JP2021175803A - Epoxy resin composition - Google Patents
Epoxy resin composition Download PDFInfo
- Publication number
- JP2021175803A JP2021175803A JP2021073790A JP2021073790A JP2021175803A JP 2021175803 A JP2021175803 A JP 2021175803A JP 2021073790 A JP2021073790 A JP 2021073790A JP 2021073790 A JP2021073790 A JP 2021073790A JP 2021175803 A JP2021175803 A JP 2021175803A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- manufactured
- resin composition
- molecule
- parts
- 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 140
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 140
- 239000000203 mixture Substances 0.000 title claims abstract description 45
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims abstract description 32
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 12
- 239000004814 polyurethane Substances 0.000 claims abstract description 12
- 229920002635 polyurethane Polymers 0.000 claims abstract description 12
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 7
- 150000004982 aromatic amines Chemical class 0.000 claims description 7
- 238000007789 sealing Methods 0.000 claims description 7
- 239000004844 aliphatic epoxy resin Substances 0.000 claims description 5
- 238000013016 damping Methods 0.000 abstract description 12
- 229920005989 resin Polymers 0.000 abstract description 9
- 239000011347 resin Substances 0.000 abstract description 9
- 229910052751 metal Inorganic materials 0.000 abstract description 4
- 239000002184 metal Substances 0.000 abstract description 4
- -1 polybutylene terephthalate Polymers 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 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 21
- 238000001723 curing Methods 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 18
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 14
- 239000000126 substance Substances 0.000 description 12
- 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 11
- 238000012360 testing method Methods 0.000 description 10
- 239000004593 Epoxy Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000853 adhesive Substances 0.000 description 7
- 230000001070 adhesive effect Effects 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 229920001707 polybutylene terephthalate Polymers 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229920005862 polyol Polymers 0.000 description 6
- 150000003077 polyols Chemical class 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000003566 sealing material Substances 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 229920000106 Liquid crystal polymer Polymers 0.000 description 4
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 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 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- ALKZAGKDWUSJED-UHFFFAOYSA-N dinuclear copper ion Chemical compound [Cu].[Cu] ALKZAGKDWUSJED-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 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 3
- 239000000944 linseed oil Substances 0.000 description 3
- 235000021388 linseed oil Nutrition 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 2
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 2
- HIGURUTWFKYJCH-UHFFFAOYSA-N 2-[[1-(oxiran-2-ylmethoxymethyl)cyclohexyl]methoxymethyl]oxirane Chemical compound C1OC1COCC1(COCC2OC2)CCCCC1 HIGURUTWFKYJCH-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- AHIPJALLQVEEQF-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1COC(C=C1)=CC=C1N(CC1OC1)CC1CO1 AHIPJALLQVEEQF-UHFFFAOYSA-N 0.000 description 2
- FAUAZXVRLVIARB-UHFFFAOYSA-N 4-[[4-[bis(oxiran-2-ylmethyl)amino]phenyl]methyl]-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC(CC=2C=CC(=CC=2)N(CC2OC2)CC2OC2)=CC=1)CC1CO1 FAUAZXVRLVIARB-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- RRDGKBOYQLLJSW-UHFFFAOYSA-N bis(2-ethylhexyl) 7-oxabicyclo[4.1.0]heptane-3,4-dicarboxylate Chemical compound C1C(C(=O)OCC(CC)CCCC)C(C(=O)OCC(CC)CCCC)CC2OC21 RRDGKBOYQLLJSW-UHFFFAOYSA-N 0.000 description 2
- NEPKLUNSRVEBIX-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,4-dicarboxylate Chemical compound C=1C=C(C(=O)OCC2OC2)C=CC=1C(=O)OCC1CO1 NEPKLUNSRVEBIX-UHFFFAOYSA-N 0.000 description 2
- XFUOBHWPTSIEOV-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) cyclohexane-1,2-dicarboxylate Chemical compound C1CCCC(C(=O)OCC2OC2)C1C(=O)OCC1CO1 XFUOBHWPTSIEOV-UHFFFAOYSA-N 0.000 description 2
- 239000002981 blocking agent Substances 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000010494 dissociation reaction Methods 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 230000020169 heat generation Effects 0.000 description 2
- NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 2
- 229920001748 polybutylene Polymers 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 229910000679 solder Inorganic materials 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XBTRYWRVOBZSGM-UHFFFAOYSA-N (4-methylphenyl)methanediamine Chemical compound CC1=CC=C(C(N)N)C=C1 XBTRYWRVOBZSGM-UHFFFAOYSA-N 0.000 description 1
- RUEBPOOTFCZRBC-UHFFFAOYSA-N (5-methyl-2-phenyl-1h-imidazol-4-yl)methanol Chemical compound OCC1=C(C)NC(C=2C=CC=CC=2)=N1 RUEBPOOTFCZRBC-UHFFFAOYSA-N 0.000 description 1
- SNVRDQORMVVQBI-UPHRSURJSA-N (z)-but-2-enedihydrazide Chemical compound NNC(=O)\C=C/C(=O)NN SNVRDQORMVVQBI-UPHRSURJSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 1
- IKYNWXNXXHWHLL-UHFFFAOYSA-N 1,3-diisocyanatopropane Chemical compound O=C=NCCCN=C=O IKYNWXNXXHWHLL-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- LHXNVCCLDTYJGT-UHFFFAOYSA-N 1-(oxiran-2-ylmethoxy)propan-2-ol Chemical compound CC(O)COCC1CO1 LHXNVCCLDTYJGT-UHFFFAOYSA-N 0.000 description 1
- YEUIMZOJSJEGFM-UHFFFAOYSA-N 1-cyclohexyl-n,n-bis(oxiran-2-ylmethyl)methanamine Chemical compound C1OC1CN(CC1CCCCC1)CC1CO1 YEUIMZOJSJEGFM-UHFFFAOYSA-N 0.000 description 1
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical group C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- ACKPSZGIQNQZLW-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxy]ethanol Chemical compound OCCOCCOCCOCC1CO1 ACKPSZGIQNQZLW-UHFFFAOYSA-N 0.000 description 1
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-UHFFFAOYSA-N 0.000 description 1
- IWRZKNMUSBNOOD-UHFFFAOYSA-N 2-methyl-4-(oxiran-2-ylmethoxy)-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C=1C=C(N(CC2OC2)CC2OC2)C(C)=CC=1OCC1CO1 IWRZKNMUSBNOOD-UHFFFAOYSA-N 0.000 description 1
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 1
- FLROJJGKUKLCAE-UHFFFAOYSA-N 3-amino-2-methylphenol Chemical compound CC1=C(N)C=CC=C1O FLROJJGKUKLCAE-UHFFFAOYSA-N 0.000 description 1
- QGNGOGOOPUYKMC-UHFFFAOYSA-N 4-hydroxy-6-methylaniline Chemical compound CC1=CC(O)=CC=C1N QGNGOGOOPUYKMC-UHFFFAOYSA-N 0.000 description 1
- XMSFNEZQRPOHAR-UHFFFAOYSA-N 4-methylazetidin-2-one Chemical compound CC1CC(=O)N1 XMSFNEZQRPOHAR-UHFFFAOYSA-N 0.000 description 1
- XKVUYEYANWFIJX-UHFFFAOYSA-N 5-methyl-1h-pyrazole Chemical compound CC1=CC=NN1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 description 1
- GJEZBVHHZQAEDB-UHFFFAOYSA-N 6-oxabicyclo[3.1.0]hexane Chemical compound C1CCC2OC21 GJEZBVHHZQAEDB-UHFFFAOYSA-N 0.000 description 1
- WPDNUCQHNPMNEO-UHFFFAOYSA-N 7-ethyloctadecanedioic acid Chemical compound OC(=O)CCCCCC(CC)CCCCCCCCCCC(O)=O WPDNUCQHNPMNEO-UHFFFAOYSA-N 0.000 description 1
- SDUZNEIVCAVWSH-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptane-3,4-dicarboxylic acid Chemical compound C1C(C(O)=O)C(C(=O)O)CC2OC21 SDUZNEIVCAVWSH-UHFFFAOYSA-N 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical class C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
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- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
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- 230000000903 blocking effect Effects 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910002026 crystalline silica Inorganic materials 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
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- CFFOYHZILKHZDE-UHFFFAOYSA-N cyclohexylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CCCCC1 CFFOYHZILKHZDE-UHFFFAOYSA-N 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- ZWLIYXJBOIDXLL-UHFFFAOYSA-N decanedihydrazide Chemical compound NNC(=O)CCCCCCCCC(=O)NN ZWLIYXJBOIDXLL-UHFFFAOYSA-N 0.000 description 1
- FSEUPUDHEBLWJY-HWKANZROSA-N diacetylmonoxime Chemical compound CC(=O)C(\C)=N\O FSEUPUDHEBLWJY-HWKANZROSA-N 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 description 1
- 229940105990 diglycerin Drugs 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- GRGBENNNGZARRZ-UHFFFAOYSA-N dodecanedihydrazide Chemical compound NNC(=O)CCCCCCCCCCC(=O)NN GRGBENNNGZARRZ-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- UFAPLAOEQMMKJA-UHFFFAOYSA-N hexane-1,2,5-triol Chemical compound CC(O)CCC(O)CO UFAPLAOEQMMKJA-UHFFFAOYSA-N 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- VLHZUYUOEGBBJB-UHFFFAOYSA-N hydroxy stearic acid Natural products OCCCCCCCCCCCCCCCCCC(O)=O VLHZUYUOEGBBJB-UHFFFAOYSA-N 0.000 description 1
- RXFZJKXZSLVQJV-UHFFFAOYSA-N icosa-8,12-dienedihydrazide Chemical compound NNC(=O)CCCCCCC=CCCC=CCCCCCCC(=O)NN RXFZJKXZSLVQJV-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 238000013035 low temperature curing Methods 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 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
- 238000000691 measurement method Methods 0.000 description 1
- AEXITZJSLGALNH-UHFFFAOYSA-N n'-hydroxyethanimidamide Chemical compound CC(N)=NO AEXITZJSLGALNH-UHFFFAOYSA-N 0.000 description 1
- IONSZLINWCGRRI-UHFFFAOYSA-N n'-hydroxymethanimidamide Chemical compound NC=NO IONSZLINWCGRRI-UHFFFAOYSA-N 0.000 description 1
- DNYZBFWKVMKMRM-UHFFFAOYSA-N n-benzhydrylidenehydroxylamine Chemical compound C=1C=CC=CC=1C(=NO)C1=CC=CC=C1 DNYZBFWKVMKMRM-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- WBHHMMIMDMUBKC-QJWNTBNXSA-N ricinoleic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-QJWNTBNXSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-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
- 239000008096 xylene Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/80—Masked polyisocyanates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
-
- 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
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
-
- 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
-
- 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
- H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Materials Engineering (AREA)
- Epoxy Resins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Sealing Material Composition (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
Abstract
Description
本発明は、エポキシ樹脂組成物に関するものである。特に、リレー、コイルに代表される小型電子部品または電気部品を封止又は固着するために用いられるエポキシ樹脂組成物に関する。 The present invention relates to an epoxy resin composition. In particular, it relates to an epoxy resin composition used for sealing or fixing a small electronic component or an electric component represented by a relay or a coil.
リレー、コイルに代表される小型電子部品または電気部品は通信機器、OA機器、家電機器、自販機等に多用されており、これら部品は昨今、プリント配線基盤に搭載されるものが主流となっている。これら部品の中でもリレーのように複数のパーツが一つのケースに収納される部品がプリント配線基板に搭載される場合、半田フラックスの侵入防止、溶剤による部品洗浄が可能であること、あるいは半田リフロー処理後に気密性を保持できること等が求められるため、樹脂等による完全気密封止が必要となる。 Small electronic parts or electrical parts represented by relays and coils are widely used in communication equipment, OA equipment, home appliances, vending machines, etc., and these parts are mainly mounted on printed wiring boards these days. .. Among these parts, when a part such as a relay in which multiple parts are stored in one case is mounted on a printed wiring board, it is possible to prevent solder flux from entering, it is possible to clean the parts with a solvent, or solder reflow processing. Since it is required that the airtightness can be maintained later, a completely airtight seal with a resin or the like is required.
斯かる完全気密封止に用いられる封止材料として、例えば、エポキシ樹脂が汎用されており、その中でも、ジシアンジアミド等の潜在性硬化剤を予めエポキシ樹脂組成物と混合しておく、いわゆる一液型エポキシ樹脂組成物が多用されている。一方、リレー等の小型電子部品または電気部品は通常、ケース及びボディは樹脂材料(ポリブチレンテレフタレート(PBT)や液晶ポリマー(LCP)等)が主体であるため、封止材料の硬化温度は120℃以下であることが望まれている。 As a sealing material used for such completely airtight sealing, for example, an epoxy resin is widely used, and among them, a latent curing agent such as dicyandiamide is mixed with an epoxy resin composition in advance, so-called one-component type. Epoxy resin compositions are often used. On the other hand, in small electronic parts such as relays or electric parts, the case and body are usually mainly made of resin material (polybutylene terephthalate (PBT), liquid crystal polymer (LCP), etc.), so the curing temperature of the sealing material is 120 ° C. It is desired that:
併せて、昨今、生活空間において前記部品を使用した電気製品から発生する騒音問題が表面化しており、特にリレーのように可動部を有する部品から発生する騒音を低減することが求められている。斯かる騒音を低減する手段の一つとして、前記した封止材料に制振性を付与させる方法が提案されている(例えば特許文献1、2)。 At the same time, in recent years, the problem of noise generated from electric appliances using the above-mentioned parts has surfaced in the living space, and it is particularly required to reduce the noise generated from parts having moving parts such as relays. As one of the means for reducing such noise, a method of imparting vibration damping property to the above-mentioned sealing material has been proposed (for example, Patent Documents 1 and 2).
しかしながら、特許文献1や特許文献2に記載のエポキシ樹脂組成物では、得られる硬化物の耐湿熱性において充分に満足できるものではなかった。 However, the epoxy resin compositions described in Patent Document 1 and Patent Document 2 are not sufficiently satisfactory in the moisture and heat resistance of the obtained cured product.
本発明は、120℃以下の温度で硬化可能であり、かつ制振性に優れ、耐湿熱性の改善された硬化物を与えるエポキシ樹脂組成物を提供することを目的とする。 An object of the present invention is to provide an epoxy resin composition that can be cured at a temperature of 120 ° C. or lower, has excellent vibration damping properties, and provides a cured product having improved moisture and heat resistance.
本発明者らは上記課題を解決するために種々検討した結果、(A)ブロックドポリウレタン、(B)1分子内に2個より多いグリシジル基を有するエポキシ樹脂、(C)1分子内に2個以下のグリシジル基を有するエポキシ樹脂及び(D)潜在性硬化剤を一定の割合で含むエポキシ樹脂組成物によれば前記課題が解決可能であることを見出した。具体的には以下の発明を含む。 As a result of various studies to solve the above problems, the present inventors have found that (A) blocked polyurethane, (B) epoxy resin having more than two glycidyl groups in one molecule, and (C) 2 in one molecule. It has been found that the above-mentioned problems can be solved by an epoxy resin composition having a glycidyl group of 1 or less and an epoxy resin composition containing (D) a latent curing agent in a certain ratio. Specifically, the following inventions are included.
〔1〕
以下(A)、(B)、(C)及び(D)を含むエポキシ樹脂組成物であって、前記(A)、(B)及び(C)の合計量100重量部に対し、(A)の含有量が20〜60重量部であり、(B)及び(C)の合計量100重量部に対し、(B)の含有量が5〜30重量部であるエポキシ樹脂組成物。
(A)ブロックドポリウレタン
(B)1分子内に2個より多いグリシジル基を有するエポキシ樹脂
(C)1分子内に2個以下のグリシジル基を有するエポキシ樹脂
(D)潜在性硬化剤
[1]
An epoxy resin composition containing the following (A), (B), (C) and (D), wherein (A) is based on 100 parts by weight of the total amount of (A), (B) and (C). The epoxy resin composition has a content of 20 to 60 parts by weight, and the content of (B) is 5 to 30 parts by weight with respect to 100 parts by weight of the total amount of (B) and (C).
(A) Blocked polyurethane (B) Epoxy resin having more than two glycidyl groups in one molecule (C) Epoxy resin having two or less glycidyl groups in one molecule (D) Latent curing agent
〔2〕
(B)1分子内に2個より多いグリシジル基を有するエポキシ樹脂が、芳香族アミン型エポキシ樹脂、アミノフェノール型エポキシ樹脂及び脂肪族系エポキシ樹脂からなる群から選ばれる少なくとも1種のエポキシ樹脂である、〔1〕記載のエポキシ樹脂組成物。
[2]
(B) The epoxy resin having more than two glycidyl groups in one molecule is at least one epoxy resin selected from the group consisting of aromatic amine type epoxy resin, aminophenol type epoxy resin and aliphatic epoxy resin. The epoxy resin composition according to [1].
〔3〕
小型電子部品または電気部品を封止または固着するためのエポキシ樹脂組成物である、〔1〕又は〔2〕記載のエポキシ樹脂組成物。
[3]
The epoxy resin composition according to [1] or [2], which is an epoxy resin composition for sealing or fixing a small electronic component or an electric component.
本発明によれば、120℃以下の温度で硬化可能であり、かつ制振性に優れ、耐湿熱性の改善された硬化物を与えるエポキシ樹脂組成物が提供可能となる。特に、本発明のエポキシ樹脂組成物は、意外にも、硬化させた際に硬化物の架橋密度が高くなることから制振性の向上に不向きであると考えられていた、1分子内に2個より多いグリシジル基を有するエポキシ樹脂を一定の割合で含有させることにより、硬化させた際に、制振性および耐湿熱性に優れると共に、耐熱性、樹脂や金属との接着性にも優れた硬化物を与える。したがって、本発明のエポキシ樹脂組成物は、リレーに代表される駆動部を有する小型電子部品または電気部品の封止材として好適に使用することができる。 According to the present invention, it is possible to provide an epoxy resin composition that can be cured at a temperature of 120 ° C. or lower, has excellent vibration damping properties, and provides a cured product having improved moisture and heat resistance. In particular, the epoxy resin composition of the present invention is unexpectedly considered to be unsuitable for improving vibration damping property because the crosslinked density of the cured product becomes high when cured, and 2 in one molecule. By containing an epoxy resin having more than one glycidyl group in a certain ratio, when cured, it is excellent in vibration damping property and moisture heat resistance, as well as excellent heat resistance and adhesion to resin and metal. Give things. Therefore, the epoxy resin composition of the present invention can be suitably used as a sealing material for small electronic parts or electric parts having a drive unit represented by a relay.
<エポキシ樹脂組成物>
本発明のエポキシ樹脂組成物は、(A)ブロックドポリウレタン、(B)1分子内に2個より多いグリシジル基を有するエポキシ樹脂、(C)1分子内に2個以下のグリシジル基を有するエポキシ樹脂及び(D)潜在性硬化剤を含有する。
<Epoxy resin composition>
The epoxy resin composition of the present invention includes (A) blocked polyurethane, (B) an epoxy resin having more than two glycidyl groups in one molecule, and (C) an epoxy having two or less glycidyl groups in one molecule. Contains a resin and (D) latent curing agent.
[(A)ブロックドポリウレタン]
本発明において(A)ブロックドポリウレタンとは、ポリエーテルポリオール、ポリエステルポリオール等のポリヒドロキシ化合物とポリイソシアネートとを反応させて得られるウレタンプレポリマーの末端にある活性なイソシアネート基を、活性水素化合物(ブロック化剤)でブロックすることにより得られる化合物のことをいう。
[(A) Blocked Polyurethane]
In the present invention, (A) blocked polyurethane is an active hydrogen compound (A), which is an active hydrogen compound (A), which is an active hydrogen compound (A), which is an active isocyanate group at the end of a urethane prepolymer obtained by reacting a polyhydroxy compound such as a polyether polyol or a polyester polyol with a polyisocyanate. A compound obtained by blocking with a blocking agent).
上記ポリエーテルポリオールは、例えば、ポリオール又はアミンとアルキレンオキシドとを反応させて得ることができる。ポリオールとしては、例えば、エチレングリコール、ジエチレングリコール、プロピレングリコール、ジ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、1,6−ヘキサンジオール等の2価アルコール、4,4’−ジヒドロキシフェニルプロパン、4,4’−ジヒドロキシフェニルメタン等のビスフェノール、グリセリン、ジグリセリン、1,1,1−トリメチロールプロパン、1,2,5−ヘキサントリオール、ペンタエリスリトール、トリエタノールアミン、ソルビトール、シュガー等の多価アルコールが挙げられ、アミンとしては、エチレンジアミン、芳香族ジアミン等のジアミン類が挙げられる。アルキレンオキシドとしては、例えば、エチレンオキシド、プロピレンオキシド、ブチレンオキシド、α−オレフィンオキシド等が挙げられる。 The above-mentioned polyether polyol can be obtained, for example, by reacting a polyol or amine with an alkylene oxide. Examples of the polyol include dihydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, 1,3-butanediol, 1,4-butanediol, and 1,6-hexanediol, and 4,4'-dihydroxy. Phenylpropane, bisphenol such as 4,4'-dihydroxyphenylmethane, glycerin, diglycerin, 1,1,1-trimethylolpropane, 1,2,5-hexanetriol, pentaerythritol, triethanolamine, sorbitol, sugar, etc. Examples of the polyhydric alcohol include diamines such as ethylene diamine and aromatic diamine. Examples of the alkylene oxide include ethylene oxide, propylene oxide, butylene oxide, α-olefin oxide and the like.
上記ポリエステルポリオールは、例えば、ポリカルボン酸とポリオールとを反応させて得ることができる。ポリカルボン酸としては、例えば、マレイン酸、フマル酸、アジピン酸、フタル酸等の2価カルボン酸およびそれらの酸無水物、リシノール酸、オキシカプロン酸、オキシカプリン酸、オキシウンデカン酸、オキシリノール酸、オキシステアリン酸、オキシヘキサンデセン酸のヒドロキシ含有長鎖脂肪酸等が挙げられる。また、ポリオールとしては上記したものの他、アルキレンオキシドと脂肪族、脂環族、芳香族アミン又はポリアミドポリアミンとの付加重合物等が挙げられる。前記付加重合物の具体例としては、フタル酸ジヒドラジド、エチレンジアミン、アジピン酸ジヒドラジド、水素添加メチレンジフェニルジアミン又はアニリンと、ポリプロピレンオキシドとの付加重合物等が挙げられる。 The polyester polyol can be obtained, for example, by reacting a polycarboxylic acid with a polyol. Examples of the polycarboxylic acid include divalent carboxylic acids such as maleic acid, fumaric acid, adipic acid, and phthalic acid and their acid anhydrides, ricinolic acid, oxycaproic acid, oxycaproic acid, oxyundecanoic acid, and oxylinolic acid. , Oxystearic acid, hydroxy-containing long-chain fatty acid of oxyhexanedecenoic acid and the like. In addition to the above-mentioned polyols, examples thereof include addition polymers of alkylene oxides and aliphatic, alicyclic, aromatic amines or polyamide polyamines. Specific examples of the addition polymer include phthalic acid dihydrazide, ethylenediamine, adipic acid dihydrazide, hydrogenated methylenediphenyldiamine or aniline, and an addition polymer of polypropylene oxide.
上記ポリイソシアネートとしては、例えば、4,4’−ジフェニルメタンジイソシアネート(4,4’−MDI)、2,4’−ジフェニルメタンジイソシアネート(2,4’−MDI)、トルエンジイソシアネート(TDI)等の芳香族イソシアネート類、トリメチレンジイソシアネート、テトラメチレンジイソシアネート、ペンタメチレンジイソシアネート、ヘキサメチレンジイソシアネート(HDI)、1,2−プロパンジイソシアネート、1,2−ブタンジイソシアネート、トリメチルヘキサメチレンジイソシアネート、イソホロンジイソシアネート(IPDI)、4,4’−ジシクロヘキシルメタンジイソシアネート、シクロヘキシレンジイソシアネート等の脂肪族イソシアネート類等が挙げられる。 Examples of the polyisocyanate include aromatic isocyanates such as 4,4'-diphenylmethane diisocyanate (4,4'-MDI), 2,4'-diphenylmethane diisocyanate (2,4'-MDI), and toluene diisocyanate (TDI). Kind, trimethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate (HDI), 1,2-propanediisocyanate, 1,2-butane diisocyanate, trimethylhexamethylene diisocyanate, isophorone diisocyanate (IPDI), 4,4' -Dicyclohexamethylene diisocyanate, aliphatic isocyanates such as cyclohexamethylene diisocyanate and the like can be mentioned.
また、上記ブロック化剤として用いられる活性水素化合物としては、例えば、ホルムアミドオキシム、アセトアミドオキシム、アセトオキシム、メチルエチルケトオキシム、ジアセチルモノオキシム、ベンゾフェノンオキシム、シクロヘキサノンオキシム等のオキシム類、フェノール、クレゾール、キシレノール、エチルフェノール、t−ブチルフェノール等のフェノール類、メタノール、エタノール、プロパノール、イソプロパノール、ブタノール、2−エチルヘキサノール等のアルコール類、ピラゾール、3−メチルピラゾール、3,5−ジメチルピラゾールのピラゾール類、アセチルアセトン等のβ−ジケトン類、マロン酸ジエチル、マロン酸ジメチル、アセト酢酸エチル、アセト酢酸メチル等のβ−ケトエステル類、ジシクロヘキシルアミン等のジアルキルアミン類、ε−カプロラクタム、δ−バレロラクタム、β−ブチロラクタム、β−プロピオラクタム等のラクタム類等が挙げられる。 Examples of the active hydrogen compound used as the blocking agent include oximes such as formamide oxime, acetamide oxime, acetoxime, methyl ethyl ketooxime, diacetyl monooxime, benzophenone oxime, and cyclohexanone oxime, phenol, cresol, xylenol, and ethyl. Phenols such as phenol and t-butylphenol, alcohols such as methanol, ethanol, propanol, isopropanol, butanol and 2-ethylhexanol, pyrazoles such as pyrazole, 3-methylpyrazole, 3,5-dimethylpyrazole, and β such as acetylacetone. -Diketones, diethyl malonate, dimethyl malonate, ethyl acetoacetate, β-ketoesters such as methyl acetoacetate, dialkylamines such as dicyclohexylamine, ε-caprolactam, δ-valerolactam, β-butyrolactam, β-pro Examples thereof include lactams such as oxime.
これらブロックドポリウレタンは市販品を用いてもよい。市販品としては、例えば、タケネートB−7005、B−7030、B−7005(以上TDI系ブロックイソシアネート、有効成分100 %、三井化学製)、タケネートB−5010(TDI系ブロックイソシアネート、有効成分100%、三井化学製)、アデカレジンQR−9466(IPDI系ブロックイソシアネート、有効成分100%、ADEKA製)等が挙げられる。 Commercially available products may be used as these blocked polyurethanes. Commercially available products include, for example, Takenate B-7005, B-7030, B-7005 (TDI-based blocked isocyanate, 100% active ingredient, manufactured by Mitsui Chemicals), Takenate B-5010 (TDI-based blocked isocyanate, 100% active ingredient). , Mitsui Chemicals), ADEKA REGIN QR-9466 (IPDI-based blocked isocyanate, 100% active ingredient, ADEKA) and the like.
上記したブロックドポリウレタンは単独で用いてもよく、2種以上を併用してもよい。 The above-mentioned blocked polyurethane may be used alone or in combination of two or more.
[(B)1分子内に2個より多いグリシジル基を有するエポキシ樹脂]
本発明に用いられる1分子内に2個より多いグリシジル基を有するエポキシ樹脂としては、例えば、2−[4−(2,3−エポキシプロポキシ)フェニル]−2−[4−[1,1−ビス[4−([2,3−エポキシプロポキシ]フェニル)]エチル]フェニル]プロパン、1,3−ビス[4−[1−[4−(2,3−エポキシプロポキシ)フェニル]−1−[4−[1−[4−(2,3−エポキシプロポキシフェニル)−1−メチルエチル]フェニル]エチル]フェノキシ]−2−プロパノール、ナフタレン型4官能エポキシ樹脂、ジシクロペンタジエン骨格を有するエポキシ樹脂、トリアジン骨格を有するエポキシ樹脂、フェノールノボラック型エポキシ樹脂、クレゾールノボラック型エポキシ樹脂、ビスフェノールA型ノボラック型エポキシ樹脂等のノボラック型エポキシ樹脂、ビフェニルアラルキル型エポキシ樹脂、テトラキスフェノールエタン型エポキシ樹脂、トリスヒドロキシフェニルメタン型エポキシ樹脂、芳香族アミン型エポキシ樹脂、脂肪族アミン型エポキシ樹脂、脂環式アミン型エポキシ樹脂、ジフェニルジアミノメタン型エポキシ樹脂、アミノフェノール型エポキシ樹脂等のグリシジルアミン型エポキシ化合物、トリメチロールプロパンポリグリジシルエーテル、ペンタエリスリトールポリグリシジルエーテル等の脂肪族系エポキシ樹脂、エポキシ変性ブタジエン、エポキシ変性アクリル‐スチレン系ポリマー等のエポキシ基含有ポリマー等が挙げられる。これらの1分子内に2個より多いグリシジル基を有するエポキシ樹脂は単独で用いてもよく、2種以上を併用してもよい。また、リレー等の電気、電子部品を気密封止又は絶縁封止する際、狭い間隔の隙間への流れ込みが向上することから、常温(25℃)で液状であることが好ましく、低粘度であることがより好ましい。また、これらエポキシ樹脂の中でも、芳香族アミン型エポキシ樹脂、アミノフェノール型エポキシ樹脂、脂肪族系エポキシ樹脂が好ましく、芳香族アミン型エポキシ樹脂(N,N,N’,N’−テトラグリシジル−4,4’−ジアミノジフェニルエーテル、テトラグリシジルメタキシレンジアミン等)、アミノフェノール型エポキシ樹脂(N,N,O−トリグリシジル−p−アミノフェノール、N,N,O−トリグリシジル−p−アミノ−m−クレゾール等)がより好ましい。
[(B) Epoxy resin having more than two glycidyl groups in one molecule]
Examples of the epoxy resin having more than two glycidyl groups in one molecule used in the present invention include 2- [4- (2,3-epoxypropoxy) phenyl] -2- [4- [1,1-]. Bis [4- ([2,3-epoxypropoxy] phenyl)] ethyl] phenyl] propane, 1,3-bis [4- [1- [4- (2,3-epoxypropoxy) phenyl] -1- [ 4- [1- [4- (2,3-epoxypropoxyphenyl) -1-methylethyl] phenyl] ethyl] phenoxy] -2-propanol, naphthalene-type tetrafunctional epoxy resin, epoxy resin having a dicyclopentadiene skeleton, Novolak type epoxy resin such as epoxy resin having triazine skeleton, phenol novolac type epoxy resin, cresol novolac type epoxy resin, bisphenol A type novolac type epoxy resin, biphenyl aralkyl type epoxy resin, tetrakisphenol ethane type epoxy resin, trishydroxyphenylmethane Glysidylamine type epoxy compounds such as type epoxy resin, aromatic amine type epoxy resin, aliphatic amine type epoxy resin, alicyclic amine type epoxy resin, diphenyldiaminomethane type epoxy resin, aminophenol type epoxy resin, trimethyl propanepoly Examples thereof include aliphatic epoxy resins such as glycisyl ether and pentaerythritol polyglycidyl ether, and epoxy group-containing polymers such as epoxy-modified butadiene and epoxy-modified acrylic-styrene-based polymers. Epoxy resins having more than two glycidyl groups in one molecule may be used alone or in combination of two or more. Further, when electrical and electronic parts such as relays are hermetically sealed or insulatedly sealed, the flow into narrow gaps is improved, so that the liquid is preferably liquid at room temperature (25 ° C.) and has a low viscosity. Is more preferable. Among these epoxy resins, aromatic amine type epoxy resins, aminophenol type epoxy resins, and aliphatic epoxy resins are preferable, and aromatic amine type epoxy resins (N, N, N', N'-tetraglycidyl-4. , 4'-diaminodiphenyl ether, tetraglycidyl metaxylene diamine, etc.), aminophenol type epoxy resin (N, N, O-triglycidyl-p-aminophenol, N, N, O-triglycidyl-p-amino-m- Cresol, etc.) is more preferable.
これら1分子内に2個より多いグリシジル基を有するエポキシ樹脂は、市販品を用いてもよい。市販品の中でも芳香族アミン型エポキシ樹脂としては、例えば、jER604(N,N,N’,N’−テトラグリシジル−4,4’−ジアミノジフェニルエーテル、三菱ケミカル社製)、スミエポキシELM−434、ELM−434VL、ELM−434L(以上N,N,N’,N’−テトラグリシジル−4,4’−ジアミノジフェニルエーテル、住友化学社製)、TETRAD−X(テトラグリシジルメタキシレンジアミン、三菱ガス化学社製)等が挙げられる。脂環族アミン型エポキシ樹脂としては、例えば、TETRAD−C(1,3’−ビス(N,N−ジグリシジルアミノメチル)シクロヘキサン、三菱ガス化学社製)等が挙げられる。アミノフェノール型エポキシ樹脂としては、例えば、jER630(N,N,O−トリグリシジル−p−アミノフェノール、三菱ケミカル社製)、スミエポキシELM−100H、ELM−100(N,N,O−トリグリシジル−p−アミノ−m−クレゾール、住友化学社製)等が挙げられる。脂肪族系エポキシ樹脂としては、例えば、デナコールEX−411(ペンタエリスリトールポリグリシジルエーテル、ナガセケムテックス社製)、SR−TMP、SR−TMPL(以下、トリメチロールプロパンポリグリシジルエーテル、阪本薬品工業社製)等が挙げられる。 Commercially available products may be used as the epoxy resin having more than two glycidyl groups in one molecule. Among the commercially available products, examples of the aromatic amine type epoxy resin include jER604 (N, N, N', N'-tetraglycidyl-4,4'-diaminodiphenyl ether, manufactured by Mitsubishi Chemical Co., Ltd.), Sumiepoxy ELM-434, and ELM. -434VL, ELM-434L (above N, N, N', N'-tetraglycidyl-4,4'-diaminodiphenyl ether, manufactured by Sumitomo Chemical Co., Ltd.), TETRAD-X (tetraglycidyl metaxylylenediamine, manufactured by Mitsubishi Gas Chemical Company, Inc.) ) Etc. can be mentioned. Examples of the alicyclic amine type epoxy resin include TETRAD-C (1,3'-bis (N, N-diglycidylaminomethyl) cyclohexane, manufactured by Mitsubishi Gas Chemical Company, Inc.) and the like. Examples of the aminophenol type epoxy resin include jER630 (N, N, O-triglycidyl-p-aminophenol, manufactured by Mitsubishi Chemical Corporation), Sumiepoxy ELM-100H, and ELM-100 (N, N, O-triglycidyl-). p-amino-m-cresol, manufactured by Sumitomo Chemical Corporation) and the like. Examples of the aliphatic epoxy resin include Denacol EX-411 (pentaerythritol polyglycidyl ether, manufactured by Nagase ChemteX Corporation), SR-TMP, SR-TMPL (hereinafter, trimethylolpropane polyglycidyl ether, manufactured by Sakamoto Pharmaceutical Co., Ltd.). ) Etc. can be mentioned.
上記した市販品の1分子内に2個より多いグリシジル基を有するエポキシ樹脂の中でも、リレー等の電気、電子部品を気密封止又は絶縁封止する際、狭い間隔の隙間への流れ込みが向上することから低粘度が好ましく、具体的には、jER630、ELM−100、TETRAD−X、SR−TMPが好ましく、jER630、ELM−100、TETRAD−Xがより好ましい。また、これら1分子内に2個より多いグリシジル基を有するエポキシ樹脂は単独で用いてもよく、2種以上を併用してもよい。 Among the above-mentioned epoxy resins having more than two glycidyl groups in one molecule of the commercially available product, when electrical and electronic parts such as relays are hermetically sealed or insulatedly sealed, the flow into narrow gaps is improved. Therefore, low viscosity is preferable, specifically, jER630, ELM-100, TETRAD-X and SR-TMP are preferable, and jER630, ELM-100 and TETRAD-X are more preferable. Further, the epoxy resins having more than two glycidyl groups in one molecule may be used alone or in combination of two or more.
<(C)1分子内に2個以下のグリシジル基を有するエポキシ樹脂>
本発明において用いられる1分子内に2個以下のグリシジル基を有するエポキシ樹脂としては、例えば、ビスフェノールA型エポキシ樹脂、ビスフェノールF型エポキシ樹脂、ビスフェノールAD型エポキシ樹脂、アルキレンオキシド変性ビスフェノールエポキシ樹脂、ナフタレン型2官能エポキシ樹脂、ビフェニル型エポキシ樹脂、脂環式エポキシ樹脂(シクロヘキセン若しくはシクロペンテン環含有化合物を酸化剤でエポキシ化することによって得られるシクロヘキセンオキシド若しくはシクロペンテンオキシド含有化合物、又は、少なくとも1個の脂環族環を有する2価以下アルコールのポリグリシジルエーテル、水添ビスフェノール型エポキシ樹脂等)、カテコール、レゾルシン等の2価フェノール、又は1,4−ブタンジオール、1,6−ヘキサンジオール、2,2−ジメチル−1,3−プロパンジオール(ネオペンチルグリコール)、(ポリ)エチレングリコール、(ポリ)プロピレングリコール等の2価アルコールとエピハロヒドリンとを反応させて得られるポリグリシジルエーテル、p−オキシ安息香酸等のヒドロキシカルボン酸とエピハロヒドリンとを反応させて得られるグリシジルエーテルエステル、フタル酸、テレフタル酸、ヘキサヒドロフタル酸、長鎖二塩基酸等の2価カルボン酸とエピハロヒドリンとを反応させて得られるポリグリシジルエステル、ゴム変性エポキシ樹脂、ウレタン変性エポキシ樹脂、エポキシ系可塑剤、単官能エポキシ化合物等が挙げられる。これら1分子内に2個以下のグリシジル基を有するエポキシ樹脂は単独で用いてもよく、2種以上を併用してもよい。
<(C) Epoxy resin having two or less glycidyl groups in one molecule>
Examples of the epoxy resin having two or less glycidyl groups in one molecule used in the present invention include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol AD type epoxy resin, alkylene oxide modified bisphenol epoxy resin, and naphthalene. Type bifunctional epoxy resin, biphenyl type epoxy resin, alicyclic epoxy resin (cyclohexene oxide or cyclopentene oxide-containing compound obtained by epoxyizing a cyclohexene or cyclopentene ring-containing compound with an oxidizing agent, or at least one alicyclic resin. Polyglycidyl ether of divalent or less alcohol having a group ring, hydrogenated bisphenol type epoxy resin, etc.), divalent phenol such as catechol, resorcin, or 1,4-butanediol, 1,6-hexanediol, 2,2- Polyglycidyl ether, p-oxybenzoic acid, etc. obtained by reacting a dihydric alcohol such as dimethyl-1,3-propanediol (neopentyl glycol), (poly) ethylene glycol, (poly) propylene glycol with epihalohydrin, etc. A polyglycidyl ester obtained by reacting a divalent carboxylic acid such as a glycidyl ether ester obtained by reacting a hydroxycarboxylic acid with an epihalohydrin, a phthalic acid, a terephthalic acid, a hexahydrophthalic acid, or a long-chain dibasic acid with an epihalohydrin. , Rubber-modified epoxy resin, urethane-modified epoxy resin, epoxy-based plasticizer, monofunctional epoxy compound and the like. These epoxy resins having two or less glycidyl groups in one molecule may be used alone or in combination of two or more.
1分子内に2個以下のグリシジル基を有するエポキシ樹脂には通常、該エポキシ樹脂の総量100重量部に対し通常50重量部以上、好ましくは70重量部以上、1分子内に2個のグリシジル基を有するエポキシ樹脂が含まれる。また、リレー等の電気、電子部品を気密封止又は絶縁封止する際、狭い間隔の隙間への流れ込みが向上することから、常温(25℃)で液状であることが好ましく、低粘度であることがより好ましい。 An epoxy resin having two or less glycidyl groups in one molecule usually has 50 parts by weight or more, preferably 70 parts by weight or more, and two glycidyl groups in one molecule with respect to 100 parts by weight of the total amount of the epoxy resin. Epoxy resin having is included. Further, when electrical and electronic parts such as relays are hermetically sealed or insulatedly sealed, the flow into narrow gaps is improved, so that the liquid is preferably liquid at room temperature (25 ° C.) and has a low viscosity. Is more preferable.
上記した1分子内に2個以下のグリシジル基を有するエポキシ樹脂の中でも、ビスフェノールA型エポキシ樹脂、ビスフェノールF型エポキシ樹脂、アルキレンオキシド変性ビスフェノールエポキシ樹脂、2価フェノール又は2価アルコールとエピハロヒドリンとを反応させて得られるポリグリシジルエーテル、2価カルボン酸とエピハロヒドリンとを反応させて得られるポリグリシジルエステル、エポキシ系可塑剤が好ましく、ビスフェノールA型エポキシ樹脂、ビスフェノールF型エポキシ樹脂、アルキレンオキシド変性ビスフェノールエポキシ樹脂、2価フェノール又は2価アルコールとエピハロヒドリンとを反応させて得られるポリグリシジルエーテル、2価カルボン酸とエピハロヒドリンとを反応させて得られるポリグリシジルエステルがより好ましい。 Among the above-mentioned epoxy resins having two or less glycidyl groups in one molecule, bisphenol A type epoxy resin, bisphenol F type epoxy resin, alkylene oxide-modified bisphenol epoxy resin, dihydric phenol or dihydric alcohol is reacted with epihalohydrin. Polyglycidyl ether obtained by reacting a divalent carboxylic acid with epihalohydrin and an epoxy-based plasticizer are preferable, and bisphenol A type epoxy resin, bisphenol F type epoxy resin, and alkylene oxide modified bisphenol epoxy resin are preferable. More preferably, a polyglycidyl ether obtained by reacting a dihydric phenol or a dihydric alcohol with an epihalohydrin, or a polyglycidyl ester obtained by reacting a divalent carboxylic acid with an epihalohydrin.
これら1分子内に2個以下のグリシジル基を有するエポキシ樹脂は、市販品を用いてもよい。市販品のビスフェノールA型エポキシ樹脂としては、例えば、D.E.R.331、D.E.R.383(以上、OLIN社製)、jER828、jER828EL(以上、三菱ケミカル社製)、エピクロン850、エピクロン850−S(以上、DIC社製)等が挙げられる。ビスフェノールF型エポキシ樹脂としては、例えば、jER807(三菱ケミカル社製)、エピクロン830、エピクロン830−S(以上、DIC社製)等が挙げられる。アルキレンオキシド変性ビスフェノールエポキシ樹脂としては、例えば、リカレジン BEO−20E(ビスフェノールAビス(プロピレングリコールグリシジルエーテル)エーテル、新日本理化社製)、リカレジンBEO−60E(ビスフェノールAビス(トリエチレングリコールグリシジルエーテル)エーテル(主成分)、新日本理化社製)、アデカレジンEP−4000、EP−4005(以上、プロピレンオキシド変性ビスフェノールエポキシ樹脂、ADEKA社製)等が挙げられる。2価フェノール又は2価アルコールとエピハロヒドリンとを反応させて得られるポリグリシジルエーテルとしては、例えば、デナコールEX−201(レゾルシノールジグリシジルエーテル、ナガセケムテックス社製)、デナコールEX−211(ネオペンチルグリコールジグリシジルエーテル、ナガセケムテックス社製)デナコールEX−212(1,6−ヘキサンジオールジグリシジルエーテル、ナガセケムテックス社製)、デナコールEX−810、811、821、830、832、841、850、851、861((ポリ)エチレングリコールジグリシジルエーテル、ナガセケムテックス社製)、デナコールEX−931(ポリプロピレングリコールジグリシジルエーテル、ナガセケムテックス社製)等が挙げられる。2価カルボン酸とエピハロヒドリンとを反応させて得られるポリグリシジルエステルとしては、例えば、デナコールEX−721(フタル酸ジグリシジルエステル、ナガセケムテックス社製)、デナコールEX−711(テレフタル酸ジグリシジルエステル、ナガセケムテックス社製)、SR−HHPA(ヘキサヒドロフタル酸ジグリシジルエステル、阪本薬品工業社製)、IPU−22G(8,13−ジメチル−8,12−エイコサジエン二酸ビス(オキシラニルメチル)エステル、岡村製油社製)、SB−20G(7−エチルオクタデカン二酸ジ(2,3−3−エポキシプロピル)、岡村製油社製)等が挙げられる。脂環式エポキシ樹脂としては、例えば、セロキサイド 2021P(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、ダイセル社製)、セロキサイド2081(ε-カプロラクトン変性 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、ダイセル社製)、セロキサイド3000(1,2,8,9−ジエポキシリモネン、ダイセル社製)、エポカリックTHI−DE(テトラヒドロインデンジエポキシド、JXTGエネルギー社製)、エポカリックDE−102(5,12−ジオキサヘキサシクロ[7.6.1.02,8.04,6.010,15.011,13]ヘキサデカン、JXTGエネルギー社製)、エポカリックDE−103(5,12−ジオキサヘプタシクロ[7.6.1.13,7.02,8.04,6.010,15.011,13]ヘプタデカン、JXTGエネルギー社製)、SR−SBA(水添ビスフェノールAジグリシジルエーテル、阪本薬品工業社製)、リカレジンDME−100 (シクロヘキサンジメタノールジグリシジルエーテル、新日本理化社)等が挙げられる。エポキシ系可塑剤としては、例えば、サンソサイザーE−PS(4,5−エポキシシクロヘキサン−1,2−ジカルボン酸ジ2−エチルヘキシル、新日本理化社製)、サンソサイザーE−PO(4,5-エポキシシクロヘキサン−1,2−ジカルボン酸ジ(9,10-エポキシステアリル)、新日本理化社製)サンソサイザーE−2000H(エポキシ化大豆油、新日本理化社製)サンソサイザーE−9000H(エポキシ化亜麻仁油、新日本理化社製)、アデカサイザーO−130P(エポキシ化大豆油、ADEKA社製)アデカサイザーO−180A(エポキシ化亜麻仁油、ADEKA社製)等が挙げられる。 Commercially available products may be used as the epoxy resin having two or less glycidyl groups in one molecule. Examples of commercially available bisphenol A type epoxy resins include D.E.R. 331, D.E.R. 383 (above, manufactured by OLIN), jER828, jER828EL (above, manufactured by Mitsubishi Chemical Corporation), Epicron 850, Epicron 850-S (above, manufactured by DIC) and the like. Examples of the bisphenol F type epoxy resin include jER807 (manufactured by Mitsubishi Chemical Corporation), Epicron 830, Epicron 830-S (manufactured by DIC Corporation) and the like. Examples of the alkylene oxide-modified bisphenol epoxy resin include ricaredin BEO-20E (bisphenol A bis (propylene glycol glycidyl ether) ether, manufactured by Shin Nihon Rika Co., Ltd.) and ricaredin BEO-60E (bisphenol A bis (triethylene glycol glycidyl ether) ether). (Main component), (manufactured by Shin Nihon Rika Co., Ltd.), Adecaledin EP-4000, EP-4005 (above, propylene oxide-modified bisphenol epoxy resin, manufactured by ADEKA) and the like. Examples of the polyglycidyl ether obtained by reacting dihydric phenol or dihydric alcohol with epihalohydrin include Denacol EX-201 (resorcinol diglycidyl ether, manufactured by Nagase ChemteX Corporation) and Denacol EX-211 (neopentyl glycol di). Glycidyl ether, manufactured by Nagase ChemteX) Denacol EX-212 (1,6-hexanediol diglycidyl ether, manufactured by Nagase Chemtex), Denacol EX-810, 811, 821, 830, 832, 841, 850, 851, Examples thereof include 861 ((poly) ethylene glycol diglycidyl ether, manufactured by Nagase ChemteX Corporation), Denacol EX-931 (polypropylene glycol diglycidyl ether, manufactured by Nagase ChemteX Corporation) and the like. Examples of the polyglycidyl ester obtained by reacting a divalent carboxylic acid with epihalohydrin include Denacol EX-721 (phthalic acid diglycidyl ester, manufactured by Nagase ChemteX Corporation) and Denacol EX-711 (terephthalic acid diglycidyl ester, terephthalic acid diglycidyl ester). Nagase ChemteX Co., Ltd.), SR-HHPA (hexahydrophthalic acid diglycidyl ester, manufactured by Sakamoto Yakuhin Kogyo Co., Ltd.), IPU-22G (8,13-dimethyl-8,12-eicosaziendiate bis (oxylanylmethyl)) Ester, manufactured by Okamura Oil Co., Ltd.), SB-20G (7-ethyloctadecanedioic acid di (2,3-3-epoxypropyl), manufactured by Okamura Oil Co., Ltd.) and the like can be mentioned. Examples of the alicyclic epoxy resin include seroxide 2021P (3', 4'-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate, manufactured by Daicel) and seroxide 2081 (ε-caprolactone modified 3', 4'-epoxy. Cyclohexylmethyl 3,4-epoxycyclohexanecarboxylate, manufactured by Daicel), Celoxide 3000 (1,2,8,9-diepoxylimonen, manufactured by Daicel), Epocalic THI-DE (tetrahydroindenediepoxide, manufactured by JXTG Energy) ), Epokarikku DE-102 (5,12-di oxa hexa cyclo [7.6.1.0 2,8 .0 4,6 .0 10,15 .0 11,13] hexadecane, manufactured JXTG energy Corporation), Epokarikku DE-103 (5,12-di oxa hept cyclo [7.6.1.1 3,7 .0 2,8 .0 4,6 .0 10,15 .0 11,13] heptadecane, JXTG energy's ), SR-SBA (hydrogenated bisphenol A diglycidyl ether, manufactured by Sakamoto Yakuhin Kogyo Co., Ltd.), epoxy resin DME-100 (cyclohexanedimethanol diglycidyl ether, Shin Nihon Rika Co., Ltd.) and the like. Examples of the epoxy-based plasticizer include Sansosizer E-PS (4,5-epoxycyclohexane-1,2-dicarboxylic acid di2-ethylhexyl, manufactured by Shin Nihon Rika Co., Ltd.) and Sansosizer E-PO (4,5-). Epoxycyclohexane-1,2-dicarboxylic acid di (9,10-epoxystearyl), manufactured by Shin Nihon Rika Co., Ltd.) Sun Sosizer E-2000H (epoxidized soybean oil, manufactured by Shin Nihon Rika Co., Ltd.) Sun Sosizer E-9000H (epoxidized) Examples thereof include flaxseed oil (manufactured by Shin Nihon Rika Co., Ltd.), Adecasizer O-130P (epoxidized soybean oil, manufactured by ADEKA), adecaseizer O-180A (epoxidized flaxseed oil, manufactured by ADEKA) and the like.
上記した市販品の1分子内に2個以下のグリシジル基を有するエポキシ樹脂の中でも、D.E.R.331、D.E.R.383、jER828、jER828EL、エピクロン850、エピクロン850−S、jER807、エピクロン830、エピクロン830−S、リカレジンBEO−60E、アデカレジンEP−4000,アデカレジンEP−4005、SR−HHPA、リカレジンDME−100、サンソサイザーE−PO、サンソサイザーE−PS、アデカサイザーO−180Aが好ましく、D.E.R.331、D.E.R.383、jER828、jER828EL、エピクロン850、エピクロン850−S、jER807、エピクロン830、エピクロン830−S、リカレジンBEO−60E、アデカレジンEP−4000,アデカレジンEP−4005、SR−HHPA、リカレジンDME−100がより好ましく、D.E.R.331、jER807、アデカレジンEP−4005、SR−HHPA、リカレジンDME−100が特に好ましい。また、1分子内に2個以下のグリシジル基を有するエポキシ樹脂は単独で用いてもよく、2種以上を併用してもよい。 Among the above-mentioned epoxy resins having two or less glycidyl groups in one molecule of the commercially available product, D.E.R. 331, D.E.R. 383, jER828, jER828EL, Epicron 850, Epicron 850-S, jER807, Epicron 830, Epicron 830-S, Rica Resin BEO-60E, Adeka Resin EP-4000, Adeka Resin EP-4005, SR-HHPA, Rika Resin DME-100, Sanso Sizar E-PO, sunsociator E-PS, and ADEKA Sizer O-180A are preferable, and D.E.R. 331, D.E.R. 383, jER828, jER828EL, Epicron 850, Epicron 850-S, jER807, Epicron 830, Epicron 830-S, Rica Resin BEO-60E, Adecaredin EP-4000, Adecaredin EP-4005, SR-HHPA, Rica Resin DME-100 are more preferable. , D.E.R. 331, jER807, Adecaledin EP-4005, SR-HHPA, and Ricaresin DME-100 are particularly preferable. Further, the epoxy resin having two or less glycidyl groups in one molecule may be used alone or in combination of two or more.
<エポキシ樹脂組成物中に含まれる(A)、(B)及び(C)の割合>
本発明のエポキシ樹脂組成物に含まれる(A)の含有量は、(A)、 (B)及び(C)の合計量100重量部に対し、20〜60重量部、好ましくは30〜45重量部である。20重量部以下の場合、得られる硬化物の室温域での損失正接(tanδ)が低下し、制振性が低下する。また、60重量部以上の場合、硬化速度が低下する。
<Ratio of (A), (B) and (C) contained in the epoxy resin composition>
The content of (A) contained in the epoxy resin composition of the present invention is 20 to 60 parts by weight, preferably 30 to 45 parts by weight, based on 100 parts by weight of the total amount of (A), (B) and (C). It is a department. When the amount is 20 parts by weight or less, the loss tangent (tan δ) of the obtained cured product in the room temperature range is reduced, and the vibration damping property is lowered. Further, when the amount is 60 parts by weight or more, the curing rate is lowered.
本発明のエポキシ樹脂組成物に含まれる(B)の含有量は、(B)及び(C)の合計量100重量部に対し、5〜30重量部、好ましくは10〜25重量部である。5重量部以下の場合、得られる硬化物の樹脂及び金属との接着性、耐湿熱性及び耐熱性が低下する。30重量部以上の場合、得られる硬化物の室温域での損失正接(tanδ)が低下し、制振性が低下する。 The content of (B) contained in the epoxy resin composition of the present invention is 5 to 30 parts by weight, preferably 10 to 25 parts by weight, based on 100 parts by weight of the total amount of (B) and (C). When the amount is 5 parts by weight or less, the adhesiveness, moisture heat resistance and heat resistance of the obtained cured product to the resin and metal are lowered. When the amount is 30 parts by weight or more, the loss tangent (tan δ) of the obtained cured product in the room temperature range is reduced, and the vibration damping property is lowered.
<(D)潜在性硬化剤>
本発明において用いられる潜在性硬化剤としては、硬化後の性能を阻害しないものであれば特に限定されない。具体的に例えば、ジヒドラジド化合物、ジシアンジアミド、イミダゾール化合物、イミダゾールアダクト系化合物、アミンアダクト系化合物、変性脂肪族ポリアミン化合物等が挙げられる。ジヒドラジド化合物としては、例えば、アジピン酸ジヒドラジド、セバシン酸ジヒドラジド、イソフタル酸ジヒドラジド、マレイン酸ジヒドラジド、ドデカン二酸ジヒドラジド、味の素テクノファイン社製のアミキュアVDH、アミキュアUDH等が挙げられる。イミダゾール化合物としては、例えば2−フェニルイミダゾール、2−フェニル−4−メチル−5−ヒドロキシメチルイミダゾール等が挙げられる。イミダゾールアダクト系化合物としては、例えば、味の素テクノファイン社製アミキュアPN−23、アミキュアPN−R等が挙げられる。アミンアダクト系化合物としては、例えば、味の素テクノファイン社製アミキュアMY−24、アミキュアMY−R、特開昭57−100127号公報又は特開2017−178981号公報に示されたアダクト系化合物等が挙げられる。変性脂肪族ポリアミン化合物としては、例えば、T&K TOKA製フジキュアーFXE−1000等が挙げられる。
<(D) Latent curing agent>
The latent curing agent used in the present invention is not particularly limited as long as it does not impair the performance after curing. Specific examples thereof include dihydrazide compounds, dicyandiamides, imidazole compounds, imidazole adduct compounds, amine adduct compounds, and modified aliphatic polyamine compounds. Examples of the dihydrazide compound include adipic acid dihydrazide, sebacic acid dihydrazide, isophthalic acid dihydrazide, maleic acid dihydrazide, dodecanedioic acid dihydrazide, Ajinomoto Technofine's Amicure VDH, and Amicure UDH. Examples of the imidazole compound include 2-phenylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole and the like. Examples of the imidazole adduct-based compound include Ajinomoto Technofine Co., Ltd. Amicure PN-23 and Amicure PN-R. Examples of the amine adduct-based compound include Ajinomoto Technofine Co., Ltd. Amicure MY-24, Amicure MY-R, and adduct-based compounds shown in JP-A-57-100127 or JP-A-2017-178981. Be done. Examples of the modified aliphatic polyamine compound include Fujicure FXE-1000 manufactured by T & K TOKA.
これら潜在性硬化剤の中でも、ジヒドラジド化合物、アミンアダクト系化合物が好ましい。また、潜在性硬化剤は、単独で用いてもよく、2種以上を併用してもよい。 Among these latent curing agents, dihydrazide compounds and amine adduct compounds are preferable. Further, the latent curing agent may be used alone or in combination of two or more.
本発明のエポキシ樹脂組成物に含まれる潜在性硬化剤の量は、例えば、(A)、(B)及び(C)の合計量100重量部に対し、3〜30重量部、好ましくは10〜20重量部である。 The amount of the latent curing agent contained in the epoxy resin composition of the present invention is, for example, 3 to 30 parts by weight, preferably 10 to 10 parts by weight, based on 100 parts by weight of the total amount of (A), (B) and (C). 20 parts by weight.
<その他の成分>
本発明のエポキシ樹脂組成物には、必要に応じて、ブロックドポリウレタン解離促進剤、有機フィラー、無機フィラー、カップリング剤、着色剤、非反応性希釈剤、消泡剤、湿潤分散剤等を配合することができる。ブロックドポリウレタン解離促進剤としては、例えば、有機錫化合物などの金属触媒、1,8−ジアザビシクロ[5,4,0]−ウンデセン−7などのアミン触媒やその塩類等が挙げられる。無機フィラーとしては、例えば、炭酸カルシウム、硫酸バリウム、溶融シリカ、結晶シリカ、ガラスフィラー、水酸化アルミニウム、水酸化マグネシウム、アルミナ等が挙げられる。カップリング剤としては、例えば、3−グリシドキシプロピルトリメトキシシラン、3−グリシドキシプロピルメチルジエトキシシラン等が挙げられる。着色剤としては、例えば、カーボンブラック、酸化チタン等が挙げられる。非反応性希釈剤としては、例えば、キシレン、セロソルブ等の有機溶剤や、フタル酸ジメチル、フタル酸ジブチル、フタル酸ジイソノニル、リン酸トリクレジル等の可塑剤等が挙げられる。
<Other ingredients>
The epoxy resin composition of the present invention may contain, if necessary, a blocked polyurethane dissociation accelerator, an organic filler, an inorganic filler, a coupling agent, a colorant, a non-reactive diluent, a defoaming agent, a wet dispersant and the like. Can be blended. Examples of the blocked polyurethane dissociation accelerator include metal catalysts such as organic tin compounds, amine catalysts such as 1,8-diazabicyclo [5,4,0] -undecene-7, and salts thereof. Examples of the inorganic filler include calcium carbonate, barium sulfate, molten silica, crystalline silica, glass filler, aluminum hydroxide, magnesium hydroxide, alumina and the like. Examples of the coupling agent include 3-glycidoxypropyltrimethoxysilane and 3-glycidoxypropylmethyldiethoxysilane. Examples of the colorant include carbon black and titanium oxide. Examples of the non-reactive diluent include organic solvents such as xylene and cellosolve, and plasticizers such as dimethyl phthalate, dibutyl phthalate, diisononyl phthalate, and tricresyl phosphate.
<エポキシ樹脂組成物の調製方法>
本発明のエポキシ樹脂組成物の調製方法は、通常のエポキシ樹脂組成物の調製方法と同様に一般的な撹拌混合装置と混合条件が適用される。使用される装置としては、ミキシングロール、ディゾルバ、プラネタリミキサ、ニーダ、押出機等である。混合の際、エポキシ樹脂等を溶解および/または低粘度化し、撹拌混合効率を向上させるために加熱してもよい。また、摩擦発熱、反応発熱等を除去するために必要に応じて冷却してもよい。撹拌混合の時問は必要により定めればよく、特に制約されることはない。
<Preparation method of epoxy resin composition>
As the method for preparing the epoxy resin composition of the present invention, a general stirring and mixing device and mixing conditions are applied in the same manner as the method for preparing an ordinary epoxy resin composition. The devices used include mixing rolls, dissolvers, planetary mixers, kneaders, extruders and the like. At the time of mixing, the epoxy resin or the like may be dissolved and / or reduced in viscosity and heated in order to improve the stirring and mixing efficiency. Further, it may be cooled as necessary to remove frictional heat generation, reaction heat generation and the like. The time of stirring and mixing may be determined as necessary and is not particularly limited.
<硬化条件>
硬化条件は特に限定されるものでないが、硬化温度は、例えば、80℃〜150℃、好ましくは90℃〜130℃である。樹脂材料(ポリブチレンテレフタレート(PBT)や液晶ポリマー(LCP)等)の接着、封止等の場合は、120℃以下が好ましい。硬化時間は、硬化温度が120℃の場合は、例えば、15分から2時間、好ましくは30分から90分である。なお、本発明のエポキシ樹脂組成物は、120℃程度の比較的低い温度でも硬化可能であることから、低温硬化用の封止材としても好適に使用することができる。
<Curing conditions>
The curing conditions are not particularly limited, but the curing temperature is, for example, 80 ° C. to 150 ° C., preferably 90 ° C. to 130 ° C. In the case of adhesion, sealing, etc. of a resin material (polybutylene terephthalate (PBT), liquid crystal polymer (LCP), etc.), 120 ° C. or lower is preferable. When the curing temperature is 120 ° C., the curing time is, for example, 15 minutes to 2 hours, preferably 30 minutes to 90 minutes. Since the epoxy resin composition of the present invention can be cured even at a relatively low temperature of about 120 ° C., it can be suitably used as a sealing material for low temperature curing.
<本発明のエポキシ樹脂の特徴>
本発明のエポキシ樹脂は、該エポキシ樹脂を上記のように硬化させて得られる硬化物の室温域での損失正接(tanδ)が通常0.10以上、好ましくは0.25以上となる。そのため、該硬化物は制振性に優れることから、小型電子部品または電気部品を封止または固着するためのエポキシ樹脂組成物、特にリレー又はコイルを封止または固着するためのエポキシ樹脂組成物として好適に用いられる。なお、本発明における室温域での損失正接(tanδ)とは、下記する実施例の項に記載する条件にて測定された値である。
<Characteristics of the epoxy resin of the present invention>
The epoxy resin of the present invention has a loss tangent (tan δ) of a cured product obtained by curing the epoxy resin as described above in a room temperature range of usually 0.10 or more, preferably 0.25 or more. Therefore, since the cured product has excellent vibration damping properties, it can be used as an epoxy resin composition for sealing or fixing small electronic parts or electric parts, particularly as an epoxy resin composition for sealing or fixing a relay or coil. It is preferably used. The loss tangent (tan δ) in the room temperature range in the present invention is a value measured under the conditions described in the section of Examples below.
また、本発明のエポキシ樹脂組成物は必要に応じ、(B)1分子以内に2個より多いグリシジル基を有するエポキシ樹脂及び/又は(C)1分子内に2個以下のグリシジル基を有するエポキシ樹脂として、25℃で液状のものを使用することにより、25℃で液状である一液型エポキシ樹脂組成物とすることができる。 Further, the epoxy resin composition of the present invention is, if necessary, (B) an epoxy resin having more than two glycidyl groups in one molecule and / or (C) an epoxy having two or less glycidyl groups in one molecule. By using a resin that is liquid at 25 ° C., a one-component epoxy resin composition that is liquid at 25 ° C. can be obtained.
以下、実施例および比較例を挙げて本発明を具体的に説明するが、本発明はこれらの実施例に何ら限定されるものではない。 Hereinafter, the present invention will be specifically described with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples.
(実施例1〜10、比較例1〜3)
表1に従って各成分をそれぞれ計量し、ミキシングロールを使って撹拌混合することで、各実施例および比較例に係るエポキシ樹脂組成物を調製した。得られたエポキシ樹脂組成物を用いて、以下の方法で各種試験を行った。得られた結果を表2に示す。なお、表1中の各数値の単位は、特に断りのない限り重量部である。また、表1中のフジEPブラック8017の量については、フジEPブラック8017に含まれるカーボンブラックの量(20重量%)を示し、jER807の量については、フジEPブラック8017に含まれるビスフェノールF型エポキシ樹脂(80重量%)を合わせた量を示した。
(Examples 1 to 10, Comparative Examples 1 to 3)
Each component was weighed according to Table 1, and the epoxy resin compositions according to each Example and Comparative Example were prepared by stirring and mixing using a mixing roll. Using the obtained epoxy resin composition, various tests were carried out by the following methods. The results obtained are shown in Table 2. The unit of each numerical value in Table 1 is a part by weight unless otherwise specified. The amount of Fuji EP Black 8017 in Table 1 indicates the amount of carbon black (20% by weight) contained in Fuji EP Black 8017, and the amount of jER807 is the bisphenol F type contained in Fuji EP Black 8017. The total amount of epoxy resin (80% by weight) is shown.
(ゲル化時間(ゲルタイム)の測定)
下記装置、条件にて測定を行い、下記の通り評価を行った。
・測定装置:熱板式ゲル化試験機GT−D(日新科学社製)
・測定方法等:スパチュラで試料0.1gを取り、100℃に設定した熱板上で加熱し、適時スパチュラで混ぜ、ひと固まりにまとまるまでの時間を測定した。結果を表2に示す。
(Measurement of gelation time (gel time))
Measurements were performed with the following equipment and conditions, and evaluation was performed as follows.
-Measuring device: Hot plate type gelling tester GT-D (manufactured by Nissin Kagaku Co., Ltd.)
-Measuring method, etc .: 0.1 g of the sample was taken with a spatula, heated on a hot plate set at 100 ° C., mixed with a spatula at appropriate times, and the time until it was put together was measured. The results are shown in Table 2.
(動的粘弾性の測定及び制振性の判定)
各実施例および比較例で得られたエポキシ樹脂組成物を、それぞれ120℃で60分間硬化させて硬化物を得た。得られた硬化物から3mm×5mm×50mmの試験片を作成し、作成した試験片について動的粘弾性試験機(SII DMS−6100(日立ハイテクサイエンス社製)を用いて、引張モード(昇温速度2℃/分)で、30℃における10Hzでの動的粘弾性を測定し、得られた損失正接(tanδ)の値に基づき、以下に示す基準に従って制振性を判定した。判定結果を表2に示す。
・損失正接(tanδ)
◎:0.25以上、〇:0.10〜0.24、×:0.09以下
(Measurement of dynamic viscoelasticity and judgment of vibration damping property)
The epoxy resin compositions obtained in each Example and Comparative Example were cured at 120 ° C. for 60 minutes to obtain a cured product. A 3 mm × 5 mm × 50 mm test piece was prepared from the obtained cured product, and the prepared test piece was subjected to a tensile mode (temperature rise) using a dynamic viscoelasticity tester (SII DMS-6100 (manufactured by Hitachi High-Tech Science Co., Ltd.)). The dynamic viscoelasticity at 10 Hz at 30 ° C. was measured at a speed of 2 ° C./min), and the vibration damping property was judged according to the criteria shown below based on the obtained loss tangent (tan δ) value. It is shown in Table 2.
・ Loss tangent (tan δ)
⊚: 0.25 or more, 〇: 0.10 to 0.24, ×: 0.09 or less
(引張剪断接着強さの測定)
各実施例および比較例で得られたエポキシ樹脂組成物を、それぞれ2枚の鋼板(1.6mm×25mm×100mm)及び2枚のPBT板(ジュラネックス(登録商標) PBT3300((GF30%強化)、ポリブラステックス社製、1.6mm×25mm×100mm)の間に塗布し、張り合わせ、120℃で60分間硬化させて試験片を作成した。作成した試験片についてJISK6850における引張剪断接着強さ(TSS)の測定方法に準拠して、PBT−PBT及び鋼―鋼での接着力を測定した。以下に示す基準に従って接着力を判定した結果を表2に示す。
・PBT−PBTのTSS(N/mm2)
◎: 4.0以上 〇:3.0〜3.9 ×:2.9以下
・鋼―鋼のTSS(N/mm2)
◎:11.0以上 〇:9.0〜10.9 ×:8.9以下
(Measurement of tensile shear adhesive strength)
The epoxy resin compositions obtained in each Example and Comparative Example were subjected to two steel plates (1.6 mm × 25 mm × 100 mm) and two PBT plates (Duranex (registered trademark) PBT3300 ((GF30% strengthened)). , Polybutylene, manufactured by Polybutylene tere, 1.6 mm × 25 mm × 100 mm), laminated, and cured at 120 ° C. for 60 minutes to prepare a test piece. The adhesive strength between PBT-PBT and steel-steel was measured according to the measurement method of TSS). Table 2 shows the results of determining the adhesive strength according to the criteria shown below.
-PBT-PBT TSS (N / mm 2 )
⊚: 4.0 or more 〇: 3.0 to 3.9 ×: 2.9 or less ・ Steel-Steel TSS (N / mm 2 )
⊚: 11.0 or more 〇: 9.0 to 10.9 ×: 8.9 or less
(高温高湿下での耐湿熱性及び判定)
各実施例および比較例で得られたエポキシ樹脂組成物を、それぞれ2枚の銅板(1.6mm×25mm×100mm)の間に塗布し、貼り合わせ、120℃で60分間硬化させて試験片を作成した。作成した試験片と、さらに温度:85℃、湿度:85%で3日間暴露させた後の試験片について、それぞれJISK6850における引張剪断接着強さの測定方法に準拠して、銅―銅接着力を測定し、測定結果から保持率を計算し、以下の基準に従って結果を判定した。判定結果を表2に示す。
・保持率({(暴露後の銅−銅接着力)/(暴露前の銅−銅接着力)}×100で計算される値、%)
〇:50%以上 ×:50%以下
(Moisture resistance and judgment under high temperature and high humidity)
The epoxy resin compositions obtained in each Example and Comparative Example were applied between two copper plates (1.6 mm × 25 mm × 100 mm), bonded, and cured at 120 ° C. for 60 minutes to prepare a test piece. Created. The prepared test piece and the test piece after further exposure at temperature: 85 ° C. and humidity: 85% for 3 days were subjected to copper-copper adhesive strength in accordance with the method for measuring tensile shear adhesive strength in JIS K6850. The measurement was performed, the retention rate was calculated from the measurement results, and the results were judged according to the following criteria. The determination results are shown in Table 2.
Retention rate ({(copper-copper adhesive strength after exposure) / (copper-copper adhesive strength before exposure)} x 100,%)
〇: 50% or more ×: 50% or less
(硬化物の耐熱性判定)
各実施例および比較例で得られたエポキシ樹脂組成物を、それぞれ120℃で60分硬化させて硬化物を得た。得られた硬化物から3mm×25mm×50mmの試験片を作成し、作成した試験片を、270℃で3分間暴露させた後、暴露後の試験片について外観の変化および柔軟性を確認し、以下の基準に従って結果を判定した。判定結果を表2に示す。
・外観
〇:変化なし △:表面の荒れあり ×:発泡、変形、べたつきあり
(Judgment of heat resistance of cured product)
The epoxy resin compositions obtained in each Example and Comparative Example were cured at 120 ° C. for 60 minutes to obtain a cured product. A 3 mm × 25 mm × 50 mm test piece was prepared from the obtained cured product, and the prepared test piece was exposed at 270 ° C. for 3 minutes, and then the appearance change and flexibility of the exposed test piece were confirmed. The results were judged according to the following criteria. The determination results are shown in Table 2.
・ Appearance 〇: No change △: Rough surface ×: Foaming, deformation, stickiness
なお、表1中の各成分は以下の通りである。
(A)ブロックドポリウレタン
・アデカレジンQR−9466:IPDI系ポリイソシアネート(ADEKA社製)
(B)1分子内に2個より多いグリシジル基を有するエポキシ樹脂
・jER630:アミノフェノール系3官能エポキシ樹脂(三菱ケミカル社製)
・SR−TMP:脂肪族系3官能エポキシ樹脂(阪本薬品工業製)
・TETRAD−X:キシレンジアミン系4官能エポキシ樹脂(三菱ガス化学社製)
・ELM−100:アミノクレゾール系3官能エポキシ樹脂(住友化学社製)
(C)1分子内に2個以下のグリシジル基を有するエポキシ樹脂
・jER807:ビスフェノールF型エポキシ樹脂(三菱ケミカル社製)
・D.E.R.331:ビスフェノールA型エポキシ樹脂(OLIN社製)
・アデカレジンEP−4005;プロピレンオキシド変性ビスフェノールA型エポキシ樹脂(ADEKA社製)
・リカレジンDME−100: シクロヘキサンジメタノールジグリシジルエーテル(新日本理化社製)
・SR−HHPA:ヘキサヒドロフタル酸ジグリシジルエーテル(阪本薬品工業社製)
・サンソサイザーE−PO:4,5-エポキシシクロヘキサン-1,2-ジカルボン酸ジ(9,10-エポキシステアリル)(新日本理化社製)
・アデカサイザーO−180A:エポキシ化亜麻仁油(ADEKA社製)
(D)潜在性硬化剤
・硬化剤A: 特開昭57−100127号公報に示されたエポキシーアミンアダクト化合物(田岡化学工業社製)
・ADH:アジピン酸ジヒドラジド(日本ファイケム社製)
・アミキュアUDH:7,11−オクタデカジエン−1,18−ジカルボヒドラジド(味の素テクノファイン社製)
(フィラー)
・アエロジル200:親水性溶融シリカ(日本アエロジル社製)
・ミクローン200:脂肪酸処理軽質炭酸カルシウム(ニューライム社製)
(着色剤)
・フジEPブラック8017:20wt%カーボンブラック含有ビスフェノールF型エポキシ樹脂分散体(富士色素社製)
Each component in Table 1 is as follows.
(A) Blocked Polyurethane ・ Adeka Resin QR-9466: IPDI Polyisocyanate (manufactured by ADEKA)
(B) Epoxy resin having more than two glycidyl groups in one molecule ・ jER630: Aminophenol-based trifunctional epoxy resin (manufactured by Mitsubishi Chemical Corporation)
-SR-TMP: Aliphatic trifunctional epoxy resin (manufactured by Sakamoto Yakuhin Kogyo)
-TETRAD-X: Xylene diamine-based tetrafunctional epoxy resin (manufactured by Mitsubishi Gas Chemical Company)
-ELM-100: Aminocresol-based trifunctional epoxy resin (manufactured by Sumitomo Chemical Co., Ltd.)
(C) Epoxy resin having two or less glycidyl groups in one molecule-jER807: Bisphenol F type epoxy resin (manufactured by Mitsubishi Chemical Corporation)
・ D.E.R. 331: Bisphenol A type epoxy resin (manufactured by OLIN)
-ADEKA REGIN EP-4005; Propylene oxide-modified bisphenol A type epoxy resin (manufactured by ADEKA)
-Ricaresin DME-100: Cyclohexanedimethanol diglycidyl ether (manufactured by Shin Nihon Rika Co., Ltd.)
-SR-HHPA: Diglycidyl hexahydrophthalate ether (manufactured by Sakamoto Yakuhin Kogyo Co., Ltd.)
・ Sansosizer E-PO: 4,5-epoxycyclohexanedi-1,2-dicarboxylic acid (9,10-epoxystearyl) (manufactured by Shin Nihon Rika Co., Ltd.)
-ADEKA Sizer O-180A: Epoxy linseed oil (manufactured by ADEKA)
(D) Latent curing agent-Curing agent A: Epoxyamine adduct compound (manufactured by Taoka Chemical Industry Co., Ltd.) shown in JP-A-57-100127.
・ ADH: Adipic acid dihydrazide (manufactured by Nippon Phychem)
・ Amicure UDH: 7,11-Octadecadien-1,18-Dicarbohydrazide (manufactured by Ajinomoto Techno Fine Co., Ltd.)
(Filler)
・ Aerosil 200: Hydrophilic fused silica (manufactured by Nippon Aerosil)
-Miclone 200: Fatty acid-treated light calcium carbonate (manufactured by New Lime)
(Colorant)
-Fuji EP Black 8017: Bisphenol F type epoxy resin dispersion containing 20 wt% carbon black (manufactured by Fuji Dye)
Claims (3)
(A)ブロックドポリウレタン
(B)1分子内に2個より多いグリシジル基を有するエポキシ樹脂
(C)1分子内に2個以下のグリシジル基を有するエポキシ樹脂
(D)潜在性硬化剤 An epoxy resin composition containing the following (A), (B), (C) and (D), wherein (A) is based on 100 parts by weight of the total amount of (A), (B) and (C). The epoxy resin composition has a content of 20 to 60 parts by weight, and the content of (B) is 5 to 30 parts by weight with respect to 100 parts by weight of the total amount of (B) and (C).
(A) Blocked polyurethane (B) Epoxy resin having more than two glycidyl groups in one molecule (C) Epoxy resin having two or less glycidyl groups in one molecule (D) Latent curing agent
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Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0629311B2 (en) * | 1986-02-21 | 1994-04-20 | 旭電化工業株式会社 | Novel curable composition |
JP2688625B2 (en) * | 1990-04-04 | 1997-12-10 | 大鹿振興株式会社 | Aqueous adhesive composition |
DE602006019836D1 (en) * | 2005-04-07 | 2011-03-10 | Asahi Kasei Chemicals Corp | epoxy resin |
EP1741734A1 (en) * | 2005-07-05 | 2007-01-10 | Sika Technology AG | Heat curable epoxy resin composition having low temperature impact strength comprising solid epoxy resins |
JP2008115198A (en) | 2006-10-11 | 2008-05-22 | Taoka Chem Co Ltd | One pack-type liquid curable composition for relay with excellent noise-reducing property |
JP5475223B2 (en) * | 2007-10-09 | 2014-04-16 | 株式会社Adeka | One-component cyanate-epoxy composite resin composition, cured product thereof and method for producing the same, and sealing material and adhesive using the same |
EP2110397A1 (en) * | 2008-04-16 | 2009-10-21 | Sika Technology AG | Polyurethane polymer based on amphiphilic block copolymers and its use as impact resistance modifier |
JP2011079957A (en) | 2009-10-07 | 2011-04-21 | Taoka Chem Co Ltd | One-pack liquid curable composition for relay having excellent noise-reducing property |
JP2011148862A (en) * | 2010-01-19 | 2011-08-04 | Hitachi Chem Co Ltd | Thermosetting resin composition, method for forming protective film of flexible wiring board and flexible wiring board |
JP5675230B2 (en) * | 2010-09-03 | 2015-02-25 | 株式会社ダイセル | Thermosetting epoxy resin composition and use thereof |
KR20140017509A (en) * | 2010-12-24 | 2014-02-11 | 가부시끼가이샤 쓰리본드 | Anaerobically curable composition |
JP6670045B2 (en) * | 2015-03-13 | 2020-03-18 | 日鉄ケミカル&マテリアル株式会社 | Oxazolidone ring-containing epoxy resin, production method thereof, epoxy resin composition and cured product |
CN107428913B (en) * | 2015-04-09 | 2019-10-18 | 株式会社钟化 | Improve the hardening resin composition containing polymer particles of impact resistance removing cementability |
TWI702204B (en) * | 2016-02-03 | 2020-08-21 | 日商田岡化學工業股份有限公司 | Bisphenol having fluorene skeleton and a method for manufacturing the same, and polyarylate resin, (meth)acrylate compound and epoxy resin derived from the bisphenol |
JPWO2018173716A1 (en) * | 2017-03-22 | 2020-02-13 | 東レ株式会社 | Epoxy resin composition, prepreg and carbon fiber reinforced composite material |
-
2021
- 2021-04-19 KR KR1020227035550A patent/KR20230008037A/en unknown
- 2021-04-19 CN CN202180020934.XA patent/CN115279814A/en active Pending
- 2021-04-19 WO PCT/JP2021/015871 patent/WO2021220864A1/en active Application Filing
- 2021-04-26 JP JP2021073790A patent/JP2021175803A/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2022137882A1 (en) | 2020-12-23 | 2022-06-30 | 日本アイキャン株式会社 | Electric hydraulic actuator |
Also Published As
Publication number | Publication date |
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KR20230008037A (en) | 2023-01-13 |
CN115279814A (en) | 2022-11-01 |
WO2021220864A1 (en) | 2021-11-04 |
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