WO2015080241A1 - メルカプトアルキルグリコールウリル類とその利用 - Google Patents
メルカプトアルキルグリコールウリル類とその利用 Download PDFInfo
- Publication number
- WO2015080241A1 WO2015080241A1 PCT/JP2014/081511 JP2014081511W WO2015080241A1 WO 2015080241 A1 WO2015080241 A1 WO 2015080241A1 JP 2014081511 W JP2014081511 W JP 2014081511W WO 2015080241 A1 WO2015080241 A1 WO 2015080241A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- epoxy resin
- resin composition
- group
- roughened
- printed wiring
- Prior art date
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- -1 mercaptomethyl group Chemical group 0.000 claims abstract description 197
- 239000003822 epoxy resin Substances 0.000 claims abstract description 157
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 157
- 239000000203 mixture Substances 0.000 claims abstract description 123
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 claims abstract description 21
- 125000005358 mercaptoalkyl group Chemical group 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 238000001723 curing Methods 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 55
- 239000004020 conductor Substances 0.000 claims description 38
- 239000000047 product Substances 0.000 claims description 36
- 239000003795 chemical substances by application Substances 0.000 claims description 33
- 239000010408 film Substances 0.000 claims description 30
- 238000010438 heat treatment Methods 0.000 claims description 26
- 239000007800 oxidant agent Substances 0.000 claims description 22
- 239000007795 chemical reaction product Substances 0.000 claims description 21
- 239000004593 Epoxy Substances 0.000 claims description 20
- 150000001412 amines Chemical class 0.000 claims description 20
- 239000002313 adhesive film Substances 0.000 claims description 19
- 238000007747 plating Methods 0.000 claims description 18
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 14
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 13
- 238000007788 roughening Methods 0.000 claims description 12
- 239000000853 adhesive Substances 0.000 claims description 11
- 230000001070 adhesive effect Effects 0.000 claims description 11
- 239000011889 copper foil Substances 0.000 claims description 11
- 238000010030 laminating Methods 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 10
- 239000000835 fiber Substances 0.000 claims description 7
- 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 claims description 7
- 239000010409 thin film Substances 0.000 claims description 7
- 230000003014 reinforcing effect Effects 0.000 claims description 6
- 238000013007 heat curing Methods 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 239000000565 sealant Substances 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 238000005530 etching Methods 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 claims 1
- 239000010410 layer Substances 0.000 description 66
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 47
- 238000006243 chemical reaction Methods 0.000 description 36
- 239000002904 solvent Substances 0.000 description 31
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 17
- 239000007983 Tris buffer Substances 0.000 description 15
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 15
- 229920005989 resin Polymers 0.000 description 15
- 239000011347 resin Substances 0.000 description 15
- 239000012948 isocyanate Substances 0.000 description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 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 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- USAIOOFEIMNEDN-UHFFFAOYSA-L disodium;carbonotrithioate Chemical compound [Na+].[Na+].[S-]C([S-])=S USAIOOFEIMNEDN-UHFFFAOYSA-L 0.000 description 10
- 238000002329 infrared spectrum Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000003700 epoxy group Chemical group 0.000 description 9
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 7
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 6
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 6
- 238000007772 electroless plating Methods 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 125000001046 glycoluril group Chemical group [H]C12N(*)C(=O)N(*)C1([H])N(*)C(=O)N2* 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229920003986 novolac Polymers 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 238000009713 electroplating Methods 0.000 description 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 239000012279 sodium borohydride Substances 0.000 description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 4
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000003431 cross linking reagent Substances 0.000 description 4
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000003607 modifier Substances 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 125000004437 phosphorous atom Chemical group 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 229960001755 resorcinol Drugs 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 3
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 3
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 3
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000003063 flame retardant Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000011810 insulating material Substances 0.000 description 3
- 239000011229 interlayer 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
- 150000002576 ketones Chemical class 0.000 description 3
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
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- 239000007787 solid Substances 0.000 description 3
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- 239000011593 sulfur Substances 0.000 description 3
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- 239000012756 surface treatment agent Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 125000001302 tertiary amino group Chemical group 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- BCMYXYHEMGPZJN-UHFFFAOYSA-N 1-chloro-2-isocyanatoethane Chemical compound ClCCN=C=O BCMYXYHEMGPZJN-UHFFFAOYSA-N 0.000 description 2
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
- GHKSKVKCKMGRDU-UHFFFAOYSA-N 2-(3-aminopropylamino)ethanol Chemical compound NCCCNCCO GHKSKVKCKMGRDU-UHFFFAOYSA-N 0.000 description 2
- SHYARJUKNREDGB-UHFFFAOYSA-N 2-ethyl-5-methyl-4,5-dihydro-1h-imidazole Chemical compound CCC1=NCC(C)N1 SHYARJUKNREDGB-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- YQLRKXVEALTVCZ-UHFFFAOYSA-N 2-isocyanato-1,3-dimethylbenzene Chemical compound CC1=CC=CC(C)=C1N=C=O YQLRKXVEALTVCZ-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
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Classifications
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- C07D487/04—Ortho-condensed systems
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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
- C08G59/66—Mercaptans
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- H05K3/10—Apparatus or processes for manufacturing printed circuits in which conductive material is applied to the insulating support in such a manner as to form the desired conductive pattern
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- H05K3/46—Manufacturing multilayer circuits
- H05K3/4644—Manufacturing multilayer circuits by building the multilayer layer by layer, i.e. build-up multilayer circuits
- H05K3/4652—Adding a circuit layer by laminating a metal foil or a preformed metal foil pattern
- H05K3/4655—Adding a circuit layer by laminating a metal foil or a preformed metal foil pattern by using a laminate characterized by the insulating layer
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Definitions
- the present invention relates to novel mercaptoalkylglycolurils and uses thereof, in particular, the use of the mercaptoalkylglycolurils as a curing agent for epoxy resins, an epoxy resin composition containing the mercaptoalkylglycolurils, and the like.
- This invention relates to the use of an epoxy resin composition.
- the use of the epoxy resin composition according to the present invention relates, in part, to an adhesive and a sealant containing the epoxy resin composition.
- the epoxy resin composition is suitable as an epoxy resin composition for an interlayer insulating material that achieves both high heat resistance and roughening properties by an oxidizing agent.
- Adhesive film and prepreg obtained using the epoxy resin composition, laminates and multilayer printed wiring boards using these, and methods for producing such laminates and multilayer printed wiring boards, in particular, conductor circuit layers
- the present invention relates to a method for manufacturing a build-up type multilayer printed wiring board in which insulating layers are alternately stacked.
- Glycolurils are heterocyclic compounds having four urea nitrogens in the ring structure, and are used for various applications and production of new functional compounds by utilizing the reactivity of the urea nitrogens. Yes.
- glycoluril is reacted with an aldehyde such as dimethoxyethanal to form an aminoplastic resin, which is used as a crosslinking agent for cellulose (see Patent Document 1).
- Patent Document 2 It is also known to use an emulsion containing a copolymer of vinyl acetate, ethylene and a self-crosslinkable monomer and tetramethylol glycoluril as a binder for a nonwoven fabric (see Patent Document 2). It is also known to use a polyhexamethylene biguanide compound, which is a water-soluble polymer antibacterial agent, as a crosslinking agent for fixing to a fiber (see Patent Document 3).
- a compound having a plurality of thiol groups in the molecule is also well known as, for example, a curing agent for epoxy resins.
- a curing agent for epoxy resins for example, an epoxy resin composition that uses a polythiol compound as a curing agent and includes a reaction product of an amine and an epoxy compound as a curing accelerator has been proposed.
- This epoxy resin composition has a long pot life and is supposed to cure quickly at a relatively low temperature (see Patent Document 5).
- An epoxy resin containing a reaction product of an isocyanate compound having one or more isocyanate groups in the molecule and a compound having at least one primary and / or secondary amino group in the molecule as a curing accelerator A composition has also been proposed, and this epoxy resin composition is also said to have a long pot life and excellent curability (see Patent Document 6).
- tris (3-mercaptopropyl) isocyanurate also called trithiol isocyanurate
- trithiol isocyanurate has been proposed as a curing agent that gives an epoxy resin cured product with excellent water resistance since it does not have an ester group in the molecule
- a compound in which a hydrogen atom on at least one nitrogen atom of a glycoluril is substituted with a mercaptoalkyl group is useful as, for example, a synthetic intermediate for a novel sulfur-containing compound, It is useful as a modifier such as a flexibility imparting agent, and is expected to be useful as a curing agent for epoxy resins.
- a modifier such as a flexibility imparting agent
- such compounds in which at least one hydrogen atom on at least one nitrogen atom of the glycoluril is substituted with a mercaptoalkyl group are not known so far.
- one of the important uses of the epoxy resin composition is in a multilayer printed wiring board.
- multilayer printed wiring boards in recent years, a build-up manufacturing technique in which organic insulating layers are alternately stacked on a conductor layer of an inner circuit board has attracted attention as a method for manufacturing a multilayer printed wiring board.
- an epoxy resin composition is applied to a circuit-formed inner layer circuit board, cured by heating, and then a roughened surface is formed on the surface with a roughening agent, and a conductor layer is formed on the roughened surface by plating.
- Patent Documents 8 and 9 A method for manufacturing a multilayer printed wiring board is disclosed (see Patent Documents 8 and 9).
- an amine curing agent such as dicyandiamide or an imidazole compound
- a curing system that is superior in heat resistance to the build-up type interlayer insulating material as well as the laminated board has been desired.
- the epoxy resin composition requires a roughening component such as a rubber component, heat resistance and electrical insulation are a problem in fields where finer fine patterns and thinner insulating layers are required. There was a case.
- a phosphorus atom-containing epoxy resin which has been attracting attention as a flame retardant epoxy resin, is used instead of a brominated epoxy resin due to recent environmental problems, a good roughened surface can be obtained with an existing resin composition.
- the peel strength of the plated conductor layer thereafter was weak.
- JP-A-8-67729 Japanese Patent Laid-Open No. 2-2611851 Japanese Unexamined Patent Publication No. 7-82665 Japanese Patent Application Laid-Open No. 11-171887 JP-A-6-211969 Japanese Patent Laid-Open No. 6-21970 JP 2012-153794 A JP-A-7-304931 Japanese Patent Laid-Open No. 7-304933 JP-A-8-64960 JP-A-11-1547
- the present invention is a novel mercaptoalkylglycoluril and its use, in particular, a modifier for an epoxy resin, for example, a diluent, a flexibility imparting agent, and a curing agent. It is another object of the present invention to provide an epoxy resin composition containing the mercaptoalkylglycoluril, and an adhesive and a sealant containing such an epoxy resin composition.
- the present invention provides an epoxy resin composition that includes the mercaptoalkylglycoluril as an application of the epoxy resin composition and provides a cured product having excellent heat resistance and adhesion to the plated conductor layer.
- the present invention provides an adhesive film, a prepreg, a laminate and a multilayer printed wiring board obtained by using an epoxy resin composition that provides a cured product having excellent heat resistance and adhesion with the plated conductor layer, It aims at providing each manufacturing method of these laminated boards and multilayer printed wiring boards.
- R 1 and R 2 each independently represent a hydrogen atom, a lower alkyl group or a phenyl group
- R 3 , R 4 and R 5 each independently represent a hydrogen atom, a mercaptomethyl group, 2-mercaptoethyl group, And a mercaptoalkyl group selected from a 3-mercaptopropyl group and n is 0, 1 or 2.
- the mercaptoalkylglycoluril represented by these is provided.
- an epoxy resin curing agent comprising the above mercaptoalkylglycoluril is provided.
- an epoxy resin composition containing an epoxy resin and the mercaptoalkylglycoluril is provided as the use of the mercaptoalkylglycoluril.
- an epoxy resin composition comprising an epoxy resin, the mercaptoalkylglycoluril and a curing accelerator.
- the curing accelerator is preferably an amine, a reaction product of an amine and an epoxy compound, an isocyanate compound having one or more isocyanate groups in the molecule, and at least one in the molecule.
- One or more reaction products with a compound having a primary and / or secondary amino group are used.
- an adhesive and a sealant containing the above-described epoxy resin composition are provided.
- the epoxy resin has a property of giving a cured product having excellent heat resistance and adhesion with the plated conductor layer
- an adhesive film comprising a support base film and a thin film of the epoxy resin composition formed thereon, (2) a prepreg comprising a sheet-like reinforcing base material comprising fibers and a semi-cured product of the epoxy resin composition impregnated therein, (3) A multilayer printed wiring board in which a plated conductor layer is formed on the roughened surface of the cured product of the epoxy resin composition, and the other surface is laminated in close contact with the patterned inner layer circuit board; (4) The epoxy resin composition is applied to a patterned inner layer circuit board, heated and cured, and the surface of the resulting cured product is roughened with an oxidizing agent, and a conductor layer is formed on the roughened surface by plating.
- Multilayer printed wiring board obtained by (5) The above adhesive film is laminated to a patterned inner layer circuit board under pressure and heating conditions, and then the epoxy resin composition is heated and cured with or without peeling off the support base film.
- a multilayer printed wiring board obtained by roughening the surface of the cured product with an oxidizing agent and forming a conductor layer on the roughened surface by plating; (6) After laminating the above prepreg on the patterned inner layer circuit board under pressure and heating conditions and integrating them, the surface of the prepreg is roughened with an oxidizing agent, and the conductor layer is plated on the roughened surface by plating.
- Multilayer printed wiring board obtained by forming, (7)
- the epoxy resin composition is applied to a patterned inner layer circuit board, heat-cured, the surface of the resulting cured product is roughened with an oxidizing agent, and a conductor layer is formed on the roughened surface by plating.
- a method for producing a multilayer printed wiring board comprising: (8) The adhesive film is laminated on a patterned inner layer circuit board under pressure and heating conditions, and then the epoxy resin composition is heated and cured with or without peeling off the support base film.
- a method for producing a multilayer printed wiring board comprising roughening the surface of the cured product with an oxidizing agent and forming a conductor layer on the roughened surface by plating; (9) After the above prepreg is laminated on the patterned inner layer circuit board under pressure and heating conditions and integrated, the surface of the prepreg is roughened with an oxidizing agent, and the conductor layer is plated on the roughened surface by plating.
- Forming a multilayer printed wiring board including forming, (10) A laminate obtained by applying the epoxy resin composition to at least one surface of an unclad plate coated with a copper foil of a double-sided copper-clad laminate and heat-curing the laminate, (11) Laminate the adhesive film on the copper foil of the double-sided copper-clad laminate or at least one surface of the unclad plate under pressure and heating conditions, and peel off and heat the support base film if necessary.
- a laminate obtained by curing (12) A laminate obtained by laminating the prepreg on at least one surface of a copper foil of a double-sided copper-clad laminate or an unclad plate under pressure and heating conditions, (13) A laminate obtained by laminating the prepreg under pressure and heating conditions, Is provided.
- the mercaptoalkyl glycoluril according to the present invention is a novel compound in which at least one of hydrogen atoms on four nitrogen atoms of the glycoluril is substituted with a mercaptoalkyl group.
- such a compound is useful as an intermediate for the synthesis of a novel sulfur-containing compound, and as described above, as a modifier or curing agent for an epoxy resin by utilizing reactivity with an epoxy group. Useful.
- those having two or more mercaptoalkyl groups in the molecule are useful, for example, as a curing agent for epoxy resins.
- 1,3,4,6-tetrakis (mercaptoalkyl) glycolurils are tetrafunctional, so that the crosslink density is higher than when conventional difunctional or trifunctional curing agents are used.
- the mercaptoalkylglycoluril according to the present invention does not have an ester group in the molecule, it provides an epoxy resin cured product having better hydrolysis resistance than conventional polythiols. Adhesives and sealants containing alkyl glycolurils and having excellent strength, heat resistance, moisture resistance and the like can be obtained.
- the epoxy resin composition containing mercaptoalkylglycoluril according to the present invention provides a cured product having excellent heat resistance and adhesion to the plated conductor layer, and is suitable for, for example, the production of laminated plates and multilayer printed wiring boards. Can be used.
- R 1 and R 2 each independently represent a hydrogen atom, a lower alkyl group or a phenyl group
- R 3 , R 4 and R 5 each independently represent a hydrogen atom, a mercaptomethyl group, 2-mercaptoethyl group, And a mercaptoalkyl group selected from a 3-mercaptopropyl group and n is 0, 1 or 2.
- the lower alkyl group when R 1 or R 2 is a lower alkyl group, the lower alkyl group usually has 1 to 5 carbon atoms, preferably 1 to 3, most preferably 1, ie a methyl group.
- mercaptoalkylglycolurils according to the present invention are preferably represented by the general formula (I ′)
- R 1 and R 2 each independently represent a hydrogen atom, a lower alkyl group or a phenyl group
- R 3 , R 4 and R 5 each independently represent a hydrogen atom or a moiety in the above general formula (I ′)
- the mercaptoalkyl glycoluril represented by the general formula (I ′) one, two or three of R 3 , R 4 and R 5 are mercaptoalkyl groups.
- the mercaptoalkyl groups of the mercaptoalkylglycoluril represented by the general formula (I ′) are all the same.
- mercaptoalkyl glycolurils include, for example, 1-mercaptomethylglycoluril, 1- (2-mercaptoethyl) glycoluril, 1- (3-mercaptopropyl) glycoluril, 1,3-bis (mercaptomethyl) glycoluril, 1,3-bis (2-mercaptoethyl) glycoluril, 1,3-bis (3-mercaptopropyl) glycoluril, 1,4-bis (mercaptomethyl) glycoluril, 1,4-bis (2-mercaptoethyl) glycoluril, 1,4-bis (3-mercaptopropyl) glycoluril, 1,6-bis (mercaptomethyl) glycoluril, 1,6-bis (2-mercaptoethyl) glycoluril, 1,6-bis (3-mercaptopropyl) glycoluril, 1,3,4-tris (mercaptomethyl) glycoluril, 1,3,4-tris (2-mercaptoe
- R 1 and R 2 are the same as defined above, and R 3 , R 4 and R 5 each independently represent a hydrogen atom or a 3-mercaptopropyl group.
- R 1 and R 2 are the same as described above, and R 6 , R 7 and R 8 each independently represent a hydrogen atom or an allyl group.
- R 6 , R 7 and R 8 each independently represent a hydrogen atom or an allyl group.
- R 1 and R 2 are the same as defined above, and R 9 , R 10 and R 11 each independently represent a hydrogen atom or a 3-acetylthiopropyl group.
- R 9 , R 10 and R 11 each independently represent a hydrogen atom or a 3-acetylthiopropyl group.
- thioacetic acid is usually used at a ratio of 1.0 to 3.0 equivalents relative to the allyl group of allyl glycoluril (a). Preferably, it is used at a ratio of 1.0 to 1.5 equivalents.
- the reaction between the allyl glycoluril (a) and thioacetic acid is carried out in the presence of a catalyst.
- a catalyst azobisisobutyronitrile and benzoyl peroxide are preferably used.
- Such a catalyst is used in a proportion of 0.001 to 0.2 equivalent, preferably in a proportion of 0.005 to 0.2 equivalent, with respect to the allyl group of allyl glycoluril (a). Used.
- the solvent is not particularly limited as long as it does not inhibit the reaction.
- water methanol, ethanol, Alcohols such as isopropyl alcohol, aliphatic hydrocarbons such as hexane and heptane, ketones such as acetone and 2-butanone, esters such as ethyl acetate and butyl acetate, benzene, toluene and xylene
- Aromatic hydrocarbons methylene chloride, chloroform, carbon tetrachloride, chlorotrifluoromethane, dichloroethane, halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl Ethers such as ether, formamide, N, N-di
- the reaction of allyl glycoluril (a) with thioacetic acid is usually performed at a temperature in the range of ⁇ 10 to 150 ° C., preferably at a temperature in the range of 0 ° C. to 100 ° C.
- the reaction time is usually in the range of 1 to 48 hours, preferably in the range of 1 to 24 hours.
- reaction mixture After completion of the reaction between the allyl glycoluril (a) and thioacetic acid, excess thioacetic acid and the solvent were distilled off from the resulting reaction mixture, and then the reaction product obtained as a residue was required. If necessary, the reaction mixture may be reduced with a borohydride compound in an appropriate solvent, and the obtained reaction mixture may be subjected to a reduction treatment with a borohydride compound in an appropriate solvent as necessary. Also good.
- borohydride compound examples include sodium borohydride, potassium borohydride, lithium borohydride, calcium borohydride, magnesium borohydride and the like. These borohydride compounds are used in a proportion of 0.5 to 10 equivalents, preferably in a proportion of 1.0 to 4.0 equivalents, with respect to the allyl group of the allyl glycoluril used. Used.
- the solvent when used, is not particularly limited unless it inhibits the reaction.
- the same solvent as the solvent used in the reaction of the allyl glycoluril (a) and thioacetic acid can be used.
- the reduction treatment with the borohydride compound is usually performed in the range of 0 ° C. to 150 ° C., preferably in the range of room temperature to 100 ° C.
- the reaction time is usually in the range of 1 to 24 hours, preferably in the range of 1 to 12 hours.
- the desired mercaptoalkylglycoluril can be obtained from the obtained reaction mixture by, for example, an extraction operation. If necessary, the desired mercaptoalkylglycoluril can be further purified by washing with a solvent such as water or activated carbon treatment.
- R 1 and R 2 are the same as defined above, and R 12 , R 13 and R 14 each independently represent a hydrogen atom or a 2-mercaptoethyl group.
- 2-ethyl mercaptoglycoluril represented by the general formula (b)
- R 1 and R 2 are the same as defined above, and R 15 , R 16 and R 17 each independently represent a hydrogen atom or a 2-hydroxyethyl group.
- the 2-hydroxyethylglycoluril (b) represented by the formula (b1) is reacted with thionyl chloride in an appropriate solvent as necessary.
- R 1 and R 2 are the same as defined above, and R 18 , R 19 and R 20 each independently represent a hydrogen atom or a 2-chloroethyl group.
- a 2-chloroethylglycoluril is obtained, and then the reaction product is treated with disodium trithiocarbonate in an appropriate solvent, if necessary, to obtain chlorine atoms. Can be obtained by substituting with a mercapto group.
- R 1 and R 2 are the same as above, and R 21 , R 22 and R 23 each independently represent a hydrogen atom or a mercaptomethyl group.
- R 21 , R 22 and R 23 each independently represent a hydrogen atom or a mercaptomethyl group.
- R 1 and R 2 are the same as described above, and R 24 , R 25 and R 26 each independently represent a hydrogen atom or a hydroxymethyl group.
- R 24 , R 25 and R 26 each independently represent a hydrogen atom or a hydroxymethyl group.
- R 1 and R 2 are the same as defined above, and R 27 , R 28 and R 29 each independently represent a hydrogen atom or a chloromethyl group.
- the reaction product is treated with disodium trithiocarbonate in an appropriate solvent as necessary to convert the chlorine atom to mercapto. It can be obtained by substituting with a group.
- thionyl chloride is 2-hydroxyethylglycoluril (b) or hydroxymethylglycoluril (c). Is usually used in a proportion of 1.0 to 10.0 equivalents, preferably in a proportion of 1.0 to 3.0 equivalents.
- the solvent is not particularly limited unless it inhibits the reaction.
- aliphatic hydrocarbons such as hexane and heptane, ketones such as acetone and 2-butanone, esters such as ethyl acetate and butyl acetate, aromatic carbon such as benzene, toluene and xylene Hydrogens, methylene chloride, chloroform, carbon tetrachloride, chlorotrifluoromethane, dichloroethane, chlorobenzene, halogenated hydrocarbons such as dichlorobenzene, diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether Ethers such as formamide, N, N-dimethylformamide,
- the reaction of the 2-hydroxyethyl glycoluril (b) or hydroxymethylglycoluril (c) with thionyl chloride is usually performed at a temperature in the range of ⁇ 10 to 150 ° C., preferably 0 ° C. to 100 ° C. At a temperature in the range of In addition, although depending on the reaction temperature, the reaction time is usually in the range of 1 to 24 hours, preferably in the range of 1 to 6 hours.
- reaction product obtained as above may be treated with disodium trithiocarbonate in an appropriate solvent, if necessary, and the above 2-hydroxyethyl glycolurils (b) or hydroxymethylglycolurils
- the obtained reaction mixture may be subjected to treatment with disodium trithiocarbonate in an appropriate solvent as necessary.
- the disodium trithiocarbonate is used in a ratio of 1.0 to 10 equivalents with respect to the hydroxy group of the 2-hydroxyethyl glycoluril (b) or hydroxymethylglycoluril (c) used, and is preferably Is used in a proportion of 1.0 to 4.0 equivalents.
- the solvent used is As long as the reaction is not inhibited, the solvent is not particularly limited.
- the same solvent as the solvent used in the reaction of the allyl glycoluril (a) and thioacetic acid can be used.
- the treatment with disodium trithiocarbonate is usually performed in the range of 0 ° C. to 150 ° C., preferably in the range of room temperature to 100 ° C.
- the reaction time is usually in the range of 1 to 24 hours, preferably in the range of 1 to 9 hours.
- the desired mercaptoalkylglycoluril can be obtained from the treated mixture, for example, by an extraction operation. If necessary, the desired mercaptoalkylglycoluril can be further purified by washing with a solvent such as water or activated carbon treatment.
- the mercaptoalkylglycoluril according to the present invention has reactivity with an epoxy group in addition to a novel intermediate for synthesis of a sulfur-containing compound. It is useful as a flexibility imparting agent and a curing agent.
- epoxy resin composition (Epoxy resin composition)
- epoxy resin composition containing the mercaptoalkyl glycoluril according to the present invention will be described.
- the epoxy resin composition according to the present invention contains mercaptoalkylglycolurils represented by the above general formula (I), and preferably further contains a curing accelerator.
- the curing accelerator examples include a curing accelerator composed of amines, a curing accelerator composed of a reaction product of amines and an epoxy compound, a compound having one or more isocyanate groups in the molecule, and at least one in the molecule.
- a curing accelerator comprising a reaction product with a compound having a primary and / or secondary amino group is used. These curing accelerators are used alone or in combination of two or more.
- the epoxy resin composition according to the present invention is preferably a mercaptoalkylglycoluril having two or more mercaptoalkyl groups in the molecule, that is, among the mercaptoalkylglycolurils represented by the general formula (I), A compound having two or more mercaptoalkyl groups in the molecule is included as a curing agent, and a curing accelerator is preferably included.
- an epoxy resin composition containing 1,3,4,6-tetrakis (mercaptoalkyl) glycoluril as a curing agent is not only excellent in hydrolysis resistance, Compared to known epoxy resin compositions, the cured epoxy resin has a higher crosslink density. Therefore, it is superior in hardness, heat resistance, moisture resistance, etc., and also has good adhesion to the plated conductor layer. Gives excellent cured epoxy resin.
- the mercaptoalkylglycoluril according to the present invention has an SH equivalent number / epoxy equivalent number ratio in the range of 0.1 to 3.0, preferably 0.5 to 2.0. It is used within the range, most preferably 0.5 to 1.2.
- Epoxy resins are typically low molecular weight prepolymers having an average of two or more epoxy groups per molecule, such as polyglycidyl ethers typically obtained by reaction of bisphenol A with epichlorohydrin.
- the epoxy resin means an epoxy compound having two or more epoxy groups per molecule on average, and therefore, not only the low molecular weight prepolymer described above but also two in the molecule.
- the monomer type epoxy compound having the above epoxy group is also included in the epoxy resin.
- examples of the epoxy resin include polyhydric phenols such as bisphenol A, bisphenol F, bisphenol S, bisphenol AD, catechol, and resorcinol, and polyvalent phenols such as glycerin and polyethylene glycol.
- the epoxy resin is not limited to the above examples. Such an epoxy resin may contain a monofunctional epoxy resin as a reactive diluent
- the epoxy resin may contain a phosphorus atom.
- the phosphorus atom containing epoxy resin which attracts attention as a flame-retardant epoxy resin can be used instead of the brominated product of an epoxy resin.
- Examples of the phosphorus atom-containing epoxy resin include those disclosed in JP-A-4-11662 and JP-A-11-166035.
- a glycidyl glycoluril compound having two or more epoxy groups in the molecule can also be used as the epoxy resin.
- examples of such glycidyl glycoluril compounds include: 1,3-diglycidyl glycoluril, 1,4-diglycidyl glycoluril, 1,6-diglycidyl glycoluril, 1,3,4-triglycidyl glycoluril, 1,3,4,6-tetraglycidylglycoluril, 1,3-diglycidyl-3a-methylglycoluril, 1,4-diglycidyl-3a-methylglycoluril, 1,6-diglycidyl-3a-methylglycoluril, 1,3,4-triglycidyl-3a-methylglycoluril, 1,3,4,6-tetraglycidyl-3a-methylglycoluril, 1,3-diglycidyl-3a, 6a-dimethylglycoluril, 1,4-diglycidyl-3a, 6a
- triglycidyl isocyanurate having three epoxy groups in the molecule can also be used as an epoxy resin, similar to the glycidyl glycolurils.
- epoxy resins can be used alone or in combination of two or more.
- the curing accelerator comprising amines in the epoxy resin composition according to the present invention has at least one active hydrogen capable of addition reaction with an epoxy group in the molecule, and a primary amino group. Any group having at least one amino group selected from a group, a secondary amino group and a tertiary amino group in the molecule may be used.
- curing accelerators composed of such amines include aliphatic amines such as diethylenetriamine, triethylenetetramine, n-propylamine, 2-hydroxyethylaminopropylamine, cyclohexylamine, and 4,4'-diaminodicyclohexylmethane.
- Aromatic amines such as 4,4'-diaminodiphenylmethane, o-methylaniline, 2-ethyl-4-methylimidazole, 2-methylimidazole, 2-ethyl-4-methylimidazoline, 2,4-dimethylimidazoline
- nitrogen-containing heterocyclic compounds such as piperidine and piperazine.
- the curing accelerator composed of amines is not limited to the above examples.
- the various hardening accelerator mentioned above can be used individually or in combination of 2 or more types.
- a reaction product of amines and an epoxy compound, or one or more isocyanate groups in the molecule in addition to the above-described curing accelerator composed of amines, a reaction product of amines and an epoxy compound, or one or more isocyanate groups in the molecule.
- a reaction product of a compound and a compound having at least one primary and / or secondary amino group in the molecule can be used as a curing accelerator.
- the reaction product of the amines and the epoxy compound is a solid insoluble in the epoxy resin at room temperature, solubilized by heating and functions as a curing accelerator, so it is also called a latent curing accelerator. Yes.
- the curing accelerator composed of a reaction product of the amines and the epoxy compound is referred to as a latent curing accelerator.
- Such a latent curing accelerator may be surface-treated with an isocyanate compound or an acidic compound.
- Examples of the epoxy compound used for the production of the latent curing accelerator are obtained by reacting a polyhydric phenol such as bisphenol A, bisphenol F, catechol, and resorcinol, or a polyhydric alcohol such as glycerin and polyethylene glycol with epichlorohydrin.
- a polyhydric phenol such as bisphenol A, bisphenol F, catechol, and resorcinol
- a polyhydric alcohol such as glycerin and polyethylene glycol
- epichlorohydrin By reacting a polycarboxylic acid such as polyglycidyl ether, p-hydroxybenzoic acid, and ⁇ -hydroxynaphthoic acid with epichlorohydrin and glycidyl ether ester, phthalic acid, terephthalic acid, and epichlorohydrin.
- the resulting polyglycidyl ester, 4,4′-diaminodiphenylmethane, m-aminophenol and the like are reacted with epichlorohydrin, and further, epoxidized phenol.
- examples include, but are not limited to, multifunctional epoxy compounds such as novolac resin, epoxidized cresol novolak resin, and epoxidized polyolefin, and monofunctional epoxy compounds such as butyl glycidyl ether, phenyl glycidyl ether, and glycidyl methacrylate. It is not a thing.
- the amines used in the production of the latent curing accelerator have at least one active hydrogen capable of addition reaction with an epoxy group in the molecule, as well as a primary amino group, a secondary amino group, and a tertiary. What is necessary is just to have at least one amino group selected from amino groups in the molecule.
- amines examples include aliphatic amines such as diethylenetriamine, triethylenetetramine, n-propylamine, 2-hydroxyethylaminopropylamine, cyclohexylamine, 4,4′-diaminodicyclohexylmethane, Aromatic amine compounds such as' -diaminodiphenylmethane, o-methylaniline, 2-ethyl-4-methylimidazole, 2-methylimidazole, 2-ethyl-4-methylimidazoline, 2,4-dimethylimidazoline, piperidine, piperazine Examples thereof include, but are not limited to, nitrogen-containing heterocyclic compounds.
- aliphatic amines such as diethylenetriamine, triethylenetetramine, n-propylamine, 2-hydroxyethylaminopropylamine, cyclohexylamine, 4,4′-diaminodicyclohexylmethane
- Aromatic amine compounds
- tertiary amines having a tertiary amino group in the molecule are raw materials that provide a latent curing accelerator having excellent curing acceleration.
- tertiary amines include, for example, dimethylaminopropylamine, diethylaminopropylamine, di-n-propylaminopropylamine, dibutylaminopropylamine, dimethylaminoethylamine, diethylaminoethylamine, N-methylpiperazine
- amines such as 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, imidazole compounds such as 2-phenylimidazole, etc.
- an active hydrogen compound having two or more active hydrogens in the molecule is added as a third component when the latent curing accelerator is produced.
- active hydrogen compounds include polyphenols such as bisphenol A, bisphenol F, bisphenol S, hydroquinone, catechol, resorcinol, pyrogallol and phenol novolac resin, polyhydric alcohols such as trimethylolpropane, adipic acid, Examples thereof include polyvalent carboxylic acids such as phthalic acid, 1,2-dimercaptoethane, 2-mercaptoethanol, 1-mercapto-3-phenoxy-2-propanol, mercaptoacetic acid, anthranilic acid, and lactic acid. It is not limited to.
- examples of the isocyanate compound used as the surface treatment agent in the production of the latent curing accelerator include monofunctional isocyanate compounds such as n-butyl isocyanate, isopropyl isocyanate, phenyl isocyanate, benzyl isocyanate, and hexamethylene.
- monofunctional isocyanate compounds such as n-butyl isocyanate, isopropyl isocyanate, phenyl isocyanate, benzyl isocyanate, and hexamethylene.
- a terminal isocyanate group-containing compound obtained by reaction of the polyfunctional isocyanate compound with an active hydrogen compound can also be used.
- examples of such compounds include addition reactants having terminal isocyanate groups obtained by reaction of toluylene diisocyanate and trimethylolpropane, addition reactants having terminal isocyanate groups obtained by reaction of toluylene diisocyanate and pentaerythritol, etc. Can be mentioned.
- the isocyanate compound used as the surface treatment agent in the production of the latent curing accelerator is not limited to the above.
- the acidic substance used as the surface treatment agent in the production of the latent curing accelerator may be any of gas, liquid, and solid, and may be any of inorganic acid and organic acid, such as carbon dioxide gas, Sulfurous acid gas, sulfuric acid, hydrochloric acid, oxalic acid, phosphoric acid, acetic acid, formic acid, propionic acid, adipic acid, caproic acid, lactic acid, succinic acid, tartaric acid, sebacic acid, p-toluenesulfonic acid, salicylic acid, boric acid, tannic acid, Examples thereof include alginic acid, polyacrylic acid, polymethacrylic acid, phenol, pyrogallol, phenol resin, resorcin resin, and the like, but are not limited thereto.
- inorganic acid and organic acid such as carbon dioxide gas, Sulfurous acid gas, sulfuric acid, hydrochloric acid, oxalic acid, phosphoric acid, acetic acid
- the above-mentioned latent curing accelerator is the above-mentioned epoxy compound, the above amines, and, if necessary, the above active hydrogen compound mixed, reacted at a temperature of room temperature to 200 ° C., then solidified and pulverized, or It can be easily obtained by reacting in a solvent such as methyl ethyl ketone, dioxane, tetrahydrofuran, etc., removing the solvent and then pulverizing the solid.
- a solvent such as methyl ethyl ketone, dioxane, tetrahydrofuran, etc.
- Alignin PN-23 (trade name of Ajinomoto Co., Inc.), “Amicure PN-H” (trade name of Ajinomoto Co., Inc.), “Amicure MY-24” (Ajinomoto Co., Inc.) Product name), “Novacure® HX-3742” (product name of Asahi Kasei Co., Ltd.), “Novacure® HX-3721” (product name of Asahi Kasei Co., Ltd.), and the like, but are not limited thereto.
- the epoxy resin composition according to the present invention can contain various additives such as a filler, a diluent, a solvent, a pigment, a flexibility imparting agent, a coupling agent, and an antioxidant as necessary.
- the adhesive strength can be improved without significantly impairing the curability of the epoxy resin composition.
- Such an isocyanate group-containing compound is not particularly limited.
- Such an isocyanate group-containing compound is usually used in the range of 0.1 to 20 parts by weight with respect to 100 parts by weight of the epoxy resin.
- the reaction product of a compound having one or more isocyanate groups in the molecule and a compound having at least one primary and / or secondary amino group in the molecule is also used as a curing accelerator. Can be used.
- Such a curing accelerator is obtained by reacting an isocyanate compound having one or more isocyanate groups in the molecule with a compound having a primary and / or secondary amino group in an organic solvent such as dichloromethane. Can do.
- Examples of the isocyanate compound having one or more isocyanate groups in the molecule include n-butyl isocyanate, isopropyl isocyanate, 2-chloroethyl isocyanate, phenyl isocyanate, p-bromophenyl isocyanate, m-chlorophenyl isocyanate, and o-chlorophenyl.
- Examples of the compound having at least one primary and / or secondary amino group in the molecule include dimethylamine, diethylamine, di-n-propylamine, di-n-butylamine, di-n- Hexylamine, di-n-octylamine, di-n-ethanolamine, dimethylaminopropylamine, diethylaminopropylamine, morpholine, piperidine, 2,6-dimethylpiperidine, 2,2,6,6-tetramethylpiperidine, piperazine Pyrrolidine, benzylamine, N-methylbenzylamine, cyclohexylamine, metaxylylenediamine, 1,3-bis (aminomethyl) cyclohexane, isophoronediamine, N-aminoethylpiperazine, 2-methylimidazole, 2-ethyl-4 -Methylimidazole, - undecylimidazole, 2-phenylimidazole, there may
- epoxy adducts of the above imidazoles, tertiary amines and guanidines, microencapsulated ones, triphenylphosphine, tetraphenylphosphonium tetraphenylborate And organic phosphine compounds such as
- the curing accelerator including the latent curing accelerator described above, is usually in the range of 0.05 to 10 parts by weight, preferably 100 parts by weight of the epoxy resin, It is used in the range of 0.1 to 10 parts by weight.
- the blending amount of the curing accelerator is less than 0.05 parts by weight, the resulting epoxy resin composition may be insufficiently cured.
- the blending amount exceeds 10 parts by weight the curing acceleration is improved. The effect almost reaches its peak, and there is a risk of impairing the heat resistance and mechanical strength of the resulting epoxy resin composition.
- the epoxy resin composition according to the present invention may contain a thermosetting resin or a commonly used additive in addition to the above-mentioned components, depending on the application and required characteristics.
- thermosetting resin examples include phenol resin, blocked isocyanate resin, xylene resin, radical generator and polymerizable resin.
- additives include barium sulfate, barium titanate, silicon oxide powder, amorphous silica, talc, clay, mica powder, aluminum hydroxide, magnesium hydroxide and other inorganic fillers, silicone powder, nylon powder, and fluorine powder.
- organic fillers thickeners such as asbestos, olben, benton, silicone type, fluorine type, polymer type antifoaming agent, leveling agent, imidazole type, thiazole type, triazole type, silane coupling agent etc.
- examples thereof include an adhesion-imparting agent and a phosphorus-based flame retardant.
- a known and commonly used colorant such as phthalocyanine / blue, phthalocyanine / green, iodin / green, disazo yellow, titanium oxide, and carbon black may be included.
- the epoxy resin composition according to the present invention is superior in hydrolysis resistance as compared with conventionally known epoxy resin compositions, and further in heat resistance and moisture resistance. It can be suitably used as an adhesive or a sealing agent. That is, the adhesive according to the present invention includes the above-described epoxy resin composition, and the sealant according to the present invention includes the above-described epoxy resin composition.
- the adhesive and sealant according to the present invention may further contain an additive.
- additives include flow behavior modifiers such as silicic acid, magnesium silicate, and barium sulfate, thermal conductivity imparting agents such as alumina, conductivity imparting agents such as silver and carbon, and coloring such as pigments and dyes. An agent etc. can be mentioned.
- flow behavior modifiers such as silicic acid, magnesium silicate, and barium sulfate
- thermal conductivity imparting agents such as alumina
- conductivity imparting agents such as silver and carbon
- coloring such as pigments and dyes.
- An agent etc. can be mentioned.
- These additives can be mixed into the above-described epoxy resin composition using a conventionally known ordinary mixer such as a three-roll or planetary mixer.
- the epoxy resin composition according to the present invention can provide a cured product having excellent heat resistance and adhesion to the plated conductor layer. Therefore, an adhesive film and a prepreg obtained using such an epoxy resin composition can be provided.
- the laminated board and the multilayer printed wiring board will be described in detail below.
- the adhesive film according to the present invention comprises a support base film and a thin film of the epoxy resin composition according to the present invention formed thereon.
- Such an adhesive film can be obtained by forming a thin film of the epoxy resin composition on a support base film.
- a support base film is used as a support, a resin varnish in which an epoxy resin composition is dissolved in a predetermined organic solvent is applied to the surface, and then the solvent is dried by heating and / or hot air blowing. If it is a thin film, an adhesive film is obtained.
- the supporting base film examples include polyolefins such as polyethylene and polyvinyl chloride, polyesters such as polyethylene terephthalate, polycarbonate, polyimide, and metal foils such as release paper, copper foil, and aluminum foil. Note that the support base film may be subjected to a release treatment in addition to the mud treatment and the corona treatment.
- organic solvent examples include ketones such as acetone, methyl ethyl ketone, and cyclohexanone, ethyl acetate, butyl acetate, cellosolve acetate, acetate esters such as propylene glycol monomethyl ether acetate and carbitol acetate, cellosolves such as cellosolve and butyl cellosolve,
- ketones such as acetone, methyl ethyl ketone, and cyclohexanone
- ethyl acetate butyl acetate
- cellosolve acetate acetate esters such as propylene glycol monomethyl ether acetate and carbitol acetate
- cellosolves such as cellosolve and butyl cellosolve
- aromatic hydrocarbons such as toluene and xylene, dimethylformamide, dimethylacetamide and the like can be used alone or in combination of two or more.
- the thickness of the epoxy resin composition layer on the support base film having a thickness of 10 to 200 ⁇ m is not less than the conductor thickness of the inner circuit board to be laminated, and is in the range of 10 to 150 ⁇ m.
- a protective film such as a support film having a thickness of 1 to 40 ⁇ m is further laminated on the surface of the film, wound into a roll and stored.
- the prepreg according to the present invention comprises a sheet-like reinforcing base material made of fibers and a semi-cured product of the epoxy resin composition according to the present invention coated and / or impregnated thereon.
- Such a prepreg according to the present invention is obtained by applying the epoxy resin composition according to the present invention to a sheet-like reinforcing substrate made of fibers by a hot melt method or a solvent method, impregnating, heating, and semi-curing. be able to.
- the sheet-like reinforcing substrate made of the above-mentioned fibers known and commonly used prepreg fibers such as glass cloth and aramid fibers can be used.
- a solvent-free resin is used, once coated on a coated paper having good releasability from the resin, and then laminated or directly applied by a die coater.
- the solvent method is a method of immersing and impregnating a sheet-like reinforcing base material in a resin varnish obtained by dissolving the epoxy resin composition in an organic solvent in the same manner as the adhesive film, and then drying it.
- the plated conductor layer is formed on the roughened surface of the cured layer of the epoxy resin composition layer according to the present invention, and the other surface is in close contact with the patterned inner layer circuit board. Are laminated.
- the multilayer printed wiring board of the present invention is coated with an epoxy resin composition on a patterned inner layer circuit board, and when it contains an organic solvent, it is dried and then heat-cured.
- an inner layer circuit board a glass epoxy board, a metal board, a polyester board, a polyimide board, a BT resin board, a thermosetting polyphenylene ether board or the like can be used, and the circuit surface is roughened in advance. Good.
- the drying conditions are preferably 70 to 130 ° C. for 5 to 40 minutes, and the heat curing conditions are preferably 130 to 180 ° C. for 15 to 90 minutes.
- the conductor layer is formed by electroless and / or electrolytic plating.
- a plating resist having a pattern opposite to that of the conductor layer may be formed, and the conductor layer may be formed only by electroless plating.
- the adhesive is applied to a patterned inner layer circuit board.
- the laminate is bonded after applying pressure and heating to a thin film of an epoxy resin composition having adhesive performance after removing the protective film.
- the laminating condition is preferably that the film and the inner circuit board are preheated as necessary, the pressure bonding temperature is 70 to 130 ° C., the pressure bonding pressure is 1 to 11 kgf / cm 2 , and lamination is performed under reduced pressure.
- the laminate may be a batch type or a continuous type with a roll.
- the support film After lamination, after cooling to near room temperature, the support film is peeled off, the epoxy resin composition is transferred onto the inner layer circuit board, and then cured by heating. Moreover, when using the support film in which the mold release process was performed, you may peel a support film, after making it heat-harden. Thereafter, in the same manner as described above, the film surface is roughened with an oxidizing agent, and the conductor layer is formed by plating to obtain a multilayer printed wiring board.
- a prepreg comprising the epoxy resin composition according to the present invention
- one prepreg is laminated on a patterned inner layer circuit board, or several sheets are laminated as necessary.
- a metal plate is sandwiched through a release film and laminated and pressed under pressure and heating conditions. Molding is preferably performed at a pressure of 5 to 40 kgf / cm 2 and a temperature of 120 to 180 ° C. for 20 to 100 minutes. Also, it can be manufactured by the above-described laminating method.
- the surface of the prepreg is roughened with an oxidizing agent, and the conductor layer is formed by plating to obtain a multilayer printed wiring board.
- an insulating layer that is a cured product of the epoxy resin composition according to the present invention is provided between the inner layer circuits. Will have.
- the patterned inner layer circuit board referred to in the present invention is a relative name to the multilayer printed wiring board. For example, when a circuit is formed on both sides of a substrate and a thin film obtained by curing an epoxy resin composition is formed on both circuit surfaces as an insulating layer, and then each circuit is formed on both surfaces, four-layer printed wiring A plate can be formed.
- the inner layer circuit board refers to a printed wiring board formed with circuits on both sides formed on the board. Furthermore, if a circuit of one layer is additionally formed on both surfaces of the four-layer printed wiring board via an insulating layer, a six-layer printed wiring board can be obtained.
- the inner layer circuit board in this case refers to the aforementioned four-layer printed wiring board.
- the laminate according to the present invention can be obtained by applying the epoxy resin composition according to the present invention to at least one surface of an uncladded plate coated with the copper foil of a double-sided copper-clad laminate and heat-cured. it can.
- the said unclad board can be obtained by using a release film etc. instead of copper foil at the time of copper clad laminated board manufacture.
- the laminated plate thus obtained is subjected to roughening treatment with an oxidizing agent such as permanganate, dichromate, ozone, hydrogen peroxide / sulfuric acid, nitric acid, etc. Further, a conductor layer can be formed directly on the surface of the laminate by electroless and / or electrolytic plating.
- an oxidizing agent such as permanganate, dichromate, ozone, hydrogen peroxide / sulfuric acid, nitric acid, etc.
- a conductor layer can be formed directly on the surface of the laminate by electroless and / or electrolytic plating.
- the laminate according to the present invention is obtained by laminating an adhesive film made of the epoxy resin composition on at least one surface of the copper clad laminate or at least one surface of an unclad plate and heat curing the adhesive film. be able to.
- the laminated plate thus obtained is subjected to roughening treatment with an oxidizing agent such as permanganate, dichromate, ozone, hydrogen peroxide / sulfuric acid, nitric acid, etc. Further, a conductor layer can be formed directly on the surface of the laminate by electroless and / or electrolytic plating.
- an oxidizing agent such as permanganate, dichromate, ozone, hydrogen peroxide / sulfuric acid, nitric acid, etc.
- a conductor layer can be formed directly on the surface of the laminate by electroless and / or electrolytic plating.
- the laminate according to the present invention is a surface obtained by laminating a predetermined number of prepregs comprising the epoxy resin composition according to the present invention, or by etching out the copper foil of a double-sided copper-clad laminate or at least one surface of an unclad plate. It can be obtained by sandwiching a metal plate through a release film and laminating and pressing under pressure and heating conditions.
- the laminated plate thus obtained is subjected to roughening treatment with an oxidizing agent such as permanganate, dichromate, ozone, hydrogen peroxide / sulfuric acid, nitric acid, etc. Further, a conductor layer can be formed directly on the surface of the laminate by electroless and / or electrolytic plating.
- an oxidizing agent such as permanganate, dichromate, ozone, hydrogen peroxide / sulfuric acid, nitric acid, etc.
- a conductor layer can be formed directly on the surface of the laminate by electroless and / or electrolytic plating.
- the obtained reaction mixture was dried under reduced pressure.
- the obtained dried product was subjected to liquid separation extraction with 400 mL of ethyl acetate and 400 mL of water.
- the ethyl acetate layer was washed with 100 mL of water and then with 100 mL of saturated brine, and then dried over anhydrous sodium sulfate.
- Ethyl acetate was distilled off under reduced pressure, and 1,3,4,6-tetraallylglycoluril 27. 4 g were obtained as a colorless oil. Yield 90%.
- the IR spectrum of the obtained 1,3-diallylglycoluril is shown in FIG.
- the 1 H-NMR spectrum (d6-DMSO) ⁇ value was as follows.
- the obtained reaction mixture was cooled and then concentrated under reduced pressure, and 10 mL of methanol was added to the obtained concentrate. After adding 189 mg (5.0 mmol) of sodium borohydride to the obtained mixture at room temperature, the mixture was stirred at 60 ° C. overnight with stirring. After completion of the reaction, the reaction mixture was cooled to 5 ° C., 30 mL of saturated aqueous ammonium chloride solution was added, and the mixture was stirred for 30 minutes.
- Example 2 Synthesis of 1,3,4,6-tetrakis (3-mercaptopropyl) glycoluril
- a 100 mL flask equipped with a thermometer was charged with 3.03 g (10.0 mmol) of 1,3,4,6-tetraallylglycoluril, 3.65 g (48.0 mmol) of thioacetic acid and 20 mL of tetrahydrofuran, and this was mixed with azobisiso After adding butyronitrile 66 mg (0.4 mmol), the reaction was carried out at 60 ° C. for 18 hours with stirring.
- the obtained reaction mixture was cooled and then concentrated under reduced pressure, and 20 mL of methanol was added to the obtained concentrate.
- To the obtained mixture 1.51 g (40.0 mmol) of sodium borohydride was added at room temperature, and then stirred at 60 ° C. overnight with stirring.
- the reaction mixture was cooled to 5 ° C., 30 mL of saturated aqueous ammonium chloride solution was added, and the mixture was stirred for 30 minutes. After performing extraction operation with 30 mL of chloroform from the obtained reaction mixture, the organic layer was washed 3 times with 15 mL of water. The obtained organic layer was concentrated under reduced pressure to obtain 3.12 g of 1,3,4,6-tetrakis (3-mercaptopropyl) glycoluril as a pale yellow oil. Yield 65%.
- Example 3 Synthesis of 1,3,4,6-tetrakis (3-mercaptopropyl) -3a, 6a-dimethylglycoluril
- a 100 mL flask equipped with a thermometer was charged with 3.30 g (10.0 mmol) of 1,3,4,6-tetraallyl-3a, 6a-dimethylglycoluril, 3.65 g (48.0 mmol) of thioacetic acid and 20 mL of tetrahydrofuran, After adding 66 mg (0.4 mmol) of azobisisobutyronitrile to this, reaction was performed at 60 ° C. for 18 hours while stirring.
- the obtained reaction mixture was cooled and then concentrated under reduced pressure, and 20 mL of methanol was added to the obtained concentrate.
- 1.51 g (40.0 mmol) of sodium borohydride was added at room temperature, and then stirred at 60 ° C. overnight with stirring.
- the reaction mixture was cooled to 5 ° C., and 30 mL of a saturated aqueous ammonium chloride solution was added, followed by stirring for 30 minutes. Extraction operation was performed with 30 mL of chloroform from the obtained reaction mixture.
- the obtained organic layer was washed with 15 mL of water three times, and the obtained organic layer was concentrated under reduced pressure to obtain 1,3,4,6-tetrakis (3-mercaptopropyl) -3a, 6a-dimethylglycoluril. 2.17 g was obtained as a pale yellow oil. Yield 46%.
- FIG. 4 shows the IR spectrum of the obtained 1,3,4,6-tetrakis (3-mercaptopropyl) -3a, 6a-dimethylglycoluril. Further, the ⁇ value in the 1 H-NMR spectrum (d6-DMSO) was as follows.
- Example 4 Synthesis of 1,3,4,6-tetrakis (2-mercaptoethyl) glycoluril
- Into a 50 mL flask equipped with a thermometer 3.18 g (10.0 mmol) of 1,3,4,6-tetrakis (2-hydroxyethyl) glycoluril and 4.76 g (40.0 mmol) of thionyl chloride were added and stirred. The reaction was carried out at 70 ° C. for 5 hours.
- the obtained reaction mixture was concentrated under reduced pressure, and 20 mL of water was added to the obtained concentrate.
- 15.4 g (40.0 mmol) of 40% aqueous solution of disodium trithiocarbonate was added dropwise at room temperature, followed by stirring at 100 ° C. for 6 hours while stirring.
- the resulting reaction mixture was cooled to 5 ° C., 50 mL of chloroform was added thereto, and the mixture was stirred for 30 minutes.
- the aqueous layer was removed from this mixture, and the resulting organic layer was concentrated under reduced pressure to obtain 3.26 g of 1,3,4,6-tetrakis (2-mercaptoethyl) glycoluril as a yellow oil. Yield 85%.
- FIG. 5 shows the IR spectrum of the obtained 1,3,4,6-tetrakis (2-mercaptoethyl) glycoluril. Further, the ⁇ value in the 1 H-NMR spectrum (CDCl 3 ) was as follows.
- Example 5 An epoxy resin composition was prepared by mixing 64 parts by weight of 1,3,4,6-tetrakis (3-mercaptopropyl) glycoluril and 3 parts by weight of a latent curing accelerator with 100 parts by weight of the epoxy resin.
- Example 6 An epoxy resin composition was prepared by mixing 56 parts by weight of 1,3,4,6-tetrakis (2-mercaptoethyl) glycoluril and 3 parts by weight of a latent curing accelerator with 100 parts by weight of the epoxy resin.
- Comparative Example 1 In the same manner as in Example 5, except that 107 parts by weight of the thiol compound (1) was used instead of 64 parts by weight of 1,3,4,6-tetrakis (3-mercaptopropyl) glycoluril, an epoxy resin composition was obtained. A product was prepared.
- the glass transition temperature (Tg) of the cured product of the epoxy resin composition obtained in Examples 5 and 6 and Comparative Examples 1 and 2 was a differential scanning calorimeter (“EXSTAR 6000” manufactured by SII NanoTechnology Inc.). It measured using. That is, the epoxy resin composition was cured by heating from 30 ° C. to 270 ° C. at a rate of temperature increase of 10 ° C./min. Subsequently, the cured product thus obtained was cooled at a rate of ⁇ 50 ° C./min. Was cooled from 270 ° C. to 10 ° C., and then heated from 10 ° C. to 100 ° C. at a rate of temperature increase of 10 ° C./min, and the glass transition temperature of the cured product was measured. The results are shown in Table 1.
- An epoxy resin composition comprising 1,3,4,6-tetrakis (3-mercaptopropyl) glycoluril and 1,3,4,6-tetrakis (2-mercaptoethyl) glycoluril according to the present invention as curing agents, respectively. It is shown that the cured product has a high glass transition temperature and excellent heat resistance as compared with the cured product of the epoxy resin composition containing the thiol compound (1) and the thiol compound (2) as curing agents.
- Example 7 100 parts by weight of a bisphenol A type epoxy resin (Mitsubishi Chemical Corporation jER828, epoxy equivalent 185) and 55 parts by weight of tetrakis (mercaptoethyl) glycoluril were heated and dissolved with stirring, and then cooled to room temperature. Subsequently, 0.8 parts by weight of 2-phenyl-4,5-bis (hydroxymethyl) imidazole (2PHZ-PW manufactured by Shikoku Chemicals Co., Ltd.), 2 parts by weight of finely pulverized silica, and 0.5 parts by weight of a silicone-based antifoaming agent An epoxy resin composition was prepared by adding parts.
- a bisphenol A type epoxy resin Mitsubishi Chemical Corporation jER828, epoxy equivalent 185
- tetrakis (mercaptoethyl) glycoluril were heated and dissolved with stirring, and then cooled to room temperature. Subsequently, 0.8 parts by weight of 2-phenyl-4,5-bis (hydroxymethyl) imidazole (2PHZ-P
- the obtained epoxy resin composition was applied to a glass epoxy double-sided copper-clad laminate having a copper foil of 35 ⁇ m and cured by heating at 170 ° C. for 30 minutes.
- a glass epoxy double-sided copper-clad laminate having a copper foil of 35 ⁇ m and cured by heating at 170 ° C. for 30 minutes.
- electroless plating and electroplating were performed, and a printed wiring board was produced according to a subtractive method. Thereafter, heat treatment (annealing treatment) was further performed at 170 ° C. for 30 minutes, and this was used as a test piece.
- Comparative Example 3 A test piece was prepared in the same manner as in Example 7, except that 30 parts by weight of phenol novolac resin (Phenolite manufactured by Dainippon Ink & Chemicals, Inc.) was used instead of tetrakis (mercaptoethyl) glycoluril.
- phenol novolac resin Phenolite manufactured by Dainippon Ink & Chemicals, Inc.
Abstract
Description
で表されるメルカプトアルキルグリコールウリル類が提供される。
(1)支持ベースフィルムとその上に形成された上記エポキシ樹脂組成物の薄膜からなる接着フィルム、
(2)繊維からなるシート状補強基材と、これに含浸された上記エポキシ樹脂組成物の半硬化物からなるプリプレグ、
(3)上記エポキシ樹脂組成物の硬化物の粗化面にメッキ導体層が形成され、他面はパターン加工された内層回路基板に密着して積層されてなる多層プリント配線板、
(4)上記エポキシ樹脂組成物をパターン加工された内層回路基板に塗工し、加熱硬化させ、得られた硬化物の表面を酸化剤により粗化し、その粗化面に導体層をメッキにより形成することによって得られる多層プリント配線板、
(5)上記接着フィルムをパターン加工された内層回路基板に加圧、加熱条件下でラミネートし、次いで、支持ベースフィルムを剥離し、又は剥離せずに、エポキシ樹脂組成物を加熱硬化させ、得られた硬化物の表面を酸化剤により粗化し、その粗化面に導体層をメッキにより形成することによって得られる多層プリント配線板、
(6)上記プリプレグをパターン加工された内層回路基板に加圧、加熱条件下で積層し、一体化させた後、酸化剤により該プリプレグ表面を粗化し、その粗化面に導体層をメッキにより形成することによって得られる多層プリント配線板、
(7)上記エポキシ樹脂組成物をパターン加工された内層回路基板に塗工し、加熱硬化させ、得られた硬化物の表面を酸化剤により粗化し、その粗化面に導体層をメッキにより形成することを含む多層プリント配線板の製造方法、
(8)上記接着フィルムをパターン加工された内層回路基板に加圧、加熱条件下でラミネートし、次いで、支持ベースフィルムを剥離し、又は剥離せずに、エポキシ樹脂組成物を加熱硬化させ、得られた硬化物の表面を酸化剤により粗化し、その粗化面に導体層をメッキにより形成することを含む多層プリント配線板の製造方法、
(9)上記プリプレグをパターン加工された内層回路基板に加圧、加熱条件下で積層し、一体化させた後、酸化剤により該プリプレグ表面を粗化し、その粗化面に導体層をメッキにより形成することを含む多層プリント配線板の製造方法、
(10)上記エポキシ樹脂組成物を両面銅張積層板の銅箔をエッチアウトした面又はアンクラッド板の少なくとも片方の面に塗工し、加熱硬化して得られる積層板、
(11)上記接着フィルムを両面銅張積層板の銅箔をエッチアウトした面又はアンクラッド板の少なくとも片方の面に、加圧、加熱条件下でラミネートし、必要により支持ベースフィルムを剥離、加熱硬化して得られる積層板、
(12)上記プリプレグを両面銅張積層板の銅箔をエッチアウトした面又はアンクラッド板の少なくとも片方の面に、加圧、加熱条件下で積層して得られる積層板、
(13)上記プリプレグを加圧、加熱条件下で積層して得られる積層板、
が提供される。
本発明によるメルカプトアルキルグリコールウリル類は、一般式(I)
で表される。
で表される。
1-メルカプトメチルグリコールウリル、
1-(2-メルカプトエチル)グリコールウリル、
1-(3-メルカプトプロピル)グリコールウリル、
1,3-ビス(メルカプトメチル)グリコールウリル、
1,3-ビス(2-メルカプトエチル)グリコールウリル、
1,3-ビス(3-メルカプトプロピル)グリコールウリル、
1,4-ビス(メルカプトメチル)グリコールウリル、
1,4-ビス(2-メルカプトエチル)グリコールウリル、
1,4-ビス(3-メルカプトプロピル)グリコールウリル、
1,6-ビス(メルカプトメチル)グリコールウリル、
1,6-ビス(2-メルカプトエチル)グリコールウリル、
1,6-ビス(3-メルカプトプロピル)グリコールウリル、
1,3,4-トリス(メルカプトメチル)グリコールウリル、
1,3,4-トリス(2-メルカプトエチル)グリコールウリル、
1,3,4-トリス(3-メルカプトプロピル)グリコールウリル、
1,3,4,6-テトラキス(メルカプトメチル)グリコールウリル、
1,3,4,6-テトラキス(2-メルカプトエチル)グリコールウリル、
1,3,4,6-テトラキス(3-メルカプトプロピル)グリコールウリル、
1-メルカプトメチル-3a-メチルグリコールウリル、
1-メルカプトメチル-6a-メチルグリコールウリル、
1-(2-メルカプトエチル)-3a-メチルグリコールウリル、
1-(2-メルカプトエチル)-6a-メチルグリコールウリル、
1-(3-メルカプトプロピル)-3a-メチルグリコールウリル、
1-(3-メルカプトプロピル)-6a-メチルグリコールウリル、
1,3-ビス(メルカプトメチル)-3a-メチルグリコールウリル、
1,3-ビス(2-メルカプトエチル)-3a-メチルグリコールウリル、
1,3-ビス(3-メルカプトプロピル)-3a-メチルグリコールウリル、
1,4-ビス(メルカプトメチル)-3a-メチルグリコールウリル、
1,4-ビス(2-メルカプトエチル)-3a-メチルグリコールウリル、
1,4-ビス(3-メルカプトプロピル)-3a-メチルグリコールウリル、
1,6-ビス(メルカプトメチル)-3a-メチルグリコールウリル、
1,6-ビス(メルカプトメチル)-6a-メチルグリコールウリル、
1,6-ビス(2-メルカプトエチル)-3a-メチルグリコールウリル、
1,6-ビス(2-メルカプトエチル)-6a-メチルグリコールウリル、
1,6-ビス(3-メルカプトプロピル)-3a-メチルグリコールウリル、
1,6-ビス(3-メルカプトプロピル)-6a-メチルグリコールウリル、
1,3,4-トリス(メルカプトメチル)-3a-メチルグリコールウリル、
1,3,4-トリス(メルカプトメチル)-6a-メチルグリコールウリル、
1,3,4-トリス(2-メルカプトエチル)-3a-メチルグリコールウリル、
1,3,4-トリス(2-メルカプトエチル)-6a-メチルグリコールウリル、
1,3,4-トリス(3-メルカプトプロピル)-3a-メチルグリコールウリル、
1,3,4-トリス(3-メルカプトプロピル)-6a-メチルグリコールウリル、
1,3,4,6-テトラキス(メルカプトメチル)-3a-メチルグリコールウリル、
1,3,4,6-テトラキス(2-メルカプトエチル)-3a-メチルグリコールウリル、
1,3,4,6-テトラキス(3-メルカプトプロピル)-3a-メチルグリコールウリル、
1-メルカプトメチル-3a,6a-ジメチルグリコールウリル、
1-(2-メルカプトエチル)-3a,6a-ジメチルグリコールウリル、
1-(3-メルカプトプロピル)-3a,6a-ジメチルグリコールウリル、
1,3-ビス(メルカプトメチル)-3a,6a-ジメチルグリコールウリル、
1,3-ビス(2-メルカプトエチル)-3a,6a-ジメチルグリコールウリル、
1,3-ビス(3-メルカプトプロピル)-3a,6a-ジメチルグリコールウリル、
1,4-ビス(メルカプトメチル)-3a,6a-ジメチルグリコールウリル、
1,4-ビス(2-メルカプトエチル)-3a,6a-ジメチルグリコールウリル、
1,4-ビス(3-メルカプトプロピル)-3a,6a-ジメチルグリコールウリル、
1,6-ビス(メルカプトメチル)-3a,6a-ジメチルグリコールウリル、
1,6-ビス(2-メルカプトエチル)-3a,6a-ジメチルグリコールウリル、
1,6-ビス(3-メルカプトプロピル)-3a,6a-ジメチルグリコールウリル、
1,3,4-トリス(メルカプトメチル)-3a,6a-ジメチルグリコールウリル、
1,3,4-トリス(2-メルカプトエチル)-3a,6a-ジメチルグリコールウリル、
1,3,4-トリス(3-メルカプトプロピル)-3a,6a-ジメチルグリコールウリル、
1,3,4,6-テトラキス(メルカプトメチル)-3a,6a-ジメチルグリコールウリル、
1,3,4,6-テトラキス(2-メルカプトエチル)-3a,6a-ジメチルグリコールウリル、
1,3,4,6-テトラキス(3-メルカプトプロピル)-3a,6a-ジメチルグリコールウリル、
1-メルカプトメチル-3a,6a-ジフェニルグリコールウリル、
1-(2-メルカプトエチル)-3a,6a-ジフェニルグリコールウリル、
1-(3-メルカプトプロピル)-3a,6a-ジフェニルグリコールウリル、
1,3-ビス(メルカプトメチル)-3a,6a-ジフェニルグリコールウリル、
1,3-ビス(2-メルカプトエチル)-3a,6a-ジフェニルグリコールウリル、
1,3-ビス(3-メルカプトプロピル)-3a,6a-ジフェニルグリコールウリル、
1,4-ビス(メルカプトメチル)-3a,6a-ジフェニルグリコールウリル、
1,4-ビス(2-メルカプトエチル)-3a,6a-ジフェニルグリコールウリル、
1,4-ビス(3-メルカプトプロピル)-3a,6a-ジフェニルグリコールウリル、
1,6-ビス(メルカプトメチル)-3a,6a-ジフェニルグリコールウリル、
1,6-ビス(2-メルカプトエチル)-3a,6a-ジフェニルグリコールウリル、
1,6-ビス(3-メルカプトプロピル)-3a,6a-ジフェニルグリコールウリル、
1,3,4-トリス(メルカプトメチル)-3a,6a-ジフェニルグリコールウリル、
1,3,4-トリス(2-メルカプトエチル)-3a,6a-ジフェニルグリコールウリル、
1,3,4-トリス(3-メルカプトプロピル)-3a,6a-ジフェニルグリコールウリル、
1,3,4,6-テトラキス(メルカプトメチル)-3a,6a-ジフェニルグリコールウリル、
1,3,4,6-テトラキス(2-メルカプトエチル)-3a,6a-ジフェニルグリコールウリル、
1,3,4,6-テトラキス(3-メルカプトプロピル)-3a,6a-ジフェニルグリコールウリル
等を挙げることができる。
で表される3-メルカプトプロピルグリコールウリル類は、一般式(a)
で表されるアリルグリコールウリル類に、必要に応じて、適宜の溶媒中、触媒の存在下にチオ酢酸を付加反応させて、一般式(a1)
で表されるチオ酢酸エステルを反応生成物として得、次いで、この反応生成物を、必要に応じて、適宜の溶媒中、水素化ホウ素化合物にて還元することによって得ることができる。
で表される2-エチルメルカプトグリコールウリル類は、一般式(b)
で表される2-ヒドロキシエチルグリコールウリル類(b)に、必要に応じて、適宜の溶媒中、塩化チオニルを反応させて、一般式(b1)
で表される反応生成物、即ち、2-クロロエチルグリコールウリル類を得、次いで、この反応生成物を、必要に応じて、適宜の溶媒中、トリチオ炭酸ジナトリウムにて処理して、塩素原子をメルカプト基に置換することによって得ることができる。
で表されるメルカプトメチルグリコールウリル類も、2-エチルメルカプトグリコールウリル類と同じ方法によって得ることができる。
で表されるヒドロキシメチルグリコールウリル類(c)に、必要に応じて、適宜の溶媒中、塩化チオニルを反応させて、一般式(c1)
で表される反応生成物、即ち、クロロメチルグリコールウリル類を得、次いで、この反応生成物を、必要に応じて、適宜の溶媒中、トリチオ炭酸ジナトリウムにて処理して、塩素原子をメルカプト基と置換することによって得ることができる。
以下、本発明によるメルカプトアルキルグリコールウリル類を含むエポキシ樹脂組成物について説明する。
1,3-ジグリシジルグリコールウリル、
1,4-ジグリシジルグリコールウリル、
1,6-ジグリシジルグリコールウリル、
1,3,4-トリグリシジルグリコールウリル、
1,3,4,6-テトラグリシジルグリコールウリル、
1,3-ジグリシジル-3a-メチルグリコールウリル、
1,4-ジグリシジル-3a-メチルグリコールウリル、
1,6-ジグリシジル-3a-メチルグリコールウリル、
1,3,4-トリグリシジル-3a-メチルグリコールウリル、
1,3,4,6-テトラグリシジル-3a-メチルグリコールウリル、
1,3-ジグリシジル-3a,6a-ジメチルグリコールウリル、
1,4-ジグリシジル-3a,6a-ジメチルグリコールウリル、
1,6-ジグリシジル-3a,6a-ジメチルグリコールウリル、
1,3,4-トリグリシジル-3a,6a-ジメチルグリコールウリル、
1,3,4,6-テトラグリシジル-3a,6a-ジメチルグリコールウリル、
1,3-ジグリシジル-3a,6a-ジフェニルグリコールウリル、
1,4-ジグリシジル-3a,6a-ジフェニルグリコールウリル、
1,6-ジグリシジル-3a,6a-ジフェニルグリコールウリル、
1,3,4-トリグリシジル-3a,6a-ジフェニルグリコールウリル、
1,3,4,6-テトラグリシジル-3a,6a-ジフェニルグリコールウリル
等を挙げることができる。
前述したように、本発明によるエポキシ樹脂組成物は、従来、知られているエポキシ樹脂組成物に比べて、耐加水分解性にすぐれており、更に、耐熱性や耐湿性等においてもすぐれており、接着剤やシール剤として好適に用いることができる。即ち、本発明による接着剤は、上述したエポキシ樹脂組成物を含み、また、本発明によるシール剤は上述したエポキシ樹脂組成物を含む。
以下において、チオ酢酸は東京化成工業(株)製、アゾビスイソブチロニトリルはシグマアルドリッチ社製、塩化チオニル及び水素化ホウ素ナトリウムは和光純薬工業(株)製、トリチオ炭酸ジナトリウム40%水溶液はBOC Science社製を用いた。
(1,3,4,6-テトラアリルグリコールウリルの合成)
特開平11-171887号公報に記載の方法に従って合成した。
(1,3,4,6-テトラアリル-3a,6a-ジメチルグリコールウリルの合成)
特開平11-171887号公報に記載の方法に従って合成した。
(1,3-ジアリルグリコールウリルの合成)
温度計を備えた100mLフラスコに尿素3.00g(50.0mmol)と40%グリオキザール水溶液8.71g(60.0mmol)を投入した。この混合物に室温で40%水酸化ナトリウム水溶液を2滴加えて、80℃にて1時間攪拌した。続いて、反応混合物を減圧下で濃縮した。得られた濃縮物にジアリルウレア7.00g(50.0mmol)、酢酸50mL及び硫酸490mg(5.0mmol)を投入し、110℃にて終夜攪拌した。次いで、反応混合物を室温まで冷却した後、アセトン50mLを加え、析出した結晶を濾別し、乾燥して、1,3-ジアリルグリコールウリルを白色の粘稠な油状物として得た。収率39%。
実施例1
(1,3-ビス(3-メルカプトプロピル)グリコールウリルの合成)
温度計を備えた50mLフラスコに、1,3-ジアリルグリコールウリル560mg(2.5mmol)、チオ酢酸457mg(6.0mmol)及びテトラヒドロフラン10mLを入れ、これにアゾビスイソブチロニトリル25mg(0.15mmol)を加えた後、攪拌しながら、60℃にて16時間反応を行った。
(1,3,4,6-テトラキス(3-メルカプトプロピル)グリコールウリルの合成)
温度計を備えた100mLフラスコに1,3,4,6-テトラアリルグリコールウリル3.02g(10.0mmol)、チオ酢酸3.65g(48.0mmol)及びテトラヒドロフラン20mLを入れ、これにアゾビスイソブチロニトリル66mg(0.4mmol)を加えた後、攪拌しながら60℃にて18時間反応を行った。
(1,3,4,6-テトラキス(3-メルカプトプロピル)-3a,6a-ジメチルグリコールウリルの合成)
温度計を備えた100mLフラスコに1,3,4,6-テトラアリル-3a,6a-ジメチルグリコールウリル3.30g(10.0mmol)、チオ酢酸3.65g(48.0mmol)及びテトラヒドロフラン20mLを入れ、これにアゾビスイソブチロニトリル66mg(0.4mmol)を投入した後、攪拌しながら60℃にて18時間反応を行った。
(1,3,4,6-テトラキス(2-メルカプトエチル)グリコールウリルの合成)
温度計を備えた50mLフラスコに1,3,4,6-テトラキス(2-ヒドロキシエチル)グリコールウリル3.18g(10.0mmol)と塩化チオニル4.76g(40.0mmol)を入れた後、攪拌しながら、70℃にて5時間反応を行った。
δ値は下記のとおりであった。
以下においては、エポキシ樹脂(三菱化学(株)製「jER828」)に上記実施例2で得られた1,3,4,6-テトラキス(3-メルカプトプロピル)グリコールウリルと上記実施例4で得られた1,3,4,6-テトラキス(2-メルカプトエチル)グリコールウリルをそれぞれ硬化剤として配合し、硬化促進剤として固体分散型アミンアダクト系潜在性硬化促進剤(味の素ファインテクノ(株)製「アミキュアPN-23」)をそれぞれ配合してエポキシ樹脂組成物を調製した。
エポキシ樹脂100重量部に1,3,4,6-テトラキス(3-メルカプトプロピル)グリコールウリル64重量部と潜在性硬化促進剤3重量部を混合して、エポキシ樹脂組成物を調製した。
エポキシ樹脂100重量部に1,3,4,6-テトラキス(2-メルカプトエチル)グリコールウリル56重量部と潜在性硬化促進剤3重量部を混合して、エポキシ樹脂組成物を調製した。
実施例5において、1,3,4,6-テトラキス(3-メルカプトプロピル)グリコールウリル64重量部に代えて、チオール化合物(1)107重量部を用いた以外は、同様にして、エポキシ樹脂組成物を調製した。
実施例5において、1,3,4,6-テトラキス(3-メルカプトプロピル)グリコールウリル64重量部に代えて、チオール化合物(2)75重量部を用いた以外は、同様にして、エポキシ樹脂組成物を調製した。
上記実施例5、6、比較例1及び2において得たエポキシ樹脂組成物の硬化物のガラス転移温度(Tg)は、示差走査熱量計(エスアイアイ・ナノテクノロジー(株)製「EXSTAR 6000」)を用いて測定した。即ち、エポキシ樹脂組成物を10℃/分の昇温速度にて30℃から270℃まで加熱して硬化させ、続いて、このようにして得られた硬化物を-50℃/分の降温速度にて270℃から10℃まで冷却し、次いで、10℃/分の昇温速度にて10℃から100℃へ加熱して、硬化物のガラス転移温度を測定した。結果を表1に示す。
ビスフェノールA型エポキシ樹脂(三菱化学社製jER828、エポキシ当量185)100重量部と、テトラキス(メルカプトエチル)グリコールウリル55重量部を攪拌しながら加熱溶解させた後、室温まで冷却した。続いて、2-フェニル-4,5-ビス(ヒドロキシメチル)イミダゾール(四国化成工業社製2PHZ-PW)0.8重量部と、微粉砕シリカ2重量部及びシリコーン系消泡剤0.5重量部を添加してエポキシ樹脂組成物を調製した。
JIS C6481に準拠して測定を行った。導体メッキ厚は約30μm。
(煮沸耐熱性試験)
試験片を2時間煮沸処理した後、260℃の半田浴に30秒間浸漬して、外観を目視により確認した。下記評価基準に従い評価した。
○;良好、×;ふくれ、はがれ又はミーズリング発生。
テトラキス(メルカプトエチル)グリコールウリルの代わりに、フェノールノボラック樹脂(大日本インキ化学工業社製フェノライト)30重量部を使用した以外は、実施例7と同様にして、試験片を作製した。
Claims (22)
- 請求項1に記載のメルカプトアルキルグリコールウリル類からなるエポキシ樹脂用硬化剤。
- エポキシ樹脂と請求項1に記載のメルカプトアルキルグリコールウリル類を含むエポキシ樹脂組成物。
- 更に、硬化促進剤を含む請求項3に記載のエポキシ樹脂組成物。
- 硬化促進剤がアミン類である請求項4に記載のエポキシ樹脂組成物。
- 硬化促進剤がアミン類とエポキシ化合物との反応生成物である請求項4に記載のエポキシ樹脂組成物。
- 硬化促進剤が分子内に1個以上のイソシアネート基を有する化合物と分子内に少なくとも1個の第1級及び/又は第2級アミノ基を有する化合物との反応生成物である請求項4に記載のエポキシ樹脂組成物。
- 請求項3から7のいずれかに記載のエポキシ樹脂組成物を含む接着剤。
- 請求項3から7のいずれかに記載のエポキシ樹脂組成物を含むシール剤。
- 支持ベースフィルムと、その上に形成された請求項3から7のいずれかに記載のエポキシ樹脂組成物の薄膜からなる接着フィルム。
- 繊維からなるシート状補強基材と、これに含浸された請求項3から7のいずれかに記載のエポキシ樹脂組成物の半硬化物からなるプリプレグ。
- 請求項3から7のいずれかに記載のエポキシ樹脂組成物の硬化物の粗化面にメッキ導体層が形成され、他面はパターン加工された内層回路基板に密着して積層されてなる多層プリント配線板。
- 請求項3から7のいずれかに記載のエポキシ樹脂組成物をパターン加工された内層回路基板に塗工し、加熱硬化させ、得られた硬化物の表面を酸化剤により粗化し、その粗化面に導体層をメッキにより形成することによって得られる多層プリント配線板。
- 請求項10に記載の接着フィルムをパターン加工された内層回路基板に加圧、加熱条件下でラミネートし、次いで、支持ベースフィルムを剥離し、又は剥離せずに、エポキシ樹脂組成物を加熱硬化させ、得られた硬化物の表面を酸化剤により粗化し、その粗化面に導体層をメッキにより形成することによって得られる多層プリント配線板。
- 請求項11に記載のプリプレグをパターン加工された内層回路基板に加圧、加熱条件下で積層し、一体化させた後、酸化剤により該プリプレグ表面を粗化し、その粗化面に導体層をメッキにより形成することによって得られる多層プリント配線板。
- 請求項3から7のいずれかに記載のエポキシ樹脂組成物をパターン加工された内層回路基板に塗工し、加熱硬化させ、得られた硬化物の表面を酸化剤により粗化し、その粗化面に導体層をメッキにより形成することを含む多層プリント配線板の製造方法。
- 請求項10に記載の接着フィルムをパターン加工された内層回路基板に加圧、加熱条件下でラミネートし、次いで、支持ベースフィルムを剥離し、又は剥離せずに、エポキシ樹脂組成物を加熱硬化させ、得られた硬化物の表面を酸化剤により粗化し、その粗化面に導体層をメッキにより形成することを含む多層プリント配線板の製造方法。
- 請求項11に記載のプリプレグをパターン加工された内層回路基板に加圧、加熱条件下で積層し、一体化させた後、酸化剤により該プリプレグ表面を粗化し、その粗化面に導体層をメッキにより形成することを含む多層プリント配線板の製造方法。
- 請求項3から7のいずれかに記載のエポキシ樹脂組成物を両面銅張積層板の銅箔をエッチアウトした面又はアンクラッド板の少なくとも片方の面に塗工し、加熱硬化して得られる積層板。
- 請求項10に記載の接着フィルムを両面銅張積層板の銅箔をエッチアウトした面又はアンクラッド板の少なくとも片方の面に、加圧、加熱条件下でラミネートし、必要により支持ベースフィルムを剥離、加熱硬化して得られる積層板。
- 請求項11に記載のプリプレグを両面銅張積層板の銅箔をエッチアウトした面又はアンクラッド板の少なくとも片方の面に、加圧、加熱条件下で積層して得られる積層板。
- 請求項11に記載のプリプレグを加圧、加熱条件下で積層して得られる積層板。
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KR20160091911A (ko) | 2016-08-03 |
EP3075736B1 (en) | 2018-08-22 |
US20160289237A1 (en) | 2016-10-06 |
US10030023B2 (en) | 2018-07-24 |
KR102267524B1 (ko) | 2021-06-18 |
TW201529577A (zh) | 2015-08-01 |
CN105764907B (zh) | 2018-05-18 |
CN105764907A (zh) | 2016-07-13 |
EP3075736A4 (en) | 2017-07-26 |
TWI635088B (zh) | 2018-09-11 |
EP3075736A1 (en) | 2016-10-05 |
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