WO2012077377A1 - Composition de résine - Google Patents

Composition de résine Download PDF

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Publication number
WO2012077377A1
WO2012077377A1 PCT/JP2011/066979 JP2011066979W WO2012077377A1 WO 2012077377 A1 WO2012077377 A1 WO 2012077377A1 JP 2011066979 W JP2011066979 W JP 2011066979W WO 2012077377 A1 WO2012077377 A1 WO 2012077377A1
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Prior art keywords
resin composition
component
compound
epoxy
equivalent
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PCT/JP2011/066979
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English (en)
Japanese (ja)
Inventor
洋平 細野
一希 岩谷
留香 横山
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ナミックス株式会社
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Publication of WO2012077377A1 publication Critical patent/WO2012077377A1/fr

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Classifications

    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00Details of semiconductor or other solid state devices
    • H01L23/28Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/29Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
    • H01L23/293Organic, e.g. plastic
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00Polycondensates 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
    • C08G59/18Macromolecules 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
    • C08G59/40Macromolecules 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
    • C08G59/50Amines
    • C08G59/56Amines together with other curing agents
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J163/00Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00Materials not provided for elsewhere
    • C09K3/10Materials in mouldable or extrudable form for sealing or packing joints or covers
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2200/00Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K2200/06Macromolecular organic compounds, e.g. prepolymers
    • C09K2200/0645Macromolecular organic compounds, e.g. prepolymers obtained otherwise than by reactions involving carbon-to-carbon unsaturated bonds
    • C09K2200/0647Polyepoxides
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/0001Technical content checked by a classifier
    • H01L2924/0002Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00

Definitions

  • the present invention relates to a resin composition having excellent low-temperature rapid curability, good storage stability (storage stability), and low Tg (glass transition point).
  • a resin composition comprising an epoxy resin, a thiol compound, and a curing accelerator is known as a resin composition having excellent low-temperature curability that can be cured at 0 ° C. to ⁇ 20 ° C.
  • resin compositions are used in various applications such as adhesives and sealants for electronic parts.
  • Patent Document 1 discloses (1) an epoxy resin having two or more epoxy groups in the molecule, (2) a thiol compound having two or more thiol groups in the molecule, (3 A resin composition containing a solid dispersion type latent curing accelerator and (4) a borate compound is disclosed.
  • Patent Document 2 discloses (1) an epoxy resin having two or more epoxy groups in the molecule, (2) a polythiol compound having two or more thiol groups in the molecule, and (3) a solid dispersion type amine adduct system latency.
  • An epoxy resin composition containing a curing accelerator is disclosed.
  • the adhesive for joining these parts needs to be flexible enough to follow the thermal deformation of the parts, and has a low Tg (glass transition point), that is, a low elastic modulus. Required.
  • the present invention has been made in view of the above problems, and is excellent in low-temperature fast curability, excellent storage stability (storage stability), and Tg (glass transition point) of a cured product. It aims at providing a low resin composition.
  • the inventors of the present invention newly added that a certain long-chain amine compound is added to a resin composition containing an epoxy resin to lower the Tg (glass transition point) of a cured product obtained by curing the resin composition. Discovered and completed the present invention.
  • the resin composition of the present invention is characterized by containing (A) an epoxy resin, (B) a long-chain amine compound, (C) a thiol compound, and (D) a latent curing agent.
  • the component (B) is preferably a compound represented by the following general formula (1).
  • the component (B) is more preferably a compound represented by the following general formula (2).
  • the component (B) is preferably a compound having a weight average molecular weight of 100 to 3000.
  • the equivalent ratio of the component (A) to the component (B) is preferably 0.1 to 0.4 in terms of amine equivalent / epoxy equivalent.
  • the equivalent ratio of the component (A) and the component (C) is preferably 0.6 to 2.0 in terms of thiol equivalent / epoxy equivalent.
  • the glass transition point of the cured product is preferably 20 ° C. or less.
  • the resin composition of the present invention preferably further contains a borate ester compound.
  • the resin composition of the present invention further includes at least one additive selected from the group consisting of a silica filler, a silane coupling agent, an ion trapping agent, a leveling agent, an antioxidant, an antifoaming agent, and a tampering agent. It is preferable to contain.
  • the present invention provides an adhesive containing any one of the above resin compositions. Moreover, this invention provides the semiconductor sealing agent containing one of said resin compositions.
  • the present invention it is possible to provide a resin composition that is excellent in low-temperature fast curability and excellent in storage stability (storage stability). Moreover, the resin composition which can make low Tg (glass transition point) of the hardened
  • the resin composition according to the embodiment of the present invention is characterized by including (A) an epoxy resin, (B) a long-chain amine compound, (C) a thiol compound, and (D) a latent curing agent.
  • the epoxy resin as the component (A) may be an epoxy resin having two or more epoxy groups per molecule.
  • examples of the epoxy resin of component (A) include polyglycidyl ethers obtained by reacting polychlorophenols such as bisphenol A, bisphenol F, bisphenol AD, catechol and resorcinol, polyhydric alcohols such as glycerin and polyethylene glycol, and epichlorohydrin.
  • Glycidyl ether ester obtained by reacting a hydroxycarboxylic acid such as p-hydroxybenzoic acid or ⁇ -hydroxynaphthoic acid with epichlorohydrin, or a polycarboxylic acid obtained by reacting a polycarboxylic acid such as phthalic acid or terephthalic acid with epichlorohydrin.
  • Epoxy resin having a naphthalene skeleton such as glycidyl ester, 1,6-bis (2,3-epoxypropoxy) naphthalene, epoxidized phenol novolac resin, epoxidized crezo Novolac resins, epoxidized polyolefins, cyclic aliphatic epoxy resins, urethane modified epoxy resins, and the like.
  • the epoxy resin of the component (A) is not limited to these.
  • the long-chain amine compound as the component (B) is a compound in which two or more amino groups (—NH 2 ) are bonded to a long-chain hydrocarbon residue.
  • the long chain hydrocarbon referred to here may be linear or branched.
  • the bond between the carbon atoms contained in the long-chain hydrocarbon may be interrupted by an oxygen atom.
  • the long-chain amine compound of the component (B) is preferably a compound represented by the following general formula (1).
  • the long-chain amine compound as the component (B) is more preferably a compound represented by the following general formula (2).
  • the weight average molecular weight of the long-chain amine compound as the component (B) is preferably 100 to 3000.
  • the weight average molecular weight can be measured by gel permeation chromatography (GPC), and can be measured using a standard polystyrene calibration curve.
  • the thiol compound as the component (C) may be a thiol compound having two or more thiol groups per molecule.
  • the thiol compound preferably has as little basic impurity content as possible from the viewpoint of storage stability.
  • Examples of the thiol compound of component (C) include trimethylolpropane tris (thioglycolate), pentaerythritol tetrakis (thioglycolate), ethylene glycol dithioglycolate, trimethylolpropane tris ( ⁇ -thiopropionate), Mention may be made of thiol compounds obtained by esterification reaction of polyols such as pentaerythritol tetrakis ( ⁇ -thiopropionate) and dipentaerythritol poly ( ⁇ -thiopropionate) with mercapto organic acids. These thiol compounds are preferable because it is not necessary to use a basic substance in the production.
  • Examples of the thiol compound of component (C) include 1,4-butanedithiol, 1,5-pentanedithiol, 1,6-hexanedithiol, 1,8-octanedithiol, 1,9-nonanedithiol, Alkyl polythiol compounds such as 1,10-decanedithiol; terminal thiol group-containing polyethers; terminal thiol group-containing polythioethers; thiol compounds obtained by reaction of epoxy compounds with hydrogen sulfide; obtained by reaction of polythiol compounds with epoxy compounds A thiol compound having a terminal thiol group; In the case of using a thiol compound produced using a basic substance as a reaction catalyst, it is preferable to reduce the alkali metal ion concentration of the thiol compound to 50 ppm or less by performing dealkalization treatment. Moreover, it is preferable to use a thiol compound having two or more thiol groups in the
  • the latent curing agent of the component (D) is a compound that is insoluble in an epoxy resin at room temperature, solubilized by heating, and functions as a curing accelerator for the epoxy resin.
  • latent curing agents include imidazole compounds that are solid at room temperature and solid-dispersed amine adduct-based latent curing accelerators.
  • solid dispersion type amine adduct-based latent curing accelerators include reaction products of amine compounds and epoxy compounds (amine-epoxy adduct systems), and reaction products of amine compounds and isocyanate compounds or urea compounds (urea) Type adduct system).
  • Examples of the epoxy compound that is one of the raw materials for producing the solid dispersion type amine adduct type latent curing accelerator include polyhydric phenols such as bisphenol A, bisphenol F, catechol, and resorcinol, Polyglycidyl ether obtained by reacting a polyhydric alcohol such as polyethylene glycol with epichlorohydrin; reacting a hydroxycarboxylic acid such as p-hydroxybenzoic acid or ⁇ -hydroxynaphthoic acid with epichlorohydrin Glycidyl ether ester obtained by reaction of polycarboxylic acid such as phthalic acid and terephthalic acid with epichlorohydrin; epichlorohydric acid such as 4,4'-diaminodiphenylmethane and m-aminophenol Glycidylamine compounds obtained by reacting with dorin; moreover, polyfunctional epoxy compounds such as epoxidized phenol novolak resin,
  • the amine compound which is one of the raw materials for producing the solid dispersion type amine adduct-based latent curing accelerator, has at least one active hydrogen capable of addition reaction with an epoxy group in the molecule, and has a primary amino group, secondary class What is necessary is just to have one or more functional groups selected from an amino group and a tertiary amino group in the molecule.
  • amine compounds examples include aliphatic amines such as diethylenetriamine, triethylenetetramine, n-propylamine, 2-hydroxyethylaminopropylamine, cyclohexylamine, 4,4'-diamino-dicyclohexylmethane; Aromatic amine compounds such as 4'-diaminodiphenylmethane and 2-methylaniline; nitrogen atoms such as 2-ethyl-4-methylimidazole, 2-ethyl-4-methylimidazoline, 2,4-dimethylimidazoline, piperidine and piperazine; A heterocyclic compound to be contained; and the like.
  • the amine compound that can be used as a raw material for producing the solid dispersion type amine adduct-based latent curing accelerator is not limited thereto.
  • an amine compound having a tertiary amino group in the molecule is a raw material for a latent curing accelerator having excellent curing acceleration ability.
  • amine compounds include amine compounds such as dimethylaminopropylamine, diethylaminopropylamine, di-n-propylaminopropylamine, dibutylaminopropylamine, dimethylaminoethylamine, diethylaminoethylamine, N-methylpiperazine, Primary or secondary amines having a tertiary amino group in the molecule, such as imidazole compounds such as 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole; Dimethylaminoethanol, 1-methyl-2-dimethylaminoethanol, 1-phenoxymethyl-2-dimethylaminoethanol, 2-diethylaminoethanol, 1-butoxymethyl-2-dimethylaminoethanol
  • the latent curing accelerator used in the present invention can be produced by addition reaction of the above epoxy compound and the above amine compound.
  • an active hydrogen compound having two or more active hydrogens in the molecule can be added as a third component.
  • the storage stability of the epoxy resin composition of the present invention can be further improved.
  • active hydrogen compounds are shown below, but are not limited thereto.
  • active hydrogen compounds include polyphenols such as bisphenol A, bisphenol F, bisphenol S, hydroquinone, catechol, resorcinol, pyrogallol, phenol novolac resin, polyhydric alcohols such as trimethylolpropane, adipic acid, phthalic acid, etc.
  • polycarboxylic acids such as 1,2-dimercaptoethane, 2-mercaptoethanol, 1-mercapto-3-phenoxy-2-propanol, mercaptoacetic acid, anthranilic acid, and lactic acid.
  • monofunctional isocyanate compounds such as n-butyl isocyanate, isopropy
  • Terminal isocyanate group-containing compounds include addition compounds having terminal isocyanate groups obtained by reaction of toluylene diisocyanate and trimethylolpropane, and terminal isocyanate groups obtained by reaction of toluylene diisocyanate and pentaerythritol. Examples thereof include, but are not limited to, addition compounds.
  • urea compounds include, but are not limited to, urea and thiourea.
  • the solid dispersion type latent curing accelerator used in the present invention can be produced by the following method. First, (a) two components of an amine compound and an epoxy compound, (b) three components of the two components and an active hydrogen compound, or (c) two or three components of an amine compound and an isocyanate compound and / or a urea compound. Mix each component in combination. Next, these components are reacted at a temperature of room temperature to 200 ° C., cooled and solidified, and then pulverized. Alternatively, these components are reacted in a solvent such as methyl ethyl ketone, dioxane, tetrahydrofuran, etc., and after removing the solvent, the solid content is pulverized. Thereby, a solid dispersion type latent hardening accelerator can be manufactured easily.
  • a solvent such as methyl ethyl ketone, dioxane, tetrahydrofuran, etc.
  • amine-epoxy adduct-based (amine adduct-based) solid dispersion type latent curing accelerators include “Amicure PN-23” (trade name of Ajinomoto Co., Inc.) and “Amicure PN-40” (Ajinomoto Co., Inc.).
  • urea-type adduct-based solid dispersion type latent curing accelerators include “Fujicure FXE-1000” (product name of Fuji Kasei Co., Ltd.), “Fujicure FXR-1030” (Fuji Kasei Co., Ltd.), etc. Can be mentioned.
  • the resin composition of the present invention preferably further contains (E) a boric acid ester compound in addition to the components (A) to (D).
  • the borate ester compound as the component (E) has an effect of further improving the storage stability of the resin composition of the present invention. It is considered that the borate ester compound exhibits such an action by reacting with the surface of the latent curing accelerator to modify and encapsulate the surface of the latent curing agent.
  • borate compound examples include trimethyl borate, triethyl borate, tri-n-propyl borate, triisopropyl borate, tri-n-butyl borate, tripentyl borate, triallyl borate, trihexyl borate, tricyclohexyl borate, Trioctyl borate, trinonyl borate, tridecyl borate, tridodecyl borate, trihexadecyl borate, trioctadecyl borate, tris (2-ethylhexyloxy) borane, bis (1,4,7,10-tetraoxaundecyl) (1,4,7,10,13-pentaoxatetradecyl) (1,4,7-trioxaundecyl) borane, tribenzyl borate, triphenyl borate, tri-o-tolyl borate, tri-m-tolyl Borate, It can be mentioned triethanol
  • the boric acid ester compound of the component (E) can be mixed simultaneously with the epoxy resin, the long chain amine compound, the thiol compound and the latent curing agent.
  • the borate ester compound can be previously mixed with a latent curing agent.
  • the boric acid ester compound and the latent curing agent can be brought into contact and mixed in a solvent such as methyl ethyl ketone or toluene, in a liquid epoxy resin, or without a solvent.
  • the resin composition of the present invention can be produced using the four components of the epoxy resin, long chain amine compound, thiol compound, and latent curing agent described above as raw materials.
  • the resin composition of the present invention can be produced by a conventionally known method.
  • the resin composition of the present invention can be produced by mixing four components with a mixer such as a Henschel mixer. The same applies to the case where the resin composition of the present invention is produced by mixing five components obtained by adding a borate compound to these four components.
  • the resin composition of the present invention can be cured by a conventionally known method, for example, it can be cured by heating.
  • the equivalent ratio of the epoxy resin to the long chain amine compound is preferably 0.1 or more and 0.4 or less in terms of amine equivalent / epoxy equivalent.
  • the Tg (glass transition point) of the cured product obtained by curing the resin composition can be effectively reduced.
  • the “epoxy equivalent” is a numerical value obtained by dividing the molecular weight of the epoxy resin by the number of epoxy groups in one molecule.
  • the “amine equivalent” is a numerical value obtained by dividing the molecular weight of the amine compound by the number of amino groups in one molecule.
  • the equivalent ratio of the epoxy resin to the thiol compound is preferably 0.6 or more and 2.0 or less in terms of thiol equivalent / epoxy equivalent.
  • the resin composition is cured while maintaining the low-temperature fast curing property and the storage stability (storage stability) of the resin composition. It is possible to effectively lower the Tg (glass transition point) of the cured product.
  • the “thiol equivalent” is a numerical value obtained by dividing the molecular weight of the thiol compound by the number of thiol groups in one molecule.
  • the resin composition of the present invention preferably has a Tg (glass transition point) of a cured product of 20 ° C. or lower.
  • Tg glass transition point
  • the resin composition is used, for example, as an adhesive for joining two components having different thermal expansion coefficients, the two components It can prevent effectively that a crack generate
  • the resin composition of the present invention is at least one selected from the group consisting of a silica filler, a silane coupling agent, an ion trapping agent, a leveling agent, an antioxidant, an antifoaming agent, and a tampering agent as necessary.
  • a silica filler e.g., a silane coupling agent, an ion trapping agent, a leveling agent, an antioxidant, an antifoaming agent, and a tampering agent as necessary.
  • One component can be contained.
  • a viscosity modifier, a flame retardant, a solvent, etc. can be contained as arbitrary components.
  • the resin composition of the present invention can be used as an adhesive for joining parts together.
  • it can be used as a sealing agent for semiconductor electronic components.
  • Resin compositions according to Examples 1 to 8 were prepared by mixing a plurality of components in the formulation shown in Table 1. A plurality of components were mixed according to the formulation shown in Table 2 to prepare resin compositions according to Comparative Examples 1 to 9.
  • the numbers in Tables 1 and 2 all represent parts by weight (excluding the amine / epoxy and thiol / epoxy equivalent ratios).
  • PEMP2 trimethylolpropane tris (3-mercaptopropionate)
  • C2 Thiol compound 2: “TMMP” manufactured by SC Organic Chemical Co., Pentaerythritol tetraxy (3-mercaptopropionate)
  • C3 Thiol compound 3: “DPMP” manufactured by SC Organic Chemical Co., dipentaerythritol hexa (3-mercaptopropionate)
  • Latent curing agent “PN23J” manufactured by Ajinomoto Fine-Techno Co., Ltd., epoxy resin amine adduct
  • E Boric acid ester compound: manufactured by Tokyo Chemical Industry Co., Ltd., triisopropyl borate
  • Fading agent manufactured by CABOT: “ TS720 ", surface-treated fumed silica (treatment agent: polydimethylsiloxane)
  • the appearance was evaluated by visual observation.
  • Tg was measured using a dynamic thermomechanical measurement (DMA) manufactured by Seiko Instruments Inc. according to a method defined in Japanese Industrial Standard JIS C 6481.
  • DMA dynamic thermomechanical measurement
  • the elastic modulus at ⁇ 40 ° C. was measured using a dynamic thermomechanical measurement (DMA) manufactured by Seiko Instruments Inc. according to the method defined in Japanese Industrial Standard JIS C6481.
  • DMA dynamic thermomechanical measurement
  • the resin composition was heated at 85 degreeC, and it evaluated by the shear strength measured after 3-minute progress. Specifically, the resin composition was applied to the upper surface of an alumina substrate (which may be an FR4 substrate) by stencil printing. Next, a 2 mm ⁇ 2 mm SiN chip was placed on the applied resin composition. Next, the resin composition was heated and cured, and the test of applying a lateral load to the SiN chip was repeated 10 times, and the average value of the load when the SiN chip peeled was measured. For measurement of the shear strength, a universal bond tester “DAGE 4000” manufactured by dage was used. And when shear strength was 1 kgf or more, it evaluated that curability was favorable ((circle)), and when shear strength was less than 1 kgf, it evaluated that curability was unsatisfactory (x).
  • the viscosity after leaving still at 25 degreeC conditions for 2 days was measured, and when the increase rate of a viscosity is 1.2 times or more, it is evaluated that it is inferior (x). When the viscosity increase rate was less than 1.2 times, it was evaluated as good ( ⁇ ).
  • the viscosity was measured using an RVDV viscometer (Brookfield) under the conditions of spindles SC4 to 14 and a rotation speed of 50 rpm / 1 minute.
  • the resin composition of the present invention is excellent in curability and pot life (storage stability), and the Tg (glass transition point) of the cured product is sufficiently high. It was low (below 0 ° C.).
  • the Tg of the cured product is 20 It was as high as °C or higher, and the elastic modulus was 4000 [MPa] or more, or measurement was impossible.

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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)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Computer Hardware Design (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • Epoxy Resins (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

L'invention concerne une composition de résine qui présente d'excellentes propriétés de durcissement rapide à basse température et une stabilité au stockage favorable (stabilité de conservation), et dont la Tg (température de transition vitreuse) est basse. La composition de résine contient (A) une résine époxy, (B) un composé d'amine à chaîne longue, (C) un composé de thiol et (D) un agent de durcissement latent. Il est préférable que le rapport équivalent entre le composant (A) et le composant (B) soit de 0,1 à 0,4, avec équivalent d'amine/équivalent d'époxy. Il est également préférable que le rapport équivalent entre le composant (A) et le composant (C) soit de 0,6 à 2,0, avec équivalent de thiol/équivalent d'époxy.
PCT/JP2011/066979 2010-12-10 2011-07-26 Composition de résine WO2012077377A1 (fr)

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JP2010-275965 2010-12-10
JP2010275965 2010-12-10

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014173007A (ja) * 2013-03-08 2014-09-22 Sekisui Chem Co Ltd エポキシ接着剤、及びレンズを備えたプリント配線板
JP2015221866A (ja) * 2014-05-23 2015-12-10 株式会社Adeka 一液型熱硬化性エポキシ樹脂組成物
JP2016050301A (ja) * 2014-08-28 2016-04-11 スリーボンドファインケミカル株式会社 熱伝導性樹脂組成物
KR20160077132A (ko) * 2013-10-25 2016-07-01 아지노모토 가부시키가이샤 유연성 에폭시 수지 조성물
JP2018503711A (ja) * 2014-12-04 2018-02-08 ピーアールシー−デソト インターナショナル,インコーポレイティド 作用時間が長いポリチオエーテルシーラント
CN110272704A (zh) * 2018-03-13 2019-09-24 松下知识产权经营株式会社 树脂组合物和包含其的各向异性导电性膜、以及电子设备

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JPH11256013A (ja) * 1998-03-12 1999-09-21 Ajinomoto Co Inc エポキシ樹脂組成物
JP2008260850A (ja) * 2007-04-12 2008-10-30 Cemedine Co Ltd エポキシ樹脂用硬化剤組成物及びエポキシ樹脂接着剤組成物

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Publication number Priority date Publication date Assignee Title
JPH02185518A (ja) * 1988-11-23 1990-07-19 Ciba Geigy Ag ポリオキシアルキレンジチオールおよびポリアミンを含有するエポキシ樹脂材料の硬化性混合物
JPH11256013A (ja) * 1998-03-12 1999-09-21 Ajinomoto Co Inc エポキシ樹脂組成物
JP2008260850A (ja) * 2007-04-12 2008-10-30 Cemedine Co Ltd エポキシ樹脂用硬化剤組成物及びエポキシ樹脂接着剤組成物

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014173007A (ja) * 2013-03-08 2014-09-22 Sekisui Chem Co Ltd エポキシ接着剤、及びレンズを備えたプリント配線板
KR20160077132A (ko) * 2013-10-25 2016-07-01 아지노모토 가부시키가이샤 유연성 에폭시 수지 조성물
JPWO2015060439A1 (ja) * 2013-10-25 2017-03-09 味の素株式会社 柔軟性エポキシ樹脂組成物
KR102217397B1 (ko) 2013-10-25 2021-02-22 아지노모토 가부시키가이샤 유연성 에폭시 수지 조성물
JP2015221866A (ja) * 2014-05-23 2015-12-10 株式会社Adeka 一液型熱硬化性エポキシ樹脂組成物
JP2016050301A (ja) * 2014-08-28 2016-04-11 スリーボンドファインケミカル株式会社 熱伝導性樹脂組成物
JP2018503711A (ja) * 2014-12-04 2018-02-08 ピーアールシー−デソト インターナショナル,インコーポレイティド 作用時間が長いポリチオエーテルシーラント
CN110272704A (zh) * 2018-03-13 2019-09-24 松下知识产权经营株式会社 树脂组合物和包含其的各向异性导电性膜、以及电子设备
CN110272704B (zh) * 2018-03-13 2022-04-15 松下知识产权经营株式会社 树脂组合物和包含其的各向异性导电性膜、以及电子设备

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