WO2010086924A1 - Composition d'adhésif durcissable à l'humidité résistant à la chaleur à un seul composant pour résine de polycarbonate - Google Patents

Composition d'adhésif durcissable à l'humidité résistant à la chaleur à un seul composant pour résine de polycarbonate Download PDF

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Publication number
WO2010086924A1
WO2010086924A1 PCT/JP2009/005103 JP2009005103W WO2010086924A1 WO 2010086924 A1 WO2010086924 A1 WO 2010086924A1 JP 2009005103 W JP2009005103 W JP 2009005103W WO 2010086924 A1 WO2010086924 A1 WO 2010086924A1
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Prior art keywords
adhesive composition
polycarbonate
group
polycarbonate resin
resistant
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PCT/JP2009/005103
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English (en)
Japanese (ja)
Inventor
馬淵俊介
堀大祐
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セメダイン株式会社
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Priority to CN2009801525076A priority Critical patent/CN102264857A/zh
Priority to KR1020117011289A priority patent/KR101413125B1/ko
Priority to JP2010548267A priority patent/JP5590325B2/ja
Publication of WO2010086924A1 publication Critical patent/WO2010086924A1/fr

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    • 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
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • 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
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/06—Polyurethanes from polyesters
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/161—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22
    • C08G18/163—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22 covered by C08G18/18 and C08G18/22
    • C08G18/165—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22 covered by C08G18/18 and C08G18/22 covered by C08G18/18 and C08G18/24
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/20—Heterocyclic amines; Salts thereof
    • C08G18/2081—Heterocyclic amines; Salts thereof containing at least two non-condensed heterocyclic rings
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/24—Catalysts containing metal compounds of tin
    • C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/44—Polycarbonates
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4825—Polyethers containing two hydroxy 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
    • 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
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • 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
    • C09J169/00—Adhesives based on polycarbonates; Adhesives based on derivatives of polycarbonates
    • 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
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/08—Polyurethanes from polyethers

Definitions

  • the present invention relates to an adhesive composition for polycarbonate resin that joins polycarbonate resins together, and particularly relates to an adhesive composition for a one-component moisture-curable polycarbonate resin that is excellent in heat resistance and adhesion to polycarbonate.
  • PC polycarbonate
  • PS polystyrene
  • PPS polyphenylene sulfite
  • PET PET
  • PBT polybutylene terephthalate
  • Patent Document 1 discloses a first component (A) composed of a mixture of a polyfunctional isocyanate compound having an isocyanate group at the end and an organotin compound, a polyfunctional mercapto compound having a mercapto group at the end, and both ends. Discloses a two-component type adhesive for polycarbonate, comprising a second component (B) comprising a mixture of polycarbonate diols having OH groups.
  • the adhesive described in Patent Document 1 has initial adhesiveness to polycarbonate, since it is a two-component type, troubles such as mixing are caused in work.
  • Patent Document 2 discloses a solvent-type adhesive for joining polycarbonate resin plates together, which is 1,4-dioxane, 1,1,1-trichloroethane, acetic acid, methyl isobutyl.
  • a solvent-type adhesive for polycarbonate resin plates is disclosed which comprises at least one solvent selected from the group consisting of ketones and n-butyl alcohol.
  • An object of the present invention is to provide a one-component moisture-curing type polycarbonate resin adhesive composition excellent in heat resistance, adhesion to polycarbonate and workability.
  • the heat-resistant one-component moisture-curable polycarbonate resin adhesive composition of the present invention is an adhesive composition for polycarbonate resin that joins polycarbonate resins together, and includes polytetramethylene glycol, modified Urethane prepolymer (A) having an isocyanate group at the terminal obtained by reacting at least one polyol selected from the group consisting of polytetramethylene glycol and polycarbonate polyol with polyisocyanate, and tertiary amine catalyst and tin It includes one or more curing catalysts (B) selected from the group consisting of catalysts.
  • polytetramethylene glycol modified Urethane prepolymer having an isocyanate group at the terminal obtained by reacting at least one polyol selected from the group consisting of polytetramethylene glycol and polycarbonate polyol with polyisocyanate
  • tertiary amine catalyst and tin It includes one or more curing catalysts (B) selected from the group consisting of catalysts.
  • the heat-resistant one-component moisture-curable polycarbonate resin adhesive composition of the present invention preferably further contains silica (C).
  • the adhesive composition of the present invention is excellent in heat resistance and adhesiveness to polycarbonate, and is used as an adhesive or fixing agent for assembly of electrical products or precision equipment that requires heat resistance and adhesiveness to polycarbonate. It has a remarkable effect that it has excellent performance and low viscosity but excellent long-term storage stability. Furthermore, since the adhesive composition of the present invention is a one-component system and is cured at room temperature by moisture in the air, it is excellent in workability.
  • the adhesive composition of the present invention is an adhesive composition for a polycarbonate resin that joins polycarbonate resins together, and is a urethane prepolymer (A) having an isocyanate group at the terminal obtained by reacting a polyol and a polyisocyanate. And one or more curing catalysts (B) selected from the group consisting of a tertiary amine catalyst and a tin catalyst, and the polyol is selected from the group consisting of polytetramethylene glycol, modified polytetramethylene glycol and polycarbonate polyol. It contains one or more selected.
  • polytetramethylene glycol known tetrahydrofuran polymers can be widely used.
  • the molecular weight of the polytetramethylene glycol is not particularly limited, but preferably has a number average molecular weight of 500 to 5000, more preferably 500 to 2000.
  • the polytetramethylene glycol may be used alone or in combination of two or more.
  • the modified polytetramethylene glycol is a copolymer of tetramethylene ether and alkylene ether, and the alkylene ether preferably has a side chain.
  • the modified polytetramethylene glycol include a copolymer of tetrahydrofuran and an alkyl-substituted tetrahydrofuran, a copolymer of tetrahydrofuran and an alkylene oxide, a copolymer of tetrahydrofuran and an alkylene ether having a side chain, and the like.
  • Preferred examples of the copolymer of tetrahydrofuran and alkyl-substituted tetrahydrofuran include a copolymer of tetrahydrofuran and 3-alkyltetrahydrofuran described in JP-A-63-235320.
  • the molecular weight of the modified polytetramethylene glycol is not particularly limited, but it is preferable to use a number average molecular weight of 500 to 5000, more preferably 1000 to 3000.
  • the modified polytetramethylene glycol may be used alone or in combination of two or more.
  • polycarbonate polyol a polyol having a structure represented by the following general formula (1) is suitable.
  • X is a hydrocarbon group
  • n is a natural number
  • R 1 is a linear alkylene group such as a methylene group, an ethylene group or an n-propylene group, an isopropylene group, sec-butylene.
  • Groups, branched alkylene groups such as tert-butylene, 1,1-cyclohexylene group, 1,2-cyclohexylene group, 1,3-cyclohexylene group, 1,4-cyclohexylene group, etc.
  • R 1 Shows alicyclic hydrocarbon group, arylene group such as phenylene group and naphthylene group, ether group such as oxymethylene group and oxypropylene group, bisphenol type skeleton such as bisphenol A, bisphenol F, bisphenol S, etc.
  • R 1 may be substituted with various substituents such as halogeno groups such as fluorine, chlorine and bromine, cyano groups, carboxyl groups, sulfonic acid groups, nitro groups, hydroxy groups and alkoxy groups.
  • R 1 represents an unsaturated group such as a vinylene group, a carbonyl group, a carboxyl group, an ether group, a thioether group, a urethane group, a urea group, a thiourea group, etc. at one end, both ends, inside or in a repeating unit. Or a plurality of them may be included. R 1 may be the same or different.
  • the molecular weight of the polycarbonate polyol is not particularly limited, but it is preferable to use one having a number average molecular weight of 300 to 3000, more preferably 500 to 2000.
  • the said polycarbonate polyol may be used independently and may be used in combination of 2 or more type.
  • the polytetramethylene glycol, the modified polytetramethylene glycol and the polycarbonate polyol may be used alone or in combination of two or more, and the combination is not particularly limited, but from the viewpoint of workability, the modified polytetramethylene. It is preferable to use glycol.
  • the urethane prepolymer (A) may be synthesized by reacting two or more polyols with a polyisocyanate. Two or more urethane prepolymers (A) having different polyol components may be synthesized. You may mix and use.
  • the total amount of the polytetramethylene glycol, the modified polytetramethylene glycol and the polycarbonate polyol is preferably 10% by mass or more, more preferably 30% by mass or more based on the total polyol.
  • the other polyol may be any active hydrogen-containing compound having two or more active hydrogen groups, and is not particularly limited.
  • other polyethers such as trifunctional or higher polyhydric alcohols, diols, and polypropylene glycol (PPG).
  • Polyols polyester polyols, polybutadiene polyols, polyisoprene polyols, polyolefin polyols, polymer polyols, polycaprolactone polyols, polyacrylate polyols, and the like. These polyols may be used alone or in combination of two or more. Also good.
  • the polyisocyanate is not particularly limited, and a known polyisocyanate compound having two or more isocyanate groups can be used.
  • diphenylmethane diisocyanate MDI
  • tolylene diisocyanate TDI
  • xylene diisocyanate XDI
  • aromatic polyisocyanates such as naphthalene diisocyanate
  • aliphatic polyisocyanates such as hexamethylene diisocyanate (HDI) and lysine methyl ester diisocyanate
  • fats such as hydrogenated diphenylmethane diisocyanate, isophorone diisocyanate, norbornane diisocyanate and hydrogenated tolylene diisocyanate Cyclic polyisocyanates are mentioned.
  • MDI is preferable from the viewpoint of cost and reactivity, but XDI is preferable in consideration of discoloration such as yellowing.
  • a method for reacting the polyol component with the polyisocyanate is not particularly limited, and a known method can be used. Specifically, the polyol component having two or more hydroxyl groups (OH) and the polyisocyanate having two or more isocyanate groups (NCO) are used so that the isocyanate groups become excessive, that is, the NCO / OH equivalent ratio is more than 1. By making it react so that it may become large, the urethane prepolymer which has an isocyanate group at the terminal is obtained.
  • the reaction conditions are not particularly limited.
  • the NCO / OH equivalent ratio is 1.3 to 10.0, more preferably 1.5 to 5.0, in a nitrogen or dry air stream.
  • the adhesive composition of the present invention may further contain other known urethane prepolymers other than the urethane prepolymer (A).
  • the total amount of the urethane prepolymer (A) is preferably 10% by mass or more based on the total urethane prepolymer in the adhesive composition of the present invention, and 30% by mass. More preferably.
  • the other urethane prepolymer a urethane prepolymer having an isocyanate group at the terminal obtained by reacting an isocyanate compound with another polyol other than polytetramethylene glycol, modified polytetramethylene glycol and polycarbonate polyol. Is mentioned.
  • the other polyol may be any active hydrogen-containing compound having two or more active hydrogen groups, and is not particularly limited.
  • other polyhydric alcohols such as trifunctional or higher polyhydric alcohols, diols, and polypropylene glycol (PPG) are used.
  • PPG polypropylene glycol
  • examples include ether polyols, polyester polyols, polybutadiene polyols, polyisoprene polyols, polyolefin polyols, polymer polyols, polycaprolactone polyols, and polyacrylate ester polyols. These polyols may be used alone or in combination of two or more. May be.
  • tertiary amine catalyst used in the curing catalyst (B) known tertiary amines can be widely used.
  • organic tin compounds can be widely used as the tin catalyst used in the curing catalyst (B).
  • divalent organic tin compounds such as tin octylate and tin naphthenate; dibutyltin dioctoate, dibutyltin 4 such as dilaurate, dibutyltin diacetate, dibutyltin dimaleate, dibutyltin distearate, dioctyltin dilaurate, dioctyltin diversate, dibutyltin oxide, dibutyltin bis (triethoxysilicate), reaction product of dibutyltin oxide and phthalate Valent organic tin compounds; tin-based chelate compounds such as dibutyltin bis (acetylacetonate);
  • the blending ratio of the curing catalyst (B) is not particularly limited, but is preferably 0.01 to 10 parts by weight, preferably 0.01 to 2 parts by weight with respect to 100 parts by weight of the urethane prepolymer (A). More preferably.
  • the tertiary amine catalyst and tin catalyst may be used alone or in combination of two or more.
  • the adhesive composition of the present invention further contains silica (C).
  • the silica (C) include fumed silica, calcined silica, precipitated silica, pulverized silica, fused silica and the like, and it is preferable to use fine powder silica.
  • the blending ratio of the silica (C) is not particularly limited, but it is preferably 0.5 to 30.0 parts by weight with respect to 100 parts by weight of the urethane prepolymer (A), preferably 3.0 to 15.0. It is more preferable to mix part by mass.
  • the adhesive composition of the present invention includes a filler, a plasticizer, a colorant, a discoloration preventing agent, an adhesion-imparting agent, a physical property modifier, a release agent, a lubricant, and a dehydrating agent (if necessary) Storage stability improver), tackifiers, sag-preventing agents, UV absorbers, antioxidants, hydrolysis stabilizers, flame retardants, radical polymerization initiators, and other additives such as high-boiling solvents May be.
  • the filler examples include organic or inorganic materials of various shapes, such as calcium carbonate, magnesium carbonate, zinc carbonate; carbon black; clay; talc; kaolin; diatomaceous earth; zeolite; titanium oxide, quicklime, iron oxide. , Zinc oxide, barium oxide, magnesium oxide; aluminum sulfate; vinyl chloride paste resin; inorganic balloons such as glass balloons, shirasu balloons, saran balloons, phenol balloons, vinylidene chloride resin balloons, etc .; or their fatty acids, fatty acid esters A processed material etc. are mentioned, It can use individually or in mixture. Moreover, you may use inorganic hollow fillers, such as a glass balloon and a silica balloon, and organic hollow fillers, such as a polyvinylidene fluoride and a polyvinylidene fluoride copolymer.
  • inorganic hollow fillers such as a glass balloon and a silica balloon
  • organic hollow fillers such as
  • plasticizer examples include dioctyl phthalate (DOP), dibutyl phthalate (DBP), dilauryl phthalate (DLP), butyl benzyl phthalate (BBP), dioctyl adipate, diisononyl phthalate, diisodecyl adipate, diisodecyl phthalate, and trioctyl phosphate.
  • DOP dioctyl phthalate
  • DBP dibutyl phthalate
  • DLP dilauryl phthalate
  • BBP butyl benzyl phthalate
  • dioctyl adipate diisononyl phthalate
  • diisodecyl adipate diisodecyl phthalate
  • trioctyl phosphate Tris (chloroethyl) phosphate, tris (dichloropropyl) phosphate
  • propylene glycol adipate polyester but
  • the ultraviolet absorber examples include benzotriazole ultraviolet absorbers such as 2- (3,5-di-tert-butyl-2-hydroxyphenyl) -5-chlorobenzotriazole, and 2- (4,6-diphenyl). -1,3,5-triazin-2-yl) -5-[(hexyl) oxy] -phenol and other triazine ultraviolet absorbers, benzophenone ultraviolet absorbers such as octabenzophene, 2,4-di-tert And benzoate ultraviolet absorbers such as -butylphenyl-3,5-di-tert-butyl-4-hydroxybenzoate.
  • benzotriazole ultraviolet absorbers such as 2- (3,5-di-tert-butyl-2-hydroxyphenyl) -5-chlorobenzotriazole, and 2- (4,6-diphenyl).
  • 2- (3,5-di-tert-butyl-2-hydroxyphenyl) -5-chlorobenzotriazole
  • antioxidants examples include hindered phenol compounds and triazole compounds.
  • hindered phenol antioxidant examples include pentaerythritol-tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], octadecyl-3- (3,5-di-tert.
  • hydrolysis stabilizer examples include aromatic carbodiimides, and carbodiimide monomers having a melting point of about 40 ° C., low molecular weight polymers having a melting point of 60 to 90 ° C., and carbodiimide polymers having a melting point of 100 to 120 ° C. are preferable.
  • the hydrolysis stabilizer is preferably blended in an amount of 0.01 to 3.0 parts by weight, more preferably 0.1 to 2.0 parts by weight with respect to 100 parts by weight of the urethane prepolymer (A). .
  • organic halogen compounds, phosphorus compounds, nitrogen-containing compounds such as (iso) cyanuric acid derivative compounds, inorganic compounds, and the like can be blended.
  • nitrogen-containing compounds such as (iso) cyanuric acid derivative compounds, inorganic compounds, and the like
  • the parts of the product can be bonded using the adhesive composition of the present invention.
  • products include electrical products such as speakers, video cassette players, televisions, radios, vending machines, refrigerators, personal computers, card-type batteries, video cameras, and other automobile parts and precision equipment.
  • Examples 1 to 14 In the formulation shown in Table 2, after stirring and mixing the urethane prepolymer, silica and diluent at room temperature under a nitrogen stream, a curing catalyst was added and stirring and mixing was performed at room temperature under a nitrogen stream to obtain an adhesive composition. It was.
  • prepolymers A1 to A3 are urethane prepolymers A1 to A3 synthesized in Synthesis Examples 1 to 3, respectively, and prepolymers X and Y are comparative synthesis examples, respectively.
  • These are urethane prepolymers X and Y synthesized in 1 and 2, and * 7 to * 10 are as follows.
  • Amine-based curing catalyst bis (morpholinoethyl) ether * 8) Tin-based curing catalyst: manufactured by Nitto Kasei Co., Ltd., trade name STANN BL, dioctyltin diversate * 9)
  • Silica manufactured by Nippon Aerosil Kogyo Co., Ltd.
  • Product name RY200S fumed silica * 10)
  • Diluent Japan Energy Co., Ltd., product name Normal Paraffin N-11
  • Adhesion test 1-1) Initial adhesion test A test was carried out in accordance with JISK6850. As the adherend, 100 ⁇ 25 ⁇ 3 mm polycarbonate (Mitsubishi Gas Chemical Co., Ltd., trade name Iupilon sheet NF2000V) was used. The adhesive composition was applied to a thickness of about 100 ⁇ m, and after bonding for 5 minutes with an open time. Then, what was aged for one week at 23 degreeC50% RH was made into the initial stage adhesive test body. The evaluation criteria are as follows.
  • Adhesive strength is 2.0 N / mm 2 or more and the fracture state indicates cohesive failure of the adhesive layer
  • Adhesive strength is 1.0 or more and less than 2.0 N / mm 2 or the fracture state is the interface of the adhesive surface With breakage
  • Ti value is 3.0 or more ⁇ : Ti value is 2.0 or more and less than 3.0 ⁇ : Ti value is 1.5 or more and less than 2.0 ⁇ : Ti value is less than 1.5
  • the adhesive composition of the present invention was excellent in initial adhesiveness and heat-resistant adhesiveness to polycarbonate, and excellent in workability, curability and storage stability.
  • Example 3 The test was conducted in the same manner as in Example 1 using a modified silicone adhesive (trade name 1530, manufactured by Three Bond Co., Ltd.). The results are shown in Table 5.
  • Example 4 A test was conducted in the same manner as in Example 1 using a urethane (polypropylene glycol-MDI) adhesive (trade name UM600V, manufactured by Cemedine Co., Ltd.). The results are shown in Table 5.
  • a urethane (polypropylene glycol-MDI) adhesive (trade name UM600V, manufactured by Cemedine Co., Ltd.). The results are shown in Table 5.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention porte sur une composition d'adhésif durcissable à l'humidité à un seul composant pour une résine de polycarbonate présentant d'excellentes qualités de résistance à la chaleur, d'adhésivité au polycarbonate et d'aptitude au façonnage. La composition d'adhésif pour une résine de polycarbonate devant être utilisée pour coller des résines de polycarbonate les unes aux autres, renferme (A) un prépolymère d'uréthane présentant un groupe isocyanate à une de ses extrémités obtenu par réaction d'un polyisocyanate avec au moins un polyol choisi dans un groupe constitué par les polytétraméthylèneglycols, les polytétraméthylèneglycols modifiés et les polycarbonate-polyols et (B) au moins catalyseur de durcissement choisi dans un groupe constitué par les catalyseurs amines tertiaires et les catalyseurs à l'étain.
PCT/JP2009/005103 2009-01-29 2009-10-02 Composition d'adhésif durcissable à l'humidité résistant à la chaleur à un seul composant pour résine de polycarbonate WO2010086924A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN2009801525076A CN102264857A (zh) 2009-01-29 2009-10-02 耐热性一液湿气固化型聚碳酸酯树脂用粘接剂组合物
KR1020117011289A KR101413125B1 (ko) 2009-01-29 2009-10-02 내열성 일액형 습기 경화형 폴리카보네이트 수지용 접착제 조성물
JP2010548267A JP5590325B2 (ja) 2009-01-29 2009-10-02 耐熱性一液湿気硬化型ポリカーボネート樹脂用接着剤組成物

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JP2009-018585 2009-01-29
JP2009018585 2009-01-29

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CN (1) CN102264857A (fr)
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WO (1) WO2010086924A1 (fr)

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KR20200047444A (ko) 2017-09-15 2020-05-07 세키스이가가쿠 고교가부시키가이샤 광습기 경화형 수지 조성물, 전자 부품용 접착제 및 표시 소자용 접착제

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CN111108245B (zh) * 2017-09-25 2022-12-30 Dic株式会社 合成皮革的制造方法

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JPH0841155A (ja) * 1994-08-03 1996-02-13 Dainippon Ink & Chem Inc 湿気硬化性ポリウレタン組成物
JPH11116652A (ja) * 1997-10-09 1999-04-27 Mitsui Chem Inc 湿気硬化性ウレタン樹脂組成物
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JPH02155979A (ja) * 1988-12-08 1990-06-15 Mitsui Toatsu Chem Inc ポリカーボネート用接着剤
JPH0616764A (ja) * 1992-04-27 1994-01-25 Asahi Glass Co Ltd ポリウレタン系硬化性組成物
JPH0841155A (ja) * 1994-08-03 1996-02-13 Dainippon Ink & Chem Inc 湿気硬化性ポリウレタン組成物
JPH11116652A (ja) * 1997-10-09 1999-04-27 Mitsui Chem Inc 湿気硬化性ウレタン樹脂組成物
JPH11263963A (ja) * 1998-03-17 1999-09-28 Konishi Co Ltd １液湿気硬化型ウレタン系液状タイプ接着剤組成物
JP2000104036A (ja) * 1998-09-28 2000-04-11 Sekisui Chem Co Ltd 湿気硬化型接着剤組成物
JP2003138239A (ja) * 2001-10-30 2003-05-14 Auto Kagaku Kogyo Kk 一液湿気硬化型ポリウレタン系接着剤及びこれを用いた床材の接着方法
JP2007153912A (ja) * 2005-11-30 2007-06-21 Sanyo Chem Ind Ltd ドライラミネート用接着剤の製造法

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Publication number Priority date Publication date Assignee Title
KR20200047444A (ko) 2017-09-15 2020-05-07 세키스이가가쿠 고교가부시키가이샤 광습기 경화형 수지 조성물, 전자 부품용 접착제 및 표시 소자용 접착제

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JP5590325B2 (ja) 2014-09-17
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TWI447196B (zh) 2014-08-01
CN102264857A (zh) 2011-11-30
TW201028450A (en) 2010-08-01

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