Priority to KR1020187030441A priority patent/KR102356381B1/ko
Priority to CN201780020027.9A priority patent/CN108884299A/zh
Publication of WO2017170883A1 publication Critical patent/WO2017170883A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • 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
    • C08G59/20—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 epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • 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
    • C08G59/20—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 epoxy compounds used
    • C08G59/32—Epoxy compounds containing three or more epoxy groups
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular 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
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/16—Cyclic ethers having four or more ring atoms
    • C08G65/18—Oxetanes
    • 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
    • C08K5/00—Use of organic 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
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/101—Esters; Ether-esters of monocarboxylic acids
    • C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
    • 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
    • C08L33/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
    • 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
    • C08L33/08—Homopolymers or copolymers of acrylic acid esters
    • 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
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers

Definitions

  • the present invention relates to a curable composition, a method for producing a cured product, and a cured product thereof, and more specifically, a curable composition having a high glass transition temperature and excellent adhesion, and a method for producing the cured product. It relates to the cured product.
  • Curable compositions are used in the fields of inks, paints, various coating agents, adhesives, optical members and the like. Various reports have been made regarding the improvement of such a curable composition.
  • Patent Documents 1 to 4 propose an energy ray curable composition containing a cationic polymerizable component and a radical polymerizable component or a cured product thereof.
  • Patent Document 1 proposes an adhesive composition for polarizing plates that is excellent in initial curability and adhesiveness.
  • patent document 2 even when it is a case where a resin film with low moisture permeability is used as a protective film, the adhesive force is expressed immediately after light irradiation, and the adhesive force after a certain period of time is good against various forces.
  • a low-viscosity photo-curing adhesive has been proposed that does not cause problems even after the endurance test and has good adhesive strength after the end of the wet heat resistance test.
  • Patent Document 3 proposes an active energy ray-polymerizable resin composition that can satisfy both high heat resistance, high refractive index and transparency, including an unsaturated alicyclic epoxy ester compound.
  • JP 2014-105218 A Japanese Patent Laying-Open No. 2015-040283 JP2015-168757A
  • an object of the present invention is to provide a curable composition having a high glass transition temperature of a hard cured product and excellent adhesion, a method for producing the cured product, and a cured product thereof.
  • the curable composition of the present invention comprises 15 to 90 parts by mass of the cationic polymerizable component (A), 1 to 10 parts by mass of the cationic polymerization initiator (B), and 10 to 50 parts by mass of the radical polymerizable component (C).
  • radical polymerization initiator (D) 1 to 10 parts by mass, the following formula (I), (Wherein X is an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aryloxy group having 6 to 12 carbon atoms, or a carbon atom)
  • the cation polymerizable component (A) includes a glycidylated product of a polyhydric alcohol or a glycidylated product of a polyhydric alcohol alkylene oxide adduct (A1) and an oxetane compound (A2) as essential components, and the cationic polymerizable component ( A), the radical polymerizable component (C), and the polymer (E) are 100 parts by mass with respect to 100 parts by mass of the glycidylated product of the polyhydric alcohol or the glycidylated product of the polyhydric alcohol alkylene oxide adduct ( A1) is 35 to 65 parts by mass,
  • the radical polymerizable component (C) is a compound (C1) having an epoxy group and an ethylenically unsaturated group, a polyhydric alcohol acrylate ester having 2 to 20 carbon atoms, or a carbon atom number 2 to 20
  • a polyhydric alcohol methacrylate (C2) is an essential component
  • the curable composition of the present invention preferably further contains an aromatic epoxy compound (A3) as the cationic polymerizable component (A).
  • the said aromatic epoxy compound (A3) is a polyfunctional aromatic epoxy compound.
  • the polymer (E) is a polymer obtained from the monomer represented by the formula (I) and the monomer represented by the formula (II).
  • X in the formula (I) is an aryl group having 6 to 12 carbon atoms
  • X ′ in the formula (II) is an alkyl group having 1 to 7 carbon atoms, It is preferred that the group is substituted with an epoxy group.
  • the method for producing a cured product of the present invention is characterized in that the curable composition of the present invention is irradiated with active energy rays or heated.
  • the cured product of the present invention is a cured product of the curable composition of the present invention.
  • the present invention it is possible to provide a curable composition having a high glass transition temperature of a hard cured product and excellent adhesion, a method for producing the cured product, and a cured product thereof.
  • the curable composition of the present invention is particularly useful for adhesives.
  • the curable composition of the present invention comprises 15 to 90 parts by mass of the cationic polymerizable component (A), 1 to 10 parts by mass of the cationic polymerization initiator (B), 10 to 50 parts by mass of the radical polymerizable component (C).
  • the cationically polymerizable component (A) essentially comprises a glycidylated product of a polyhydric alcohol or a glycidylated product of a polyhydric alcohol alkylene oxide adduct (A1), and an oxetane compound (A2).
  • the glycidylated product (A1) of the oxide adduct is 35 to 65 parts by mass.
  • the radical polymerizable component (C) is a compound having an epoxy group and an ethylenically unsaturated group (C1), an acrylate ester of a polyhydric alcohol having 2 to 20 carbon atoms, or 2 to 20 carbon atoms.
  • a polyhydric alcohol methacrylate (C2) is an essential component.
  • X is an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aryl group having 6 to 12 carbon atoms.
  • An oxy group or an alicyclic hydrocarbon group having 6 to 10 carbon atoms, or a hydrogen atom in these groups is one or more groups selected from the group consisting of an epoxy group, an oxetane group, a hydroxyl group and a carboxyl group; Has been replaced.
  • R 1 represents a hydrogen atom, a methyl group or a halogen atom
  • X ′ represents an alkyl group having 1 to 7 carbon atoms, an aryl group having 6 to 12 carbon atoms or a carbon atom.
  • An alicyclic hydrocarbon group of 6 to 10 or a hydrogen atom in these groups substituted with one or more groups selected from the group consisting of an epoxy group, an oxetane group, a hydroxyl group and a carboxyl group is there.
  • the cationically polymerizable component (A) according to the curable composition of the present invention is a compound that undergoes polymerization or crosslinking reaction by a cationic polymerization initiator activated by irradiation with energy rays or heating.
  • a cationic polymerization initiator activated by irradiation with energy rays or heating.
  • An epoxy compound, an oxetane compound, a vinyl ether compound, etc. are mentioned.
  • the cationically polymerizable component (A) according to the curable composition of the present invention comprises a glycidylated product of a polyhydric alcohol or a glycidylated product of a polyhydric alcohol alkylene oxide adduct (A1) and an oxetane compound (A2) as essential components.
  • aromatic epoxy compounds (A3) and alicyclic epoxy compounds (A4) can also be used as other epoxy compounds.
  • Examples of the glycidylated product of the polyhydric alcohol or the glycidylated product (A1) of the polyhydric alcohol alkylene oxide adduct include those obtained by glycidylating a polyhydric alcohol or polyhydric alcohol alkylene oxide adduct, and the molecular weight of the glycidylated product is 250. The above is preferable.
  • Examples of the glycidylated polyhydric alcohol or the glycidylated polyhydric alcohol alkylene oxide adduct (A1) include 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, neopentyl glycol diglycidyl ether.
  • glycidylated product of a polyhydric alcohol or a polyhydric alcohol alkylene oxide adduct (A1) a monoglycidyl ether of a higher aliphatic alcohol, a glycidyl ester of a higher fatty acid, epoxidized soybean oil, octyl epoxy stearate, Examples include epoxy butyl stearate, epoxidized soybean oil, and epoxidized polybutadiene.
  • glycidylated product of the polyhydric alcohol or the glycidylated product (A1) of the polyhydric alcohol alkylene oxide adduct those having a saturated condensed ring are preferable because the curability and adhesion of the cured product are improved.
  • glycidylated product of polyhydric alcohol or the glycidylated product (A1) of a polyhydric alcohol alkylene oxide adduct commercially available products can be used.
  • Examples of the oxetane compound (A2) include 3,7-bis (3-oxetanyl) -5-oxa-nonane, 1,4-bis [(3-ethyl-3-oxetanylmethoxy) methyl] benzene, 1,2- Bis [(3-ethyl-3-oxetanylmethoxy) methyl] ethane, 1,3-bis [(3-ethyl-3-oxetanylmethoxy) methyl] propane, ethylene glycol bis (3-ethyl-3-oxetanylmethyl) ether Triethylene glycol bis (3-ethyl-3-oxetanylmethyl) ether, tetraethylene glycol bis (3-ethyl-3-oxetanylmethyl) ether, 1,4-bis (3-ethyl-3-oxetanylmethoxy) butane, Bifunctional aliphatic oxygen such as 1,6-bis (3-ethyl-3-o
  • oxetane compound (A2) commercially available products can be used.
  • the aromatic epoxy compound (A3) refers to an epoxy compound containing an aromatic ring, and specific examples of the aromatic epoxy compound (A3) include polyphenols having at least one aromatic ring such as phenol, cresol, and butylphenol. Mono- or polyglycidyl etherified products of polyhydric phenols or alkylene oxide adducts thereof, such as glycidyl etherified products of epoxy compounds and bisphenol A, bisphenol F, or compounds obtained by further adding alkylene oxide to these, epoxy novolac resins; resorcinol, hydroquinone, catechol, etc.
  • the aromatic epoxy compound (A3) commercially available products can be used.
  • Denacol EX-146, Denacol EX-147, Denacol EX-201, Denacol EX-203, Denacol EX-711, Denacol EX -721, on-coat EX-1020, on-coat EX-1030, on-coat EX-1040, on-coat EX-1050, on-coat EX-1051, on-coat EX-1010, on-coat EX-1011, on-coat 1012 (Nagase Chemtex Co., Ltd.); Ogsol PG-100, Ogsol EG-200, Ogsol EG-210, Ogsol EG-250 (Osaka Gas Chemical Co., Ltd.); HP4032, HP4032D, HP4700 (DIC Corporation) ESN-475 (Manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.); Epicoat YX8800 (manufactured by Mitsubishi Chemical Corporation); Marproof G-0105SA,
  • the alicyclic epoxy compound (A4) refers to a saturated ring having an oxirane ring directly without a bonding group.
  • Specific examples of the alicyclic epoxy compound (A4) are obtained by epoxidizing a polyglycidyl etherified product of a polyhydric alcohol having at least one alicyclic ring or a cyclohexene or cyclopentene ring-containing compound with an oxidizing agent. Examples include cyclohexene oxide and cyclopentene oxide-containing compounds.
  • 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate 3,4-epoxy-1-methylcyclohexyl-3,4-epoxy-1-methylhexanecarboxylate, 6-methyl-3,4 -Epoxycyclohexylmethyl-6-methyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-3-methylcyclohexylmethyl-3,4-epoxy-3-methylcyclohexanecarboxylate, 3,4-epoxy-5 -Methylcyclohexylmethyl-3,4-epoxy-5-methylcyclohexanecarboxylate, bis (3,4-epoxycyclohexylmethyl) adipate, 3,4-epoxy-6-methylcyclohexanecarboxylate, methylenebis (3,4-epoxy Cyclohexane), propane-2,2-diyl-bis (3,
  • alicyclic epoxy compound (A4) 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate or 3,4-epoxy-1-methylcyclohexyl-3,4-epoxy-1-methylhexanecarboxyl
  • the rate is preferable from the viewpoint of improving adhesion.
  • alicyclic epoxy compound (A4) Commercially available products can be used as the alicyclic epoxy compound (A4), and examples thereof include Celoxide 2021P, Celoxide 2081, Celoxide 2000, and Celoxide 3000 (manufactured by Daicel Corporation).
  • Examples of the vinyl ether compound include diethylene glycol monovinyl ether, triethylene glycol divinyl ether, n-dodecyl vinyl ether, cyclohexyl vinyl ether, 2-ethylhexyl vinyl ether, 2-chloroethyl vinyl ether, ethyl vinyl ether, isobutyl vinyl ether, triethylene glycol vinyl ether, 2- Examples thereof include hydroxyethyl vinyl ether, 4-hydroxybutyl vinyl ether, 1,6-cyclohexanedimethanol monovinyl ether, ethylene glycol divinyl ether, 1,4-butanediol divinyl ether, 1,6-cyclohexanedimethanol divinyl ether.
  • the ratio of the compound (A4) and the vinyl ether compound used is such that the total of the cationic polymerizable component (A), the radical polymerizable component (C), and the polymer (E) is 100 parts by mass of the polyhydric alcohol.
  • the compound (A4) is 0 to 30 parts by mass and the vinyl ether compound is 0 to 20 parts by mass. Viscosity, coating property, is preferably improved reactivity and curability.
  • the cationic polymerization initiator (B) may be any compound as long as it can release a substance that initiates cationic polymerization by energy ray irradiation or heating.
  • it is a double salt that is an onium salt that releases a Lewis acid upon irradiation with energy rays, or a derivative thereof.
  • Representative examples of such compounds include the following general formula: [A] r + [B] r- And cation and anion salts represented by the formula:
  • the cation [A] r + is preferably onium, and the structure thereof is, for example, the following general formula: [(R 2 ) a Q] r + Can be expressed as
  • R 2 is an organic group having 1 to 60 carbon atoms and any number of atoms other than carbon atoms.
  • a is an integer of 1 to 5.
  • the a R 2 s are independent and may be the same or different.
  • at least one is preferably an organic group as described above having an aromatic ring.
  • the anion [B] r- is preferably a halide complex, and the structure thereof is, for example, the following general formula: [LY b ] r- Can be expressed as
  • L is a metal or metalloid which is a central atom of a halide complex
  • B P, As, Sb, Fe, Sn, Bi, Al, Ca, In, Ti, Zn, Sc, V, Cr, Mn, Co and the like.
  • Y is a halogen atom.
  • b is an integer of 3 to 7.
  • anion [LY b ] r- of the above general formula examples include tetrakis (pentafluorophenyl) borate, tetra (3,5-difluoro-4-methoxyphenyl) borate, tetrafluoroborate (BF 4 ) ⁇ , Examples include hexafluorophosphate (PF 6 ) ⁇ , hexafluoroantimonate (SbF 6 ) ⁇ , hexafluoroarsenate (AsF 6 ) ⁇ , hexachloroantimonate (SbCl 6 ) ⁇ and the like.
  • the anion [B] r- is represented by the following general formula [LY b-1 (OH)] r-
  • the thing of the structure represented by can also be used preferably. L, Y, and b are the same as described above.
  • Other anions that can be used include perchlorate ion (ClO 4 ) ⁇ , trifluoromethylsulfite ion (CF 3 SO 3 ) ⁇ , fluorosulfonate ion (FSO 3 ) ⁇ , and toluenesulfonate anion.
  • Trinitrobenzenesulfonate anion camphor sulfonate, nonafluorobutane sulfonate, hexadecafluorooctane sulfonate, tetraarylborate, tetrakis (pentafluorophenyl) borate and the like.
  • the onium salts it is particularly effective to use the following aromatic onium salts (a) to (c).
  • aromatic onium salts (a) to (c) one of them can be used alone, or two or more of them can be mixed and used.
  • Aryl diazonium salts such as phenyldiazonium hexafluorophosphate, 4-methoxyphenyldiazonium hexafluoroantimonate, 4-methylphenyldiazonium hexafluorophosphate, etc.
  • Diaryls such as diphenyliodonium hexafluoroantimonate, di (4-methylphenyl) iodonium hexafluorophosphate, di (4-tert-butylphenyl) iodonium hexafluorophosphate, and tricumyliodonium tetrakis (pentafluorophenyl) borate Iodonium salt
  • Sulfonium salts such as sulfonium cations represented by the following group I or group II and hexafluoroantimony ions, hexafluorophosphate ions, tetrakis (pentafluorophenyl) borate ions, etc.
  • Aromatic sulfonium salts having the following structure are used as cationic polymerization initiators (B ) It is more preferable to contain at least 0.1% by mass with respect to 100% by mass.
  • R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and R 20 are each independently a hydrogen atom, a halogen atom, or a carbon atom number.
  • R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 26 , R 27 , R 28 , R 29 , R 35 , R 36 , R 37 , R 38 and R 39 are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, or 1 carbon atom.
  • R 30 , R 31 , R 32 , R 33 and R 34 each independently represents a hydrogen atom, a halogen atom or 1 to 10 carbon atoms. Represents an alkyl group.
  • the halogen atom include fluorine, chlorine, bromine and iodine.
  • R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 and R 39 Is methyl, ethyl, propyl, isopropyl, butyl, s-butyl, t-butyl, isobutyl, amyl, isoamyl, t-amyl, hexyl, cyclohexyl, heptyl, octyl, nonyl, ethyloctyl, 2-methoxyethyl, 3- Methoxypropyl, 4-methoxybutyl, 2-
  • the alkoxy group having 1 to 10 carbon atoms includes methoxy, ethoxy, propyloxy, isopropyloxy, butyloxy, s-butyloxy, t-butyloxy, isobutyloxy, pentyloxy, isoamyloxy, t-amyloxy, hexyloxy, cyclohexyloxy, cyclohexylmethyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, 2-methoxyethyloxy, 3-methoxypropyloxy, 4- Methoxybutyloxy, 2-butoxye
  • R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 26 , R 27 , R 28 R 29 , R 35 , R 36 , R 37 , R 38 and R 39 are ester groups having 2 to 10 carbon atoms such as methoxycarbonyl, ethoxycarbonyl, isopropyloxycarbonyl, phenoxycarbonyl, acetoxy, propionyl Examples include oxy, butyryloxy, chloroacetyloxy, dichloroacetyloxy, trichloroacetyloxy, trifluoroacetyloxy, t-butylcarbonyloxy, methoxyacetyloxy, benzoyloxy and the like.
  • the radical polymerizable component (C) according to the curable composition of the present invention is a compound (C1) having an epoxy group and an ethylenically unsaturated group, an acrylate ester of an alcohol having 2 to 20 carbon atoms, or the number of carbon atoms.
  • the methacrylic acid ester (C2) of alcohol 2 to 20 is an essential component.
  • Examples of the compound (C1) having an epoxy group and an ethylenically unsaturated group include epoxy acrylate or epoxy methacrylate.
  • epoxy acrylate or epoxy methacrylate Specifically, conventionally known aromatic epoxy resins, alicyclic epoxy resins, An acrylate obtained by reacting an aliphatic epoxy resin or the like with acrylic acid or methacrylic acid.
  • epoxy acrylates or epoxy methacrylates particularly preferred are acrylates or methacrylates of glycidyl ethers of alcohols.
  • Examples of the acrylate of alcohol having 2 to 20 carbon atoms or the methacrylate (C2) of alcohol having 2 to 20 carbon atoms include aromatic or aliphatic alcohols having at least one hydroxyl group in the molecule, and alkylenes thereof. Examples thereof include acrylates or methacrylates obtained by reacting an oxide adduct with acrylic acid or methacrylic acid.
  • radically polymerizable component (C) a compound that is polymerized or cross-linked by a radical polymerization initiator activated by energy ray irradiation or heating other than (C1) or (C2) can be used. Examples include urethane compounds, unsaturated polyester compounds, and styrene compounds.
  • the proportion of the component (C1) and the component (C2) in the radical polymerizable component (C) is preferably 50% by mass or more.
  • the radical initiator (D) according to the curable composition of the present invention is not particularly limited, and known ones can be used.
  • ketone compounds such as acetophenone compounds, benzyl compounds, benzophenone compounds, and thioxanthone compounds, oxime compounds, and the like can be used.
  • the polymer (E) according to the curable composition of the present invention is a polymer obtained from the monomer represented by the above formula (I), a polymer obtained from the monomer represented by the above formula (II), Polymer obtained from two or more monomers selected from monomers represented by formula (I), two or more monomers selected from monomers represented by formula (II) Selected from the group consisting of a polymer obtained from the above, a monomer represented by the above formula (I) and a polymer obtained from the monomer represented by the above formula (II), and the weight average molecular weight is in terms of polystyrene 1,000 to 30,000.
  • alkyl group having 1 to 7 carbon atoms represented by X in the formula (I) examples include methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, tert-butyl, iso-butyl, amyl, Examples include iso-amyl, tert-amyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 4-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, iso-heptyl, tert-heptyl and the like.
  • an alkyl group having 1 to 4 carbon atoms, or 1 to 1 carbon atom partially substituted with one or more groups selected from the group consisting of an epoxy group, an oxetane group, a hydroxyl group and a carboxyl group 4 alkyl groups are preferable from the viewpoint of curability.
  • alkoxy group having 1 to 7 carbon atoms represented by X in the formula (I) examples include methoxy, ethoxy, propyloxy, iso-propyloxy, butyloxy, sec-butyloxy, tert-butyloxy, iso-butyloxy, Amyloxy, iso-amyloxy, tert-amyloxy, hexyloxy, 2-hexyloxy, 3-hexyloxy, cyclohexyloxy, 4-methylcyclohexyloxy, heptyloxy, 2-heptyloxy, 3-heptyloxy, iso-heptyloxy, and tert-heptyloxy.
  • an alkoxy group having 1 to 4 carbon atoms, or 1 to 1 carbon atoms partially substituted with one or more groups selected from the group consisting of an epoxy group, an oxetane group, a hydroxyl group and a carboxyl group 4 alkoxy groups are preferred from the viewpoint of curability.
  • Examples of the aryl group having 6 to 12 carbon atoms represented by X in the above formula (I) include phenyl, methylphenyl, naphthyl and the like.
  • Examples of the aryloxy group having 6 to 12 carbon atoms represented by X in the above formula (I) include phenyloxy, methylphenyloxy, naphthyloxy and the like.
  • Examples of the alicyclic hydrocarbon group having 6 to 10 carbon atoms represented by X in the formula (I) include cyclohexyl, methylcyclohexyl, norbornyl, bicyclopentyl, bicyclooctyl, trimethylbicycloheptyl, tricyclooctyl. , Tricyclodecanyl, spirooctyl, spirobicyclopentyl, adamantyl, isobornyl and the like.
  • alkyl group, alkoxy group, aryl group, aryloxy group, and alicyclic hydrocarbon group are selected from the group consisting of an epoxy group, an oxetane group, a hydroxyl group, and a carboxyl group in which the hydrogen atom in these groups is 1 It may be substituted with more than one group.
  • examples of the monomer represented by the formula (I) include the following formulas (1) to (3): The monomer represented by these is mentioned.
  • R 3 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and m is an integer of 1 to 6.
  • R 4 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and n is an integer of 1 to 6.
  • R 5 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and s is an integer of 1 to 6.
  • examples of the halogen atom represented by R 1 include fluorine, chlorine, bromine and iodine.
  • the alkyl group having 1 to 7 carbon atoms, the aryl group having 6 to 12 carbon atoms, or the alicyclic hydrocarbon group having 6 to 10 carbon atoms as X ′ can be represented by the above formula (I ).
  • R 1 is the same as in the above formula (II)
  • R 6 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • t is an integer of 1 to 6 It is.
  • R 1 is the same as in Formula (II) above, R 7 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and q is an integer of 1 to 6 It is.
  • R 1 is the same as in the above formula (II)
  • R 8 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • y is an integer of 1 to 6 It is.
  • the proportion of the monomer constituting the polymer is such that X is a carbon substituted with one or more groups selected from the group consisting of epoxy groups, oxetane groups, hydroxyl groups and carboxyl groups.
  • X is a carbon substituted with one or more groups selected from the group consisting of epoxy groups, oxetane groups, hydroxyl groups and carboxyl groups.
  • an alkyl group having 1 to 7 atoms, an aryl group having 6 to 12 carbon atoms, or an alicyclic hydrocarbon group having 6 to 10 carbon atoms the single group represented by the above (I) or (II) It is preferable to use the polymer in an amount of 10 to 100% by mass because the adhesiveness is improved.
  • the cationic polymerizable component (A) is 15 to 90 parts by mass, preferably 50 to 80 parts by mass
  • the cationic polymerization initiator (B) is 1 to 10 parts by mass, preferably 1 To 6 parts by weight, 10 to 50 parts by weight, preferably 10 to 20 parts by weight of the radical polymerizable component (C), and 1 to 10 parts by weight, preferably 1 to 5 parts by weight of the radical polymerization initiator (D).
  • the polymer (E) is 1 to 20 parts by mass, preferably 5 to 15 parts by mass. If the blending ratio is other than the above, the curability and adhesion of the cured product may be deteriorated. In addition, the sum total of a cationically polymerizable component (A), a radically polymerizable component (C), and a polymer (E) is 100 mass parts.
  • a sensitizer and / or a sensitization aid can be further used as necessary.
  • the sensitizer is a compound that exhibits maximum absorption at a wavelength longer than the maximum absorption wavelength indicated by the cationic polymerization initiator (B) and promotes the polymerization initiation reaction by the cationic polymerization initiator (B).
  • the sensitization aid is a compound that further promotes the action of the sensitizer.
  • Sensitizers and sensitizers include anthracene compounds and naphthalene compounds.
  • anthracene compound examples include those represented by the following formula (7).
  • R 50 and R 51 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or an alkoxyalkyl group having 2 to 12 carbon atoms
  • R 52 represents a hydrogen atom. Or an alkyl group having 1 to 6 carbon atoms.
  • anthracene compound represented by the above formula (7) include the following compounds.
  • naphthalene compound examples include those represented by the following formula (8).
  • R 53 and R 54 each independently represents an alkyl group having 1 to 6 carbon atoms.
  • naphthalene compound represented by the above formula (8) include the following compounds.
  • 4-methoxy-1-naphthol 4-ethoxy-1-naphthol, 4-propoxy-1-naphthol, 4-butoxy-1-naphthol, 4-hexyloxy-1-naphthol, 1,4-dimethoxynaphthalene
  • Examples thereof include 1-ethoxy-4-methoxynaphthalene, 1,4-diethoxynaphthalene, 1,4-dipropoxynaphthalene, 1,4-dibutoxynaphthalene and the like.
  • the use ratio of the sensitizer and the sensitization aid to the cationic polymerizable component (A) is not particularly limited, and may be used at a generally normal use ratio within a range not inhibiting the purpose of the present invention. From the viewpoint of improving curability, the amount of the sensitizer and the sensitizer is 0.1 to 3 parts by mass with respect to 100 parts by mass of the cationic polymerizable component (A).
  • a silane coupling agent can be used as necessary.
  • the silane coupling agent include dimethyldimethoxysilane, dimethyldiethoxysilane, methylethyldimethoxysilane, methylethyldiethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, and ethyltrimethoxysilane.
  • Alkyl-functional alkoxysilanes vinyltrichlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane, allyltrimethoxysilane, and other alkenyl-functional alkoxysilanes, 3-methacryloxypropyltriethoxysilane, 3-methacryloxypropyltrimethoxy Silane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 2-methacryloxypropyltrimethoxysilane, ⁇ Epoxy-functional alkoxysilanes such as glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropylmethyldiethoxysilane, ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxysilane, N- ⁇ (aminoethyl) - ⁇ Aminofunctional alkoxysilanes such as amino
  • the amount of the silane coupling agent used is not particularly limited, but is usually in the range of 0.01 to 20 parts by mass with respect to 100 parts by mass of the total amount of solids in the curable composition.
  • the properties of the cured product can be improved by using a thermoplastic organic polymer as necessary.
  • the thermoplastic organic polymer include polystyrene, polymethyl methacrylate, methyl methacrylate ethyl acrylate copolymer, methyl methacrylate glycidyl methacrylate copolymer, poly (meth) acrylic acid, styrene- (meth) acrylic acid copolymer, Examples include (meth) acrylic acid-methyl methacrylate copolymer, glycidyl (meth) acrylate-polymethyl (meth) acrylate copolymer, polyvinyl butyral, cellulose ester, polyacrylamide, and saturated polyester.
  • the UV-absorbing agent is inactivated at room temperature, and the protective group is released by heating to a predetermined temperature, light irradiation, acid, etc. and activated.
  • a compound exhibiting ultraviolet absorbing ability can also be used.
  • coloring agents such as polyols, inorganic fillers, organic fillers, pigments, dyes, antifoaming agents, thickeners, surfactants, leveling agents, difficulty
  • resin additives such as flame retardants, thixotropic agents, diluents, plasticizers, stabilizers, polymerization inhibitors, UV absorbers, antioxidants, antistatic agents, flow regulators, adhesion promoters, etc. may be added. it can.
  • the curable composition of the present invention is not particularly limited, and a solvent that can dissolve or disperse the components (A), (B), (C), (D) and (E) which are usually used is used.
  • a solvent that can dissolve or disperse the components (A), (B), (C), (D) and (E) which are usually used is used.
  • the solvent include ketones such as methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone and 2-heptanone; ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1 Ether solvents such as 1,2-diethoxyethane, propylene glycol monomethyl ether, dipropylene glycol dimethyl ether; methyl acetate, ethyl acetate, acetic acid-n
  • Paraffin solvents Paraffin solvents; halogenated aliphatic hydrocarbon solvents such as carbon tetrachloride, chloroform, trichloroethylene, methylene chloride, and 1,2-dichloroethane; halogenated aromatic hydrocarbon solvents such as chlorobenzene; propylene carbonate, carbitol solvents Aniline, triethylamine, pyridine, acetic acid, acetonitrile, carbon disulfide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, water and the like. These solvents can be used as one or a mixture of two or more.
  • the water content is preferably 5 parts by mass or less, and more preferably 3 parts by mass or less because the curability, adhesiveness, and liquid storage stability are improved. Too much moisture is not preferred because it may cause cloudiness or components may precipitate.
  • the curable composition of the present invention is applied onto a support substrate by a known means such as a roll coater, a curtain coater, various types of printing, and immersion. Moreover, after once applying on support bases, such as a film, it can also transfer on another support base
  • the material for the support substrate is not particularly limited and may be any commonly used material, such as inorganic materials such as glass; diacetyl cellulose, triacetyl cellulose (TAC), propionyl cellulose, butyryl cellulose, acetylpropionyl.
  • inorganic materials such as glass
  • Cellulose esters such as cellulose and nitrocellulose; polyamide; polyimide; polyurethane; epoxy resin; polycarbonate; polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, poly-1,4-cyclohexanedimethylene terephthalate, polyethylene-1,2-diphenoxy Polyesters such as ethane-4,4′-dicarboxylate and polybutylene terephthalate; polystyrene; polyethylene, polypropylene, polymethylpente Polyolefin such as polyvinyl acetate, polyvinyl compounds such as polyvinyl chloride and polyvinyl fluoride, acrylic resins such as polymethyl methacrylate and polyacrylate, polycarbonate, polysulfone, polyethersulfone, polyetherketone, polyetherimide, polyoxy Polymer materials such as ethylene, norbornene resin, and cycloolefin polymer (COP) can be used.
  • the support substrate may
  • examples of energy rays include ultraviolet rays, electron beams, X-rays, radiation, high frequencies, and the like, and ultraviolet rays are most preferable economically.
  • examples of the ultraviolet light source include an ultraviolet laser, a mercury lamp, a xenon laser, and a metal halide lamp.
  • the conditions for the method of curing the curable composition of the present invention by heating are 70 to 250 ° C. and 1 to 100 minutes. After performing pre-baking (PAB), pressurization and post-baking (PEB) may be performed, or baking may be performed at several different temperatures.
  • the heating conditions vary depending on the type and mixing ratio of each component, but are, for example, 70 to 180 ° C., 5 to 15 minutes for an oven, and 1 to 5 minutes for a hot plate.
  • a cured film can be obtained by heat treatment at 180 to 250 ° C., preferably 200 to 250 ° C., for 30 to 90 minutes for an oven and 5 to 30 minutes for a hot plate.
  • curable composition of the present invention or a cured product thereof include adhesives, glasses, optical materials represented by imaging lenses, paints, coating agents, lining agents, inks, resists, liquid resists, printing Plates, color TVs, PC monitors, personal digital assistants, digital cameras, organic EL, touch panels and other display elements, insulating varnishes, insulating sheets, laminates, printed boards, semiconductor devices, LED packages, liquid crystal inlets, organic Sealants for EL, optical elements, electrical insulation, electronic parts, separation membranes, molding materials, putty, glass fiber impregnating agents, sealants, passivation films for semiconductors and solar cells, interlayers Insulating film, protective film, prism lens sheet used for backlight of liquid crystal display device, Fresnel label used for screen of projection TV, etc. Lens parts of lens sheets such as lens sheets, lenticular lens sheets, or backlights using such sheets, optical lenses such as micro lenses, optical elements, optical connectors, optical waveguides, castings for optical modeling, etc. Can be mentioned
  • the display device of the present invention includes a transparent support, an undercoat layer, an antireflection layer, a polarizing element layer, a retardation layer, a birefringence layer, a light scattering layer, a hard coat layer, a lubricating layer, and a protective layer as necessary.
  • cured material of this invention can be used for each layer.
  • Examples 1 to 19 Comparative Examples 1 to 8
  • the components shown in [Table 1] to [Table 6] below were mixed thoroughly to obtain the curable compositions of Examples 1 to 19 and the curable compositions of Comparative Examples 1 to 8, respectively.
  • the unit of an Example and a comparative example is a mass part.
  • Compound (A1-1) Neopentyl glycol diglycidyl ether
  • Compound (A1-2) 1,4-butanediol diglycidyl ether
  • Compound (A2-1) Aron oxetane OXT-221 (manufactured by Toagosei Co., Ltd.)
  • Compound (A3-1) Bisphenol type diglycidyl ether
  • the following compound (B-1) was used as the cationic polymerization initiator (B).
  • Compound (B-1) 50% propylene carbonate solution of a mixture of a compound represented by the following formula (9) and a compound represented by the following formula (10)
  • Polymer (E) As the polymer (E), the following compounds (E-1) and (E-2) were used.
  • Polymer (E-1) copolymer of 75 parts by mass of methyl methacrylate and glycidyl methacrylate 25 (weight average molecular weight 7,000)
  • the following compounds (E′-1) and (E′-2) were used.
  • Compound (E′-1) copolymer of 75 parts by mass of methyl methacrylate and glycidyl methacrylate 25 (weight average molecular weight 800)
  • Compound (E′-2 Copolymer of 75 parts by mass of methyl methacrylate and glycidyl methacrylate 25 (weight average molecular weight 35,000)
  • the curable composition of the present invention has a high glass transition temperature and excellent adhesion.

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)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

La présente invention décrit une composition durcissable qui fournit un produit durci présentant une température de transition vitreuse élevée et une excellente adhésion, un procédé de production d'un produit durci, et un produit durci à partir de ce dernier. La composition durcissable comprend de 15 à 90 parties en masse d'un constituant cationiquement polymérisable (A), de 1 à 10 parties en masse d'un initiateur de polymérisation cationique (B), de 10 à 50 parties en masse d'un constituant polymérisable par voie radicalaire (C), de 1 à 10 parties en masse d'un initiateur de polymérisation radicalaire (D), et de 1 à 20 parties en masse d'un polymère (E) ayant un poids moléculaire moyen en poids de 1 000 à 30 000 et sélectionné dans le groupe constitué d'un polymère obtenu à partir du monomère représenté par la formule (I) et d'un polymère obtenu à partir du monomère représenté par la formule (II), les constituants étant présents d'une manière telle que le total des constituants (A), (C), et (E) représente 100 parties en masse. Le constituant (A) comprend, comme constituants essentiels, un produit glycidylé (A1) d'un polyalcool hydrique, et d'un composé oxétane (A2), avec de 35 à 65 parties en masse de (A1) étant incorporés en son sein. Le constituant polymérisable par voie radicalaire (C) comprend, comme constituant essentiel, un composé (C1) qui présente un groupe époxy et un groupe éthyléniquement insaturé.
PCT/JP2017/013288 2016-03-30 2017-03-30 Composition durcissable, procédé de production d'un produit durci, et son produit durci WO2017170883A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN202410291187.9A CN118185235A (zh) 2016-03-30 2017-03-30 固化性组合物、固化物的制造方法、及其固化物
KR1020187030441A KR102356381B1 (ko) 2016-03-30 2017-03-30 경화성 조성물, 경화물의 제조 방법, 및 그 경화물
CN201780020027.9A CN108884299A (zh) 2016-03-30 2017-03-30 固化性组合物、固化物的制造方法、及其固化物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2016-069796 2016-03-30
JP2016069796A JP6993766B2 (ja) 2016-03-30 2016-03-30 硬化性組成物、硬化物の製造方法、およびその硬化物

Publications (1)

Publication Number Publication Date
WO2017170883A1 true WO2017170883A1 (fr) 2017-10-05

Family

ID=59965991

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2017/013288 WO2017170883A1 (fr) 2016-03-30 2017-03-30 Composition durcissable, procédé de production d'un produit durci, et son produit durci

Country Status (5)

Country Link
JP (1) JP6993766B2 (fr)
KR (1) KR102356381B1 (fr)
CN (2) CN108884299A (fr)
TW (1) TWI788285B (fr)
WO (1) WO2017170883A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001022165A1 (fr) * 1999-09-17 2001-03-29 Hitachi Chemical Co., Ltd. Compositions a base de resine photosensibles, element photosensible contenant ces compositions, procede de production d'un motif de reserve et procede de production de carte a circuit imprime
JP2006057078A (ja) * 2004-07-22 2006-03-02 Mitsui Chemicals Inc 光硬化型樹脂組成物及びそれからなるプラスチック用樹脂組成物
JP2013209607A (ja) * 2011-07-05 2013-10-10 Jsr Corp 樹脂組成物、重合体、硬化膜および電子部品
WO2015068454A1 (fr) * 2013-11-07 2015-05-14 積水化学工業株式会社 Agent d'étanchéité pour éléments d'affichage électroluminescents organiques
JP2015143352A (ja) * 2013-12-25 2015-08-06 東亞合成株式会社 光硬化性接着剤組成物、偏光板とその製造法、光学部材及び液晶表示装置
JP2015179210A (ja) * 2014-03-19 2015-10-08 富士フイルム株式会社 重合性非線形光学材料、非線形光学膜、光学素子、光変調素子、及び非線形光学膜の製造方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5296575B2 (ja) * 2009-03-06 2013-09-25 住友化学株式会社 光硬化性接着剤組成物、偏光板とその製造法、光学部材及び液晶表示装置
JP6103687B2 (ja) 2012-11-22 2017-03-29 チェイル インダストリーズ インコーポレイテッド 偏光板用接着剤組成物
JP6075237B2 (ja) * 2013-07-12 2017-02-08 東亞合成株式会社 プラスチック製フィルム又はシート用活性エネルギー線硬化型接着剤組成物
JP6164609B2 (ja) 2013-08-23 2017-07-19 東亞合成株式会社 光硬化性接着剤組成物、偏光板とその製造法、光学部材及び液晶表示装置
JP6284721B2 (ja) * 2013-08-26 2018-02-28 株式会社Adeka エネルギー線感受性組成物
JP6337523B2 (ja) 2014-03-07 2018-06-06 東洋インキＳｃホールディングス株式会社 活性エネルギー線重合性樹脂組成物および積層体
JP6292400B2 (ja) * 2014-06-06 2018-03-14 東亞合成株式会社 プラスチック製フィルム又はシート用活性エネルギー線硬化型接着剤組成物

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001022165A1 (fr) * 1999-09-17 2001-03-29 Hitachi Chemical Co., Ltd. Compositions a base de resine photosensibles, element photosensible contenant ces compositions, procede de production d'un motif de reserve et procede de production de carte a circuit imprime
JP2006057078A (ja) * 2004-07-22 2006-03-02 Mitsui Chemicals Inc 光硬化型樹脂組成物及びそれからなるプラスチック用樹脂組成物
JP2013209607A (ja) * 2011-07-05 2013-10-10 Jsr Corp 樹脂組成物、重合体、硬化膜および電子部品
WO2015068454A1 (fr) * 2013-11-07 2015-05-14 積水化学工業株式会社 Agent d'étanchéité pour éléments d'affichage électroluminescents organiques
JP2015143352A (ja) * 2013-12-25 2015-08-06 東亞合成株式会社 光硬化性接着剤組成物、偏光板とその製造法、光学部材及び液晶表示装置
JP2015179210A (ja) * 2014-03-19 2015-10-08 富士フイルム株式会社 重合性非線形光学材料、非線形光学膜、光学素子、光変調素子、及び非線形光学膜の製造方法

Also Published As

Publication number Publication date
CN118185235A (zh) 2024-06-14
CN108884299A (zh) 2018-11-23
TW201803909A (zh) 2018-02-01
KR102356381B1 (ko) 2022-01-26
JP2017179163A (ja) 2017-10-05
KR20180132724A (ko) 2018-12-12
TWI788285B (zh) 2023-01-01
JP6993766B2 (ja) 2022-01-14

Similar Documents

Publication Publication Date Title
JP7071262B2 (ja) 硬化性組成物、硬化物の製造方法、およびその硬化物
KR102272147B1 (ko) 경화성 조성물, 경화물의 제조 방법, 및 그 경화물
KR102265025B1 (ko) 경화성 조성물, 경화물의 제조 방법, 및 그 경화물
JP2019026774A (ja) 硬化性組成物、硬化物の製造方法、およびその硬化物
JP2019026775A (ja) 硬化性組成物、硬化物の製造方法、およびその硬化物
KR102278179B1 (ko) 경화성 조성물, 경화물의 제조 방법, 및 그 경화물
JP6949458B2 (ja) 硬化性組成物、硬化物の製造方法、およびその硬化物
JP7008398B2 (ja) 硬化性組成物、硬化物の製造方法、およびその硬化物
JP2018172494A (ja) 硬化性組成物、硬化物の製造方法、その硬化物、およびこれを用いた接着剤
JP6993766B2 (ja) 硬化性組成物、硬化物の製造方法、およびその硬化物
JP6910347B2 (ja) 硬化性組成物、硬化物の製造方法、およびその硬化物
JP2018012765A (ja) 硬化性組成物、硬化物の製造方法、その硬化物および接着剤
JP2017115103A (ja) 硬化性組成物、その硬化方法、これにより得られる硬化物および接着剤
JP2018012766A (ja) 硬化性組成物、硬化物の製造方法、およびその硬化物

Legal Events

Date Code Title Description
NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 20187030441

Country of ref document: KR

Kind code of ref document: A

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 17775417

Country of ref document: EP

Kind code of ref document: A1

122 Ep: pct application non-entry in european phase

Ref document number: 17775417

Country of ref document: EP

Kind code of ref document: A1