WO2012081192A1 - マスターバッチ型エポキシ樹脂用潜在性硬化剤及びそれを用いたエポキシ樹脂組成物 - Google Patents
マスターバッチ型エポキシ樹脂用潜在性硬化剤及びそれを用いたエポキシ樹脂組成物 Download PDFInfo
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- WO2012081192A1 WO2012081192A1 PCT/JP2011/006794 JP2011006794W WO2012081192A1 WO 2012081192 A1 WO2012081192 A1 WO 2012081192A1 JP 2011006794 W JP2011006794 W JP 2011006794W WO 2012081192 A1 WO2012081192 A1 WO 2012081192A1
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- Prior art keywords
- epoxy resin
- curing agent
- type epoxy
- latent curing
- masterbatch
- Prior art date
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002923 metal particle Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- MILHQHDXRQFQCW-UHFFFAOYSA-N n',n'-dicyclohexylethane-1,2-diamine Chemical compound C1CCCCC1N(CCN)C1CCCCC1 MILHQHDXRQFQCW-UHFFFAOYSA-N 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- CPCHVLBDLZEKTD-UHFFFAOYSA-N n'-(2-phenylethyl)ethane-1,2-diamine Chemical compound NCCNCCC1=CC=CC=C1 CPCHVLBDLZEKTD-UHFFFAOYSA-N 0.000 description 1
- HUWUUMUEMQWJKZ-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-benzylpropane-1,3-diamine Chemical compound NCCCN(CCCN)CC1=CC=CC=C1 HUWUUMUEMQWJKZ-UHFFFAOYSA-N 0.000 description 1
- CMDGBXZMCXCQFG-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-butylpropane-1,3-diamine Chemical compound CCCCN(CCCN)CCCN CMDGBXZMCXCQFG-UHFFFAOYSA-N 0.000 description 1
- BQUQUASUHNZZLS-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-cyclohexylpropane-1,3-diamine Chemical compound NCCCN(CCCN)C1CCCCC1 BQUQUASUHNZZLS-UHFFFAOYSA-N 0.000 description 1
- ZKKMLXOYLORBLV-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-ethylpropane-1,3-diamine Chemical compound NCCCN(CC)CCCN ZKKMLXOYLORBLV-UHFFFAOYSA-N 0.000 description 1
- RQSHNRYXVUXSJC-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-hexylpropane-1,3-diamine Chemical compound CCCCCCN(CCCN)CCCN RQSHNRYXVUXSJC-UHFFFAOYSA-N 0.000 description 1
- LUZCQJHUWNIZNZ-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-pentylpropane-1,3-diamine Chemical compound CCCCCN(CCCN)CCCN LUZCQJHUWNIZNZ-UHFFFAOYSA-N 0.000 description 1
- CSIOOUSJMRKIAQ-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-propylpropane-1,3-diamine Chemical compound NCCCN(CCC)CCCN CSIOOUSJMRKIAQ-UHFFFAOYSA-N 0.000 description 1
- LFEPPILEVCKNJN-UHFFFAOYSA-N n'-(cyclohexylmethyl)ethane-1,2-diamine Chemical compound NCCNCC1CCCCC1 LFEPPILEVCKNJN-UHFFFAOYSA-N 0.000 description 1
- IZDWJSKWDHFHSF-UHFFFAOYSA-N n'-(cyclohexylmethyl)propane-1,3-diamine Chemical compound NCCCNCC1CCCCC1 IZDWJSKWDHFHSF-UHFFFAOYSA-N 0.000 description 1
- RFLHDXQRFPJPRR-UHFFFAOYSA-N n'-benzylpropane-1,3-diamine Chemical compound NCCCNCC1=CC=CC=C1 RFLHDXQRFPJPRR-UHFFFAOYSA-N 0.000 description 1
- HVOYZOQVDYHUPF-UHFFFAOYSA-N n,n',n'-trimethylethane-1,2-diamine Chemical compound CNCCN(C)C HVOYZOQVDYHUPF-UHFFFAOYSA-N 0.000 description 1
- NYIODHFKZFKMSU-UHFFFAOYSA-N n,n-bis(methylamino)ethanamine Chemical compound CCN(NC)NC NYIODHFKZFKMSU-UHFFFAOYSA-N 0.000 description 1
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 description 1
- NGRXSVVLBWDAHG-UHFFFAOYSA-N n,n-bis(propan-2-ylamino)ethanamine Chemical compound CC(C)NN(CC)NC(C)C NGRXSVVLBWDAHG-UHFFFAOYSA-N 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
- WLNSKTSWPYTNLY-UHFFFAOYSA-N n-ethyl-n',n'-dimethylethane-1,2-diamine Chemical compound CCNCCN(C)C WLNSKTSWPYTNLY-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 229940057402 undecyl alcohol Drugs 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
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
- 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
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
-
- 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
- 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
- C08G59/182—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 using pre-adducts of epoxy compounds with curing agents
- C08G59/184—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 using pre-adducts of epoxy compounds with curing agents with amines
-
- 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
- C08G59/50—Amines
- C08G59/56—Amines together with other curing agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/20—Compounding polymers with additives, e.g. colouring
- C08J3/22—Compounding polymers with additives, e.g. colouring using masterbatch techniques
- C08J3/226—Compounding polymers with additives, e.g. colouring using masterbatch techniques using a polymer as a carrier
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
- C08J3/241—Preventing premature crosslinking by physical separation of components, e.g. encapsulation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
- C08J5/243—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using carbon fibres
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
- C08J5/244—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using glass fibres
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/249—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs characterised by the additives used in the prepolymer mixture
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08L63/04—Epoxynovolacs
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2463/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
Definitions
- the present invention relates to a latent curing agent for a masterbatch type epoxy resin and an epoxy resin composition using the same, and in particular, fine particles composed of a mixture of a glycidyl ether type epoxy resin, an adduct-modified amine and a phenol compound, an active hydrogen compound,
- the present invention also relates to a latent curing agent for a masterbatch type epoxy resin, which is obtained from an isocyanate compound and has excellent curability and stability.
- Epoxy resins have excellent adhesion to various substrates, and cured products obtained by curing epoxy resins with curing agents have relatively good heat resistance, chemical resistance, electrical properties, mechanical properties, etc. Therefore, it is widely used for paints, adhesives, various molding materials, etc.
- epoxy resin compositions have mainly been two-component systems in which a curing agent or a curing accelerator is added immediately before use.
- the two-component system has the characteristics that it can be cured at room temperature or low temperature, but on the other hand, it must be weighed and mixed immediately before use, and the usable time is short, so it can be applied to automatic machines. There is a problem that the use conditions are limited, such as being difficult. In order to solve such problems, a one-component curable epoxy resin composition is desired.
- a curing agent that does not react at room temperature but has a property of starting and curing by heating
- a so-called latent curing agent is required.
- the latent curing agent for example, dicyandiamide, dibasic acid dihydrazide, boron trifluoride amine complex salt, guanamines, melamine, imidazoles and the like have been proposed.
- a mixture of dicyandiamide, melamine, and guanamine with an epoxy resin is excellent in storage stability, but requires a high temperature of 150 ° C. or higher for a long time to cure. have.
- microcapsule-type latent curing agents for epoxy resins obtained by surface treatment of amine-based curing agents such as amine-epoxy adducts with polyisocyanate have been proposed, but storage stability, heat-curing properties, etc. are still available. No satisfactory product has been obtained in terms of performance.
- a microcapsule type curing agent having a curing agent as a core component and a thermoplastic resin as a shell component (Patent Document 1), a compound having a primary amino group or a secondary amino group, and a tertiary amino group but having a primary amino group Curing agent for epoxy resin obtained by reacting an isocyanate compound with a fine powder comprising a mixture of an amino group and a compound having no secondary amino group (Patent Document 2), or a solid adduct synthesized from an amine compound and an epoxy compound
- Patent Document 3 a powder curing agent for epoxy resin having a spherical shape
- the first object of the present invention is to provide a latent curing agent for an epoxy resin that can impart excellent storage stability and heat curability to the epoxy resin.
- the second object of the present invention is to provide a one-component curable epoxy resin composition having excellent storage stability and heat curability.
- the present inventors have used a latent curing agent for a masterbatch type epoxy resin containing a specific component, thereby achieving a one-part type curing having excellent storage stability and heat curability.
- the present inventors have found that a functional epoxy resin composition can be obtained and have reached the present invention.
- the present invention comprises a latent curing agent for a masterbatch type epoxy resin obtained from the following components (A) to (D), and an epoxy resin and a latent curing agent for the masterbatch type epoxy resin.
- This is a one-component curable epoxy resin composition.
- % Of the mixture fine particles (C) an active hydrogen compound, and (D) Isocyanate compound.
- the latent curing agent for masterbatch type epoxy resin of the present invention may be one obtained by reacting the component (D) with the mixed system of (A) to (C).
- the chlorine concentration in the glycidyl ether type epoxy resin used for the component (A) is preferably 2000 ppm or less.
- the latent curing agent for masterbatch type epoxy resin of the present invention preferably has a viscosity of 20 Pa ⁇ s / 25 ° C. to 400 Pa ⁇ s / 25 ° C.
- An epoxy resin composition excellent in storage stability and curability can be obtained by the latent curing agent for masterbatch type epoxy resin of the present invention.
- the latent curing agent for masterbatch type epoxy resin of the present invention is obtained from components (A) to (D) described below.
- the component (A) and glycidyl ether type epoxy resin include polyglycidyl ether compounds of mononuclear polyhydric phenol compounds such as hydroquinone, resorcin, pyrocatechol or phloroglucinol; dihydroxynaphthalene, biphenol, methylene bisphenol (bisphenol F) ), Methylene bis (orthocresol), ethylidene bisphenol, isopropylidene bisphenol (common name: bisphenol A), isopropylidene bis (orthocresol), tetrabromobisphenol A, 1,3-bis (4-hydroxycumylbenzene), 1 , 4-bis (4-hydroxycumylbenzene), 1,1,3-tris (4-hydroxyphenyl) butane, 1,1,2,2-tetra (4-hydroxyphenyl) ethane, Poly
- the chlorine concentration in the component (A) glycidyl ether type epoxy resin is preferably 2000 ppm or less.
- the component (B) is fine particles of a mixture of (B-1) an adduct-modified amine obtained by reacting a glycidyl ether type epoxy resin and a polyamine compound, and (B-2) a phenol compound.
- the glycidyl ether type epoxy resin include the compounds exemplified as the component (A).
- the chlorine concentration is preferably 2000 ppm or less as in the case of the component (A).
- polyamines examples include ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, hexamethylenediamine, isophoronediamine, bis (4-amino-3-methylcyclohexyl) methane, diaminodicyclohexylmethane, metaxylenediamine, diaminodiphenylmethane, Diaminodiphenylsulfone, metaphenylenediamine, 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-isopropylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-phenylimidazole, 2-phenyl-4- Imidazoles such as methylimidazole and 2-aminopropylimidazole; N, N-dimethylaminoethylamine, N, N-diethylaminoethyl Ruamine, N, N
- reaction method is not particularly limited, but for example, a compound having a secondary or tertiary amino group is dissolved in a solvent, and a glycidyl ether type epoxy resin is added little by little, and further, 100 ° C. or higher. There is a method of reacting by heating.
- Examples of the solvent used for the reaction of the polyamine and the glycidyl ether type epoxy resin include hydrocarbons such as benzene, toluene, xylene, cyclohexene, mineral spirit, and naphtha; ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone.
- the (B-2) phenol compound is not particularly limited.
- 2,2-bis (4-hydroxyphenyl) propane (common name: bisphenol A) or phenol synthesized from phenols and aldehydes.
- Resin examples include phenol, cresol, ethylphenol, n-propylphenol, isopropylphenol, butylphenol, tert-butylphenol, octylphenol, nonylphenol, dodecylphenol, cyclohexylphenol, phenylphenol, chlorophenol, bromophenol, xylenol, resorcinol Catechol, hydroquinone, 2,2-bis (4-hydroxyphenyl) propane, 4,4′-thiodiphenol, dihydroxydiphenylmethane, naphthol, terpenephenol, phenolized dicyclopentadiene, and the like.
- Examples include formaldehyde.
- the particles of the mixture of component (B) are usually obtained by heating and mixing the components (B-1) and (B-2) in a solvent, then distilling off the solvent and pulverizing.
- the solvent used here include hydrocarbons such as benzene, toluene, xylene, cyclohexene, mineral spirit, and naphtha; ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; ethyl acetate, n-butyl acetate, Examples include esters such as propylene glycol monomethyl ethyl ether acetate; alcohols such as methanol, isopropanol, n-butanol, butyl cellosolve, and butyl carbitol.
- the mixing ratio of the component (B-1) and the component (B-2) is 50% by mass to 99% by mass for the component (B-1) and 1% by mass to 50% by mass for the component (B-2).
- the component (B-1) is preferably 70% by mass to 90% by mass
- the component (B-2) is preferably 10% by mass to 30% by mass.
- the mixing ratio of the component (B-2) is less than 1% by mass, the viscosity of the latent curing agent for masterbatch type epoxy resin is increased, and the handleability is lowered.
- the component (B-2) exceeds 50% by mass, the curing temperature of the epoxy resin increases, and the curability decreases.
- the volume average particle size of the mixture fine particles of the component (B) is required to be 100 ⁇ m or less, and preferably 0.1 to 10 ⁇ m.
- Examples of the active hydrogen compound of the component (C) include water, a compound having one or more primary and / or secondary amino groups in one molecule, and a compound having one or more hydroxyl groups in one molecule. It is done.
- Examples of the compound having one or more primary and / or secondary amino groups in one molecule include aliphatic amines, alicyclic amines, aromatic amines and the like.
- Examples of the aliphatic amine include alkylamines such as methylamine, ethylamine, propylamine, butylamine, and dibutylamine, alkylenediamines such as ethylenediamine, propylenediamine, butylenediamine, and hexamethylenediamine, diethylenetriamine, triethylenetetramine, and tetraethylenepenta.
- Examples include polyalkylene polyamines such as min, polyoxyalkylene polyamines such as polyoxypropylene diamine and polyoxyethylene diamine.
- alicyclic amines examples include cyclopropylamine, cyclobutylamine, cyclopentylamine, cyclohexylamine, isophoronediamine, and examples of aromatic amines include aniline, toluidine, benzylamine, naphthylamine, diaminodiphenylmethane. And diaminodiphenyl sulfone.
- Examples of the compound having one or more hydroxyl groups in one molecule include an alcohol compound and a phenol compound.
- the alcohol compound include methyl alcohol, propyl alcohol, butyl alcohol, amyl alcohol, hexyl alcohol, heptyl alcohol, octyl alcohol, nonyl alcohol, decyl alcohol, undecyl alcohol, lauryl alcohol, dodecyl alcohol, stearyl alcohol, and eicosyl.
- Monoalcohols such as alcohol, allyl alcohol, crotyl alcohol, propargyl alcohol, cyclopentanol, cyclohexanol, benzyl alcohol, cinnamyl alcohol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether, diethylene glycol monobutyl , Ethylene glycol, polyethylene glycol, plastic Propylene glycol, polypropylene glycol, 1,3-butanediol, 1,4-butanediol, hydrogenated bisphenol A, neopentyl glycol, glycerol, trimethylolpropane, polyhydric alcohols such as pentaerythritol. Further, examples of the phenol compound and the like include the compounds exemplified as the component (B-1).
- Examples of the isocyanate compound as the component (D) include propane-1,2-diisocyanate, 2,3-dimethylbutane-2,3-diisocyanate, 2-methylpentane-2,4-diisocyanate, and octane-3,6.
- adduct type polyisocyanates such as isocyanurate type polyisocyanate, biuret type polyisocyanate, urethane type polyisocyanate and allophanate type polyisocyanate can also be used as component (D).
- the isocyanurate-type polyisocyanate can be obtained by cyclization of the aforementioned isocyanate compound with a quaternary ammonium salt or the like to trimerize it.
- Biuret type polyisocyanate is obtained by reacting the above-described isocyanate compound with a biuret agent such as water.
- urethane type and / or allophanate type polyisocyanate is obtained by making the isocyanate compound mentioned above react with monoalcohol and / or polyol.
- Examples of monoalcohols used here include n-butanol, 2-ethylhexanol, butyl cellosolve, polyethylene glycol monoethyl ether, etc., and polyols include ethylene glycol, propylene glycol, 1,3 butanediol, and 1,4 butanediol. , Diethylene glycol, polyethylene glycol, polypropylene glycol, polytetramethylene glycol, trimethylolpropane and the like. These monoalcohols or polyols may be used alone or in combination of two or more.
- the latent curing agent for masterbatch type epoxy resins of the present invention may be obtained by reacting the mixture of the components (A), (B) and (C) with the component (D). Specifically, component (D) was added to the mixed system of components (A), (B), and (C), and the mixture was reacted by heating at 40 to 60 ° C. to confirm that the absorption of isocyanate groups by IR disappeared. After that, aging reaction is further performed at 40 to 60 ° C. for 2 to 12 hours.
- the blending ratio of each component is 50-78.9% by mass for component (A), 20-48.9% by mass for component (B), 0.1-1.5% by mass for component (C), and component (D) is 1 to 15% by mass.
- the latent curing agent for masterbatch type epoxy resin obtained by the present invention preferably has a viscosity of 20 Pa ⁇ s / 25 ° C. to 400 Pa ⁇ s / 25 ° C. from the viewpoint of workability and ease of blending. .
- the one-pack type curable epoxy resin composition of the present invention comprises the latent curing agent for masterbatch type epoxy resin of the present invention and an epoxy resin.
- the epoxy resin used in the one-component curable epoxy resin composition of the present invention include polyglycidyl ether compounds of mononuclear polyhydric phenol compounds such as hydroquinone, resorcin, pyrocatechol, and phloroglucinol; dihydroxynaphthalene, Biphenol, methylene bisphenol (common name: bisphenol F), methylene bis (orthocresol), ethylidene bisphenol, isopropylidene bisphenol (common name: bisphenol A), isopropylidene bis (orthocresol), tetrabromobisphenol A, 1,3-bis (4-hydroxycumylbenzene), 1,4-bis (4-hydroxycumylbenzene), 1,1,3-tris (4-hydroxyphenyl) butane, 1,1,2,2-tetra (4-
- epoxy resins may be internally cross-linked by a prepolymer having an isocyanate at the end, or have a high molecular weight by a polyvalent active hydrogen compound such as a polyhydric phenol, polyamine, carbonyl group-containing compound, or polyphosphate ester. It may be made.
- a polyvalent active hydrogen compound such as a polyhydric phenol, polyamine, carbonyl group-containing compound, or polyphosphate ester. It may be made.
- the curable epoxy resin composition of the present invention includes a curing catalyst; a reactive or non-reactive diluent (such as monoglycidyl ethers, dioctyl phthalate, dibutyl phthalate, benzyl alcohol, coal tar) as necessary.
- a reactive or non-reactive diluent such as monoglycidyl ethers, dioctyl phthalate, dibutyl phthalate, benzyl alcohol, coal tar
- Plasticizer glass fiber, carbon fiber, cellulose, silica sand, cement, kaolin, clay, aluminum hydroxide, bentonite, talc, silica, fine powder silica, titanium dioxide, carbon black, graphite, iron oxide, bituminous substance, metal Particles, fillers or pigments such as resin particles coated with metal; thickeners; thixotropic agents; flame retardants; antifoaming agents; rust preventives; containing conventional additives such as colloidal silica and colloidal alumina Furthermore, you may contain adhesive resins, such as a xylene resin and a petroleum resin.
- adhesive resins such as a xylene resin and a petroleum resin.
- Adeka Resin EP-4100E (produced by ADEKA Corp., Bisphenol A at 60-100 ° C.) 190 g (0.5 mol) of diglycidyl ether type epoxy resin: epoxy equivalent 190) was added while being divided, and the mixture was aged. Subsequently, it heated to 180 degreeC and methylpropylene glycol was removed, and solid substance (b) with melting
- Production Example 6 [Production of mixture fine particles F] Mixed fine particles F having a volume average particle diameter of 5 ⁇ m were obtained in the same manner as in Production Example 3 except that cresol novolac resin (OH equivalent 90, melting point 110 ° C.) was used instead of phenol novolac resin.
- Adeka Resin EP-4100L (manufactured by ADEKA Corporation, bisphenol A diglycidyl ether type epoxy resin: epoxy equivalent 170 g / eq, chlorine concentration 600 ppm), 700 g of water, and mixture fine particles C obtained in Production Example 3 were mixed. After adding 300 g and mixing uniformly, 30.0 g (0.34 mol) of tolylene diisocyanate (TDI) was added and reacted at 40 to 50 ° C. for 2 hours. After confirming the absence of NCO absorption by IR, the mixture was further aged at 40 to 50 ° C. under reduced pressure for 2 hours to obtain a masterbatch type latent curing agent for epoxy resins.
- TDI tolylene diisocyanate
- a latent curing agent for a masterbatch type epoxy resin was obtained in the same manner as in Example 1 except that the mixture fine particles D were used instead of the mixture fine particles C.
- a latent curing agent for a masterbatch type epoxy resin was obtained in the same manner as in Example 1 except that the mixed fine particles E were used instead of the mixed fine particles C.
- Example 1 A latent curing agent for a masterbatch type epoxy resin was obtained in the same manner as in Example 1 except that the fine particles A were used instead of the mixed fine particles C.
- Comparative Example 2 A latent curing agent for a masterbatch type epoxy resin was obtained in the same manner as in Example 1 except that the fine particles B were used instead of the mixed fine particles C.
- Adeka Resin EP-4100 (Adeka Co., Ltd., bisphenol A diglycidyl ether type epoxy resin: epoxy equivalent 190 g / eq, chlorine concentration 2,500 ppm) instead of Adeka Resin EP-4100L, the same as Example 1 was used. Thus, a latent curing agent for masterbatch type epoxy resin was obtained.
- a latent curing agent for a masterbatch type epoxy resin was obtained in the same manner as in Example 1 except that the mixture fine particles F were used.
- Adeka Resin EP-4100L (manufactured by ADEKA Corporation, bisphenol A diglycidyl ether type epoxy resin: epoxy equivalent 170 g / eq, chlorine concentration 600 ppm), 700 g of glycerin and the mixture fine particles C obtained in Production Example 3
- 30.0 g (0.34 mol) of tolylene diisocyanate (TDI) was added and reacted at 40-50 ° C. for 2 hours, after which it was confirmed that NCO absorption disappeared by IR did. Thereafter, the mixture was further aged at 40 to 50 ° C. under reduced pressure for 2 hours to obtain a masterbatch type epoxy resin latent curing agent.
- Adeka Resin EP-4100L (manufactured by ADEKA Corporation, bisphenol A diglycidyl ether type epoxy resin: epoxy equivalent 170 g / eq, chlorine concentration 600 ppm), 700 g of water, and mixture fine particles C obtained in Production Example 3 were mixed. After 300 g was added and mixed uniformly, 34.7 g (0.34 mol) of norbornene diisocyanate (NBDI) was added and reacted at 40-50 ° C. for 2 hours, after which it was confirmed by IR that there was no NCO absorption. . Thereafter, the mixture was further aged at 40 to 50 ° C. under reduced pressure for 2 hours to obtain a masterbatch type epoxy resin latent curing agent.
- NBDI norbornene diisocyanate
- Epoxy equivalent means the mass (g) of an epoxy resin containing 1 equivalent of an epoxy group.
- the epoxy equivalent of the diglycidyl ether type epoxy resin used in each example and comparative example was measured according to JIS K-7236.
- [Chlorine concentration] The diglycidyl ether type epoxy resin used in each example and comparative example was burned and oxidized in an Ar / O 2 atmosphere, and the generated hydrogen chloride was collected in an absorbing solution, and then a potential difference determination device was used. The chlorine concentration was measured by silver ions, and the chlorine concentration in the epoxy resin was calculated.
- Adeka Resin EP-4901E (produced by ADEKA, bisphenol F diglycidyl ether type epoxy resin: epoxy equivalent 170) is mixed uniformly with a master batch type latent curing agent 120 g, and a one-part epoxy resin composition is prepared. Manufactured. 100 parts by mass of this one-part epoxy resin composition and 20 parts by mass of a mixed solvent of toluene / ethyl acetate (mass ratio 1/1) were mixed to prepare a mixed varnish.
- the viscosity at 25 degreeC was measured using the BM type
- the evaluation method of the solvent stability was ⁇ when the viscosity increase rate was less than 2 times, ⁇ when the viscosity was 2 times or more and less than 4 times, and ⁇ when the gelation was 4 times or more.
- the masterbatch type epoxy resin latent curing agent of the present invention is a one-part type curing that combines low viscosity with excellent curability and solvent stability by combining with an epoxy resin. It was confirmed that a functional epoxy resin composition can be obtained. It was also confirmed that the curability of the mixture particles composed of the components (B-1) and (B-2) was lowered when the component (B-2) exceeded 50% by mass. In particular, when an epoxy adduct using a glycidyl ether type epoxy resin having a chlorine concentration of 2000 ppm or less is used, it is confirmed that the latent curing agent for the masterbatch type epoxy resin itself has a low viscosity. It was also confirmed that by using the latent curing agent for epoxy resin itself, a one-part curable epoxy resin composition having excellent storage stability can be obtained.
- the latent curing agent for masterbatch type epoxy resin of the present invention is excellent in storage stability and curability, and is an adhesive, a paste-like composition, a film-like composition, an anisotropic conductive material, a sealing material, A one-component curable epoxy resin composition useful for the production of paint materials, prepregs, and the like can be provided.
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Abstract
Description
しかしながら、例えば、ジシアンジアミド、メラミン、グアナミン類をエポキシ樹脂と混合したものは、貯蔵安定性には優れているが、硬化させるためには150℃以上の高温を長時間かけることを必要とするという問題を有している。
一方、二塩基酸ジヒドラジドやイミダゾール類は比較的低温で硬化するが、貯蔵安定性に乏しい。三フッ化ホウ素アミン錯塩は貯蔵安定性に優れ硬化時間は短いという長所があるが、耐水性に劣るばかりでなく、金属に対する腐食性を持つ等の問題を有している。
また、本発明の第二の目的は、優れた保存安定性及び加熱硬化性を有する一液型硬化性エポキシ樹脂組成物を提供することにある。
(A)グリシジルエーテル型エポキシ樹脂、
(B)(B-1)グリシジルエーテル型エポキシ樹脂及びポリアミン化合物を反応させて得られるアダクト変性アミンを50質量%~99質量%、及び、(B-2)フェノール化合物を50質量%~1質量%含有する混合物の微粒子、
(C)活性水素化合物、及び、
(D)イソシアネート化合物。
本発明のマスターバッチ型エポキシ樹脂用潜在性硬化剤は、前記(A)~(C)の混合系に前記成分(D)を反応させたものでもよい。
前記成分(A)に使用されるグリシジルエーテル型エポキシ樹脂中の塩素濃度は、2000ppm以下であることが好ましい。
また、本発明のマスターバッチ型エポキシ樹脂用潜在性硬化剤は、粘度が20Pa・s/25℃~400Pa・s/25℃であることが好ましい。
前記成分(A)、グリシジルエーテル型エポキシ樹脂としては、例えば、ハイドロキノン、レゾルシン、ピロカテコール又はフロログルシノール等の単核多価フェノール化合物のポリグリシジルエーテル化合物;ジヒドロキシナフタレン、ビフェノール、メチレンビスフェノール(ビスフェノールF)、メチレンビス(オルトクレゾール)、エチリデンビスフェノール、イソプロピリデンビスフェノール(慣用名:ビスフェノールA)、イソプロピリデンビス(オルトクレゾール)、テトラブロモビスフェノールA、1,3-ビス(4-ヒドロキシクミルベンゼン)、1,4-ビス(4-ヒドロキシクミルベンゼン)、1,1,3-トリス(4-ヒドロキシフェニル)ブタン、1,1,2,2-テトラ(4-ヒドロキシフェニル)エタン、チオビスフェノール、スルホビスフェノール、オキシビスフェノール、フェノールノボラック、オルソクレゾールノボラック、エチルフェノールノボラック、ブチルフェノールノボラック、オクチルフェノールノボラック、レゾルシンノボラック又はテルペンフェノール等の多核多価フェノール化合物のポリグリシジルエーテル化合物;ビスフェノールA-エチレンオキシド付加物、エチレングリコール、プロピレングリコール、ブチレングリコール、ヘキサンジオール、ポリグリコール、チオジグリコール、グリセリン、トリメチロールプロパン、ペンタエリスリトール又はソルビトール等の多価アルコール類のポリグリシジルエーテル等が挙げられる。
成分(A)グリシジルエーテル型エポキシ樹脂において、塩素濃度が高いと、得られるマスターバッチ型エポキシ樹脂用潜在性硬化剤の粘度が高くなり、取り扱い性が低下すると共に、保存安定性も低下することから、成分(A)グリシジルエーテル型エポキシ樹脂中の塩素濃度は2000ppm以下であることが好ましい。
前記グリシジルエーテル型エポキシ樹脂の例としては、前記成分(A)として例示された化合物が挙げられる。また、(B-1)に使用されるグリシジルエーテル型エポキシ樹脂においても、前記成分(A)と同様、塩素濃度は2000ppm以下であることが好ましい。
反応方法は、特に制限されるものではないが、例えば、溶剤中に2級もしくは3級アミノ基を有する化合物を溶解させ、そこにグリシジルエーテル型エポキシ樹脂を少量ずつ添加し、さらに100℃以上に加熱して反応させる方法がある。
フェノール類の例としては、フェノール、クレゾール、エチルフェノール、n-プロピルフェノール、イソプロピルフェノール、ブチルフェノール、第三ブチルフェノール、オクチルフェノール、ノニルフェノール、ドデシルフェノール、シクロヘキシルフェノール、フェニルフェノール、クロロフェノール、ブロモフェノール、キシレノール、レゾルシン、カテコール、ハイドロキノン、2,2-ビス(4-ヒドロキシフェニル)プロパン、4,4’-チオジフェノール、ジヒドロキシジフェニルメタン、ナフトール、テルペンフェノール、フェノール化ジシクロペンタジエン等が挙げられ、アルデヒド類としては、ホルムアルデヒド等が挙げられる。
ここで使用される溶剤としては、例えば、ベンゼン、トルエン、キシレン、シクロヘキセン、ミネラルスピリット、ナフサ等の炭化水素類;アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類;酢酸エチル、酢酸-n-ブチル、プロピレングリコールモノメチルエチルエーテルアセテート等のエステル類;メタノール、イソプロパノール、n-ブタノール、ブチルセルソルブ、ブチルカルビトール等のアルコール類等が挙げられる。
また、(B)成分の混合物微粒子の体積平均粒径は、100μm以下であることが必要であり、0.1~10μmであることが好ましい。
脂肪族アミンとしては、例えば、メチルアミン、エチルアミン、プロピルアミン、ブチルアミン、ジブチルアミン等のアルキルアミン、エチレンジアミン、プロピレンジアミン、ブチレンジアミン、ヘキサメチレンジアミン等のアルキレンジアミン、ジエチレントリアミン、トリエチレンテトラミン、テトラエチレンペンタミン等のポリアルキレンポリアミン、ポリオキシプロピレンジアミン、ポリオキシエチレンジアミン等のポリオキシアルキレンポリアミン類等が挙げられる。
また、脂環式アミンの例としては、シクロプロピルアミン、シクロブチルアミン、シクロペンチルアミン、シクロヘキシルアミン、イソホロンジアミン等が挙げられ、芳香族アミンの例としては、アニリン、トルイジン、ベンジルアミン、ナフチルアミン、ジアミノジフェニルメタン、ジアミノジフェニルスルホン等が挙げられる。
アルコール化合物としては、例えば、メチルアルコール、プロピルアルコール、ブチルアルコール、アミルアルコール、ヘキシルアルコール、ヘプチルアルコール、オクチルアルコール、ノニルアルコール、デシルアルコール、ウンデシルアルコール、ラウリルアルコール、ドテシルアルコール、ステアリルアルコール、エイコシルアルコール、アリルアルコール、クロチルアルコール、プロパルギルアルコール、シクロペンタノール、シクロヘキサノール、ベンジルアルコール、シンナミルアルコール、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノエチルエーテル、ジエチレングリコールモノブチル等のモノアルコール類、エチレングリコール、ポリエチレングリコール、プロピレングリコール、ポリプロピレングリコール、1,3-ブタンジオール、1,4-ブタンジオール、水添ビスフェノールA、ネオペンチルグリコール、グリセリン、トリメチロールプロパン、ペンタエリスリトール等の多価アルコール類等が挙げられる。
また、フェノール化合物等の例としては、前記成分(B-1)として例示された化合物が挙げられる。
また、ビウレット型ポリイソシアネートは、前述したイソシアネート化合物を、水等のビウレット化剤と反応させることにより得られる。
また、ウレタン型及び/又はアロハネート型ポリイソシアネートは、前述したイソシアネート化合物を、モノアルコール及び/又はポリオールと反応させることにより得られる。
ここで用いられるモノアルコールの例としては、n-ブタノール、2-エチルヘキサノール、ブチルセロソルブ、ポリエチレングリコールモノエチルエーテル等、ポリオールとしては、エチレングリコール、プロピレングリコール、1,3ブタンジオール、1,4ブタンジオール、ジエチレングリコール、ポリエチレングリコール、ポリプロピレングリコール、ポリテトラメチレングリコール、トリメチロールプロパン等が挙げられる。これらのモノアルコール又はポリオールは単独で使用しても、2種以上を併用してもよい。
各成分の配合比は、成分(A)が50~78.9質量%、成分(B)が20~48.9質量%、成分(C)が0.1~1.5質量%、及び成分(D)が1~15質量%である。
本発明の一液型硬化性エポキシ樹脂組成物に使用されるエポキシ樹脂としては、例えば、ハイドロキノン、レゾルシン、ピロカテコール、フロログルシノール等の単核多価フェノール化合物のポリグリシジルエーテル化合物;ジヒドロキシナフタレン、ビフェノール、メチレンビスフェノール(慣用名:ビスフェノールF)、メチレンビス(オルトクレゾール)、エチリデンビスフェノール、イソプロピリデンビスフェノール(慣用名:ビスフェノールA)、イソプロピリデンビス(オルトクレゾール)、テトラブロモビスフェノールA、1,3-ビス(4-ヒドロキシクミルベンゼン)、1,4-ビス(4-ヒドロキシクミルベンゼン)、1,1,3-トリス(4-ヒドロキシフェニル)ブタン、1,1,2,2-テトラ(4-ヒドロキシフェニル)エタン、チオビスフェノール、スルホビスフェノール、オキシビスフェノール、フェノールノボラック、オルソクレゾールノボラック、エチルフェノールノボラック、ブチルフェノールノボラック、オクチルフェノールノボラック、レゾルシンノボラック、テルペンフェノール等の多核多価フェノール化合物のポリグリシジルエーテル化合物;ビスフェノールA-エチレンオキシド付加物、エチレングリコール、プロピレングリコール、ブチレングリコール、ヘキサンジオール、ポリグリコール、チオジグリコール、グリセリン、トリメチロールプロパン、ペンタエリスリトール、ソルビトール等の多価アルコール類のポリグリシジルエーテル;マレイン酸、フマル酸、イタコン酸、コハク酸、グルタル酸、スベリン酸、アジピン酸、アゼライン酸、セバシン酸、ダイマー酸、トリマー酸、フタル酸、イソフタル酸、テレフタル酸、トリメリット酸、トリメシン酸、ピロメリット酸、テトラヒドロフタル酸、ヘキサヒドロフタル酸、エンドメチレンテトラヒドロフタル酸等の脂肪族、芳香族または脂環族多塩基酸のグリシジルエステル類およびグリシジルメタクリレートの単独重合体または共重合体;N,N-ジグリシジルアニリン、ビス(4-(N-メチル-N-グリシジルアミノ)フェニル)メタン、ジグリシジルオルトトルイジン等のグリシジルアミノ基を有するエポキシ化合物;ビニルシクロヘキセンジエポキシド、ジシクロペンタンジエンジエポキシド、3,4-エポキシシクロヘキシルメチル-3,4-エポキシシクロヘキサンカルボキシレート、3,4-エポキシ-6-メチルシクロヘキシルメチル-6-メチルシクロヘキサンカルボキシレート、ビス(3,4-エポキシ-6-メチルシクロヘキシルメチル)アジペート等の環状オレフィン化合物のエポキシ化物;エポキシ化ポリブタジエン、エポキシ化スチレン-ブタジエン共重合物等のエポキシ化共役ジエン重合体、トリグリシジルイソシアヌレート等の複素環化合物が挙げられる。
メチルプロピレングリコール150g中に2‐メチルイミダゾールを164g(2.0mol)溶解し、60~100℃でアデカレジンEP-4100E((株)ADEKA製の商品名、ビスフェノールAジグリシジルエーテル型エポキシ樹脂:エポキシ当量190)380g(1.0mol)を分割しながら添加し、熟成反応させた。次いで、180℃まで加熱してメチルプロピレングリコールを除去し、融点100℃の固形物(a)を得た。得られた固形物(a)を粉砕し、体積平均粒径5μmの微粒子Aを得た。
メチルプロピレングリコール150g中に2‐メチルイミダゾール82g(1.0mol)を溶解し、60~100℃でアデカレジンEP‐4100E((株)ADEKA製 ビスフェノールAジグリシジルエーテル型エポキシ樹脂:エポキシ当量190)190g(0.5mol)を分割しながら添加した後、更にN,N‐ジメチルアミノプロピルアミンを102g(1.0mol)溶解し、同様に60~100℃でアデカレジンEP‐4100E((株)ADEKA製 ビスフェノールAジグリシジルエーテル型エポキシ樹脂:エポキシ当量190)190g(0.5mol)を分割しながら添加し、熟成反応させた。次いで、180℃まで加熱してメチルプロピレングリコールを除去し、融点90℃の固形物(b)を得た。得られた固形物(b)を粉砕し、体積平均粒径5μmの微粒子Bを得た。
メチルプロピレングリコール150g中に製造例1にて得られた固形物(a)480gを溶解させながら180℃まで加熱し、次いでフェノールノボラック樹脂(OH当量78、融点95℃)を120g添加した。次いで、減圧工程にてメチルプロピレングリコールを除去し、融点100℃の固形物を得た。得られた固形物を粉砕し、体積平均粒径5μmの混合物微粒子Cを得た。
メチルプロピレングリコール150g中に製造例2で得られた固形物(b)480gを溶解させながら180℃まで加熱し、次いでフェノールノボラック樹脂(OH当量78、融点95℃)を120g添加した。その後、減圧工程にてメチルプロピレングリコールを除去し、融点95℃の固形物を得た。得られた固形物を粉砕し、体積平均粒径5μmの混合物微粒子Dを得た。
メチルプロピレングリコール150g中に製造例2にて得られた固形物(b)360gを溶解させながら180℃まで加熱し、次いでフェノールノボラック樹脂(OH当量78、融点95℃)を240g添加した。その後、減圧工程にてメチルプロピレングリコールを除去し、融点100℃の固形物を得た。得られた固形物を粉砕し、体積平均粒径5μmの混合物微粒子Eを得た。
フェノールノボラック樹脂の代わりにクレゾールノボラック樹脂(OH当量90、融点110℃)を使用したこと以外は製造例3と同様にして、体積平均粒径5μmの混合物微粒子Fを得た。
メチルプロピレングリコール150g中に製造例2にて得られた固形物(b)240gを溶解させながら180℃まで加熱し、次いでフェノールノボラック樹脂(OH当量78、融点95℃)を360g添加した。その後、減圧工程にてメチルプロピレングリコールを除去し、融点100℃の固形物を得た。得られた固形物を粉砕し、体積平均粒径5μmの混合物微粒子Gを得た。
混合物微粒子Cの代わりに微粒子Aを用いたこと以外は実施例1と同様にして、マスターバッチ型エポキシ樹脂用潜在性硬化剤を得た。
[比較例2]
混合物微粒子Cの代わりに微粒子Bを用いたこと以外は実施例1と同様にして、マスターバッチ型エポキシ樹脂用潜在性硬化剤を得た。
混合物微粒子Cの代わりに混合物微粒子Gを用いたこと以外は実施例1と同様にして、マスターバッチ型エポキシ樹脂用潜在性硬化剤を得た。
[エポキシ当量]
「エポキシ当量」とは、1当量のエポキシ基を含むエポキシ樹脂の質量(g)を意味する。各実施例及び比較例で使用したジグリシジルエーテル型エポキシ樹脂のエポキシ当量は、JIS K‐7236に従って測定した。
[塩素濃度]
各実施例及び比較例で使用したジグリシジルエーテル型エポキシ樹脂を、Ar/O2雰囲気下で燃焼して酸化し、生成した塩化水素を吸収液に捕集した後、電位差適定装置を用いて、銀イオンによって塩素濃度を測定し、エポキシ樹脂中の塩素濃度を算出した。
[粘度]
製造直後のマスターバッチ型エポキシ樹脂用潜在性硬化剤の、25℃における粘度を、BM型粘度計を使用して測定した。
[融点]
Yanaco製の融点測定器を用いて融点を測定した。
[マスターバッチ型エポキシ樹脂用潜在性硬化剤の硬化性]
アデカレジンEP‐4901E((株)ADEKA製 ビスフェノールFジグリシジルエーテル型エポキシ樹脂:エポキシ当量170)100gに対して、得られたマスターバッチ型硬化剤120gを均一に混合し、DSC(昇温速度10℃/分)にて測定した。得られたDSCの発熱挙動チャートから読み取られる発熱最大温度を硬化温度とした。
[マスターバッチ型エポキシ樹脂用潜在性硬化剤の保存安定性]
各実施例及び比較例にて得られたマスターバッチ型硬化剤を、40℃雰囲気下にて保存し、1箇月経過した後、BM型粘度計を使用して粘度を測定し、製造直後の粘度に対する増粘率を算出した。
評価方法は、増粘率が2倍未満のものを◎、2倍以上4倍未満のものを○、4倍以上のものを△、ゲル化したものを×とした。
アデカレジンEP‐4901E((株)ADEKA製 ビスフェノールFジグリシジルエーテル型エポキシ樹脂:エポキシ当量170)100gに対して、マスターバッチ型潜在性硬化剤120gを均一に混合し、一液性エポキシ樹脂組成物を製造した。
この一液性エポキシ樹脂組成物100質量部と、トルエン/酢酸エチル(質量比が1/1)の混合溶媒20質量部とを混合し、混合ワニスを作製した。
この混合ワニスについて、混合溶媒との混合直後、及び、40℃で6時間静置した後の、25℃における粘度をBM型粘度計を使用して測定し、増粘率を算出した。
また、同様にして酢酸エチル/MEK=1/1質量比の混合溶媒を使用した場合の増粘率も算出した。
溶剤安定性の評価方法は、増粘率が2倍未満のものを◎、2倍以上4倍未満のものを○、4倍以上のものを△、ゲル化したものを×とした。
また、(B-1)及び(B-2)成分からなる混合物粒子であっても、(B‐2)成分が50質量%を超えると、硬化性が低下することも確認された。
特に、塩素濃度が2000ppm以下のグリシジルエーテル型エポキシ樹脂を用いたエポキシアダクトを使用した場合には、マスターバッチ型エポキシ樹脂用潜在性硬化剤自体が低粘度であることが確認され、このマスターバッチ型エポキシ樹脂用潜在性硬化剤自体を用いることによって、保存安定性が優れた一液硬化型エポキシ樹脂組成物が得られることも確認された。
Claims (5)
- 下記の成分(A)~(D)から得られることを特徴とするマスターバッチ型エポキシ樹脂用潜在性硬化剤;
(A)グリシジルエーテル型エポキシ樹脂、
(B)(B-1)グリシジルエーテル型エポキシ樹脂及びポリアミン化合物を反応させて得られるアダクト変性アミンを50質量%~99質量%、及び、(B-2)フェノール化合物を50質量%~1質量%含有する混合物の微粒子、
(C)活性水素化合物、及び、
(D)イソシアネート化合物。 - 前記成分(A)~(C)の混合系に前記成分(D)を反応させて得られる、請求項1に記載されたマスターバッチ型エポキシ樹脂用潜在性硬化剤。
- 前記成分(A)に使用されるグリシジルエーテル型エポキシ樹脂中の塩素濃度が2000ppm以下である、請求項1又は2に記載されたマスターバッチ型エポキシ樹脂用潜在性硬化剤。
- 粘度が20Pa・s/25℃~400Pa・s/25℃である、請求項1~3の何れかに記載されたマスターバッチ型エポキシ樹脂用潜在性硬化剤。
- 請求項1~4の何れかに記載されたマスターバッチ型エポキシ樹脂用潜在性硬化剤及びエポキシ樹脂を含有してなることを特徴とする、一液型硬化性エポキシ樹脂組成物。
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CA2821878A CA2821878C (en) | 2010-12-17 | 2011-12-05 | Masterbatch-type latent curing agent for epoxy resin, and epoxy resin composition using the same |
US13/994,441 US9464161B2 (en) | 2010-12-17 | 2011-12-05 | Masterbatch-type latent curing agent for epoxy resin, and epoxy resin composition using the same |
EP11849608.2A EP2653492B1 (en) | 2010-12-17 | 2011-12-05 | Masterbatch-type latent curing agent for epoxy resin, and epoxy resin composition using the same |
CN201180060717.XA CN103261284B (zh) | 2010-12-17 | 2011-12-05 | 母料型环氧树脂用潜在性硬化剂、及使用其的环氧树脂组合物 |
KR1020137015559A KR101813743B1 (ko) | 2010-12-17 | 2011-12-05 | 마스터 배치형 에폭시 수지용 잠재성 경화제 및 그것을 사용한 에폭시수지 조성물 |
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WO2016093253A1 (ja) * | 2014-12-08 | 2016-06-16 | 株式会社スリーボンド | 熱硬化性樹脂組成物 |
US11008455B2 (en) | 2016-07-08 | 2021-05-18 | Tesa Se | Curable adhesive compound and reactive adhesive tapes based thereon |
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JP5605516B2 (ja) * | 2012-03-29 | 2014-10-15 | Dic株式会社 | 導電性インキ組成物、導電性パターンの製造方法及び導電性回路 |
WO2019107070A1 (ja) * | 2017-11-29 | 2019-06-06 | 協立化学産業株式会社 | 硬化性樹脂組成物及びその製造方法 |
JP2019189833A (ja) * | 2018-04-27 | 2019-10-31 | 旭化成株式会社 | エポキシ樹脂組成物 |
CN114423801B (zh) * | 2019-07-19 | 2024-08-06 | 蓝立方知识产权有限责任公司 | 用于环氧粉末涂料的酚醛硬化剂 |
KR20220155260A (ko) * | 2020-03-31 | 2022-11-22 | 나믹스 가부시끼가이샤 | 경화 촉매, 수지 조성물, 봉지재, 접착제, 및 경화물 |
CN111484729A (zh) * | 2020-06-16 | 2020-08-04 | 江苏科技大学 | 一种三网络共聚的母线槽用浇注料 |
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WO2016093253A1 (ja) * | 2014-12-08 | 2016-06-16 | 株式会社スリーボンド | 熱硬化性樹脂組成物 |
JPWO2016093253A1 (ja) * | 2014-12-08 | 2017-09-14 | 株式会社スリーボンド | 熱硬化性樹脂組成物 |
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TW201226430A (en) | 2012-07-01 |
KR20130141597A (ko) | 2013-12-26 |
US9464161B2 (en) | 2016-10-11 |
CN103261284A (zh) | 2013-08-21 |
TWI506052B (zh) | 2015-11-01 |
BR112013015074B1 (pt) | 2020-12-29 |
CN103261284B (zh) | 2014-07-23 |
EP2653492B1 (en) | 2021-03-03 |
US20130267663A1 (en) | 2013-10-10 |
CA2821878A1 (en) | 2012-06-21 |
JP2012126859A (ja) | 2012-07-05 |
JP5717434B2 (ja) | 2015-05-13 |
KR101813743B1 (ko) | 2017-12-29 |
EP2653492A4 (en) | 2017-01-04 |
BR112013015074A2 (pt) | 2016-09-13 |
CA2821878C (en) | 2018-04-17 |
EP2653492A1 (en) | 2013-10-23 |
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