WO2011036836A1 - 無溶剤一液型シアン酸エステル-エポキシ複合樹脂組成物 - Google Patents
無溶剤一液型シアン酸エステル-エポキシ複合樹脂組成物 Download PDFInfo
- Publication number
- WO2011036836A1 WO2011036836A1 PCT/JP2010/004721 JP2010004721W WO2011036836A1 WO 2011036836 A1 WO2011036836 A1 WO 2011036836A1 JP 2010004721 W JP2010004721 W JP 2010004721W WO 2011036836 A1 WO2011036836 A1 WO 2011036836A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- resin composition
- cyanate ester
- composite resin
- general formula
- epoxy composite
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 36
- 239000004593 Epoxy Substances 0.000 title claims abstract description 21
- 239000000805 composite resin Substances 0.000 title claims abstract description 19
- 150000002148 esters Chemical class 0.000 title abstract 3
- 239000003822 epoxy resin Substances 0.000 claims abstract description 31
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 31
- -1 guanidine compound Chemical class 0.000 claims abstract description 23
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims abstract description 10
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims abstract description 10
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000002989 phenols Chemical class 0.000 claims abstract description 7
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 30
- 239000004643 cyanate ester Substances 0.000 claims description 16
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 230000001070 adhesive effect Effects 0.000 claims description 8
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
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- 239000011347 resin Substances 0.000 claims description 6
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- XSTITJMSUGCZDH-UHFFFAOYSA-N 4-(4-hydroxy-2,6-dimethylphenyl)-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1C1=C(C)C=C(O)C=C1C XSTITJMSUGCZDH-UHFFFAOYSA-N 0.000 claims description 3
- NJYZCEFQAIUHSD-UHFFFAOYSA-N acetoguanamine Chemical compound CC1=NC(N)=NC(N)=N1 NJYZCEFQAIUHSD-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims 1
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
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- PEHXKUVLLWGBJS-UHFFFAOYSA-N 2-[1-(2-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=CC=C(O)C=1C(C)C1=CC=CC=C1O PEHXKUVLLWGBJS-UHFFFAOYSA-N 0.000 description 1
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- 238000004040 coloring Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002483 hydrogen compounds Chemical class 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical group 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 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
- 238000005259 measurement Methods 0.000 description 1
- 239000002923 metal particle Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical class [H]C([H])([H])* 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
- 239000003607 modifier Substances 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
- CXXISLZOPXKTTK-UHFFFAOYSA-N n-methyl-4-[[4-[methyl(oxiran-2-ylmethyl)amino]phenyl]methyl]-n-(oxiran-2-ylmethyl)aniline Chemical compound C=1C=C(CC=2C=CC(=CC=2)N(C)CC2OC2)C=CC=1N(C)CC1CO1 CXXISLZOPXKTTK-UHFFFAOYSA-N 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000642 polymer Polymers 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
- 239000000843 powder Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000012945 sealing adhesive Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- LZOZLBFZGFLFBV-UHFFFAOYSA-N sulfene Chemical compound C=S(=O)=O LZOZLBFZGFLFBV-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 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
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- 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
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
- H01L23/295—Organic, e.g. plastic containing a filler
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- 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
- C08G59/5006—Amines aliphatic
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- 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
- C08G59/5033—Amines 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
- C08G59/50—Amines
- C08G59/5046—Amines heterocyclic
-
- 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
- C08G59/686—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 nitrogen
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
- C08G73/065—Preparatory processes
- C08G73/0655—Preparatory processes from polycyanurates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- 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
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/52—Encapsulations
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/52—Encapsulations
- H01L33/56—Materials, e.g. epoxy or silicone resin
-
- 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
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/36—Pre-polymer
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/0001—Technical content checked by a classifier
- H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00
Definitions
- the present invention relates to a cyanate ester-epoxy composite resin composition, and in particular, contains a cyanate ester, an epoxy resin, a guanidine compound, and a biphenyl compound, and is excellent in storage stability, low-temperature curability, and heat resistance.
- the present invention relates to a solvent one-component cyanate ester-epoxy composite resin composition.
- epoxy resin compositions have been used in various applications in the electric / electronic field because they have excellent electrical performance and adhesive strength.
- a cyanate ester-epoxy composite resin composition obtained by mixing an epoxy resin and a cyanate ester is used. It is widely used as a resin composition used for semiconductor sealing and molding applications that require heat resistance.
- Patent Document 1 a resin composition composed of a cyanate ester, an epoxy resin, dicyandiamide and the like has already been proposed (Patent Document 1), but there are drawbacks such as a high temperature and a long time required for curing, and it is still satisfactory. There are no characteristics that can be achieved.
- a first object of the present invention is a solvent-free one-component cyanate ester-epoxy resin composition obtained by combining a cyanate ester and an epoxy resin, which is excellent in storage stability and curability and has high heat resistance.
- a second object of the present invention is to provide a solvent-free one-component cyanate ester-epoxy resin composition excellent in storage stability and suitable for semiconductor encapsulation and molding applications.
- a third object of the present invention is to provide a solvent-free one-component cyanate ester-epoxy composite resin composition excellent in storage stability, low-temperature curability, and heat resistance, which is suitable as an adhesive composition. It is in.
- the present inventors obtain good results when a specific phenol compound is contained together with a cyanate ester, an epoxy resin and a guanidine compound.
- the present invention has been found.
- the present invention provides at least one phenol compound selected from the group consisting of (A) cyanate ester, (B) epoxy resin, (C) guanidine compound, and (D) a phenol compound represented by the following general formula:
- the guanidine compound of component (C) is preferably at least one selected from the group of compounds represented by the following general formula, and particularly selected from acetoguanamine, benzoguanamine, and dicyandiamide. It is preferable that it is at least one kind.
- the phenol compound as component (D) is preferably 4,4′-biphenol and / or 3,3 ′, 5,5′-tetramethyl-4,4′-biphenol
- the cyanate ester (A) is preferably at least one selected from the group consisting of the following general formulas (1) and (2) and prepolymers thereof.
- General formula (1) R 1 ′′ in the general formula (1) represents an unsubstituted or fluorine-substituted divalent hydrocarbon group, —O—, —S—, or a single bond, and R 2 ′ and R 3 are Each is independently a phenylene group which is unsubstituted or substituted with 1 to 4 alkyl groups.
- n ′ represents a positive number from 1 to 100
- R represents an unsubstituted or fluorine-substituted divalent hydrocarbon group.
- R 4 and R 5 are a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
- the cyanate ester-epoxy resin composition of the present invention is excellent in low temperature curability and heat resistance in spite of excellent storage stability.
- concrete, cement mortar, various metals, leather, glass, rubber, plastic, wood It can be used for a wide range of applications such as paints or adhesives for cloth, paper and the like.
- it since it has high heat resistance and excellent adhesiveness, it is suitable for use in electronic materials such as semiconductor protective sealing and adhesion of electronic parts, and automotive materials.
- the cyanate ester which is the component (A) used in the present invention is not particularly limited, the compound represented by the following general formula (1) or (2), and the cyanate group in these compounds It is preferable to use a prepolymer partially formed with a triazine ring.
- General formula (1): R 1 ′′ in the above general formula represents an unsubstituted or fluorine-substituted divalent hydrocarbon group, —O—, —S—, or a single bond, and R 2 ′ and R 3 are each independently unsubstituted. Or a phenylene group substituted with 1 to 4 alkyl groups.
- n ′ represents a positive number from 1 to 100
- R represents an unsubstituted or fluorine-substituted divalent hydrocarbon group.
- R 4 and R 5 are a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
- the following compounds are particularly preferable in the present invention.
- the prepolymer include those obtained by trimerizing all or part of the compound represented by the general formula (1).
- More preferred cyanate esters in the present invention are compounds represented by the following general formula (3) and prepolymers thereof, and in particular, 4,4′-ethylidenebisphenylene cyanate, 2,2-bis (4-silane). Anatophenyl) propane and bis (4-cyanato-3,5-dimethylphenyl) methane are preferred.
- General formula (3): R 5 ′ in the general formula (3) is selected from the following groups.
- R 6 to R 11 are each independently a hydrogen atom or an unsubstituted or fluorine-substituted methyl group, and n ′′ is an integer of 4 to 12.
- these cyanate esters can be used alone or in combination of two or more.
- epoxy resin of component (B) used in the present invention examples include polyglycidyl ether compounds of mononuclear polyhydric phenol compounds such as hydroquinone, resorcin, pyrocatechol, and phloroglucinol; dihydroxynaphthalene, biphenol, methylene bisphenol ( Bisphenol F), methylene bis (orthocresol), ethylidene bisphenol, isopropylidene bisphenol (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, thiobisphenol Polyglycidyl ether compounds of polynuclear polyhydric phenol compounds such as sulfene, sulfobisphenol,
- epoxy resins may be those internally crosslinked by terminal isocyanate prepolymers or those having a high molecular weight with polyvalent active hydrogen compounds (polyhydric phenols, polyamines, carbonyl group-containing compounds, polyphosphates, etc.). Good.
- the polyepoxy compound described above preferably has an epoxy equivalent of 70 to 3000, more preferably 90 to 2000. If the epoxy equivalent is less than 70, the curability may be lowered, and if it is greater than 3000, sufficient film properties may not be obtained.
- Examples of the guanidine compound (C) used in the present invention include compounds represented by the following general formula.
- m represents an integer of 1 to 5
- R 1 ′ represents an amino group or an unsubstituted or fluorine-substituted monovalent hydrocarbon group having 1 to 15 carbon atoms
- R 2 represents a hydrogen atom or carbon number. 1 to 4 alkyl groups are represented.
- guanidine compounds it is preferable to use acetoguanamine, benzoguanamine, or dicyandiamide, which has an excellent balance between stability and reactivity.
- the phenol compound of component (D) used in the present invention is, for example, a compound represented by the following general formula.
- l represents an integer of 0 to 4
- R 1 represents an unsubstituted or fluorine-substituted monovalent hydrocarbon group.
- 4,4′-biphenol and / or 3,3 ′, 5,5′-tetramethyl-4,4′-biphenol is used from the viewpoint of a balance between reactivity and stability. Is preferred.
- the amount of component (A) and component (B) used in the cyanate ester-epoxy resin composition of the present invention is 1 to 10,000 parts by weight, preferably 100 parts by weight of component (A), The amount is 10 to 1000 parts by mass, more preferably 20 to 500 parts by mass.
- the amount of the component (C) used in the cyanate ester-epoxy resin composition of the present invention is 3 to 60 parts by weight, preferably 5 parts per 100 parts by weight of the total amount of the components (A) and (B). ⁇ 50 parts by mass.
- the amount of the component (D) used in the cyanate ester-epoxy resin composition of the present invention is preferably 0.1 to 50 parts by mass, preferably 100 parts by mass of the total amount of the components (A) and (B). Is 1 to 30 parts by mass.
- the following additives are appropriately added within a range not to impair the effects of the present invention (10% by mass or less).
- Surfactants such as viscosity modifiers and surface modifiers, fluxing agents used to remove solder oxide films, coloring dyes and pigments, internal additives such as carnauba wax, phenolic and sulfur oxidizing agents
- Deterioration preventives such as inhibitors, hindered amine radical trapping agents, and UV absorbers.
- the cyanate ester-epoxy resin composition of the present invention may contain glass fiber, carbon fiber, cellulose, silica sand, cement, kaolin, clay, aluminum hydroxide, bentonite, talc, silica, fine powder silica, if necessary.
- additives such as colloidal silica and colloidal alumina, in addition to sticky resins such as xylene resin and petroleum resin, etc. Can do.
- the ratio of use of these additives and the like and the cyanate ester-epoxy resin composition of the present invention may be appropriately determined according to the application.
- the cyanate ester-epoxy resin composition of the present invention in a solvent-free one-part type, for example, it is possible to suppress the generation of VOC, so that it is possible to provide a highly safe material with reduced environmental load.
- the solvent-free one-component cyanate ester-epoxy resin composition of the present invention includes a wide range of paints or adhesives for concrete, cement mortar, various metals, leather, glass, rubber, plastic, wood, cloth, paper, etc. Can be used for various purposes. In particular, since it has high heat resistance and excellent adhesiveness, it is suitable for use in electronic materials such as semiconductor protective sealing and adhesion of electronic parts, and automotive materials.
- the above compounds were blended as shown in the following [Table 1], and the following tests were conducted to evaluate the storage stability, curability and glass transition point. The results are shown in [Table 1]. Street.
- a DSC chart was obtained using a differential scanning calorimeter (trade name: DSC 6220) manufactured by SII Nano Technologies, Inc. with a temperature increase rate of 10 ° C./min and a scanning temperature range of 25 to 300 ° C. Further, the secondary temperature was raised under the same conditions, and the glass transition point was measured from the inflection point of the heat capacity curve.
- the solvent-free one-component cyanate ester-epoxy resin composition of the present invention has excellent storage stability and curability, and can provide a highly safe material with reduced environmental load. Since it has an advantage that it can be applied to uses where a solvent cannot be used, such as permeation and curing, it is extremely useful industrially.
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Abstract
Description
本発明の第2の目的は、半導体封止や成形用途などに好適な、貯蔵安定性に優れた無溶剤一液型シアン酸エステル-エポキシ樹脂組成物を提供することにある。
本発明の第3の目的は、接着剤組成物として好適な、貯蔵安定性、低温硬化性、及び耐熱性に優れた、無溶剤一液型シアン酸エステル-エポキシ複合樹脂組成物を提供することにある。
一般式:
但し、上記一般式中のlは0~4の整数、R1は、非置換又はフッ素置換の1価の炭化水素基を表す。
一般式:
但し、上記一般式中のmは1~5の整数、R1’は、アミノ基又は非置換若しくはフッ素置換の炭素数1~15の1価の炭化水素基、R2は水素原子又は炭素数1~4のアルキル基である。
更に本発明においては、前記(D)成分のフェノール化合物が、4,4’-ビフェノール及び/又は3,3’,5,5’-テトラメチル-4,4’-ビフェノールであることが好ましく、前記(A)のシアン酸エステルが、下記一般式(1)、(2)及びこれらのプレポリマーからなる群から選択される少なくとも1種であることが好ましい。
一般式(1):
但し、上記一般式(1)中のR1”は、非置換又はフッ素置換の2価の炭化水素基、-O-、-S-、又は単結合を表し、R2’及びR3は、それぞれ独立に非置換又は1~4個のアルキル基で置換されているフェニレン基である。
一般式(2):
但し、上記一般式(2)中のn’は1~100の正数、Rは、非置換又はフッ素置換の2価の炭化水素基を表す。R4及びR5は水素原子又は炭素数1~4のアルキル基である。
本発明に使用される(A)成分であるシアン酸エステルは特に限定されるものではないが、下記一般式(1)又は(2)で表される化合物、及び、これらの化合物におけるシアネート基の一部がトリアジン環を形成したプレポリマーを使用することが好ましい。
一般式(1):
上記一般式中のR1”は、非置換又はフッ素置換の2価の炭化水素基、-O-、-S-、又は単結合を表し、R2’及びR3はそれぞれ独立して非置換又は1~4個のアルキル基で置換されているフェニレン基である。
一般式(2):
但し、上記一般式(2)中のn’は1~100の正数、Rは、非置換又はフッ素置換の2価の炭化水素基を表す。R4及びR5は水素原子又は炭素数1~4のアルキル基である。これらの中でも、本発明においては、特に下記の化合物が好ましい。
また、前記プレポリマーとしては、例えば、前記一般式(1)で表される化合物の全部又は一部が3量化したものが挙げられる。
一般式(3):
上記一般式(3)中のR5’は、下記の基の中から選択される。
上記のR6~R11は、それぞれ独立に水素原子又は非置換若しくはフッ素置換のメチル基、n”は4~12の整数である。
上記一般式中のmは1~5の整数、R1’は、アミノ基又は非置換若しくはフッ素置換の炭素数1~15の1価の炭化水素基を表し、R2は水素原子又は炭素数1~4のアルキル基を表す。
粘性調整剤や表面調整剤等の界面活性剤、はんだの酸化皮膜除去用等に用いるフラックス剤;着色用の染料や顔料;カルナバワックス等の内添離型剤;フェノール系、硫黄系等の酸化防止剤、ヒンダードアミン系ラジカルトラップ剤、紫外線吸収剤等の劣化防止剤。
エポキシ樹脂(EP):(株)ADEKA社製のEP-4901E(ビスフェノールF型エポキシ樹脂、エポキシ当量168の商品名)
ベンゾグアナミン(BG):日本カーバイド工業(株)社製のBG(商品名)
ジシアンジアミド(DICY):(株)ADEKA社製のEH-3636AS(商品名)
4,4’-ビフェノール(44BP):東京化成工業(株)社製の4,4’-ビフェノール
ビス(4-ヒドロキシフェニル)スルホン(BPS):東京化成工業(株)社製のビス(4-ヒドロキシフェニル)スルホン
上記の化合物を下記〔表1〕に示した如く配合し、以下の試験を実施して貯蔵安定性、硬化性及びガラス転移点を評価した結果は、〔表1〕に示した通りである。
ブルックフィールドE型回転粘度計を用いて、5rpmで25℃における粘度を測定した。
各測定温度に保たれた熱盤上に、得られた組成物を0.5g滴下し、スパチュラなどでかき混ぜながら、流動性がなくなるまでの時間を測定した。
SIIナノテクノロジーズ社製の示差走査熱量計(商品名:DSC6220)を用いて、昇温速度10℃/分、走査温度範囲を25~300℃として測定し、DSCチャートを得た。更に、同条件で2次昇温を行い、熱容量曲線の変曲点からガラス転移点を測定した。
JIS K 6850に準拠した方法によって、120℃×1時間硬化後の鋼板/鋼板の剪断接着力を求めた。
Claims (10)
- 前記(C)成分のグアニジン化合物が、アセトグアナミン、ベンゾグアナミン、ジシアンジアミドの中から選ばれる少なくとも一種である、請求項2に記載された無溶剤一液型シアン酸エステル-エポキシ複合樹脂組成物。
- 前記(D)成分のフェノール化合物が、4,4’-ビフェノール及び/又は3,3’,5,5’-テトラメチル-4,4’-ビフェノールである、請求項1又は2に記載された無溶剤一液型シアネート-エポキシ複合樹脂組成物。
- 前記(A)のシアン酸エステルが、下記一般式(1)、(2)及びこれらのプレポリマーからなる群から選択される少なくとも1種である、請求項1に記載された無溶剤一液型シアン酸エステル-エポキシ複合樹脂組成物;
一般式(1):
但し、上記一般式(1)中のR1”は、非置換又はフッ素置換の2価の炭化水素基、-O-、-S-、又は単結合を表し、R2’及びR3は、それぞれ独立に非置換又は1~4個のアルキル基で置換されているフェニレン基である。
一般式(2):
但し、上記一般式(2)中のn’は1~100の正数、Rは、非置換又はフッ素置換の2価の炭化水素基を表す。R4及びR5は水素原子又は炭素数1~4のアルキル基である。 - 請求項1に記載されたシアン酸エステル-エポキシ複合樹脂組成物を重合硬化させてなることを特徴とする硬化物。
- 請求項1に記載されたシアン酸エステル-エポキシ複合樹脂組成物と、充填剤、顔料、増粘剤、チキソトロピック剤、難燃剤、消泡剤、防錆剤、コロイダルシリカ、コロイダルアルミナ、及び粘着性樹脂類からなる群の中から選択された少なくとも1種からなる均一混合物を、硬化させてなることを特徴とする硬化物。
- 請求項1に記載されたシアン酸エステル-エポキシ複合樹脂組成物からなることを特徴とする封止用材料。
- 請求項1に記載されたシアン酸エステル-エポキシ複合樹脂組成物からなることを特徴とする接着剤。
- 請求項1に記載されたシアン酸エステル-エポキシ複合樹脂組成物を型内で硬化させることを特徴とする、硬化物の製造方法。
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KR1020177002361A KR101811184B1 (ko) | 2009-09-25 | 2010-07-23 | 무용제 일액형 시안산 에스테르-에폭시 복합 수지 조성물 |
US13/497,811 US9601401B2 (en) | 2009-09-25 | 2010-07-23 | Solventless one liquid type cyanate ester-epoxy composite resin composition |
KR1020127007200A KR20120088673A (ko) | 2009-09-25 | 2010-07-23 | 무용제 일액형 시안산 에스테르-에폭시 복합 수지 조성물 |
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US20220289973A1 (en) | 2019-09-09 | 2022-09-15 | Adeka Corporation | Curable resin composition |
WO2021193233A1 (ja) | 2020-03-25 | 2021-09-30 | 株式会社Adeka | 硬化性樹脂組成物、及び硬化性樹脂組成物の硬化収縮を抑制する方法 |
US20240141095A1 (en) | 2021-03-08 | 2024-05-02 | Adeka Corporation | Curable resin composition, cured product and adhesive |
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TW201114796A (en) | 2011-05-01 |
CN102574987B (zh) | 2014-04-23 |
KR101811184B1 (ko) | 2017-12-20 |
US9601401B2 (en) | 2017-03-21 |
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