CN117413002A - 环氧树脂组合物 - Google Patents
环氧树脂组合物 Download PDFInfo
- Publication number
- CN117413002A CN117413002A CN202280038767.6A CN202280038767A CN117413002A CN 117413002 A CN117413002 A CN 117413002A CN 202280038767 A CN202280038767 A CN 202280038767A CN 117413002 A CN117413002 A CN 117413002A
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- CN
- China
- Prior art keywords
- epoxy resin
- resin composition
- epoxy
- bis
- mercaptomethylthio
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 239000003822 epoxy resin Substances 0.000 title claims abstract description 56
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 56
- 239000000203 mixture Substances 0.000 title claims abstract description 51
- 239000004593 Epoxy Substances 0.000 claims abstract description 57
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 54
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 11
- 229940126062 Compound A Drugs 0.000 claims abstract description 8
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 66
- 150000001412 amines Chemical class 0.000 claims description 25
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 150000003573 thiols Chemical class 0.000 claims description 6
- 239000000463 material Substances 0.000 abstract description 11
- 230000007613 environmental effect Effects 0.000 abstract description 3
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical group C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 abstract description 2
- -1 mold Substances 0.000 description 138
- 239000000047 product Substances 0.000 description 43
- 239000000306 component Substances 0.000 description 35
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 19
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- 101710082399 Alpha-protein kinase 3 Proteins 0.000 description 18
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 17
- 238000000034 method Methods 0.000 description 17
- 229920005989 resin Polymers 0.000 description 16
- 239000011347 resin Substances 0.000 description 16
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 229920000768 polyamine Polymers 0.000 description 12
- 229920003986 novolac Polymers 0.000 description 11
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 229920001568 phenolic resin Polymers 0.000 description 9
- 239000005011 phenolic resin Substances 0.000 description 9
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- 239000007983 Tris buffer Substances 0.000 description 8
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- 125000003118 aryl group Chemical group 0.000 description 7
- 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 7
- 125000003700 epoxy group Chemical group 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
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- 238000010538 cationic polymerization reaction Methods 0.000 description 6
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- 239000006087 Silane Coupling Agent Substances 0.000 description 5
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 5
- 239000003444 phase transfer catalyst Substances 0.000 description 5
- 239000003505 polymerization initiator Substances 0.000 description 5
- JOLVYUIAMRUBRK-UHFFFAOYSA-N 11',12',14',15'-Tetradehydro(Z,Z-)-3-(8-Pentadecenyl)phenol Natural products OC1=CC=CC(CCCCCCCC=CCC=CCC=C)=C1 JOLVYUIAMRUBRK-UHFFFAOYSA-N 0.000 description 4
- YLKVIMNNMLKUGJ-UHFFFAOYSA-N 3-Delta8-pentadecenylphenol Natural products CCCCCCC=CCCCCCCCC1=CC=CC(O)=C1 YLKVIMNNMLKUGJ-UHFFFAOYSA-N 0.000 description 4
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- PTFIPECGHSYQNR-UHFFFAOYSA-N cardanol Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
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- 239000002184 metal Substances 0.000 description 4
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
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- 239000001294 propane Substances 0.000 description 4
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- HHRACYLRBOUBKM-UHFFFAOYSA-N 2-[(4-tert-butylphenoxy)methyl]oxirane Chemical compound C1=CC(C(C)(C)C)=CC=C1OCC1OC1 HHRACYLRBOUBKM-UHFFFAOYSA-N 0.000 description 3
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- 239000000347 magnesium hydroxide Substances 0.000 description 1
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- QPGRDTXELAFGRG-UHFFFAOYSA-N n',n'-di(propan-2-yl)propane-1,3-diamine Chemical compound CC(C)N(C(C)C)CCCN QPGRDTXELAFGRG-UHFFFAOYSA-N 0.000 description 1
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- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-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
- YFQPICDSUBYACX-UHFFFAOYSA-N n'-(2-phenylethyl)propane-1,3-diamine Chemical compound NCCCNCCC1=CC=CC=C1 YFQPICDSUBYACX-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
- LUZCQJHUWNIZNZ-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-pentylpropane-1,3-diamine Chemical compound CCCCCN(CCCN)CCCN LUZCQJHUWNIZNZ-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
- HUQLOABSMDKQBW-UHFFFAOYSA-N n'-benzyl-n-methylethane-1,2-diamine Chemical compound CNCCNCC1=CC=CC=C1 HUQLOABSMDKQBW-UHFFFAOYSA-N 0.000 description 1
- IWUHWRSKHTWKHZ-UHFFFAOYSA-N n'-cyclohexyl-n-methylethane-1,2-diamine Chemical compound CNCCNC1CCCCC1 IWUHWRSKHTWKHZ-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
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- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
- VSWALKINGSNVAR-UHFFFAOYSA-N naphthalen-1-ol;phenol Chemical compound OC1=CC=CC=C1.C1=CC=C2C(O)=CC=CC2=C1 VSWALKINGSNVAR-UHFFFAOYSA-N 0.000 description 1
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- WSKHYOXDVZCOJP-UHFFFAOYSA-N naphthalene-1,6-diamine Chemical compound NC1=CC=CC2=CC(N)=CC=C21 WSKHYOXDVZCOJP-UHFFFAOYSA-N 0.000 description 1
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- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
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- 235000012239 silicon dioxide Nutrition 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
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- 235000019385 spermaceti wax Nutrition 0.000 description 1
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- 239000011029 spinel Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
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- 229940014800 succinic anhydride Drugs 0.000 description 1
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- QMHKMLUVKWZPCH-UHFFFAOYSA-N sulfanylmethylsulfanyl-[3-[3-(sulfanylmethylsulfanyl)propylsulfanylmethylsulfanylmethylsulfanylmethylsulfanyl]propylsulfanyl]methanethiol Chemical compound SCSCCCSCSCSCSCCCSC(S)SCS QMHKMLUVKWZPCH-UHFFFAOYSA-N 0.000 description 1
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- 235000007586 terpenes Nutrition 0.000 description 1
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- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
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- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000005028 tinplate Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 125000005628 tolylene group Chemical group 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- NLSXASIDNWDYMI-UHFFFAOYSA-N triphenylsilanol Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(O)C1=CC=CC=C1 NLSXASIDNWDYMI-UHFFFAOYSA-N 0.000 description 1
- DSROZUMNVRXZNO-UHFFFAOYSA-K tris[(1-naphthalen-1-yl-3-phenylnaphthalen-2-yl)oxy]alumane Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CC2=C(C=2C3=CC=CC=C3C=CC=2)C=1O[Al](OC=1C(=C2C=CC=CC2=CC=1C=1C=CC=CC=1)C=1C2=CC=CC=C2C=CC=1)OC(C(=C1C=CC=CC1=C1)C=2C3=CC=CC=C3C=CC=2)=C1C1=CC=CC=C1 DSROZUMNVRXZNO-UHFFFAOYSA-K 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229940045860 white wax Drugs 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
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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
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/223—Di-epoxy compounds together with monoepoxy compounds
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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
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
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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
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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
- C08G59/5046—Amines heterocyclic
- C08G59/5053—Amines heterocyclic containing only nitrogen as a heteroatom
- C08G59/5073—Amines heterocyclic containing only nitrogen as a heteroatom having two nitrogen atoms in the ring
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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
- C08G59/66—Mercaptans
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- Epoxy Resins (AREA)
Abstract
本发明的目的在于提供用于得到为了即使在环境变化大的状况下也维持可靠性而弹性模量降低的固化物的环氧系材料。本发明为一种环氧树脂组合物,其包含(A)下述通式(1)所表示的环氧化合物A、(B)取代有碳原子数6~20的烃基的苯基缩水甘油醚、(C)固化剂。在通式(1)中,R1及R2分别独立地表示碳原子数2~4的亚烷基,R3表示亚甲基或‑C(CH3)2‑,a及b分别独立地表示1~10的数。
Description
技术领域
本发明涉及将2种特定的环氧化合物组合而成的环氧树脂组合物。
背景技术
环氧树脂在粘接剂、涂料、电绝缘材料、土木建筑材料等广泛的用途中发挥优异的特性。其中,在电气·电子领域中的密封剂、铸型、粘接剂中,有效使用环氧树脂的特征即粘接性、耐热性等特征,但在上述的用途中大多要求即使在温度差大的环境、高湿度下也维持粘接性、耐热性。
廉价且获得容易而通用的双酚型环氧树脂通过利用固化剂固化而能够得到具有粘接性、耐热性的固化物,但由于固化物的弹性模量过大,因此存在在温度差大的环境、高湿度下的环境中产生裂纹或从基材剥离这样的问题。
作为解决上述问题的手段之一,考虑降低固化物的弹性模量的方法,具体而言可列举出并用增塑剂等的方法,但不被纳入环氧树脂的固化体系中的增塑剂会在固化后渗出而降低粘接性。作为维持粘接性、同时一定程度降低弹性模量而提高固化物的可靠性的手段,可列举出并用具有环氧基和长链烷基的化合物的方法(例如专利文献1等)。然而获知,就该方法而言,虽然可产生一定程度的柔软性,但不具有可耐受上述环境程度的柔软性。
现有技术文献
专利文献
专利文献1:US5683627A
发明内容
发明所要解决的课题
因此,本发明所要解决的课题在于提供用于得到为了在环境变化大的状况下也维持可靠性而弹性模量降低的固化物的环氧系材料。
用于解决课题的手段
于是,本发明者等进行深入研究,发现将2种特定的环氧化合物并用的环氧树脂组合物,达到本发明。即,本发明为一种环氧树脂组合物,其包含(A)下述通式(1)所表示的环氧化合物A、(B)下述通式(2)所表示的环氧化合物B、(C)固化剂。
[化学式1]
通式(1)中,R1及R2分别独立地表示碳原子数2~4的亚烷基,R3表示亚甲基或-C(CH3)2-,a及b分别独立地表示1~10的数。
[化学式2]
通式(2)中,R4表示碳原子数6~20的烃基。
发明效果
本发明的效果在于提供具有为了在环境变化大的状况下也维持可靠性所需的低弹性模量的环氧树脂组合物。该环氧树脂组合物可以适宜用于电气·电子领域的密封剂、铸型、粘接剂等各种用途。
具体实施方式
本发明的环氧树脂组合物含有(A)下述通式(1)所表示的环氧化合物A、(B)下述通式(2)所表示的环氧化合物B、及(C)固化剂。
[化学式3]
通式(1)中,R1及R2分别独立地表示碳原子数2~4的亚烷基,R3表示亚甲基或-C(CH3)2-,a及b分别独立地表示1~10的数。
[化学式4]
通式(2)中,R4表示碳原子数6~20的烃基。
在本发明的(A)成分即环氧化合物A中,R1及R2分别独立地为碳原子数2~4的亚烷基,例如可列举出亚乙基、亚丙基、异亚丙基、亚丁基、异亚丁基等。它们中,从能够得到低弹性模量的固化物的观点出发,优选为亚乙基、亚丙基、异亚丙基,特别优选为异亚丙基。此外,R1、R2可以为相同的基团,也可以为不同的基团,但从能够容易地合成的方面出发,优选为相同的基团。
在本发明的(A)成分即环氧化合物A中,a及b分别独立地为1~10的数,从弹性模量与固化性的平衡的观点出发优选为1~3。此外,a及b可以为相同的数,也可以为不同的数,但从能够容易地合成的方面出发,优选为相同的数。进而,在使用2种以上的环氧化合物A的情况下a及b的平均值分别优选为1~3。
环氧化合物A可以通过公知的方法来制造。具体而言,例如可以相对于双酚A、双酚F等双酚系化合物使用氢氧化钠等碱催化剂而加成环氧烷烃后,使用环氧氯丙烷进行环氧化而得到。若使用双酚A,则可得到R3为-C(CH3)2-的环氧化合物A,若使用双酚F,则可得到R3为亚甲基的环氧化合物A。
作为上述环氧烷烃,例如可列举出环氧乙烷、环氧丙烷、环氧丁烷等。需要说明的是,通过相对于上述双酚系化合物1摩尔调整环氧烷烃的加成摩尔数,能够调整a及b的数,例如在加成2摩尔环氧丙烷的情况下,a及b的数在理论上分别成为1。
作为使用上述环氧氯丙烷进行环氧化时的方法,例如可列举出下述方法:相对于双酚系化合物的环氧烷烃加成物1摩尔,使用1.6~3摩尔氢氧化钠等碱性化合物、2~20摩尔环氧氯丙烷、及根据需要的相转移催化剂,在常压或减压条件下在40~90℃下进行环氧化。此时,剩余的环氧氯丙烷优选通过蒸馏操作而除去。
作为上述相转移催化剂,例如可列举出四甲基铵盐、四丁基铵盐等。在使用相转移催化剂的情况下,相对于双酚系化合物的环氧烷烃加成物1摩尔,优选使用0.001~0.1摩尔的相转移催化剂。
作为环氧化的其他方法,可列举出下述方法:相对于双酚系化合物的环氧烷烃加成物1摩尔,使用氯化锡等路易斯酸作为催化剂,同时使2~4摩尔环氧氯丙烷反应而制造醇体后,使用1.6~3摩尔氢氧化钠等碱性化合物、及根据需要的溶剂进行闭环反应,由此进行环氧化。
作为上述溶剂,例如可列举出甲乙酮、甲基戊基酮、二乙基酮、丙酮、甲基异丙基酮、丙二醇单甲基醚乙酸酯、环己酮等酮类;四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷、丙二醇单甲基醚等醚类;乙酸乙酯、乙酸正丁酯等酯类;苯、甲苯、二甲苯等芳香族烃;四氯化碳、氯仿、三氯乙烯、二氯甲烷等卤代脂肪族烃;氯苯等卤代芳香族烃。
所得到的环氧化合物A也可以通过使用水或有机溶剂的油水分离、过滤、浓缩、蒸馏、提取、晶析、重结晶、吸附、及柱色谱法等分离精制手段、或将它们组合的手段进行分离精制。
作为本发明的(A)成分即环氧化合物A,也可以使用市售品,例如可列举出(株)ADEKA制的ADEKA RESIN系列的EP-4000、EP-4003、EP-4005、EP-4000S、EP-4003S、EP-4010S、EP-4000L等。
在本发明的(B)成分即环氧化合物B中,R4为碳原子数6~20的烃基,作为那样的烃基,例如可列举出正己基、环己基、1,3-二甲基丁基、1-异丙基丙基、1,2-二甲基丁基、正庚基、2-庚基、1,4-二甲基戊基、叔庚基、2-甲基-1-异丙基丙基、1-乙基-3-甲基丁基、正辛基、叔辛基、2-乙基己基、2-甲基己基、2-丙基己基、正壬基、异壬基、正癸基、异癸基、正十一烷基、异十一烷基、正十二烷基、异十二烷基、正十三烷基、异十三烷基、正十四烷基、异十四烷基、正十五烷基、异十五烷基、正十六烷基、异十六烷基、正十七烷基、异十七烷基、正十八烷基、异十八烷基、正十九烷基、异十九烷基、正二十烷基、异二十烷基、环庚基、环辛基、环十二烷基等。此外,上述列举的烃基中的一部分也可以不饱和化。
从获得容易、可得到更低弹性的固化物的观点出发,本发明的(B)成分即环氧化合物B优选为腰果酚型环氧化合物。腰果酚是通过天然存在的槚如酸中的任一者发生热分解而得到的苯酚脂质,具体而言具有下述通式(3)所表示的化学结构。
[化学式5]
通式(3)中,R为括弧右边所示的任一基团,*表示与芳香环键合的部位。
通常,天然来源的腰果酚为上述通式(3)所示的酚系化合物的混合物,各个化合物的比例因从天然采集的化合物、精制的条件等而不同,但例如可列举出具有作为饱和基的碳原子数15的正十五烷基的化合物为约5质量%、具备具有1个不饱和基的(8Z)-8,11-十五烯基的化合物为约35质量%、具备具有2个不饱和基的(8Z,11Z)-8,11-戊二烯基的化合物为约20质量%、具备具有3个不饱和基的(8Z,11Z)-8,11,14-戊三烯基的化合物为约40质量%的混合物。
本发明的(B)成分即环氧化合物B的优选的方式是将上述的腰果酚环氧化而得到的化合物。环氧化的方法没有特别限制,可以使用公知的方法,例如可列举出上述(A)成分即环氧化合物A的制造方法中例示的方法。即可列举出相对于腰果酚1摩尔使用氢氧化钠等碱性化合物0.8~1.5摩尔、环氧氯丙烷2~20摩尔、及根据需要的相转移催化剂在常压或减压条件下、在40~90℃下进行环氧化的方法。此时,剩余的环氧氯丙烷优选通过蒸馏操作而除去。
所得到的环氧化合物B也可以通过使用水或有机溶剂的油水分离、过滤、浓缩、蒸馏、提取、晶析、重结晶、吸附、及柱色谱法等分离精制手段、或将它们组合而成的手段进行分离精制。
作为本发明的(B)成分即环氧化合物B,也可以使用市售品,例如可列举出Cardolite公司制的NC 513、Ultra LITE 513、LITE 513E等。
在本发明的环氧树脂组合物中,从固化性与固化物的弹性模量的平衡的观点出发,(A)成分与(B)成分的质量比A/B优选为90/10~10/90,更优选为80/20~20/80,进一步优选为70/30~30/70,特别优选为60/40~40/60。
本发明的环氧树脂组合物也可以使用上述(A)成分及(B)成分以外的具有环氧基的化合物(以下,称为其他的环氧化合物)。作为那样的化合物,例如可列举出正丁基缩水甘油醚、C12~C14烷基缩水甘油醚、烯丙基缩水甘油醚、2-乙基己基缩水甘油醚、氧化苯乙烯、苯基缩水甘油醚、甲苯基缩水甘油醚、对仲丁基苯基缩水甘油醚、叔丁基苯基缩水甘油醚、甲基丙烯酸缩水甘油酯、及叔羧酸缩水甘油酯等具有1个环氧基的反应性稀释剂;氢醌、间苯二酚、焦儿茶酚、间苯三酚等单核多元酚化合物的聚缩水甘油醚化物;二羟基萘、联苯酚、亚甲基双酚(双酚F)、亚甲基双(邻甲酚)、亚乙基双酚、异亚丙基双酚(双酚A)、异亚丙基双(邻甲酚)、四溴双酚A、1,3-双(4-羟基枯基苯)、1,4-双(4-羟基枯基苯)、1,1,3-三(4-羟基苯基)丁烷、1,1,2,2-四(4-羟基苯基)乙烷、硫代双酚、磺基双酚、氧代双酚、苯酚酚醛清漆、邻甲酚酚醛清漆、乙基苯酚酚醛清漆、丁基苯酚酚醛清漆、辛基苯酚酚醛清漆、间苯二酚酚醛清漆、萜烯酚等多核多元酚化合物的聚缩水甘油醚化物;乙二醇、丙二醇、丁二醇、己二醇、聚乙二醇、硫二甘醇、二环戊二烯二甲醇、2,2-双(4-羟基环己基丙烷(氢化双酚A)、甘油、三羟甲基丙烷、季戊四醇、山梨糖醇等多元醇类的聚缩水甘油醚;马来酸、富马酸、衣康酸、琥珀酸、戊二酸、辛二酸、己二酸、壬二酸、癸二酸、二聚物酸、三聚物酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸、偏苯三酸、均苯三甲酸、均苯四甲酸、四氢邻苯二甲酸、六氢邻苯二甲酸、桥亚甲基四氢邻苯二甲酸等脂肪族、芳香族或脂环族多元酸的缩水甘油酯类及甲基丙烯酸缩水甘油酯的均聚物或共聚物;N,N-二缩水甘油基苯胺、双(4-(N-甲基-N-缩水甘油基氨基)苯基)甲烷、二缩水甘油基邻甲苯胺、N,N-双(2,3-环氧丙基)-4-(2,3-环氧丙氧基)-2-甲基苯胺、N,N-双(2,3-环氧丙基)-4-(2,3-环氧丙氧基)苯胺、N,N,N’,N’-四(2,3-环氧丙基)-4,4’-二氨基二苯基甲烷等具有缩水甘油基氨基的环氧化合物;乙烯基环己烯二环氧化物、二环戊二烯二环氧化物、3,4-环氧环己基甲基-3,4-环氧环己烷羧酸酯、3,4-环氧-6-甲基环己基甲基-6-甲基环己烷羧酸酯、双(3,4-环氧-6-甲基环己基甲基)己二酸酯等环状烯烃化合物的环氧化物;环氧化聚丁二烯、环氧化苯乙烯-丁二烯共聚物等环氧化共轭二烯聚合物、异氰脲酸三缩水甘油酯等杂环化合物。
作为其他的环氧化合物,也可以使用对环氧树脂赋予了氨基甲酸酯骨架的氨基甲酸酯改性环氧树脂。氨基甲酸酯改性环氧树脂是在分子内具有环氧基和氨基甲酸酯键的树脂,例如可以通过使具有异氰酸酯基的化合物相对于在分子内具有羟基的环氧化合物反应而获得,可以通过日本特开2016-210922号公报等中记载的公知的方法而获得。
作为其他的环氧化合物,也可以使用使CTBN和/或ATBN与环氧树脂反应而得到的橡胶改性环氧树脂等。
作为其他的环氧化合物,从树脂组合物的作业性与固化物的弹性模量的平衡的观点出发,优选为具有1个环氧基的反应性稀释剂、单核多元酚化合物的聚缩水甘油醚,更优选为双酚A型环氧树脂、双酚F型环氧树脂及叔丁基苯基缩水甘油醚。
从固化性与固化物的弹性模量的平衡的观点出发,使用其他的环氧化合物的情况的使用量相对于具有环氧基的化合物的总量,优选为0~90质量%,更优选为0~60质量%,进一步优选为0~30质量%。
作为本发明的(C)固化剂,例如可列举出胺系固化剂、硫醇系固化剂、酸酐、酚醛树脂类、阳离子聚合引发剂等。通过使(A)成分、(B)成分及任意使用的其他环氧化合物的混合物利用(C)固化剂而固化,能够得到固化性优异且柔软性良好的固化物。
作为上述胺系固化剂,例如可列举出乙二胺、二亚乙基三胺、三亚乙基四胺、四亚乙基五胺、聚氧亚丙基二胺、聚氧亚丙基三胺等脂肪族多胺;异佛尔酮二胺、薄荷烯二胺、双(4-氨基-3-甲基二环己基)甲烷、二氨基二环己基甲烷、双(氨基甲基)环己烷、N-氨基乙基哌嗪、3,9-双(3-氨基丙基)-2,4,8,10-四氧杂螺(5.5)十一烷等脂环式多胺;间苯二胺、对苯二胺、甲苯-2,4-二胺、甲苯-2,6-二胺、均三甲苯-2,4-二胺、均三甲苯-2,6-二胺、3,5-二乙基甲苯-2,4-二胺、3,5-二乙基甲苯-2,6-二胺等单核多胺;联苯二胺、4,4-二氨基二苯基甲烷、2,5-萘二胺、2,6-萘二胺等芳香族多胺等。它们可以单独使用,也可以将2种以上并用。
胺系固化剂也可以为使胺化合物与环氧化合物与根据需要的异氰酸酯化合物或尿素反应而得到的改性胺。
作为上述胺化合物,可列举出乙二胺、1,2-二氨基丙烷、1,3-二氨基丙烷、1,3-二氨基丁烷、1,4-二氨基丁烷、六亚甲基二胺等亚烷基二胺类;二亚乙基三胺、三亚乙基三胺、四亚乙基五胺等多烷基多胺类;1,4-二氨基环己烷、1,3-二氨基环己烷、1,3-二氨基甲基环己烷、1,2-二氨基环己烷、1,4-二氨基-3,6-二乙基环己烷、4,4’-二氨基二环己基甲烷、1,3-双(氨基甲基)环己烷、1,4-双(氨基甲基)环己烷、4,4’-二氨基二环己基丙烷、双(4-氨基环己基)砜、4,4’-二氨基二环己基醚、2,2’-二甲基-4,4’-二氨基二环己基甲烷、异佛尔酮二胺、降冰片烯二胺等脂环式多胺类;间苯二甲基二胺、二氨基二苯基甲烷、二氨基二苯基砜、二乙基甲苯二胺、1-甲基-3,5-二乙基-2,4-二胺苯、1-甲基-3,5-二乙基-2,6-二氨基苯、1,3,5-三乙基-2,6-二氨基苯、3,3’-二乙基-4,4’-二氨基二苯基甲烷、3,5,3’、5’-四甲基-4,4’-二氨基二苯基甲烷等芳香族多胺类;苯并胍胺、乙酰胍胺等胍胺类;2-甲基咪唑、2-乙基-4-甲基咪唑、2-异丙基咪唑、2-十一烷基咪唑、2-十七烷基咪唑、2-苯基咪唑、2-苯基-4-甲基咪唑、2-氨基丙基咪唑等咪唑类;草酸二酰肼、丙二酸二酰肼、琥珀酸二酰肼、戊二酸二酰肼、己二酸二酰肼、辛二酸二酰肼、壬二酸二酰肼、癸二酸二酰肼、邻苯二甲酸二酰肼等二酰肼类;N,N-二甲基氨基乙基胺、N,N-二乙基氨基乙基胺、N,N-二异丙基氨基乙基胺、N,N-二烯丙基氨基乙基胺、N,N-苄基甲基氨基乙基胺、N,N-二苄基氨基乙基胺、N,N-环己基甲基氨基乙基胺、N,N-二环己基氨基乙基胺、N-(2-氨基乙基)吡咯烷、N-(2-氨基乙基)哌啶、N-(2-氨基乙基)吗啉、N-(2-氨基乙基)哌嗪、N-(2-氨基乙基)-N’-甲基哌嗪、N,N-二甲基氨基丙基胺、N,N-二乙基氨基丙基胺、N,N-二异丙基氨基丙基胺、N,N-二烯丙基氨基丙基胺、N,N-苄基甲基氨基丙基胺、N,N-二苄基氨基丙基胺、N,N-环己基甲基氨基丙基胺、N,N-二环己基氨基丙基胺、N-(3-氨基丙基)吡咯烷、N-(3-氨基丙基)哌啶、N-(3-氨基丙基)吗啉、N-(3-氨基丙基)哌嗪、N-(3-氨基丙基)-N’-甲基哌啶、4-(N,N-二甲基氨基)苄基胺、4-(N,N-二乙基氨基)苄基胺、4-(N,N-二异丙基氨基)苄基胺、N,N,-二甲基异佛尔酮二胺、N,N-二甲基双氨基环己烷、N,N,N’-三甲基乙二胺、N’-乙基-N,N-二甲基乙二胺、N,N,N’-三甲基乙二胺、N’-乙基-N,N-二甲基丙烷二胺、N’-乙基-N,N-二苄基氨基丙基胺;N,N-(双氨基丙基)-N-甲基胺、N,N-双氨基丙基乙基胺、N,N-双氨基丙基丙基胺、N,N-双氨基丙基丁基胺、N,N-双氨基丙基戊基胺、N,N-双氨基丙基己基胺、N,N-双氨基丙基-2-乙基己基胺、N,N-双氨基丙基环己基胺、N,N-双氨基丙基苄基胺、N,N-双氨基丙基烯丙基胺、双〔3-(N,N-二甲基氨基丙基)〕胺、双〔3-(N,N-二乙基氨基丙基)〕胺、双〔3-(N,N-二异丙基氨基丙基)〕胺、双〔3-(N,N-二丁基氨基丙基)〕胺等。它们可以单独使用,也可以将2种以上并用。
作为用于得到上述改性胺的环氧化合物,例如可列举出上述其他的环氧化合物中例示的化合物,此外,也可以使用(A)成分及(B)成分。
作为用于得到上述改性胺的异氰酸酯化合物,例如可列举出2,4-甲苯撑二异氰酸酯、2,6-甲苯撑二异氰酸酯、二苯基甲烷-4,4’-二异氰酸酯、苯二异氰酸酯、苯二甲基二异氰酸酯、四甲基苯二甲基二异氰酸酯、1,5-萘二异氰酸酯、1,5-四氢萘二异氰酸酯、3,3’-二甲基二苯基-4,4’-二异氰酸酯、二茴香胺二异氰酸酯、四甲基苯二甲基二异氰酸酯等芳香族二异氰酸酯;异佛尔酮二异氰酸酯、二环己基甲烷-4,4’-二异氰酸酯、反式-1,4-环己基二异氰酸酯、降冰片烯二异氰酸酯等脂环式二异氰酸酯;四亚甲基二异氰酸酯、1,6-六亚甲基二异氰酸酯、2,2,4-三甲基六亚甲基二异氰酸酯、2,4,4-三甲基六亚甲基二异氰酸酯、赖氨酸二异氰酸酯等脂肪族二异氰酸酯;上述例示的二异氰酸酯的异氰脲酸酯三聚物、缩二脲三聚物、三羟甲基丙烷加合化物等;三苯基甲烷三异氰酸酯、1-甲基苯-2,4,6-三异氰酸酯、二甲基三苯基甲烷四异氰酸酯等。
作为使胺化合物、环氧化合物、尿素反应而得到的改性胺的制造方法,例如可列举出日本特公平06-006620号公报、日本专利第3837134号公报等中记载的公知的方法。
上述胺系固化剂也可以为胺系潜伏性固化剂。作为潜伏性固化剂,可列举出双氰胺型、咪唑型、多胺型化合物等在室温下与环氧树脂混合时混合物的粘度变化、物性变化小的潜伏性固化剂。
作为上述双氰胺型潜伏性固化剂,可列举出双氰胺单独、或根据需要并用了后述的固化促进剂的物质。
上述咪唑型潜伏性固化剂例如可以通过相对于含有活泼氢的咪唑化合物在50~150℃下、根据需要使用溶剂使环氧化合物反应1~20小时而获得。在使用溶剂的情况下,在反应结束后,在常压或减压下、在80~200℃下除去溶剂。
作为上述咪唑型潜伏性固化剂的制造中使用的咪唑化合物,例如可列举出2-甲基咪唑、2-乙基-4-甲基咪唑、2-十一烷基咪唑、2-十七烷基咪唑、2-苯基咪唑等。
作为上述咪唑型潜伏性固化剂的制造中使用的环氧化合物,例如可列举出上述其他的环氧化合物中例示的化合物,此外,也可以使用(A)成分及(B)成分。
作为上述咪唑型潜伏性固化剂的制造中使用的溶剂,可列举出甲乙酮、甲基戊基酮、二乙基酮、丙酮、甲基异丙基酮、丙二醇单甲基醚乙酸酯、环己酮等酮类;四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷、丙二醇单甲基醚等醚类;乙酸乙酯、乙酸正丁酯等酯类;苯、甲苯、二甲苯等芳香族烃;四氯化碳、氯仿、三氯乙烯、二氯甲烷等卤代脂肪族烃;氯苯等卤代芳香族烃。
上述多胺型潜伏性固化剂例如可以通过相对于多胺在50~150℃下根据需要使用溶剂使环氧化合物反应1~20小时而获得。在使用溶剂的情况下,在反应结束后,在常压或减压下、在80~200℃下除去溶剂。
作为上述多胺型潜伏性固化剂的制造中使用的多胺,例如可列举出上述列举的改性胺中使用的胺化合物中具有至少2个氨基的化合物。
作为上述多胺型潜伏性固化剂的制造中使用的环氧化合物及溶剂,可列举出与上述咪唑型潜伏性固化剂的制造中使用的物质同样的物质。
为了提高组合物的贮藏稳定性,上述胺系潜伏性固化剂也可以并用后述的酚醛树脂类。并用时的酚醛树脂类的使用量例如相对于胺系潜伏性固化剂总质量为10~50质量%。
作为上述胺系固化剂,也可以使用市售品,例如可列举出Adeka Hardener EH-3636AS((株)ADEKA制;双氰胺型潜伏性固化剂)、Adeka Hardener EH-4351S((株)ADEKA制;双氰胺型潜伏性固化剂)、Adeka Hardener EH-5011S((株)ADEKA制;咪唑型潜伏性固化剂)、Adeka Hardener EH-5046S((株)ADEKA制;咪唑型潜伏性固化剂)、Adeka HardenerEH-4357S((株)ADEKA制;多胺型潜伏性固化剂)、Adeka Hardener EH-5057P((株)ADEKA制;多胺型潜伏性固化剂)、Adeka Hardener EH-5057PK((株)ADEKA制;多胺型潜伏性固化剂)、Amicure PN-23(Ajinomoto Finetechno(株)制;胺加合系潜伏性固化剂)、Amicure PN-40(Ajinomoto Finetechno(株)制;胺加合系潜伏性固化剂)、Amicure VDH(AjinomotoFinetechno(株)制;酰肼系潜伏性固化剂)、Fujicure FXR-1020((株)T&KTOKA制;脲型潜伏性固化剂)等。
从固化性与固化物的弹性模量的平衡的观点出发,本发明的(C)固化剂中使用胺系固化剂时的使用量相对于(A)成分、(B)成分、及其他的环氧化合物的合计质量100质量份优选为1~100质量份,更优选为5~60质量份。
作为上述硫醇系固化剂,例如可列举出季戊四醇四(3-巯基丙酸酯)、季戊四醇四(巯基乙酸酯)、二季戊四醇六(3-巯基丙酸酯)、二季戊四醇六(3-巯基丁酸酯)、1,3,4,6-四(2-巯基乙基)-1,3,4,6-四氮杂八氢戊搭烯-2,5-二酮、1,3,5-三(3-巯基丙基)-1,3,5-三嗪-2,4,6(1H,3H,5H)-三酮、4-巯基甲基-1,8-二巯基-3,6-二硫杂辛烷、4,8-、4,7-或5,7-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷、1,3,4,6-四(2-巯基乙基)甘脲、1,2,3-三(巯基甲基硫代)丙烷、1,2,3-三(2-巯基乙基硫代)丙烷、1,2,3-三(3-巯基丙基硫代)丙烷、4-巯基甲基-1,8-二巯基-3,6-二硫杂辛烷、5,7-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷、4,7-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷、4,8-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷、四(巯基甲基硫代甲基)甲烷、四(2-巯基乙基硫代甲基)甲烷、四(3-巯基丙基硫代甲基)甲烷、1,1,3,3-四(巯基甲基硫代)丙烷、1,1,2,2-四(巯基甲基硫代)乙烷、4,6-双(巯基甲基硫代)-1,3-二噻烷、1,1,5,5-四(巯基甲基硫代)-3-硫杂戊烷、1,1,6,6-四(巯基甲基硫代)-3,4-二硫杂己烷、2,2-双(巯基甲基硫代)乙烷硫醇、3-巯基甲基硫代-1,7-二巯基-2,6-二硫杂庚烷、3,6-双(巯基甲基硫代)-1,9-二巯基-2,5,8-三硫杂壬烷、3-巯基甲基硫代-1,6-二巯基-2,5-二硫杂己烷、1,1,9,9-四(巯基甲基硫代)-5-(3,3-双(巯基甲基硫代)-1-硫杂丙基)3,7-二硫杂壬烷、三(2,2-双(巯基甲基硫代)乙基)甲烷、三(4,4-双(巯基甲基硫代)-2-硫杂丁基)甲烷、四(2,2-双(巯基甲基硫代)乙基)甲烷、四(4,4-双(巯基甲基硫代)-2-硫杂丁基)甲烷、3,5,9,11-四(巯基甲基硫代)-1,13-二巯基-2,6,8,12-四硫杂十三烷、3,5,9,11,15,17-六(巯基甲基硫代)-1,19-二巯基-2,6,8,12,14,18-六硫杂十九烷、9-(2,2-双(巯基甲基硫代)乙基)-3,5,13,15-四(巯基甲基硫代)-1,17-二巯基-2,6,8,10,12,16-六硫杂十七烷、3,4,8,9-四(巯基甲基硫代)-1,11-二巯基-2,5,7,10-四硫杂十一烷、3,4,8,9,13,14-六(巯基甲基硫代)-1,16-二巯基-2,5,7,10,12,15-六硫杂十六烷、8-[双(巯基甲基硫代)甲基]-3,4,12,13-四(巯基甲基硫代)-1,15-二巯基-2,5,7,9,11,14-六硫杂十五烷、4,6-双[3,5-双(巯基甲基硫代)-7-巯基-2,6-二硫杂庚基硫代]-1,3-二噻烷、4-[3,5-双(巯基甲基硫代)-7-巯基-2,6-二硫杂庚基硫代]-6-巯基甲基硫代-1,3-二噻烷、1,1-双[4-(6-巯基甲基硫代)-1,3-二噻烷基硫代]-1,3-双(巯基甲基硫代)丙烷、1-[4-(6-巯基甲基硫代)-1,3-二噻烷基硫代]-3-[2,2-双(巯基甲基硫代)乙基]-7,9-双(巯基甲基硫代)-2,4,6,10-四硫杂十一烷、1,5-双[4-(6-巯基甲基硫代)-1,3-二噻烷基硫代]-3-[2-(1,3-二硫杂环丁烷基)]甲基-2,4-二硫杂戊烷、3-[2-(1,3-二硫杂环丁烷基)]甲基-7,9-双(巯基甲基硫代)-1,11-二巯基-2,4,6,10-四硫杂十一烷、9-[2-(1,3-二硫杂环丁烷基)]甲基-3,5,13,15-四(巯基甲基硫代)-1,17-二巯基-2,6,8,10,12,16-六硫杂十七烷、3-[2-(1,3-二硫杂环丁烷基)]甲基-7,9,13,15-四(巯基甲基硫代)-1,17-二巯基-2,4,6,10,12,16-六硫杂十七烷、3,7-双[2-(1,3-二硫杂环丁烷基)]甲基-1,9-二巯基-2,4,6,8-四硫杂壬烷、4,6-双{3-[2-(1,3-二硫杂环丁烷基)]甲基-5-巯基-2,4-二硫杂戊基硫代}-1,3-二噻烷、4,6-双[4-(6-巯基甲基硫代)-1,3-二噻烷基硫代]-6-[4-(6-巯基甲基硫代)-1,3-二噻烷基硫代]-1,3-二噻烷、4-[3,4,8,9-四(巯基甲基硫代)-11-巯基-2,5,7,10-四硫杂十一烷基]-5-巯基甲基硫代-1,3-二硫杂环戊烷、4,5-双[3,4-双(巯基甲基硫代)-6-巯基-2,5-二硫杂己基硫代]-1,3-二硫杂环戊烷、4-[3,4-双(巯基甲基硫代)-6-巯基-2,5-二硫杂己基硫代]-5-巯基甲基硫代-1,3-二硫杂环戊烷、4-[3-双(巯基甲基硫代)甲基-5,6-双(巯基甲基硫代)-8-巯基-2,4,7-三硫杂辛基]-5-巯基甲基硫代-1,3-二硫杂环戊烷、2-{双[3,4-双(巯基甲基硫代)-6-巯基-2,5-二硫杂己基硫代]甲基}-1,3-二硫杂环丁烷、2-[3,4-双(巯基甲基硫代)-6-巯基-2,5-二硫杂己基硫代]巯基甲基硫代甲基-1,3-二硫杂环丁烷、2-[3,4,8,9-四(巯基甲基硫代)-11-巯基-2,5,7,10-四硫杂十一烷基硫代]巯基甲基硫代甲基-1,3-二硫杂环丁烷、2-[3-双(巯基甲基硫代)甲基-5,6-双(巯基甲基硫代)-8-巯基-2,4,7-三硫杂辛基]巯基甲基硫代甲基-1,3-二硫杂环丁烷、4,5-双{1-[2-(1,3-二硫杂环丁烷基)]-3-巯基-2-硫杂丙基硫代}-1,3-二硫杂环戊烷、4-{1-[2-(1,3-二硫杂环丁烷基)]-3-巯基-2-硫杂丙基硫代}-5-[1,2-双(巯基甲基硫代)-4-巯基-3-硫杂丁基硫代]-1,3-二硫杂环戊烷、2-{双[4-(5-巯基甲基硫代-1,3-二硫杂环戊烷基)硫代]甲基}-1,3-二硫杂环丁烷、4-[4-(5-巯基甲基硫代-1,3-二硫杂环戊烷基)硫代]-5-{1-[2-(1,3-二硫杂环丁烷基)]-3-巯基-2-硫杂丙基硫代}-1,3-二硫杂环戊烷等。它们可以单独使用,也可以将2种以上并用。
从固化性与固化物的弹性模量的平衡的观点出发,本发明的(C)固化剂中使用硫醇系固化剂时的使用量相对于(A)成分、(B)成分、及其他的环氧化合物的合计质量100质量份优选为1~100质量份,更优选为40~80质量份。
作为上述酸酐,例如可列举出降冰片烯二酸酐、邻苯二甲酸酐、马来酸酐、甲基降冰片烯二酸酐、琥珀酸酐、四氢邻苯二甲酸酐、六氢邻苯二甲酸酐、甲基四氢邻苯二甲酸酐、甲基六氢邻苯二甲酸酐、三烷基四氢邻苯二甲酸酐-马来酸酐加成物、二苯甲酮四羧酸酐、偏苯三酸酐、均苯四甲酸酐、及氢化甲基纳迪克酸酐等。
从固化性与固化物的弹性模量的平衡的观点出发,本发明的(C)固化剂中使用酸酐时的使用量相对于(A)成分、(B)成分、及其他的环氧化合物的合计质量100质量份优选为30~300质量份,更优选为50~100质量份。
作为上述酚醛树脂类,例如可列举出苯酚酚醛清漆树脂、甲酚酚醛清漆树脂、芳香族烃甲醛树脂改性酚醛树脂、二环戊二烯苯酚加成型树脂、苯酚芳烷基树脂(Xylok树脂)、萘酚芳烷基树脂、三苯酚基甲烷树脂、四苯酚基乙烷树脂、萘酚酚醛清漆树脂、萘酚-苯酚共缩合酚醛清漆树脂、萘酚-甲酚共缩合酚醛清漆树脂、联苯改性酚醛树脂(苯酚核以双亚甲基连结而成的多元酚化合物)、联苯改性萘酚树脂(苯酚核以双亚甲基连结而成的多元萘酚化合物)、氨基三嗪改性酚醛树脂(在分子结构中具有苯酚骨架、三嗪环及伯氨基的化合物)、及含烷氧基的芳香环改性酚醛清漆树脂(苯酚核及含烷氧基的芳香环以甲醛连结而成的多元酚化合物)等多元酚化合物。
从固化性与固化物的弹性模量的平衡的观点出发,本发明的(C)固化剂中使用酚醛树脂类时的使用量相对于(A)成分、(B)成分、及其他的环氧化合物的合计质量100质量份优选为10~200质量份,更优选为50~100质量份。
上述阳离子聚合引发剂是通过热或能量射线的照射而能够放出引发阳离子聚合的物质的化合物。特别优选的阳离子系引发剂是通过热或光照射而放出路易斯酸的鎓盐即复盐或其衍生物。作为所述化合物的代表性例子,可列举出下述的通式所表示的阳离子与阴离子的盐。
[A]m+[B]m-
阳离子[A]m+优选为鎓,其结构例如可以以通式[(R5)pQ]m+表示。
其中,R5为碳原子数为1~60、并且可包含几个除碳原子以外的原子的有机基,p为1~5的整数。p个R5分别独立,可以相同,也可以不同。此外,至少1个优选为具有芳香环的上述的有机基。Q为选自由S、N、Se、Te、P、As、Sb、Bi、O、I、Br、Cl、F、N=N构成的组中的原子或原子团。此外,在将阳离子[A]m+中的Q的原子价设定为q时,成为m=p-q的关系必须成立(其中,N=N作为原子价0来处理)。
此外,阴离子[B]m-优选为卤化物络合物,其结构例如可以以通式[LXr]m-表示。
这里,L为作为卤化物络合物的中心原子的金属或半金属(Metalloid),为B、P、As、Sb、Fe、Sn、Bi、Al、Ca、In、Ti、Zn、Sc、V、Cr、Mn、Co等,X为卤素原子。r为3~7的整数,在将阴离子[B]m-中的L的原子价设定为s时,成为m=r-s的关系必须成立。
作为上述通式所表示的阴离子[LXr]m-的具体例子,可列举出四氟硼酸根(BF4)-、六氟磷酸根(PF6)-、六氟锑酸根(SbF6)-、六氟砷酸根(AsF6)-、六氯锑酸根(SbCl6)-等。
此外,作为阴离子[B]m-,也可以优选使用[LXr -1(OH)]m-所表示的结构的阴离子。其中,L、X、及r与上述同样。此外,作为本发明中可使用的其他阴离子,可列举出高氯酸根离子(ClO4)-、三氟甲基亚硫酸根离子(CF3SO3)-、氟磺酸根离子(FSO3)-、甲苯磺酸根阴离子、三硝基苯磺酸根阴离子等。
作为上述鎓盐,例如可以使用下述的1)~3)的芳香族鎓盐。此外,可以单独使用它们中的1种,或将2种以上混合使用。
1)苯基重氮鎓六氟磷酸盐、4-甲氧基苯基重氮鎓六氟锑酸盐、4-甲基苯基重氮鎓六氟磷酸盐等芳基重氮鎓盐
2)二苯基碘鎓六氟锑酸盐、二(4-甲基苯基)碘鎓六氟磷酸盐、二(4-叔丁基苯基)碘鎓六氟磷酸盐等二芳基碘鎓盐
3)三苯基锍六氟锑酸盐、三(4-甲氧基苯基)锍六氟磷酸盐、二苯基-4-硫代苯氧基苯基锍六氟锑酸盐、二苯基-4-硫代苯氧基苯基锍六氟磷酸盐、4,4’-双(二苯基锍基)苯基硫化物-双-六氟锑酸盐、4,4’-双(二苯基锍基)苯基硫化物-双-六氟磷酸盐、4,4’-双[二(β-羟基乙氧基)苯基锍基]苯基硫化物-双-六氟锑酸盐、4,4’-双[二(β-羟基乙氧基)苯基锍基]苯基硫化物-双-六氟磷酸盐、4-[4’-(苯甲酰基)苯基硫代]苯基-二-(4-氟苯基)锍六氟锑酸盐、4-[4’-(苯甲酰基)苯基硫代]苯基-二-(4-氟苯基)锍六氟磷酸盐等三芳基锍盐
此外,作为上述以外的阳离子聚合引发剂,还可列举出(η5-2,4-环戊二烯-1-基)〔(1,2,3,4,5,6,-η)-(1-甲基乙基)苯〕-铁-六氟磷酸盐等铁-芳烃络合物、三(乙酰丙酮)铝、三(乙基丙酮乙酸)铝、三(水杨醛)铝等铝络合物与三苯基硅烷醇等硅烷醇类的混合物等。
进而,例如也可以使用日本特开平6-41215号公报、日本特开平6-65310号公报、日本特开平6-206862号公报、日本特开平6-247925号公报、日本专利第2699188号公报、日本专利第2706833号公报、日本专利第2709625号公报、日本专利第2782093号公报、日本专利2782104号公报、日本专利第2782106号公报、日本特开2006-282633号公报、日本特开2007-91702号公报等中记载的阳离子聚合引发剂。
此外,作为阳离子聚合引发剂的市售品,例如可列举出KAYARAD PCI-220(日本化药(株)制)、KAYARAD PCI-620(日本化药(株)制)、UVI-6990(Union Carbide公司制)、ADEKAOPTOMER SP-150((株)ADEKA制)、ADEKA OPTOMER SP-170((株)ADEKA制)、CI-5102(日本曹达(株)制)、CIT-1370(日本曹达(株)制)、CIT-1682(日本曹达(株)制)、CIP-1866S(日本曹达(株)制)、CIP-2048S(日本曹达(株)制)、CIP-2064S(日本曹达(株)制)、DPI-101(MidoriKagaku(株)制)、DPI-102(Midori Kagaku(株)制)、DPI-103(Midori Kagaku(株)制)、DPI-105(Midori Kagaku(株)制)、MPI-103(Midori Kagaku(株)制)、MPI-105(Midori Kagaku(株)制)、BBI-101(Midori Kagaku(株)制)、BBI-102(Midori Kagaku(株)制)、BBI-103(Midori Kagaku(株)制)、BBI-105(Midori Kagaku(株)制)、TPS-101(Midori Kagaku(株)制)、TPS-102(Midori Kagaku(株)制)、TOS-103(Midori Kagaku(株)制)、TPS-105(MidoriKagaku(株)制)、MDS-103(Midori Kagaku(株)制)、MDS-105(Midori Kagaku(株)制)、DTS-102(Midori Kagaku(株)制)、DTS-103(Midori Kagaku(株)制)、PI-2074(RHODIA公司制)、SI-60L(三新化学(株)制)、SI-80L(三新化学(株)制)、SI-100L(三新化学(株)制)等。
从固化性与固化物的弹性模量的平衡的观点出发,本发明的(C)固化剂中使用光聚合引发剂时的使用量相对于(A)成分、(B)成分、及其他的环氧化合物的合计质量100质量份优选为0.1~20质量份,更优选为1~7质量份。
上述列举的固化剂中,从可低温固化的观点出发,优选胺系固化剂、或硫醇系固化剂。
本发明的环氧树脂组合物也可以并用固化促进剂。通过并用固化促进剂,能够提高固化速度。作为固化促进剂,例如可例示出三苯基膦等膦类;四苯基溴化鏻等鏻盐;2-甲基咪唑、2-苯基咪唑、2-乙基-4-甲基咪唑、2-十一烷基咪唑、1-氰基乙基-2-甲基咪唑等咪唑类;上述咪唑类与偏苯三酸、异氰脲酸、硼等的盐即咪唑盐类;苄基二甲基胺、2,4,6-三(二甲基氨基甲基)苯酚等胺类;三甲基氯化铵等季铵盐类;3-(对氯苯基)-1,1-二甲基脲、3-(3,4-二氯苯基)-1,1-二甲基脲、3-苯基-1,1-二甲基脲、异佛尔酮二异氰酸酯-二甲基脲、甲苯撑二异氰酸酯-二甲基脲等脲类;及三氟化硼与胺类或醚化合物等的络合物等。这些固化促进剂可以单独使用,也可以将2种以上并用。固化促进剂的含量没有特别限制,可以根据本发明的环氧树脂组合物的用途而适当设定。
上述固化促进剂也可以为芯壳型的物质,具体而言可列举出日本特公平07-005708号公报、日本专利第4405741号公报等中记载的使以固形状的叔胺作为芯成分且以环氧树脂与胺化合物的反应产物作为壳的物质分散到环氧树脂中而得到的母料型固化促进剂。从环氧树脂组合物的贮藏稳定性的观点出发,这些固化促进剂特别优选与硫醇系固化剂、或酸酐并用。
上述母料型固化促进剂也可以使用市售品,例如可列举出旭化成(株)制的NOVACURE系列即HX-3742、HX-3721、HXA9322HP、HXA3922HP、HXA3932HP、HXA5945HP、HXA9382HP等。
本发明的环氧树脂组合物也可以任选地包含硅烷偶联剂。作为硅烷偶联剂,例如可列举出γ-氨基丙基三乙氧基硅烷、N-β-(氨基乙基)-γ-氨基丙基三乙氧基硅烷、N-β-(氨基乙基)-N’-β-(氨基乙基)-γ-氨基丙基三乙氧基硅烷、γ-苯胺基丙基三乙氧基硅烷、γ-环氧丙氧基丙基三乙氧基硅烷、β-(3,4-环氧环己基)乙基三乙氧基硅烷、乙烯基三乙氧基硅烷、N-β-(N-乙烯基苄基氨基乙基)-γ-氨基丙基三乙氧基硅烷、γ-甲基丙烯酰氧基丙基三甲氧基硅烷、γ-氯丙基三甲氧基硅烷、γ-巯基丙基三甲氧基硅烷、γ-异氰酸酯丙基三乙氧基硅烷等。
作为上述硅烷偶联剂,从提高使用本发明的环氧树脂组合物作为粘接剂时的粘接性的观点出发,优选具有环氧基的硅烷偶联剂。
上述硅烷偶联剂也可以使用市售品,例如可以使用信越化学工业(株)制的KBM-403、KBE-403、KBM-402等。
作为使用上述硅烷偶联剂时的使用量,从固化性与固化物的弹性模量的平衡的观点出发,相对于(A)成分、(B)成分、及其他的环氧化合物的合计质量100质量份优选为0.1~20质量份,更优选为0.2~5质量份。
在本发明的环氧树脂组合物中,根据需要也可以添加无机填充剂。作为这样的无机填充剂,例如可列举出熔融二氧化硅、结晶二氧化硅、气相二氧化硅等二氧化硅、氢氧化镁、氢氧化铝、硼酸锌、钼酸锌、碳酸钙、氮化硅、碳化硅、氮化硼、硅酸钙、钛酸钾、氮化铝、氧化铍、氧化锆、锆石、镁橄榄石、块滑石、尖晶石、莫来石、二氧化钛等粉体、或将它们球形化而得到的珠子、及玻璃纤维等。
在本发明的环氧树脂组合物中,也可以根据需要并用上述无机填充剂以外的添加剂。作为上述添加剂,例如可列举出邻苯二甲酸二辛酯、邻苯二甲酸二丁酯、苄基醇、煤焦油等非反应性的稀释剂(增塑剂);玻璃纤维、纸浆纤维、合成纤维、陶瓷纤维等纤维质填充材;玻璃布/芳族聚酰胺布、碳纤维等增强材料;颜料;小烛树蜡、巴西棕榈蜡、木蜡、白蜡、蜂蜡、羊毛脂、鲸蜡、褐煤蜡、石油蜡、脂肪族蜡、脂肪族酯、脂肪族醚、芳香族酯、芳香族醚等润滑剂;增稠剂;触变剂;抗氧化剂;光稳定剂;紫外线吸收剂;阻燃剂;消泡剂;防锈剂;胶体二氧化硅、胶体氧化铝等常用的添加物。本发明中,也可以进一步并用二甲苯树脂、石油树脂等粘合性的树脂类。
本发明的环氧树脂组合物中,从高温高湿下的可靠性的观点出发,总氯量优选少,具体而言,总氯量优选为2000ppm,更优选为1000ppm以下。总氯量优选少,因此总氯量的理想值为0ppm。需要说明的是,本发明中总氯量可以通过燃烧-电量测定法来测定。
本发明的环氧树脂组合物从作业性的观点出发,粘度优选为20~600mPa·s,更优选为50~400mPa·s。需要说明的是,粘度可以通过锥板型旋转粘度计(E型粘度计)来进行测定。
本发明的环氧树脂组合物可以通过将(A)~(C)成分、及根据需要添加的任意的成分根据需要一边加热处理一边进行搅拌、熔融、混合、分散来制造。该情况的搅拌、熔融、混合、分散中使用的装置没有特别限定,在本发明中,可以使用具备搅拌器、加热装置的擂溃机、三辊磨、球磨机、行星混合器、珠磨机、行星搅拌机等。此外,也可以将这些装置适当组合而使用。
本发明的环氧树脂组合物可以适用于针对混凝土、水泥、灰浆、各种金属、皮革、玻璃、橡胶、塑料、木、布、纸等的涂料;印制电路布线基板用层叠板、积层基板用层间绝缘材料、积层用粘接膜、芯片贴装剂、倒装片安装用底部填充材料、球顶(Glob top)封装材料、TCP用液状密封材料、导电性粘接剂、液晶密封材料、柔性基板用保护层、抗蚀油墨等电子电路基板用树脂材料;半导体密封材料;光波导、光学膜等光学用材料;树脂铸型材料;粘接剂;LED、光电晶体管、光电二极管、光耦合器、CCD、EPROM、光电传感器等各种光半导体装置;CFRP等纤维强化树脂成形品等各种用途。
本发明的环氧树脂组合物由于具有环氧树脂本来的粘接性,并且通过弹性模量低而固化物的可靠性也良好,因此特别是可以应用于电子电路基板用树脂材料、半导体密封材料、电子部件用粘接剂,特别是可以适宜用于相机模块用部件的粘接剂·密封剂。
实施例
以下通过实施例对本发明具体地进行说明。需要说明的是,在以下的实施例等中%只要没有特别记载则为质量基准。
<制造例1>
在20L的SUS制反应容器中加入双酚A的环氧丙烷加成物((株)ADEKA制AdekaPolyether BPX-11)3.4kg(羟基的mol数:18.9mol)、环氧氯丙烷8.8kg(95.1mol)、50%四甲基氯化铵水溶液22.0g(0.096mol),加温至55~60℃后,开始减压。调整减压度,在55~60℃下确认环氧氯丙烷回流。确认后,按照反应温度成为55~60℃的方式滴加48%氢氧化钠水溶液1.9kg(22.6mol)。滴加完成后,在55~60℃下搅拌至回收的水成为1.2kg以上为止。之后,将反应溶液冷却至成为室温以下为止,通过过滤将无用的固体除去后,在减压下除去环氧氯丙烷,得到4.4kg环氧化合物A-1(收率90%、环氧当量:257g/eq.、粘度(25℃):2100mPa·s、总氯量:2300ppm、可皂化氯量:40ppm)。
<制造例2>
将4.0kg的制造例1中得到的环氧化合物A-1使用刮板式薄膜蒸馏机以蒸馏生产线的温度为180℃、减压度为15Pa以下、环氧化合物A-1的给料速度为0.55kg/h的条件进行蒸馏精制,得到环氧化合物A-2(收率:87.4%、环氧当量:273g/eq.、粘度(25℃):2540mPa·s、总氯量:500ppm)。
实施例中使用的原料如下所述。
A-2:上述制造例2中制造的环氧化合物(包含通式(1)中R1及R2为异亚丙基、R3为-C(CH3)2-、a及b的平均值分别为1的化合物作为主要成分)
D-1:ADEKA RESIN EP-4100E、双酚型环氧树脂((株)ADEKA制)
D-2:ADEKA GLYCIROL ED-509S、叔丁基苯基缩水甘油醚((株)ADEKA制)
B-1:LITE 513E、腰果酚型环氧化合物(Cardolite公司制)
C-1:Adeka Hardener EH-5011S、咪唑型潜伏性固化剂((株)ADEKA制)
E-1:RY-200S、疏水性气相二氧化硅(NIPPON AEROSIL(株)制)
[实施例1~5、比较例1~4]
以表1中所示那样的配合比,在500mL一次性杯中加入各种材料,用刮勺搅拌10分钟后,利用行星搅拌机进行搅拌,制造实施例及比较例的环氧树脂组合物。对所得到的环氧树脂组合物分别通过以下的评价方法进行固化性、柔软性、作业性、总氯量及粘度的评价。将结果示于表1中。
<固化性>
将所得到的环氧树脂组合物2g分别放入120℃的恒温槽中静置2小时。在将加热后的树脂组合物用刮勺触碰时,将没有流动性的环氧树脂组合物设定为合格,将具有流动性的环氧树脂组合物设定为不合格。
<柔软性>
依据JIS K5600-5-1,在镀锡铁皮板上以厚度1mm涂布环氧树脂组合物后,在120℃用2小时使环氧树脂组合物固化。之后,将心轴的直径设定为2mm而测定耐弯曲性。将即使折弯到180度也没有开裂、也没有确认到裂痕的环氧树脂组合物设定为合格,将开裂的环氧树脂组合物、或确认到裂痕的环氧树脂组合物设定为不合格。
<作业性>
将粘度低于600mPa的环氧树脂组合物设定为合格,将600mPa以上的环氧树脂组合物设定为不合格。
<总氯量>
使用NITTOSEIKO ANALYTECH(株)制、全有机卤素测定装置TOX-2100来测定总氯量。
<粘度>
使用E型粘度计测定25℃下的粘度。
表1
实施例1 | 实施例2 | 实施例3 | 实施例4 | 实施例5 | 比较例1 | 比较例2 | 比较例3 | 比较例4 | |
A-2 | 50 | 20 | 40 | 60 | 80 | - | 50 | - | 100 |
D-1 | - | - | - | - | - | 50 | - | - | - |
D-2 | - | - | - | - | - | - | 50 | - | - |
B-1 | 50 | 80 | 60 | 40 | 20 | 50 | - | 100 | - |
C-1 | 20 | 20 | 20 | 20 | 20 | 20 | 20 | 20 | 20 |
E-1 | 4 | 4 | 4 | 4 | 4 | 4 | 4 | 4 | 4 |
固化性 | 合格 | 合格 | 合格 | 合格 | 合格 | 合格 | 合格 | 不合格 | 合格 |
柔软性 | 合格 | 合格 | 合格 | 合格 | 合格 | 不合格 | 不合格 | - | 不合格 |
作业性 | 合格 | 合格 | 合格 | 合格 | 合格 | 合格 | 合格 | 合格 | 不合格 |
总氯量(ppm) | 810 | 883 | 835 | 786 | 738 | 1093 | 609 | 931 | 689 |
粘度(mPa·s) | 120 | 51 | 86 | 186 | 496 | 169 | 126 | 29 | 2000 |
如表1的结果中所示的那样,获知本发明的环氧树脂组合物的固化性、柔软性的平衡优异。在没有使用本发明的环氧树脂组合物的比较例1~4中,固化性、柔软性中的某一项目没有得到满意的结果。在比较例3中,由于没有以120℃、2小时的固化条件进行固化,因此无法进行柔软性的评价。
Claims (6)
1.一种环氧树脂组合物,其包含(A)下述通式(1)所表示的环氧化合物A、(B)下述通式(2)所表示的环氧化合物B、及(C)固化剂,
通式(1)中,R1及R2分别独立地表示碳原子数2~4的亚烷基,R3表示亚甲基或-C(CH3)2-,a及b分别独立地表示1~10的数,
通式(2)中,R4表示碳原子数6~20的烃基。
2.根据权利要求1所述的环氧树脂组合物,其中,(B)成分为腰果酚型环氧化合物。
3.根据权利要求1所述的环氧树脂组合物,其中,(A)成分与(B)成分的质量比A/B为90/10~10/90。
4.根据权利要求1所述的环氧树脂组合物,其中,(C)成分为选自胺系固化剂及硫醇系固化剂中的至少1种。
5.根据权利要求1所述的环氧树脂组合物,其中,总氯量为2000ppm以下。
6.一种固化物,其是使权利要求1~5中任一项所述的环氧树脂组合物固化而成的。
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