WO2019198792A1 - Composition adhésive - Google Patents

Composition adhésive Download PDF

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Publication number
WO2019198792A1
WO2019198792A1 PCT/JP2019/015781 JP2019015781W WO2019198792A1 WO 2019198792 A1 WO2019198792 A1 WO 2019198792A1 JP 2019015781 W JP2019015781 W JP 2019015781W WO 2019198792 A1 WO2019198792 A1 WO 2019198792A1
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WO
WIPO (PCT)
Prior art keywords
group
adhesive composition
meth
unsubstituted
substituted
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PCT/JP2019/015781
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English (en)
Japanese (ja)
Inventor
太軌 山手
祐一 立石
侑弥 長尾
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日本曹達株式会社
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Priority to JP2020513450A priority Critical patent/JPWO2019198792A1/ja
Publication of WO2019198792A1 publication Critical patent/WO2019198792A1/fr

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Classifications

    • 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
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04—Homopolymers or copolymers of esters
    • 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
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/24—Homopolymers or copolymers of amides or imides
    • 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
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/24—Homopolymers or copolymers of amides or imides
    • C09D133/26—Homopolymers or copolymers of acrylamide or methacrylamide
    • 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
    • C09D201/00—Coating compositions based on unspecified macromolecular compounds
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/24—Homopolymers or copolymers of amides or imides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/24—Homopolymers or copolymers of amides or imides
    • C09J133/26—Homopolymers or copolymers of acrylamide or methacrylamide
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J201/00—Adhesives based on unspecified macromolecular compounds

Definitions

  • the present invention relates to a novel adhesive composition, in particular, an adhesive composition excellent in adhesion to a plastic substrate, etc., and an adhesive composition that can be used as a coating agent or an adhesive.
  • Patent Document 1 describes that a polymerizable compound having a methyl group or a silyl group substituted with a plurality of aryl groups becomes a coating agent having excellent adhesion to a cycloolefin resin.
  • the present inventors have found that a copolymer having a repeating unit derived from a kind of polymerizable compound exhibits excellent adhesion to a cycloolefin resin and solubility in various solvents and resins, thereby completing the present invention.
  • Formula (I) YN (Ar) (R) Formula (I) (Where Ar represents an unsubstituted or substituted C6-C14 aryl group or an unsubstituted or substituted C6-C10 aryl C1-C3 alkyl group. R represents an unsubstituted or substituted C1-C6 alkyl group, an unsubstituted or substituted C3-C6 cycloalkyl group, an unsubstituted or substituted C6-C14 aryl group, or unsubstituted. Or a C6-C10 aryl C1-C3 alkyl group having a substituent.
  • Y represents a polymerizable functional group.
  • the substituent on Ar and the substituent on R may be combined to form a divalent organic group.
  • the adhesive composition according to (4), wherein the plastic substrate is a polyolefin resin substrate.
  • the adhesive composition according to (4), wherein the plastic substrate is a cycloolefin resin substrate.
  • the adhesive composition according to (4), wherein the adhesive composition is a coating agent.
  • the adhesive composition according to (7), wherein the coating agent is a primer.
  • the adhesive composition according to (4), wherein the adhesive composition is an adhesive.
  • a coating film having excellent adhesion to a plastic substrate particularly a plastic substrate such as a cycloolefin resin
  • a functional film that could not be directly formed on a plastic substrate can be laminated via the coating film of the present invention.
  • the plastic substrates can be bonded to each other through the coating film. Since it is not necessary to modify the surface of the plastic substrate by UV ozone treatment or the like, the initial characteristics of the plastic substrate can be maintained.
  • the adhesive composition of the present invention can also be used as an adhesive.
  • the adhesive composition of the present invention is excellent in solubility in various solvents and resins.
  • Adhesive composition (copolymer)
  • the adhesive composition of the present invention comprises a repeating unit derived from the polymerizable compound represented by formula (I) (hereinafter sometimes referred to as repeating unit A), (meth) acrylic acid ester and (meth) acrylamide. It contains a copolymer having a repeating unit derived from at least one polymerizable compound selected (hereinafter may be referred to as repeating unit B).
  • repeating unit A the polymerizable compound represented by formula (I)
  • (meth) acrylic acid ester and (meth) acrylamide contains a copolymer having a repeating unit derived from at least one polymerizable compound selected (hereinafter may be referred to as repeating unit B).
  • repeating unit B a copolymer having a repeating unit derived from at least one polymerizable compound selected
  • Ar represents an unsubstituted or substituted C6-C14 aryl group or an unsubstituted or substituted C6-C10 aryl C1-C3 alkyl group.
  • Specific examples of the C6 to C14 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, and the like.
  • Examples of the C6 to C10 aryl C1 to C3 alkyl group include a benzyl group, a phenethyl group, and a naphthalen-1-ylmethyl group.
  • the “substituent” in “unsubstituted or substituted” specifically includes a halogeno group, a hydroxyl group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a C3-C6 cycloalkyl group, C6-C10 aryl group, benzyl group, ⁇ , ⁇ -dimethylbenzyl group, mercapto group, C1-C6 alkylthio group, amino group, C1-C6 alkylamino group, C1-C6 dialkylamino group, nitro group, or A cyano group is mentioned.
  • the number of substituents is not limited as long as it is within a chemically acceptable range.
  • halogeno group examples include a fluoro group, a chloro group, a bromo group, and an iodo group.
  • C1-C20 alkyl group examples include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, a t-butyl group, An n-pentyl group, n-hexyl, n-octyl group and the like can be mentioned.
  • C1-C20 alkoxy group examples include a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group, a t-butoxy group, Examples thereof include an n-pentoxy group, an n-hexoxy group, and an n-octoxy group.
  • Specific examples of the C3-C6 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like.
  • C6 to C10 aryl group examples include a phenyl group and a naphthyl group.
  • Specific examples of the C1-C6 alkylthio group include methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, s-butylthio group, i-butylthio group, t-butylthio group, Examples include n-pentylthio group and n-hexylthio group.
  • C1-C6 alkylamino group examples include methylamino group, ethylamino group, n-propylamino group, i-propylamino group, n-butylamino group, i-butylamino group, and t-butyl.
  • An amino group, n-pentylamino group, n-hexylamino group and the like can be mentioned.
  • Specific examples of the C1-C6 dialkylamino group include an N, N-dimethylamino group, an N, N-diethylamino group, and an ethyl (methyl) amino group.
  • Ar is preferably an unsubstituted or substituted C6-C10 aryl group.
  • a C1-C12 alkyl group and a C1-C12 alkoxy group are preferable, and a C1-C6 alkyl group and a C1-C6 alkoxy group are more preferable.
  • R is an unsubstituted or substituted C1-C6 alkyl group, an unsubstituted or substituted C3-C6 cycloalkyl group, an unsubstituted or substituted C6-C14 aryl group Or an unsubstituted or substituted C6-C10 aryl C1-C3 alkyl group.
  • C1-C6 alkyl group examples include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, a t-butyl group, Examples thereof include an n-pentyl group and an n-hexyl group.
  • Specific examples of the C3-C6 cycloalkyl group, the C6-C14 aryl group, the C6-C10 aryl C1-C3 alkyl group and the substituents thereof are the same as those exemplified for Ar above.
  • R is preferably an unsubstituted or substituted C6-C14 aryl group, more preferably an unsubstituted or substituted C6-C10 aryl group.
  • substituent a C1-C12 alkyl group and a C1-C12 alkoxy group are preferable, and a C1-C6 alkyl group and a C1-C6 alkoxy group are more preferable.
  • the substituent on Ar and the substituent on R may be combined to form a divalent organic group.
  • the divalent organic group include a methylene group, a dimethylene group, an oxo group, a sulfenyl group, a carbonyl group, an imino group, and a C1-C6 alkylimino group.
  • Y represents a polymerizable functional group.
  • polymerizable functional groups include acryloyl group, methacryloyl group, vinyloxycarbonyl group, prop-1-en-2-yloxycarbonyl group, allyloxycarbonyl group, vinyl group, allyl group, propen-2-yl group, etc. And a group having a polymerizable carbon-carbon double bond.
  • Y is preferably an acryloyl group or a methacryloyl group.
  • N N-diphenylacrylamide, N, N-diphenylmethacrylamide, N, N-bis (4-octylphenyl) acrylamide, N, N-bis (4-octylphenyl) methacrylamide, N, N-bis [4- ( ⁇ , ⁇ -dimethylbenzyl) phenyl] acrylamide, N, N-bis [4- ( ⁇ , ⁇ -dimethylbenzyl) Phenyl] methacrylamide.
  • Examples of the (meth) acrylic acid ester and (meth) acrylamide used in the present invention include the following.
  • the content of the repeating unit A and the repeating unit B is not particularly limited.
  • the repeating unit A and the repeating unit B have a molar ratio of 1:99 to 99: 1, 20:80 to 95: 5, 25:75 to 90:10, 30:70 to 85:25 (number of moles of the repeating unit A) : The number of moles of the repeating unit B) can be selected.
  • the copolymer used in the present invention comprises a repeating unit derived from a polymerizable compound represented by the formula (I) and a repeating unit derived from at least one polymerizable compound selected from (meth) acrylic acid ester and (meth) acrylamide. If it has, it can use without a restriction
  • the polymerizable compound represented by the formula (I), the (meth) acrylic acid ester, and the polymerizable compound other than (meth) acrylamide may be appropriately selected according to the desired physical properties such as melting point, viscosity, or refractive index. Although not particularly limited, specific examples include the following.
  • Vinyl compounds such as styrene, vinyl acetate, vinyl chloride, vinylidene chloride, acrylonitrile, vinyl ether, acrolein, divinylbenzene; Olefin compounds such as ethylene, propylene and butadiene.
  • the copolymer contained in the adhesive composition of the present invention comprises at least one polymer selected from a repeating unit derived from the polymerizable compound represented by formula (I), (meth) acrylic acid ester, and (meth) acrylamide.
  • a repeating unit derived from the polymerizable compound represented by formula (I) Any of repeating units derived from a compound may be randomly arranged, alternately arranged, or block arranged. Among these, those arranged in a block are particularly preferable.
  • the molecular chain of the copolymer of the present invention may be linear or branched.
  • Examples of the branched chain include a branched chain branched at one point (star type) and a branched chain branched at a plurality of points (graft type).
  • the polymerization reaction of the copolymer in the present invention can be performed by a known method. Depending on the chemical reaction point, for example, radical polymerization, anionic polymerization, cationic polymerization, coordination polymerization, ring-opening polymerization and the like can be used.
  • the polymerization reaction of the copolymer in the present invention for example, it can be synthesized using a known living polymerization. Reaction of the polymerizable compound represented by the formula (I) and the polymerizable compound of (meth) acrylic acid ester was carried out by anionic polymerization using a Zr-based initiator (J. Am. Chem. Soc., 2007, 129, 6724). ) Etc. can be used. Moreover, the reaction of the polymerizable compound represented by the formula (I) and the polymerizable compound of ((meth) acrylamide) is a living polymerization using triisopropylaluminum as an initiator (Macromol.molRapid Commun. 2005, 26, 1499.) Etc. can be used.
  • the molecular weight of the copolymer used in the adhesive composition of the present invention is not limited as long as it is within a range that can be applied onto a substrate. For example, 1,000 to 300,000, 5,000 to 200,000, Mention may be made of copolymers having a number average molecular weight (Mn) in the range of 10,000 to 150,000, 20,000 to 100,000 and the like.
  • the molecular weight distribution (PDI) of the copolymer according to the present invention is preferably a ratio of weight average molecular weight / number average molecular weight (Mw / Mn), preferably 1.0 to 5.0, more preferably 1.0 to 4. 0, most preferably 1.0 to 3.0.
  • the weight average molecular weight and the number average molecular weight are values obtained by converting data measured by gel permeation chromatography (GPC) using DMF as a solvent based on the molecular weight of polymethyl methacrylate used as a standard.
  • the adhesive composition of the present invention is not particularly limited as long as it contains a copolymer having a repeating unit derived from at least one polymerizable compound selected from (meth) acrylic acid ester and (meth) acrylamide. It can also contain other components.
  • various components can be added depending on the purpose within a range not impairing the effects of the present invention.
  • Such components include binder resins, polymerization initiators, solvents, dehydrating agents, flame retardants, thermal stabilizers, antioxidants, lubricants, antistatic agents, ultraviolet absorbers, colorants and release agents, organic Examples include condensates of silane compounds, metal compounds, and the like. These can be used in combination of two or more.
  • the binder resin contained in the adhesive composition of the present invention includes (meth) acrylic resin, melamine resin, urethane resin, epoxy resin, silicone resin, polyester resin, polyamic acid resin, polyimide resin Resins, styrene maleic acid resins, styrene maleic anhydride resins, and the like can be used.
  • a curable resin such as an ionizing radiation curable resin or a thermosetting resin can also be used as the binder resin.
  • ionizing radiation curable resin refers to a resin that is cured by irradiation with ionizing radiation including all electromagnetic waves such as infrared rays, visible rays, ultraviolet rays, X-rays, and electron beams.
  • the ionizing radiation curable resin or thermosetting resin is not particularly limited, and monomers, prepolymers, oligomers, polymers, and the like having a vinyl group, a (meth) acryloyl group, an epoxy group, or an oxetanyl group can be used. . Among these, it is preferable to use a polyfunctional resin.
  • “(meth) acryloyl group” means “acryloyl group” and / or “methacryloyl group”.
  • the ionizing radiation curable resin and thermosetting resin include polyfunctional or monofunctional (meth) acrylate monomers or acrylate oligomers.
  • it preferably contains a polyfunctional acrylate having two or more polymerizable unsaturated groups.
  • the monofunctional acrylate monomer is a monomer having one (meth) acrylate group in the molecule, and examples thereof include tricyclodecane acrylate, isobornyl acrylate, tetrahydrofurfuryl acrylate, and phenoxyethyl acrylate.
  • (meth) acrylate group means “acrylate group” and / or “methacrylate group”.
  • the polyfunctional acrylate monomer is a monomer having 2 or more (preferably 2 to 6) (meth) acrylate groups in the molecule, such as tricyclodecane dimethylol diacrylate, neopentyl glycol diacrylate, Hydroxypivalate neopentyl glycol diacrylate, dioxane glycol diacrylate, trimethylolpropane triacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, ditrimethylolpropane tetraacrylate, bisphenol A type polyethoxylate diacrylate, dipentaerythritol pentaacrylate And dipentaerythritol hexaacrylate.
  • tricyclodecane dimethylol diacrylate such as tricyclodecane dimethylol diacrylate, neopentyl glycol diacrylate, Hydroxypivalate neopentyl glycol diacrylate
  • acrylate oligomer examples include an epoxy acrylate oligomer, a polyester polyacrylate oligomer, and a urethane acrylate oligomer.
  • polyfunctional or monofunctional (meth) acrylate monomers or oligomers can be used alone or in combination of two or more.
  • the adhesive composition of the present invention contains a polymerization initiator.
  • the polymerization initiator include a photopolymerization initiator and a thermal polymerization initiator.
  • Examples of the photopolymerization initiator that can be used in the present invention include 4- (2-hydroxyethoxy) phenyl (2-hydroxy-2-propyl) ketone [Darocur (registered trademark) -2959: manufactured by Merck & Co., Ltd.]; ⁇ -hydroxy - ⁇ , ⁇ '-dimethylacetophenone [Darocur (registered trademark) -1173: manufactured by Merck & Co., Ltd.]; Agents; benzoin ether initiators such as benzoin ethyl ether and benzoin isopropyl ether; other examples include halogenated ketones, acyl phosphinoxides, and acyl phosphonates.
  • the thermal polymerization initiator that can be used in the present invention includes an azo-based initiator and a peroxide-based initiator.
  • azo initiator examples include azobisisobutyronitrile, 1,1 ′ -azobis (cyclohexane-1-carbonitrile), 2,2 ′ -azobis ⁇ 2-methyl-N- [1,1- Bis (hydroxymethyl) ethyl] propionamide ⁇ , 2,2 ′]-azobis [2-methyl-N- (2-hydroxyethyl) propionamide], 2,2 ′ -azobis [2- (hydroxymethyl) propionitrile 2,2′2-azobis (2,4-dimethylvaleronitrile), 2,2 ′ -azobis (4-methoxy-2,4-dimethylvaleronitrile), dimethyl 2,2 ′ -azobisisobutyrate, 2,2 '-Azobis [2- (2-imidazolin-2-yl) propane], 2,2' -azobis ⁇ 2-methyl-N- [1,1-bis (hydroxymethyl) -2-hydro Xoxyethyl] propionamide ⁇ and the like.
  • peroxide-based initiators examples include benzoyl peroxide, isobutyryl peroxide, cumyl peroxyoctoate, and the like.
  • peroxide-based initiator one having a short thermal polymerization time and a stable reactive composition before polymerization can be appropriately selected.
  • the amount of the polymerization initiator used in the adhesive composition of the present invention is preferably 0.01 to 20% by weight, more preferably 0.1 to 10% by weight, based on the total amount of the curable resin. preferable.
  • the adhesive composition of the present invention may further contain a solvent.
  • a solvent for example, inorganic solvents, such as water, and an organic solvent can be used, These solvents may be used independently and may be used in combination of 2 or more type.
  • the adhesive composition of the present invention can contain an organic solvent.
  • organic solvents that can be used include ether-based, ester-based, aliphatic hydrocarbon-based, aromatic hydrocarbon-based, ketone-based, and organic halide-based solvents.
  • relatively inactive organic solvents such as propylene glycol monomethyl ether and propylene glycol monoethyl ether can also be used.
  • ester systems such as volatile acetates such as propyl acetate, butyl acetate, isoamyl acetate, heptyl acetate, ethyl butyrate, isoamyl isovalerate, etc.
  • the organic solvent is preferable.
  • dehydrating agent examples include methyl orthoformate, methyl orthoacetate, and tetraethoxysilane.
  • a brominated flame retardant usually used for thermoplastic resins is preferable, and an inorganic flame retardant may be used in combination.
  • brominated flame retardants include aliphatic types, aromatic types, phenol types, epoxy types, bisphenol types, biphenyl types, and the like.
  • the inorganic flame retardant include antimony trioxide, tin oxide, molybdenum oxide, and zinc borate.
  • heat stabilizer examples include phosphorus heat stabilizers such as phosphites and phosphates.
  • phosphites include triphenyl phosphite, trisnonylphenyl phosphite, tris (2,4-di-tert-butylphenyl) phosphite, trinonyl phosphite, tridecyl phosphite, trioctyl phosphite , Trioctadecyl phosphite, distearyl pentaerythritol diphosphite, tricyclohexyl phosphite, monobutyl diphenyl phosphite, monooctyl diphenyl phosphite, distearyl pentaerythritol diphosphite, bis (2,4-di-tert-butyl Phenyl) pentaeryth
  • phosphate esters include trimethyl phosphate, triethyl phosphate, tributyl phosphate, trioctyl phosphate, triphenyl phosphate, tricresyl phosphate, tris (nonylphenyl) phosphate, 2-ethylphenyldiphenyl phosphate, tetrakis (2,4-di-). tert-butylphenyl) -4,4-diphenylene phosphonite.
  • antioxidant examples include phenolic antioxidants, phosphorus antioxidants, phosphite antioxidants, thiourea antioxidants, and the like.
  • lubricant examples include higher fatty acids, ester waxes, polyethylene waxes, metal soaps and the like.
  • Antistatic agent examples include fatty acid amines, fatty acid alcohols, fatty acid esters, fatty acid amides, and sulfonic acid compounds.
  • UV absorber examples include benzotriazole compounds such as salicylic acid derivative compounds, benzophenone compounds, and benzotriazole derivatives, and cyanoacrylate compounds.
  • Examples of the colorant include organic pigments, inorganic pigments, dyes, and brighteners.
  • organic pigments include phthalocyanine, benzimidazolone, azo, azomethine azo, azomethine, anthraquinone, perinone / perylene, indigo / thioindigo, dioxazine, quinacridone, isoindoline, Examples thereof include indolinone pigments and carbon black pigments.
  • Examples of the inorganic pigments include extender pigments, titanium oxide pigments, iron oxide pigments, and spinnel pigments.
  • insoluble azo pigments such as Toluidine Red, Toluidine Maroon, Hansa Yellow, Benzidine Yellow, and Pyrazolone Red
  • soluble azo pigments such as Ritol Red, Helio Bordeaux, Pigment Scarlet, and Permanent Red 2B
  • phthalocyanine blue phthalocyanine green
  • Quinacridone series such as phthalocyanine, quinacridone red, quinacridone magenta, perylene series such as perylene red and perylene scarlet, isoindolinone series such as isoindolinone yellow and isoindolinone orange
  • pyranthrone series such as pyranthrone red and pyranthrone orange
  • Thioindigo condensed azo, benzimidazolone, quinophthalone yellow, nickel azo yellow, perinone orange, anthrone orange Dianthraquinonyl red
  • conventionally known pigments such as dioxazine violet
  • the dye conventionally known dyes such as direct dyes, basic dyes, cationic dyes, acid dyes, mordant dyes, acid mordant dyes, sulfur dyes, naphthol dyes, disperse dyes and reactive dyes can be used.
  • the brightening agent include aluminum paste, mica, and flake iron oxide.
  • release agent examples include at least one compound selected from aliphatic carboxylic acids, esters of aliphatic carboxylic acids and alcohols, aliphatic hydrocarbon compounds having a number average molecular weight of 200 to 15000, and polysiloxane silicone oils. Can do.
  • aliphatic carboxylic acid examples include saturated or unsaturated aliphatic monovalent, divalent or trivalent carboxylic acid.
  • the aliphatic carboxylic acid includes alicyclic carboxylic acid.
  • aliphatic carboxylic acid examples include palmitic acid, stearic acid, caproic acid, capric acid, lauric acid, arachidic acid, behenic acid, lignoceric acid, serotic acid, mellicic acid, tetrariacontanoic acid, montanic acid, adipic acid And azelaic acid.
  • the aliphatic carboxylic acid in the ester of an aliphatic carboxylic acid and an alcohol the same one as the aliphatic carboxylic acid can be used.
  • the alcohol that reacts with the aliphatic carboxylic acid to form an ester examples include saturated or unsaturated monohydric alcohols and saturated or unsaturated polyhydric alcohols.
  • aliphatic includes alicyclic compounds.
  • these alcohols include octanol, decanol, dodecanol, stearyl alcohol, behenyl alcohol, ethylene glycol, diethylene glycol, glycerin, pentaerythritol, 2,2-dihydroxyperfluoropropanol, neopentylene glycol, ditrimethylolpropane, dipentaerythritol. And so on.
  • These ester compounds of aliphatic carboxylic acids and alcohols may contain aliphatic carboxylic acids and / or alcohols as impurities, or may be a mixture of a plurality of compounds.
  • esters of aliphatic carboxylic acids and alcohols include beeswax (a mixture based on myricyl palmitate), stearyl stearate, behenyl behenate, stearyl behenate, glycerin monopalmitate, glycerin monostearate Mention may be made of rate, glycerol distearate, glycerol tristearate, pentaerythritol monopalmitate, pentaerythritol monostearate, pentaerythritol distearate, pentaerythritol tristearate, pentaerythritol tetrastearate.
  • Examples of the aliphatic hydrocarbon having a number average molecular weight of 200 to 15000 include liquid paraffin, paraffin wax, microwax, polyethylene wax, Fischer-Tropsch wax, and ⁇ -olefin oligomer having 3 to 12 carbon atoms.
  • an alicyclic hydrocarbon is also included.
  • these hydrocarbon compounds may be partially oxidized.
  • Examples of the polysiloxane silicone oil include dimethyl silicone oil, phenylmethyl silicone oil, diphenyl silicone oil, and fluorinated alkyl silicone. These may be used alone or in combination of two or more.
  • the adhesive composition of the present invention may contain a condensate of an organosilane compound for the purpose of making the coating film surface inorganic.
  • a glassy hard coat layer can be laminated on the surface of the plastic substrate.
  • the condensate of the organic silane compound can be produced by using a known silanol condensation method for the organic silane compound represented by the formula (A).
  • R 4 represents a C1-C30 alkyl group, a C2-C8 alkenyl group, or a C6-C10 aryl group optionally substituted with an epoxy group, a glycidyloxy group or a (meth) acryloxy group, R 3 represents a hydroxyl group or a hydrolyzable group.
  • n represents 1 or 2.
  • Examples of the C1-C30 alkyl group in R 4 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, n-pentyl group, isopentyl group.
  • neopentyl group 2-methylbutyl group, 2,2-dimethylpropyl group, n-hexyl group, isohexyl group, n-heptyl group, n-octyl group, nonyl group, isononyl group, decyl group, lauryl group, tridecyl group , Myristyl group, pentadecyl group, palmityl group, heptadecyl group, stearyl group and the like.
  • Examples of the C2-C8 alkenyl group include a vinyl group, an allyl group, and a 1-propenyl group.
  • the C6 to C10 aryl group include a phenyl group and a naphthyl group.
  • the hydrolyzable group of R 3 is a group that can be hydrolyzed to form a silanol group by heating at 25 ° C. to 100 ° C. under non-catalytic conditions or in the presence of excess water.
  • examples of the C1-C4 alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a t-butoxy group, and the like, and a C1-C6 acyloxy group.
  • examples of the halogeno group include a fluoro group, a chloro group, a bromo group, and an iodo group.
  • organic silane compound represented by the formula (A) examples include vinyltrichlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltributoxysilane, vinyltriisopropoxysilane, allyltrimethoxysilane, 3 -Butenyltrimethoxysilane, divinyldichlorosilane, divinyldiacetoxysilane, divinyldimethoxysilane, diallyldimethoxysilane, di-3-butenyldimethoxysilane, vinylmethyldimethoxysilane, vinylethyldiethoxysilane, methyltri (meth) acryloxysilane , Methyltris [2- (meth) acryloxyethoxy] silane, methyltriglycidyloxysilane, methyltris (3-methyl-3-oxetanemethoxy) silane, methyltrichlorosilane, methyltrime
  • silanol condensation method examples include a method using a silanol condensation catalyst.
  • the silanol condensation catalyst is not particularly limited as long as it hydrolyzes a hydrolyzable group in the compound represented by the formula (A) and condenses silanol to form a siloxane bond.
  • a silanol condensation catalyst can be used individually by 1 type or in combination of 2 or more types.
  • organic metal examples include alkyl metal compounds such as tetramethyl titanium and tetrapropyl zirconium; metal alcoholates such as tetraisopropoxy titanium and tetrabutoxy zirconium; and the like.
  • the organic acid metal salt is a compound composed of a salt obtained from a metal ion and an organic acid.
  • the organic acid include carboxylic acids such as acetic acid, oxalic acid, tartaric acid and benzoic acid; and sulfur-containing organic materials such as sulfonic acid and sulfinic acid. Examples include acids, phenolic compounds, enol compounds, oxime compounds, imide compounds, aromatic sulfonamides, and the like. Specific examples include carboxylic acid metal salts, sulfonic acid metal salts, phenol metal salts, and the like.
  • a metal hydroxide is a metal compound having a hydroxide ion as an anion.
  • the metal complex is preferably a metal complex having a hydroxyl group or a hydrolyzable group, and more preferably a metal complex having two or more hydroxyl groups or hydrolyzable groups.
  • having two or more hydroxyl groups or hydrolyzable groups means that the sum of hydrolyzable groups and hydroxyl groups is 2 or more.
  • the hydrolyzable group include an alkoxy group, an acyloxy group, a halogen group, and an isocyanate group, and a C1-C4 alkoxy group and a C1-C4 acyloxy group are preferable.
  • ⁇ -ketocarbonyl compounds ⁇ -ketoester compounds, and ⁇ -hydroxyester compounds are preferable.
  • methyl acetoacetate, n-propyl acetoacetate, isopropyl acetoacetate, n-acetoacetate ⁇ -ketoesters such as butyl, sec-butyl acetoacetate, t-butyl acetoacetate; acetylacetone, hexane-2,4-dione, heptane-2,4-dione, heptane-3,5-dione, octane ⁇ -diketones such as 2,4-dione, nonane-2,4-dione, and 5-methyl-hexane-2,4-dione; hydroxycarboxylic acids such as glycolic acid and lactic acid are coordinated to metal elements Compounds.
  • organic acid metal salts organic acid metal salts, metal hydroxides, and metal complexes, titanium (Ti), zirconium (Zr), aluminum (Al), silicon (Si), germanium (Ge), indium (In), tin (Sn), tantalum (Ta), zinc (Zn), tungsten (W), lead (Pb), etc.
  • titanium (Ti), zirconium (Zr), aluminum (Al) Tin (Sn) is preferable, and titanium (Ti) is particularly preferable. These may be used alone or in combination of two or more.
  • acids include organic acids and mineral acids.
  • organic acids include acetic acid, formic acid, oxalic acid, phthalic acid, trifluoroacetic acid, p-toluenesulfonic acid, and methanesulfonic acid.
  • mineral acids include hydrochloric acid and nitric acid. , Carbonic acid, boric acid, borohydrofluoric acid and the like.
  • a photoacid generator that generates an acid by light irradiation, specifically, diphenyliodonium hexafluorophosphate, triphenylphosphonium hexafluorophosphate, and the like are also included in the acid.
  • the base examples include strong bases such as tetramethylguanidine and tetramethylguanidylpropyltrimethoxysilane; organic amines, carboxylic acid neutralized salts of organic amines, quaternary ammonium salts, and the like.
  • the compounding ratio of the silanol condensation catalyst is 1:99 to 99: 1, preferably 1:99 to 50:50 with respect to the mass of the organosilane compound.
  • Metal compounds, etc. A metal compound can be added to the adhesive composition of the present invention for the purpose of increasing the refractive index and hardness of the coating film.
  • the metal compound include the organic silane compounds described above, organic metals exemplified as silanol condensation catalysts, organic acid metal salts, metal hydroxides, and metal complexes.
  • Other metal compounds include metal oxides. Specifically, metal oxide particles of silicon dioxide, titanium oxide, aluminum oxide, chromium oxide, manganese oxide, iron oxide, zirconium oxide (zirconia), cobalt oxide, and the like can be given. Zirconium oxide is particularly preferable.
  • colloidal metal oxide particles can also be used as the metal oxide particles of the present invention. Specific examples include colloidal silica and colloidal zirconium, and water-dispersed colloidal or organic solvent-dispersed colloidal metal oxide particles such as methanol or isopropanol.
  • additives such as various surfactants, other silane coupling agents, titanium coupling agents, dyes, dispersants, thickeners, and leveling agents are added to the adhesive composition of the present invention. If necessary, additive components such as a sensitizer, a rust inhibitor, and a preservative can be blended.
  • the copolymer of the present invention is excellent in solubility.
  • the adhesive composition of the present invention is also excellent in moldability.
  • the adhesive composition in the present invention is usually at least one selected from a repeating unit derived from a polymerizable compound represented by formula (I) in an organic solvent, (meth) acrylic acid ester, and (meth) acrylamide.
  • a copolymer having a repeating unit derived from a polymerizable compound it is prepared by mixing the polymerizable compound, a condensate of the organosilane compound, a photopolymerization initiator, a metal compound, and the like, if necessary.
  • the solid content in the adhesive composition of the present invention is preferably 1 to 90% by mass, and more preferably 5 to 60% by mass.
  • Molded body The molded body of the present invention is obtained by directly applying a film (coating film) obtained by applying the adhesive composition onto a plastic substrate and curing the adhesive composition. is there.
  • the base material on which the adhesive composition of the present invention can be used is preferably a plastic base material.
  • cycloolefin resins such as cycloolefin polymers and cycloolefin copolymers; polyethylene, polypropylene, polyisoprene, polybutadiene, polymethyl Polyolefin resins such as pentene, polycarbonate resins, polyisocyanate resins, polyimide resins, polyester resins, acrylic resins, methacrylic resins, epoxy resins, polyethylene terephthalate resins, and aromatic polyether ketone resins.
  • cycloolefin resin and polyolefin resin are preferably used.
  • the adhesive composition of the present invention since the copolymer adheres firmly to the surface of the substrate, a coating film can be formed only by heating and drying after applying the adhesive composition.
  • the adhesive composition further contains a polymerizable compound (binder resin), it is preferable to perform an ultraviolet irradiation treatment using a photopolymerization initiator in combination or a heat treatment using a thermal polymerization initiator in combination. Since it is not necessary to modify the substrate surface by UV ozone treatment or the like, the initial characteristics of the plastic substrate can be maintained.
  • a coating method of the adhesive composition As a coating method of the adhesive composition, a known coating method can be used, and a dipping method, a spray method, a bar coating method, a roll coating method, a spin coating method, a curtain coating method, a gravure printing method, a silk screen method, An ink jet method is exemplified. Further, the thickness of the coating film to be formed is not particularly limited, and is about 0.1 to 200 ⁇ m.
  • the heat drying treatment of the coating film is preferably performed at 40 to 200 ° C. for about 0.5 to 120 minutes, more preferably at 60 to 120 ° C. for about 1 to 60 minutes.
  • Irradiation with ultraviolet rays can be performed using a known apparatus such as a high-pressure mercury lamp, a low-pressure mercury lamp, a metal halide lamp, or an excimer lamp.
  • the heat treatment can be performed continuously with the drying treatment.
  • the coating film of the present invention Since the coating film of the present invention has very good adhesion to a plastic substrate, the coating film of the present invention can be used as a primer layer. Thereby, the functional film that could not be directly formed on the conventional plastic substrate can be laminated via the coating film of the present invention. A plurality of layers can be laminated, and the coating agent of the present invention can be further applied on the plurality of layers and further laminated.
  • Examples of the functional film include a conductive film, an antireflection film, a gas barrier film, a hard coat film, a water repellent film, and a hydrophilic film.
  • Examples of the conductive film include an indium oxide film doped with tin (ITO film), a tin oxide film doped with fluorine (FTO film), a zinc oxide film doped with antimony, and a zinc oxide film doped with indium. Can be mentioned.
  • the gas barrier film is not particularly limited as long as it has gas barrier properties such as oxygen and water vapor, but is preferably a thin film of an inorganic compound, in particular, titanium, zirconium, aluminum, silicon, germanium, indium, tin, tantalum, zinc, A thin film of a metal oxide, metal nitride, metal carbide or a composite thereof having a metal element selected from the group consisting of tungsten and lead is preferred.
  • the thickness of these functional films is usually 10 to 300 nm, preferably 10 to 200 nm, more preferably 10 to 100 nm.
  • a method for forming a conductive film, a gas barrier film, or the like made of an inorganic compound on the coating film of the present invention can be formed by a known method, such as a sputtering method, a vacuum deposition method, an ion plating method, etc. Or a chemical method such as a spray method, a dipping method, a thermal CVD method, or a plasma CVD method.
  • a film made of silicon oxide can be formed by using a silicon compound sintered in the presence of oxygen gas as a target, and metal silicon can be used as a target in the presence of oxygen.
  • a film can also be formed by reactive sputtering.
  • a film made of silicon oxynitride can be formed on a substrate by supplying silane gas together with oxygen gas and nitrogen gas into a chamber in which plasma is generated and reacting them.
  • a film made of silicon oxide can be formed by using an organic solvent solution containing a silicon compound as an evaporant.
  • the functional film it is particularly preferable to form the functional film by sputtering, vacuum deposition, ion plating, or plasma CVD. Further, when forming the functional film, the surface of the coating film of the present invention may be previously subjected to plasma treatment or UV ozone treatment as necessary.
  • the coating film of the present invention can also be used as an adhesive layer used when bonding plastic substrates to each other or between a plastic substrate and another molded sheet.
  • Molded sheets include: polyvinyl chloride resin, cellulose resin, polyethylene resin, polystyrene resin, ABS resin, polyamide resin, polyester resin, polyurethane resin, cycloolefin resin, etc .; plastic sheet; polarizing plate, retardation Examples thereof include optical films such as films and antireflection films; metal foils such as aluminum, copper and silicone;
  • DPAA N, N-diphenylacrylamide
  • DEAA diethylacrylamide
  • Mn 27,300
  • Mw / Mn 1.88
  • Example 1 A 10 wt% cyclohexanone solution was prepared for (Example 1), (Example 2), (Example 3), (Example 4), and (Example 5). This solution was applied onto a substrate by a bar coating method. A cross-cut tape peeling test (JIS K5400) was performed on the coating film dried at 80 ° C. for 3 minutes and cooled to room temperature. The evaluation results are shown in Table 1. The same results were obtained in Example 1 even at a drying time of 120 ° C.
  • the adhesive composition of the present invention is excellent in adhesiveness and solubility in various solvents and resins.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

La présente invention aborde le problème consistant à fournir une composition adhésive présentant une excellente adhérence à des résines de cyclooléfine, et analogues. La composition adhésive de l'invention contient un copolymère comportant : un motif répétitif dérivé d'un composé polymérisable représenté par la formule ((I) (formule (I) : Y-N(Ar)(R)) (dans la formule : Ar représente un groupe aryle en C6-C14 non substitué ou substitué ou un groupe (aryle en C6-C10)(alkyle en C1-C3) non substitué ou substitué ; R représente un groupe alkyle en C1-C6 non substitué ou substitué, un groupe cycloalkyle en C3-C6 non substitué ou substitué, un groupe aryle en C6-C14 non substitué ou substitué, ou un groupe (aryle en C6-C10)(alkyle en C1-C3) non substitué ou substitué ; Y représente un groupe fonctionnel polymérisable ; et le substituant sur Ar et le substituant sur R peuvent former ensemble un groupe organique divalent) ; et un motif répétitif dérivé d'au moins un composé polymérisable choisi parmi les esters de l'acide (méth)acrylique et le (méth)acrylamide.
PCT/JP2019/015781 2018-04-13 2019-04-11 Composition adhésive WO2019198792A1 (fr)

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WO2020071456A1 (fr) * 2018-10-05 2020-04-09 日本曹達株式会社 Composition adhésive
WO2020262423A1 (fr) * 2019-06-27 2020-12-30 日本曹達株式会社 Composition adhésive
US20230118487A1 (en) * 2020-04-03 2023-04-20 Nippon Soda Co., Ltd. Two-component adhesive composition
EP4130166A4 (fr) * 2020-04-03 2024-04-10 Nippon Soda Co., Ltd. Composition adhésive

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JP2004217697A (ja) * 2003-01-09 2004-08-05 Asahi Kasei Corp アミド系ブロック共重合体
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020071456A1 (fr) * 2018-10-05 2020-04-09 日本曹達株式会社 Composition adhésive
US11834390B2 (en) 2018-10-05 2023-12-05 Nippon Soda Co., Ltd. Adhesive composition
WO2020262423A1 (fr) * 2019-06-27 2020-12-30 日本曹達株式会社 Composition adhésive
US20230118487A1 (en) * 2020-04-03 2023-04-20 Nippon Soda Co., Ltd. Two-component adhesive composition
EP4130166A4 (fr) * 2020-04-03 2024-04-10 Nippon Soda Co., Ltd. Composition adhésive

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