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WO2015005211A1 - Composition polymérisable par voie cationique - Google Patents

Composition polymérisable par voie cationique Download PDF

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Publication number
WO2015005211A1
WO2015005211A1 PCT/JP2014/067779 JP2014067779W WO2015005211A1 WO 2015005211 A1 WO2015005211 A1 WO 2015005211A1 JP 2014067779 W JP2014067779 W JP 2014067779W WO 2015005211 A1 WO2015005211 A1 WO 2015005211A1
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Prior art keywords
epoxy compound
polymerizable composition
compound
cationically polymerizable
composition according
Prior art date
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English (en)
Japanese (ja)
Inventor
俊輔 高日
和彦 松土
智幸 岩島
浩之 五十嵐
英里 本間
智志 渡辺
泰延 大野
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Adeka Corp
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Adeka Corp
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Application filed by Adeka Corp filed Critical Adeka Corp
Priority to CN201480005618.5A priority Critical patent/CN104955866B/zh
Priority to JP2015526295A priority patent/JP6400006B2/ja
Priority to KR1020157020637A priority patent/KR102219443B1/ko
Publication of WO2015005211A1 publication Critical patent/WO2015005211A1/fr
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    • 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
    • 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

Definitions

  • the present invention relates to a cationic polymerizable composition and a cured product obtained by irradiating the cationic polymerizable composition with active energy rays.
  • the cationically polymerizable composition is particularly useful for adhesives.
  • Cationic polymerizable compositions are used in the fields of inks, paints, various coating agents, adhesives, optical members and the like.
  • Patent Documents 1 to 3 disclose various photocurable adhesives.
  • An object of the present invention is to provide a cationically polymerizable composition having excellent curability, adhesion and water resistance.
  • the present invention has been made on the basis of the above findings, and includes (1) an aromatic epoxy compound (1A) as a main component as a cationically polymerizable organic substance, and further an aliphatic epoxy compound (1B) or an alicyclic type.
  • an aromatic epoxy compound (1A) as a main component as a cationically polymerizable organic substance
  • an aliphatic epoxy compound (1B) or an alicyclic type By providing a cationically polymerizable composition characterized by comprising a cationically polymerizable organic substance mixture containing at least one of the epoxy compound (1C) and (2) an energy ray-sensitive cationic polymerization initiator. Is achieved.
  • the present invention also provides an adhesive comprising the above cationic polymerizable composition.
  • the cationically polymerizable composition of the present invention is particularly useful as an adhesive because it is excellent in curability, adhesiveness and water resistance.
  • the cationic polymerizable organic substance constituting the mixture is polymerized or crosslinked by an energy ray sensitive cationic polymerization initiator activated by light irradiation.
  • An epoxy compound is preferable.
  • an aromatic epoxy compound (1A), an alicyclic epoxy compound (1C), an aliphatic epoxy compound (1B), or a high molecular weight compound (1D) having an epoxy group and having a weight average molecular weight of 1,000 to 1,000,000 is used. be able to.
  • a vinyl ether compound or an oxetane compound (1E) is used as the cationically polymerizable organic substance.
  • the aromatic epoxy compound (1A) refers to an epoxy compound containing an aromatic ring, and specific examples of the aromatic epoxy compound include monovalent phenols having at least one aromatic ring such as phenol, cresol, and butylphenol.
  • mono / polyglycidyl etherified products of the alkylene oxide adducts such as bisphenol A, bisphenol F, or glycidyl etherified products of compounds obtained by further adding alkylene oxide to these and epoxy novolac resins; two such as resorcinol, hydroquinone and catechol Glycidyl ethers of aromatic compounds having the above phenolic hydroxyl groups; mono / polyglycidic aromatic compounds having two or more alcoholic hydroxyl groups such as benzenedimethanol, benzenediethanol, and benzenedibutanol Ruetherified products: glycidyl esters of polybasic acid aromatic compounds having two or more carboxylic acids such as phthalic acid, terephthalic acid, trimellitic acid, gly
  • glycidyl ethers of phenols glycidyl ethers of aromatic compounds having two or more alcoholic hydroxyl groups
  • glycidyl ethers of polyphenols glycidyl esters of benzoic acids
  • glycidyl esters of polybasic acids glycidyl esters of polybasic acids
  • styrene oxide or divinyl It is preferable to contain at least one selected from the group of epoxidized benzene from the viewpoint of reducing the viscosity of the composition.
  • aromatic epoxy compound those having an epoxy equivalent of 80 to 500 are preferable because of excellent curability.
  • the aromatic epoxy compound (1A) commercially available products can be used.
  • the aromatic epoxy compound (1A) preferably contains at least one polyfunctional epoxy compound from the viewpoints of curability and adhesiveness.
  • the cationically polymerizable composition of the present invention preferably contains 25 to 70 parts by mass of the polyfunctional aromatic epoxy compound (1A) with respect to 100 parts by mass of (1) the cationically polymerizable organic substance mixture, More preferably, 60 parts by mass is contained.
  • the amount of (1A) includes the amount corresponding to (1D).
  • alicyclic epoxy compound (1C) is 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. And cyclopentene oxide-containing compounds.
  • alicyclic epoxy compound (1C) Commercially available products can be used as the alicyclic epoxy compound (1C), and examples thereof include Celoxide 2021P, Celoxide 2081, Celoxide 2000, and Celoxide 3000 (manufactured by Daicel Corporation).
  • the aliphatic epoxy compound (1B) refers to an epoxy compound that is not classified as the aromatic epoxy compound (1A) or the alicyclic epoxy compound (1C).
  • Specific examples of the aliphatic epoxy compound include aliphatic alcohols.
  • An epoxy compound is mentioned.
  • Representative compounds include allyl glycidyl ether, butyl glycidyl ether, 2-ethylhexyl glycidyl ether, C 1 2-13 mixed alkyl glycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, Triglycidyl ether of glycerin, triglycidyl ether of trimethylolpropane, tetraglycidyl ether of sorbitol, hexaglycidyl ether of dipentaerythritol, diglycidyl ether of polyethylene glycol, glycidyl ether of polyhydric alcohol such as diglycidyl ether of polypropylene glycol, In addition, one or two or more alkyl polyhydric alcohols such as propylene glycol, trimethylolpropane and glycerin are used.
  • Polyglycidyl ethers of polyether polyols obtained by adding emission oxide include diglycidyl esters of aliphatic long-chain dibasic acids. Furthermore, monoglycidyl ethers of higher aliphatic alcohols, glycidyl esters of higher fatty acids, epoxidized soybean oil, octyl epoxy stearate, butyl epoxy stearate, epoxidized soybean oil, epoxidized polybutadiene and the like. As the aliphatic epoxy compound (1B), those having an epoxy equivalent of 80 to 500 are preferable.
  • aliphatic epoxy compound (1B) commercially available products can be used.
  • the cationically polymerizable composition of this invention contains at least 1 type of a polyfunctional epoxy compound as said aliphatic epoxy compound (1B) or alicyclic epoxy compound (1C).
  • the cationically polymerizable composition of the present invention is (1) the sum of the polyfunctional aliphatic epoxy compound (1B) and the polyfunctional alicyclic epoxy compound (1C) with respect to 100 parts by mass of the cationically polymerizable organic substance mixture.
  • the amount is preferably 10 to 65 parts by mass, particularly 20 to 50 parts by mass.
  • the content of the polyfunctional aliphatic epoxy compound (1B) is preferably 10 to 45 parts by mass with respect to (1) 100 parts by mass of the cation polymerizable organic substance mixture, and the polyfunctional alicyclic epoxy compound
  • the content of (1C) is preferably 0 to 10 parts by mass.
  • the amounts of (1B) and (1C) are amounts including those corresponding to (1D).
  • Examples of the high molecular weight polymer (1D) having a weight average molecular weight of 1,000 to 1,000,000 having an epoxy group include a polymer obtained by radical polymerization, and homopolymerizing one kind of ethylenically unsaturated monomer having a cationic polymerizable substituent. Preferred is a polymer copolymerized with an ethylenically unsaturated monomer that does not have a polymer or a cationically polymerizable substituent.
  • the ethylenically unsaturated monomer constituting the high molecular weight product (1D) having a weight average molecular weight of 1,000 to 1,000,000 having the epoxy group is not particularly limited, and known ones can be used.
  • an example of an ethylenically unsaturated monomer having no cationically polymerizable substituent includes a group represented by the following general formula (1), and an ethylenically unsaturated group having a cationically polymerizable substituent.
  • the monomer one or more hydrogen atoms in the alkyl group, aryl group or alicyclic hydrocarbon group in the following general formula (1) are substituted with an epoxy group, an oxetane group or a vinyl ether group. Groups.
  • R 11 , R 12 , R 13 and R 14 are each independently a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, or 6 to 12 carbon atoms.
  • An aryl group or an alicyclic hydrocarbon group having 6 to 10 carbon atoms, and a methylene group in these groups may be substituted with —CO—, —O— or —COO—)
  • the high molecular weight body (1D) contains 10 to 10 ethylenically unsaturated monomers having a structure substituted with a cationic polymerizable substituent such as an epoxy group, an oxetane group or a vinyl ether group.
  • methyl group, ethyl group or branched alkyl group having 3 to 7 carbon atoms, aryl group having 6 to 12 carbon atoms, 6 to 10 carbon atoms, which is not substituted with a cationic polymerizable substituent The content of the ethylenically unsaturated monomer substituted with an alicyclic hydrocarbon group is preferably 20 to 90% by mass, and the total together with other ethylenically unsaturated monomers is preferably 100% by mass.
  • the high molecular weight product (1D) having a weight average molecular weight of 1,000 to 1,000,000 having an epoxy group preferably has a weight average molecular weight of 5,000 to 100,000, more preferably 7,000 to 70,000.
  • Examples of the vinyl ether compound or oxetane compound (1E) include ethylene glycol divinyl 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.
  • the vinyl ether compound preferably has a molecular weight of 58 to 500, more preferably 70 to 300.
  • the oxetane compound preferably has a molecular weight of 100 to 1000, more preferably 110 to 500.
  • the vinyl ether compound or oxetane compound (1E) may be monofunctional or polyfunctional, but has one or two vinyl ether groups or oxetane groups having one or two vinyl ether groups. It is preferable to use an oxetane compound.
  • vinyl ether compound or oxetane compound (1E) commercially available products mainly composed of a cationic polymerizable monomer can be used.
  • the molecular weight (1D), vinyl ether compound, or oxetane compound (1E) is used in an amount of (1) 25 to 70 parts by mass, especially 30 parts by mass of the aromatic epoxy compound (1A) with respect to 100 parts by mass of the cationic polymerizable organic substance mixture.
  • the amounts of (1B) and (1C) are amounts excluding those corresponding to the above (1D), and the amount of (1A) is an amount including those corresponding to (1D).
  • the main component means a mixture of several types of epoxy compounds and the largest total amount of the same type of epoxy compounds, and the cationically polymerizable organic substance mixture contains a cationically polymerizable organic substance other than the epoxy compound.
  • the total amount of the several types of epoxy compounds having the largest total amount is greater than the total amount of the cationically polymerizable organic material other than the epoxy compound.
  • the total amount of each type of epoxy compound includes those corresponding to (1D).
  • the (2) energy ray-sensitive cationic polymerization initiator used in the present invention may be any compound that can release a substance that initiates cationic polymerization by irradiation with energy rays, but is preferably 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: Listed is a salt of a cation and an anion represented by [A] r + [B] r- (wherein A represents a cation species, B represents an anion species, and r represents a valence). be able to.
  • the cation [A] r + is preferably onium, and the structure thereof is, for example, the following general formula: [(R 1 ) a Q] r + It can be expressed as
  • R 1 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 1 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.
  • anion [B] r- is preferably a halide complex, and the structure thereof is, for example, the following general formula: [LX b ] r- It 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.
  • X is a halogen atom.
  • b is an integer of 3 to 7.
  • anion [LX b ] r- in 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: [LX b-1 (OH)] r-
  • L, X, and b are the same as described above.
  • Other anions that can be used include perchlorate ion (ClO 4 ) ⁇ , trifluoromethyl sulfite 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.
  • 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
  • preferable examples include ( ⁇ 5 -2,4-cyclopentadien-1-yl) [(1,2,3,4,5,6- ⁇ )-(1-methylethyl) benzene] -iron.
  • -Iron-arene complexes such as hexafluorophosphate
  • aluminum complexes such as tris (acetylacetonato) aluminum, tris (ethylacetonatoacetato) aluminum, tris (salicylaldehyde) aluminum, and silanols such as triphenylsilanol
  • silanols such as triphenylsilanol
  • aromatic iodonium salts aromatic sulfonium salts, and iron-arene complexes are preferably used from the viewpoints of practical use and photosensitivity.
  • the use ratio of the (2) energy ray sensitive cationic polymerization initiator to the above (1) cationic polymerizable organic substance mixture is not particularly limited, and may be used at a generally normal use ratio within a range not impairing the object of the present invention.
  • a silane coupling agent can be used as necessary.
  • the silane coupling agent include dimethyldimethoxysilane, dimethyldiethoxysilane, methylethyldimethoxysilane, methylethyldiethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, and ethyltrimethoxysilane.
  • the amount of the silane coupling agent used is not particularly limited, but is usually in the range of 1 to 20 parts by mass with respect to 100 parts by mass of the total amount of solids in the cationic polymerizable composition.
  • thermal polymerization initiator is a compound that generates a cationic species or Lewis acid by heating, such as a salt of sulfonium salt, thiophenium salt, thiolanium salt, benzylammonium, pyridinium salt, hydrazinium salt; diethylenetriamine, triethylenetriamine, tetraethylenepenta Polyalkylpolyamines such as min; alicyclic polyamines such as 1,2-diaminocyclohexane, 1,4-diamino-3,6-diethylcyclohexane, isophoronediamine; m-xylylenediamine, diaminodiphenylmethane, diaminodiphenylsulfone Aromatic polyamines such as; such polyamines; phenyl glycidyl ether, butyl glycid
  • Mannich-modified products produced by reacting phenols having sex sites by a conventional method polyvalent carboxylic acids (oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelain Acid, sebacic acid, Decanedioic acid, 2-methylsuccinic acid, 2-methyladipic acid, 3-methyladipic acid, 3-methylpentanedioic acid, 2-methyloctanedioic acid, 3,8-dimethyldecanedioic acid, 3,7-dimethyldecane Aliphatic dicarboxylic acids such as diacid, hydrogenated dimer acid and dimer acid; aromatic dicarboxylic acids such as phthalic acid, terephthalic acid, isophthalic acid and naphthalenedicarboxylic acid; alicyclic dicarboxylic acids such as cyclohexanedicarboxylic acid; trimellitic acid, Tri
  • thermal polymerization initiator Commercially available products may be used as the thermal polymerization initiator.
  • Adeka Opton® CP77 Adeka Opton CP66 (manufactured by ADEKA), CI-2539, CI-2624 (manufactured by Nippon Soda Co., Ltd.), Sun-Aid® SI-60L, Sun-Aid SI -80L, Sun Aid SI-100L (manufactured by Sanshin Chemical Industry Co., Ltd.) and the like.
  • the amount of the thermal polymerization initiator used is not particularly limited, but is usually in the range of 0.001 to 10 parts by mass with respect to 100 parts by mass of the total amount of solids in the cationic polymerizable composition.
  • an initiator it is preferable to heat the cationically polymerizable composition of the present invention at 130 to 180 ° C. for 20 minutes to 1 hour.
  • a cured product can be obtained by using a thermoplastic organic polymer (excluding a high molecular weight polymer (1D) having a weight average molecular weight of 1,000 to 1,000,000 having an epoxy group) as necessary. It is possible to improve the characteristics.
  • a thermoplastic organic polymer excluding a high molecular weight polymer (1D) having a weight average molecular weight of 1,000 to 1,000,000 having an epoxy group
  • thermoplastic organic polymer examples include polystyrene, polymethyl methacrylate, methyl methacrylate-ethyl acrylate copolymer, poly (meth) acrylic acid, styrene- (meth) acrylic acid copolymer, (meth) acrylic acid- Examples include methyl methacrylate copolymer, glycidyl (meth) acrylate-polymethyl (meth) acrylate copolymer, polyvinyl butyral, cellulose ester, polyacrylamide, and saturated polyester.
  • the cationically polymerizable composition of the present invention is not particularly limited, and a solvent that can dissolve or disperse the components (1) and (2) that are usually used can be used.
  • a solvent that can dissolve or disperse the components (1) and (2) that are usually used can be used.
  • methyl ethyl ketone, methyl amyl ketone, Ketones such as diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone, 2-heptanone; ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, propylene glycol monomethyl ether, Ether solvents such as dipropylene glycol dimethyl ether; ester solvents such as methyl acetate, ethyl acetate, acetic acid-n-propyl, isopropyl acetate,
  • BTX solvents aliphatic hydrocarbon solvents such as hexane, heptane, octane, cyclohexane; terpenes such as turpentine oil, D-limonene, and pinene Hydrocarbon oils; paraffinic solvents such as mineral spirits, Swazol # 310 (Cosmo Matsuyama Oil Co., Ltd.), Solvesso # 100 (Exxon Chemical Co., Ltd.); carbon tetrachloride, chloroform, trichloroethylene, methylene chloride, 1,2- Halogenated aliphatic hydrocarbon solvents such as dichloroethane; Halogenated aromatic hydrocarbon solvents such as chlorobenzene; Propylene carbonate, carbitol solvents, aniline, triethylamine, pyridine, acetic acid, acetonitrile, carbon disulfide, N, N- Examples thereof include dimethylformamide, N, N-dimethylacetamide, N-methylpyrrol
  • the total amount of optional components other than (1) the cationic polymerizable organic substance mixture and (2) the energy ray sensitive cationic polymerization initiator depends on the use of the present invention, etc. From the viewpoint of further enhancing the effects of the present invention, (1) it is preferably 20 parts by mass or less, particularly 10 parts by mass or less with respect to 100 parts by mass of the cationically polymerizable organic substance mixture.
  • the cationically polymerizable composition of the present invention has a water content of preferably 5% by mass or less, and more preferably 3% by mass or less from the viewpoints of curability, adhesiveness, and liquid storage stability. Too much moisture is not preferable because it may cause cloudiness or components may precipitate. The amount of water is measured by the method described in the examples described later.
  • the cationic polymerizable composition of the present invention preferably has a viscosity of 200 mPa ⁇ s or less, more preferably 10 to 150 mPa ⁇ s, from the viewpoint of coating properties.
  • This viscosity is a viscosity at 25 ° C., and is measured by the method described in Examples described later.
  • the cationically polymerizable composition of the present invention is applied onto a supporting 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 Polyester such as ethane-4,4′-dicarboxylate, polybutylene terephthalate, etc .; polystyrene; polyethylene, polypropylene, polymethylpentene, etc.
  • Polyolefins Vinyl compounds such as polyvinyl acetate, polyvinyl chloride, and polyvinyl fluoride; Acrylic resins such as polymethyl methacrylate and polyacrylate; Polycarbonate; Polysulfone; Polyethersulfone; Polyetherketone; Polyetherimide; Polymer materials such as oxyethylene, norbornene resin, and cycloolefin polymer (COP) can be used.
  • the support substrate may be subjected to surface activation treatment such as corona discharge treatment, flame treatment, ultraviolet treatment, high frequency treatment, glow discharge treatment, active plasma treatment, laser treatment and the like.
  • the cationic polymerizable composition of the present invention is cured by irradiation with active energy rays.
  • active energy rays include ultraviolet rays, electron beams, X-rays, radiation, and high frequencies, and ultraviolet rays are the most economical.
  • ultraviolet light source include an ultraviolet laser, a mercury lamp, a xenon laser, and a metal halide lamp.
  • cationically polymerizable composition of the present invention include glasses, optical materials represented by imaging lenses, paints, coating agents, lining agents, inks, resists, liquid resists, adhesives, printing plates, and insulation. Varnish, insulating sheet, laminate, printed circuit board, sealing agent for molding of semiconductor devices, LED packages, liquid crystal inlets, organic EL, optical elements, electrical insulation, electronic components, separation membranes, etc. Materials, putty, glass fiber impregnating agent, sealant, semiconductor / solar cell passivation film, interlayer insulating film, protective film, prism lens sheet used for backlight of liquid crystal display, screen for projection TV, etc.
  • the lens portion of a lens sheet such as a Fresnel lens sheet or a lenticular lens sheet, or a bag using such a sheet.
  • a lens sheet such as a Fresnel lens sheet or a lenticular lens sheet, or a bag using such a sheet.
  • Examples include light, optical lenses such as microlenses, optical elements, optical connectors, optical waveguides, optical molding casting agents, etc.
  • substrates that can be used as coating agents include metals, wood, rubber, and plastics. , Glass, ceramic products and the like.
  • cationic polymerizable composition of the present invention and the cured product obtained by curing the cationic polymerizable composition will be described in detail with reference to examples, evaluation examples, and comparative examples.
  • “part” means “part by mass”
  • “%” means “% by mass”.
  • Examples 1-30, Comparative Examples 1-2 The components shown in [Table 1] to [Table 3] below were mixed thoroughly to obtain Example Compositions 1 to 30 and Comparative Compositions 1 and 2, respectively.
  • Compound 1A-1 Resorcinol diglycidyl ether compound 1A-2: Diglycidyl o-phthalate compound 1A-3: Divinylbenzene oxide compound 1A-4: Phenyl glycidyl ether compound 1A-5: Styrene oxide compound 1A-6: EP-4100L ( Bisphenol A epoxy: manufactured by ADEKA) Compound 1A-7: Adeka Resin EP-4901L Compound 1A-8: Adeka Resin EP-4000L Compound 1A-9: TECHMORE VG-3101L Compound 1A-10: Adekaglycil ED-509S (manufactured by ADEKA) Compound 1A-11: Adekaglycilol ED-501 (manufactured by ADEKA) Compound 1A-12: Adekaglycil ED-529 (manufactured by ADEKA) Compound 1B-1: Neopentyl glycol diglycidyl ether compound 1B-2: Triglycid
  • Example Compositions 1 to 30 and Comparative Compositions 1 to 2 were applied to a COP (cycloolefin polymer) film that had been subjected to corona discharge treatment, and then the film was laminated using a laminator.
  • COP cycloolefin polymer
  • a test piece was obtained by bonding to another COP (cycloolefin polymer) film that had been subjected to corona discharge treatment, and using an electrodeless ultraviolet lamp to irradiate with 1000 mJ / cm 2 of energy.
  • a 90 degree peel test is performed on the obtained test piece.
  • a specimen having a strength of 2.0 N / cm or more is indicated by ⁇ , a specimen having a strength of 1.0 to 2.0 N / cm is ⁇ , and a specimen having a strength of 1.0 N / cm or less.
  • the results are shown in [Table 1] to [Table 5].
  • (amount of water) The water content of each of the obtained practical compositions 1-30 and the comparative compositions 1-2 was measured according to the Karl Fischer method. The results are shown in the above [Table 1] to [Table 5].

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  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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  • Polymers & Plastics (AREA)
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  • Adhesives Or Adhesive Processes (AREA)
  • Polyethers (AREA)

Abstract

La composition polymérisable par voie cationique de l'invention comprend : un mélange de matière organique polymérisable par voie cationique comprenant à son tour en tant que matière organique polymérisable par voie cationique (1), un composé époxy aromatique (1A) servant de composant principal, et au moins un composé époxy aliphatique (1B) ou un composé époxy alicyclique (1C); et un initiateur de polymérisation par voie cationique sensible aux rayonnements d'énergie (2). De préférence, la composition de l'invention comprend au moins une sorte de composé époxy polyfonctionnel, en tant que composé époxy aliphatique (1B) ou composé époxy alicyclique (1C).
PCT/JP2014/067779 2013-07-09 2014-07-03 Composition polymérisable par voie cationique Ceased WO2015005211A1 (fr)

Priority Applications (3)

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CN201480005618.5A CN104955866B (zh) 2013-07-09 2014-07-03 阳离子聚合性组合物
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