WO2020137246A1 - 硬化性組成物及び電子機器 - Google Patents

硬化性組成物及び電子機器 Download PDF

Info

Publication number
WO2020137246A1
WO2020137246A1 PCT/JP2019/044990 JP2019044990W WO2020137246A1 WO 2020137246 A1 WO2020137246 A1 WO 2020137246A1 JP 2019044990 W JP2019044990 W JP 2019044990W WO 2020137246 A1 WO2020137246 A1 WO 2020137246A1
Authority
WO
WIPO (PCT)
Prior art keywords
curable composition
epoxy
isocyanate
compound
case
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2019/044990
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
奥平　浩之
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Denso Corp
Original Assignee
Denso Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Denso Corp filed Critical Denso Corp
Priority to DE112019006551.3T priority Critical patent/DE112019006551T5/de
Priority to CN201980085725.6A priority patent/CN113228203A/zh
Publication of WO2020137246A1 publication Critical patent/WO2020137246A1/ja
Priority to US17/354,715 priority patent/US20210317251A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • 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
    • C08G18/70—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
    • 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
    • C08G18/003—Polymeric products of isocyanates or isothiocyanates with epoxy compounds having no active hydrogen
    • 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
    • C08G18/166—Catalysts not provided for in the groups C08G18/18 - C08G18/26
    • C08G18/168—Organic compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • 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
    • C08G18/246—Catalysts containing metal compounds of tin tin salts of carboxylic acids containing also tin-carbon bonds
    • 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
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/36—Hydroxylated esters of higher fatty 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
    • C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
    • C08G18/4063—Mixtures of compounds of group C08G18/62 with other macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • 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
    • C08G18/58—Epoxy resins
    • 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
    • C08G18/58—Epoxy resins
    • C08G18/581—Reaction products of epoxy resins with less than equivalent amounts of compounds containing active hydrogen added before or during the reaction with the isocyanate component
    • 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
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6204—Polymers of olefins
    • C08G18/6208—Hydrogenated polymers of conjugated dienes
    • 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
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
    • C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
    • C08G18/6225—Polymers of esters of acrylic or methacrylic acid
    • C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
    • 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
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • 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
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/8064—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy compounds
    • C08G18/8067—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy compounds phenolic compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • 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
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
    • C08G18/8074—Lactams
    • 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
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
    • C08G18/8077—Oximes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • C08G59/245—Di-epoxy compounds carbocyclic aromatic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
    • C08G59/4014—Nitrogen containing compounds
    • C08G59/4028—Isocyanates; Thioisocyanates
    • 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
    • C08G59/68—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 catalysts used
    • C08G59/688—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 catalysts used containing phosphorus
    • 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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
    • H01B3/302—Polyurethanes or polythiourethanes; Polyurea or polythiourea
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K5/00—Casings, cabinets or drawers for electric apparatus
    • H05K5/06—Hermetically-sealed casings
    • H05K5/065—Hermetically-sealed casings sealed by encapsulation, e.g. waterproof resin forming an integral casing, injection moulding

Definitions

  • the present disclosure relates to curable compositions and electronic devices.
  • the urethane resin may be, for example, a casting material for filling the case containing the electronic component to protect the electronic component, or an adhesive material for bonding the case containing the electronic component and the lid member. Is used for.
  • a method of forming this type of urethane resin a method of heating a curable composition containing a blocked isocyanate compound protected by a blocking agent is known.
  • Patent Document 1 describes a thermosetting coating composition containing a polyol or a polyamine and a scavenger for the thermosetting coating as essential components.
  • the scavenger for thermosetting coating material is composed of a blocked isocyanate obtained by reacting an isocyanate compound having two or more isocyanate groups in one molecule with a phenol compound. When this coating composition is heated, the phenol compound as a blocking agent is desorbed from the blocked isocyanate to produce an isocyanate compound. The coating composition is cured by the reaction of this isocyanate compound with the polyol or polyamine.
  • the blocking agent released from the blocked isocyanate may volatilize from the coating composition and contaminate the surroundings.
  • the blocking agent released from the blocked isocyanate may remain in the cured product of the coating composition. In this case, problems such as alteration of the cured product of the coating composition by the blocking agent and contamination of the surface of the cured product due to bleed-out of the blocking agent may occur.
  • An object of the present disclosure is to provide a curable composition capable of suppressing volatilization of a blocking agent, bleed-out, and deterioration of a cured product due to the blocking agent, and an electronic component using the curable composition.
  • One aspect of the present disclosure is a blocked isocyanate compound having a plurality of isocyanate groups protected by phenols, Including an epoxy compound having a plurality of epoxy groups, A curable composition containing no isocyanate scavenger capable of reacting with an isocyanate group and an epoxy scavenger capable of reacting with an epoxy group.
  • Another aspect of the present disclosure is an electronic component, A case accommodating the electronic component, A casting material filled in the case, The casting material is an electronic device including a cured product of the curable composition of the above aspect.
  • Yet another aspect of the present disclosure is an electronic component, A case having an opening and containing the electronic component; A lid that covers the opening, And an adhesive which is interposed between the case and the lid, and bonds the two together,
  • the adhesive comprises a cured product of the curable composition of the above aspect.
  • the curable composition contains a blocked isocyanate compound containing phenols as a blocking agent, an epoxy compound, and an isocyanate scavenger capable of reacting with an isocyanate group and an epoxy scavenger capable of reacting with an epoxy group. Not included.
  • the curing reaction of the curable composition proceeds as follows.
  • the curable composition When the curable composition is heated, phenols are desorbed from the blocked isocyanate compound, resulting in phenols and an isocyanate compound having a plurality of isocyanate groups. The phenols released from the blocked isocyanate compound react with the epoxy groups of the epoxy compound. At this time, an alcoholic hydroxyl group is formed in the reaction product of the epoxy compound and the phenol by the ring opening of the epoxy group. Then, the curing of the curable composition proceeds by reacting the alcoholic hydroxyl group with the isocyanate compound.
  • the phenols desorbed from the blocked isocyanate compound can be incorporated into the molecular structure of the cured product.
  • the phenols incorporated in the molecular structure form a chemical bond with the structural unit derived from the epoxy compound. Therefore, volatilization of phenols during the curing reaction and bleed-out of phenols from the cured product after curing can be suppressed. Furthermore, since the phenolic hydroxyl group of the phenol is consumed during the reaction with the epoxy group, it is possible to suppress the deterioration of the cured product due to the phenolic hydroxyl group.
  • curable composition capable of suppressing volatilization of the blocking agent, bleed-out, and alteration of the cured product due to the blocking agent, and an electronic component using the curable composition.
  • FIG. 1 shows (a) a reaction in which a phenol is desorbed from a blocked isocyanate compound, (b) a reaction in which a phenol and an epoxy compound are bonded, and (c) an isocyanate compound is bonded to an alcoholic hydroxyl group in Embodiment 1.
  • FIG. 2 is a cross-sectional view showing a main part of an electronic device in which an electronic component is covered with a sealing part according to the second embodiment
  • FIG. 3 is a cross-sectional view showing a main part of an electronic device in which an adhesive is interposed between a case and a lid in the third embodiment.
  • the curable composition includes a blocked isocyanate compound PhI having a plurality of isocyanate groups protected by phenols Ph shown in FIG. 1(a) and an epoxy compound E having a plurality of epoxy groups shown in FIG. 1(b). Includes and. Further, the curable composition does not contain an isocyanate scavenger capable of reacting with an isocyanate group and an epoxy scavenger capable of reacting with an epoxy group.
  • the blocked isocyanate compound PhI has a skeleton structure derived from an isocyanate compound having a plurality of isocyanate groups, and a phenol group as a protective group bonded to the isocyanate group. ..
  • the blocked isocyanate compound for example, a compound obtained by reacting the isocyanate compound I with a phenol Ph can be used.
  • isocyanate compound examples include aromatic diisocyanates such as toluene diisocyanate (TDI) and diphenylmethane diisocyanate (MDI), aliphatic diisocyanates such as hexamethylene diisocyanate (HDI) and isophorone diisocyanate (IPDI), buret type polyisocyanate, isocyanurate type. It is possible to use a multimer of diisocyanate such as polyisocyanate, an adduct type polyisocyanate, a urethane prepolymer containing a structural unit derived from polyisocyanate and a structural unit derived from polyol, and the like. These isocyanate compounds may be used alone or in combination of two or more.
  • aromatic diisocyanates such as toluene diisocyanate (TDI) and diphenylmethane diisocyanate (MDI)
  • aliphatic diisocyanates such as hexam
  • the blocked isocyanate compound preferably has a skeleton structure derived from the urethane prepolymer. That is, the blocked isocyanate compound is preferably a compound obtained by reacting a urethane prepolymer with phenols. In this case, the physical properties of the cured product of the curable composition can be more easily adjusted according to the molecular weight of the urethane prepolymer and the structural unit contained in the urethane prepolymer.
  • the weight average molecular weight of the urethane prepolymer as the isocyanate compound can be appropriately set within the range of 200 to 10,000, for example. If the weight average molecular weight of the urethane prepolymer is excessively small, the concentration of urethane bonds will be high, which may increase the viscosity of the curable composition. As a result, workability may be deteriorated in the work of applying the curable composition, the work of casting, and the like. Further, when the weight average molecular weight of the urethane prepolymer is excessively large, the entanglement of the urethane prepolymers may increase the viscosity of the curable composition. As a result, workability may be deteriorated in the work of applying the curable composition, the work of casting, and the like.
  • the weight average molecular weight of the urethane prepolymer is more preferably 500 to 8,000, further preferably 800 to 5,000.
  • the structural unit derived from the polyol in the urethane prepolymer is not particularly limited.
  • the urethane prepolymer may have a structural unit derived from, for example, polyether polyol, polyester polyol, (meth)acrylic polyol, castor oil-based polyol, polyolefin polyol, or the like.
  • the urethane prepolymer may have one type of these structural units, or may have two or more types.
  • polyether polyol for example, a polymer obtained by addition-polymerizing an alkylene oxide with a polyhydric alcohol such as ethylene glycol, glycerin, or pentaerythritol can be used.
  • a polyhydric alcohol such as ethylene glycol, glycerin, or pentaerythritol
  • polyester polyol for example, a polymer obtained by condensing a polyhydric alcohol and a polycarboxylic acid such as adipic acid or phthalic acid can be used.
  • (meth)acrylic polyol for example, polymers obtained by addition-polymerizing acrylic acid and/or methacrylic acid and olefin, and hydrogenated products of these polymers can be used.
  • castor oil-based polyol for example, castor oil or a castor oil derivative can be used.
  • Castor oil has an ester of a fatty acid containing ricinoleic acid as a main component and glycerin as a main component, and has a hydroxyl group derived from ricinoleic acid and a double bond.
  • the castor oil derivative include a partially dehydrated condensate of castor oil, a transesterification product of castor oil and a low molecular weight polyol, a polyether polyol, a polyester polyol, or the like, or a hydrogenated product thereof.
  • polyolefin polyol for example, a polyolefin polyol containing a double bond, or by adding hydrogen to the polyolefin polyol containing a double bond, the amount of double bonds in the main chain is reduced, or the double bonds are completely eliminated.
  • a single bond hydrogenated polyolefin polyol or the like can be used.
  • Specific examples of the hydrogenated polyolefin polyol include hydrogenated polybutadiene and hydrogenated polyisoprene.
  • the urethane prepolymer preferably has a structural unit derived from castor oil-based polyol, (meth)acrylic polyol or polyolefin polyol, which has excellent insulation and moisture resistance.
  • ⁇ Phenolics as blocking agents are bonded to the isocyanate groups in the blocked isocyanate compounds.
  • phenols for example, unsubstituted phenols such as phenol and naphthol, and phenols having a hydrocarbon group such as cresol, ethylphenol and propylphenol can be used. These phenols may be used alone or in combination of two or more.
  • -Phenols preferably have a chain hydrocarbon group bonded to an aromatic ring.
  • the elimination of phenols from the isocyanate group is likely to occur at a relatively low temperature.
  • volatilization of phenols during the curing reaction and bleed-out of phenols from the cured product after curing can be suppressed more effectively.
  • the structure of the chain hydrocarbon group may be a straight chain structure or a branched structure. Further, the chain hydrocarbon group may have an unsaturated bond or may not have an unsaturated bond.
  • phenols having a chain hydrocarbon group having 8 or more carbon atoms examples include octylphenol, nonylphenol, and decylphenol. It is also possible to use a mixture of phenols having a chain hydrocarbon group having 8 or more carbon atoms, such as cardanol and hydrogenated cardanol.
  • the chain hydrocarbon group is arranged at the meta position with respect to the phenolic hydroxyl group.
  • the content of isocyanate groups in the curable composition is preferably 0.8 to 1.2 times the content of epoxy groups in molar ratio.
  • the amount of phenols released from the blocked isocyanate compound and the amount of epoxy groups are approximately the same, so the phenols released from the blocked isocyanate compound can be more easily incorporated into the cured product.
  • volatilization of the phenols during the curing reaction, bleed-out of the phenols from the cured product, and alteration of the cured product by the phenols can be suppressed more effectively.
  • the isocyanate compound and the reaction product of the epoxy compound and the phenols can be more efficiently produced. It can react. As a result, the amount of unreacted material in the cured product can be further reduced, and the variation in the physical properties of the cured product can be further reduced.
  • the epoxy compound (E) has a plurality of epoxy groups in one molecule as shown in Fig. 1(b).
  • the epoxy compound for example, glycidyl ether type epoxy resin, glycidyl amine type epoxy resin, glycidyl ester type epoxy resin, polyether, polyester, polybutadiene, high molecular weight epoxy resin having an epoxy group bonded to the polymer terminal such as polyurethane, naphthalene, An epoxy resin having a polyaromatic ring such as biphenyl can be used.
  • These epoxy compounds may be used alone or in combination of two or more.
  • the epoxy compound it is preferable to use a glycidyl ether type or glycidyl amine type epoxy resin having an epoxy equivalent of 150 to 2000 and having a bisphenol skeleton such as bisphenol or bisphenol F.
  • These epoxy resins can be easily mixed when mixed with other resins.
  • the curable composition containing these epoxy resins tends to be liquid at room temperature.
  • a cured product having higher strength can be obtained by curing a curable composition containing these epoxy resins.
  • the above-mentioned epoxy equivalent is a value determined by the method specified in JIS K7236:2009.
  • a filler in addition to the blocked isocyanate compound and the epoxy compound as essential components, a filler, a flame retardant, a flame retardant aid, and a mold release agent as long as the above-mentioned effects are not impaired.
  • Additives such as agents and catalysts may be included.
  • the curable composition contains an isocyanate scavenger capable of reacting with an isocyanate group or an epoxy scavenger capable of reacting with an epoxy group
  • the above-mentioned effects may be impaired.
  • the isocyanate scavenger include alcohol, amine, carboxylic acid and the like.
  • the epoxy scavenger include primary amine, secondary amine, tertiary amine, acid anhydride and phenols.
  • the isocyanate group of the isocyanate compound I generated by the reaction in the first step can react with the isocyanate scavenger.
  • the isocyanate group is consumed by the reaction with the isocyanate scavenger, the progress of the reaction in the third stage may be hindered. As a result, it becomes difficult to sufficiently cure the curable composition, and the amount of unreacted material in the cured product may increase. Further, in this case, since the isocyanate compound I and the isocyanate scavenger react after the phenol Ph is desorbed from the blocked isocyanate compound PhI, there is a possibility that storage stability may be lowered.
  • the epoxy group of the epoxy compound E may react with the epoxy scavenger.
  • the progress of the reaction in the second stage may be hindered.
  • it becomes difficult to sufficiently cure the curable composition and the amount of unreacted material in the cured product may increase.
  • volatilization and bleed-out of the phenol Ph desorbed from the blocked isocyanate compound Ph, and deterioration of the cured product due to the phenol Ph may easily occur.
  • the content of the isocyanate scavenger and the content of the epoxy scavenger in the curable composition are preferably as small as possible, and it is particularly preferable that the isocyanate scavenger and the epoxy scavenger are not contained in the curable composition. ..
  • the concept of "isocyanate scavenger and epoxy scavenger are not included" means that the isocyanate scavenger content and the epoxy scavenger content are zero, the isocyanate scavenger and/or the epoxy scavenger are not contained. However, it is included in such a case that the above-mentioned effects are not impaired.
  • the isocyanate scavenger when the number of moles of active hydrogen of the isocyanate scavenger is 1/10 or less of the number of moles of isocyanate groups in the blocked isocyanate compound, the isocyanate scavenger has almost no effect on the curing reaction. It may be regarded as containing no scavenger.
  • the active site of the epoxy scavenger that is, the number of moieties capable of reacting with the epoxy group is 1/10 or less of the number of moles of the epoxy group in the epoxy compound, the epoxy scavenger has almost no influence on the curing reaction. Since it does not, it may be considered that the epoxy scavenger is not included.
  • the curable composition containing a blocked isocyanate compound and an epoxy compound and not containing an isocyanate scavenger or an epoxy scavenger, the occurrence of the above-mentioned problems is avoided, and the blocking agent volatilizes or bleeds out and is cured by the blocking agent. It is possible to suppress alteration of the material.
  • the electronic device 1 In this embodiment, an embodiment of an electronic device in which the curable composition according to the first embodiment is used as a casting material will be described.
  • the electronic device 1 according to the present embodiment has an electronic component 2, a case 3 that accommodates the electronic component 2, and a casting material 4 that is filled in the case 3.
  • the casting material 4 is composed of a cured product of the curable composition.
  • the case 3 in the electronic device 1 of the present embodiment has a bottomed box shape, and one surface of the case 3 is open.
  • the electronic component 2 is housed in the case 3.
  • the case 3 is filled with the casting material 4, and the entire surface of the electronic component 2 is covered with the casting material 4.
  • the electronic component 2 may have wirings, terminals, and the like that project to the outside of the casting material 4 and are electrically connected to peripheral devices of the electronic device 1.
  • the electronic component 2 may be, for example, an electronic control device such as an engine control unit.
  • the electronic device 1 of this embodiment can be manufactured, for example, as follows. First, after housing the electronic component 2 in the case 3, the curable composition is injected into the case 3. After the entire surface of the electronic component 2 is covered with the curable composition, the injection of the curable composition is stopped.
  • the casting material 4 can be formed by heating the electronic device 1 to cure the curable composition.
  • the curable composition does not need to take in moisture or oxygen from the outside of the curable composition in order to proceed with the curing reaction, and is excellent in deep curability. Therefore, by using the curable composition, the electronic component 2 in the case 3 can be protected by the sufficiently hardened casting material 4.
  • the electronic device 102 includes the electronic component 2 and the opening 31, the case 302 that houses the electronic component 2, the lid 5 that covers the opening 31, and the case 302 and the lid 5 that are interposed therebetween. , And an adhesive 6 for bonding the both.
  • the adhesive 6 is composed of a cured product of the curable composition.
  • the electronic component 2 As shown in FIG. 3, the electronic component 2 according to the present embodiment is housed in a box-shaped case 302 having an opening on one side.
  • the electronic component 2 may be an electronic control device such as an engine control unit as in the second embodiment.
  • the case 302 has a flange portion 32 extending outward from the edge of the opening 31.
  • the lid portion 5 is arranged so as to cover the flange portion 32 and the opening 31 of the case 302.
  • An adhesive 6 is arranged between the flange portion 32 and the lid portion 5 so as to extend over the entire circumference of the flange portion 32.
  • the electronic device 102 of this embodiment can be manufactured, for example, as follows. First, after disposing the electronic component 2 in the case 302, the curable composition is applied over the entire circumference of the flange portion 32. Then, after the lid 5 is placed on the case 302, the electronic device 102 is heated to cure the curable composition. As a result, the adhesive 6 can be formed between the lid 5 and the flange 32 to bond the case 302 and the lid 5 together.
  • Example 1 A specific example of the composition of the curable composition will be described.
  • the polyol shown in Table 1 and an isocyanate were reacted in the presence of a tin catalyst to prepare a urethane prepolymer as an isocyanate compound.
  • the “isocyanate group content” in Table 1 shows the content of isocyanate groups in each urethane prepolymer.
  • the compounds used for preparing the urethane prepolymer are specifically as follows.
  • Acrylic polyol "ARUFON (registered trademark) UH-2000” manufactured by Toagosei Co., Ltd.
  • -Hydrogenated polybutadiol "GI-1000” manufactured by Nippon Soda Co., Ltd.
  • -Modified MDI "Millionate MTL” manufactured by Tosoh Corporation
  • ⁇ Tin catalyst dibutyltin dilaurate
  • a blocking isocyanate compound was prepared by reacting 100 parts by mass of the urethane prepolymer with the amount of the blocking agent shown in Table 2. Epoxy compounds and other compounds were added to this blocked isocyanate compound in the ratios shown in Tables 2 and 3 to prepare curable compositions.
  • the "NCO/epoxy" column in Tables 2 and 3 shows the molar ratio of the amount of isocyanate groups to the amount of epoxy groups in the curable composition.
  • the other compounds are specifically as follows.
  • the test agents 1 to 9 include the blocked isocyanate compound and the epoxy resin as the epoxy compound, and the isocyanate scavenger and the epoxy scavenger are not included. Therefore, these test agents can suppress volatilization of phenols from the cured product. In addition, these test agents are excellent in storage stability and curability. From these results, it can be understood that in the test agents 1 to 9, the phenols desorbed from the blocked isocyanate compound can be incorporated into the cured product.
  • test agent 10 used methyl ethyl ketone oxime, which is not a phenol, as the blocking agent, the storage stability decreased, the curability deteriorated, and the volatilization amount of the blocking agent increased.
  • the test agent 11 used ⁇ -caprolactam, which is not a phenol, as the blocking agent, so that the curability was deteriorated.
  • the test agent 12 does not contain an epoxy compound but contains octanediol which can react with an isocyanate group. Therefore, the blocking agent desorbed from the blocked isocyanate compound was not incorporated into the cured product and was easily volatilized from the cured product.
  • test agent 13 contains an epoxy compound, it also contains octanediol. Therefore, the blocking agent desorbed from the blocked isocyanate compound was not incorporated into the cured product and was easily volatilized from the cured product. Further, the curability was slightly lowered by the unreacted epoxy compound.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Organic Insulating Materials (AREA)
PCT/JP2019/044990 2018-12-27 2019-11-18 硬化性組成物及び電子機器 Ceased WO2020137246A1 (ja)

Priority Applications (3)

Application Number Priority Date Filing Date Title
DE112019006551.3T DE112019006551T5 (de) 2018-12-27 2019-11-18 Härtbare zusammensetzung und elektronische vorrichtung
CN201980085725.6A CN113228203A (zh) 2018-12-27 2019-11-18 固化性组合物和电子设备
US17/354,715 US20210317251A1 (en) 2018-12-27 2021-06-22 Curable composition and electronic device

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2018-244012 2018-12-27
JP2018244012A JP7119991B2 (ja) 2018-12-27 2018-12-27 硬化性組成物及び電子機器

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US17/354,715 Continuation US20210317251A1 (en) 2018-12-27 2021-06-22 Curable composition and electronic device

Publications (1)

Publication Number Publication Date
WO2020137246A1 true WO2020137246A1 (ja) 2020-07-02

Family

ID=71126558

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2019/044990 Ceased WO2020137246A1 (ja) 2018-12-27 2019-11-18 硬化性組成物及び電子機器

Country Status (5)

Country Link
US (1) US20210317251A1 (https=)
JP (1) JP7119991B2 (https=)
CN (1) CN113228203A (https=)
DE (1) DE112019006551T5 (https=)
WO (1) WO2020137246A1 (https=)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2024020844A (ja) * 2022-08-02 2024-02-15 サカタインクス株式会社 ウレタン（メタ）アクリレート化合物、組成物、硬化物及びウレタン（メタ）アクリレート化合物の製造方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50146700A (https=) * 1974-05-16 1975-11-25
JPS51145598A (en) * 1975-06-09 1976-12-14 Asahi Denka Kogyo Kk Curable epoxy resin composition
JPS5310652A (en) * 1976-07-19 1978-01-31 Asahi Denka Kogyo Kk Curable epoxy resin compositions
JPS60262818A (ja) * 1984-06-08 1985-12-26 Idemitsu Petrochem Co Ltd エポキシ樹脂組成物
JPS62195013A (ja) * 1986-02-21 1987-08-27 Asahi Denka Kogyo Kk 硬化性組成物
JPS63243123A (ja) * 1987-03-30 1988-10-11 Asahi Denka Kogyo Kk 硬化性エポキシブロツクドウレタン組成物
JP2008231142A (ja) * 2007-03-16 2008-10-02 Nippon Paint Co Ltd カチオン電着塗料組成物、補給用カチオン電着塗料組成物および電着塗料組成物の補給方法

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE790295A (fr) * 1971-10-22 1973-04-19 Bayer Ag Matieres plastiques elastifiees
US4396753A (en) * 1981-12-28 1983-08-02 Ford Motor Company Diblocked diisocyanate diurea oligomers and coating compositions comprising same
DE68921092T2 (de) * 1988-05-13 1995-08-03 Nippon Paint Co Ltd Hitzehärtende Harzzusammensetzung und Herstellung von hitzebeständigen Überzügen und Gegenständen auf der Basis dieser Zusammensetzung.
US4892756A (en) * 1988-06-06 1990-01-09 Lord Corporation Flock adhesive composition
US4835226A (en) * 1988-06-06 1989-05-30 Lord Corporation Flock adhesive composition
US5446077A (en) * 1993-05-17 1995-08-29 Nippon Paint Company, Ltd. Oxazolidone ring-containing modified epoxy resins and cathodic electrodeposition paints containing same
IT1264960B1 (it) * 1993-11-11 1996-10-17 Eniricerche Spa Composizioni isocianato/epossido polimerizzabili mediante microonde per applicazioni tecnicamente impegnative
CA2115533C (en) * 1994-02-11 2002-06-18 Hiroshi Uchida Urethane modified epoxy resin compositions
KR100221035B1 (ko) * 1996-03-01 1999-09-15 후지이 히로시 음극 전착도료
DE19816570A1 (de) * 1998-04-15 1999-10-21 Bayer Ag Reaktivsysteme und ihre Verwendung zur Herstellung von Beschichtungen, Klebstoffen, Dichtungsmassen, Vergußmassen oder Formteilen
JP3819254B2 (ja) 2001-05-23 2006-09-06 新日鐵化学株式会社 熱硬化型塗料用硬化剤及び塗料組成物
DE102010030924A1 (de) * 2010-06-21 2011-12-22 Endress + Hauser Flowtec Ag Elektronik-Gehäuse für ein elektronisches Gerät bzw. damit gebildetes Gerät
JP5969405B2 (ja) * 2013-01-30 2016-08-17 日立オートモティブシステムズ株式会社 車載用電子モジュール
MY174272A (en) * 2013-08-23 2020-04-01 Mitsui Chemicals Inc Blocked isocyanate, coating composition, adhesive composition, and article

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50146700A (https=) * 1974-05-16 1975-11-25
JPS51145598A (en) * 1975-06-09 1976-12-14 Asahi Denka Kogyo Kk Curable epoxy resin composition
JPS5310652A (en) * 1976-07-19 1978-01-31 Asahi Denka Kogyo Kk Curable epoxy resin compositions
JPS60262818A (ja) * 1984-06-08 1985-12-26 Idemitsu Petrochem Co Ltd エポキシ樹脂組成物
JPS62195013A (ja) * 1986-02-21 1987-08-27 Asahi Denka Kogyo Kk 硬化性組成物
JPS63243123A (ja) * 1987-03-30 1988-10-11 Asahi Denka Kogyo Kk 硬化性エポキシブロツクドウレタン組成物
JP2008231142A (ja) * 2007-03-16 2008-10-02 Nippon Paint Co Ltd カチオン電着塗料組成物、補給用カチオン電着塗料組成物および電着塗料組成物の補給方法

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2024020844A (ja) * 2022-08-02 2024-02-15 サカタインクス株式会社 ウレタン（メタ）アクリレート化合物、組成物、硬化物及びウレタン（メタ）アクリレート化合物の製造方法
JP7847055B2 (ja) 2022-08-02 2026-04-16 サカタインクス株式会社 ウレタン（メタ）アクリレート化合物、組成物、硬化物及びウレタン（メタ）アクリレート化合物の製造方法

Also Published As

Publication number Publication date
US20210317251A1 (en) 2021-10-14
CN113228203A (zh) 2021-08-06
JP2020105315A (ja) 2020-07-09
JP7119991B2 (ja) 2022-08-17
DE112019006551T5 (de) 2021-09-16

Similar Documents

Publication Publication Date Title
KR101782885B1 (ko) 카르복실기 함유 변성 에스테르 수지를 포함하는 열경화성 수지 조성물
TWI482797B (zh) (Poly) carbonate polyol and a carboxyl group-containing polyurethanes using the (poly) carbonate polyol as a raw material
JP7031824B2 (ja) ポリカルボジイミド共重合体
CN107922570B (zh) 用于环氧树脂胶粘剂的封端型聚氨基甲酸酯增韧剂
KR102351716B1 (ko) 콘크리트용 무용제 이액형 프라이머 조성물
TWI622602B (zh) 硬化性組成物、硬化物、保護膜、被覆可撓性電路板及其製造方法
DE19733643A1 (de) Lösbare Klebstoffe
TWI500695B (zh) Thermosetting composition
CN101679575A (zh) 单组分、湿固化聚氨酯粘合剂
WO2020137246A1 (ja) 硬化性組成物及び電子機器
KR102469706B1 (ko) 에폭시 수지 조성물
US20110315223A1 (en) Coating having improved hydrolytic resistance
CN101289604A (zh) 用于蒸馏袋的层压粘合剂
TW201038667A (en) Curable composition
KR20200044820A (ko) 폴리카르보디이미드 화합물 및 열경화성 수지 조성물
CN115279814B (zh) 环氧树脂组合物
JP7230525B2 (ja) 硬化性組成物及び電子機器
JP2017137407A (ja) 硬化性組成物及び電子デバイス
RU2477291C2 (ru) Отверждаемая композиция смолы
NL2037879B1 (en) A multicomponent polyester resin composition, for potting and encapsulating, and a removable polybutadiene polyester potting compound made therefrom
JP6882263B2 (ja) 硬化性組成物、該組成物を用いる硬化膜およびオーバーコート膜
US6812315B2 (en) Oxazolidine compound and curable resin composition
JP2021175765A (ja) イミド樹脂、硬化性樹脂組成物、イミド樹脂の製造方法、硬化性樹脂組成物の製造方法、硬化物、及び硬化物の製造方法
KR20130037841A (ko) 연성회로 기판용 접착제 조성물, 이를 이용한 접착시트 및 그의 제조방법
KR20140073334A (ko) 화합물, 이중 경화형 조성물, 이중 경화형 가교 고분자의 제조 방법 및 이중 경화형 가교 고분자

Legal Events

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

Ref document number: 19906076

Country of ref document: EP

Kind code of ref document: A1

122 Ep: pct application non-entry in european phase

Ref document number: 19906076

Country of ref document: EP

Kind code of ref document: A1