JP2020164628A - 樹脂組成物 - Google Patents
樹脂組成物 Download PDFInfo
- Publication number
- JP2020164628A JP2020164628A JP2019065763A JP2019065763A JP2020164628A JP 2020164628 A JP2020164628 A JP 2020164628A JP 2019065763 A JP2019065763 A JP 2019065763A JP 2019065763 A JP2019065763 A JP 2019065763A JP 2020164628 A JP2020164628 A JP 2020164628A
- Authority
- JP
- Japan
- Prior art keywords
- bis
- resin
- resin composition
- mercaptomethylthio
- epoxy
- 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.)
- Granted
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 63
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 48
- 239000003822 epoxy resin Substances 0.000 claims abstract description 47
- 229920005989 resin Polymers 0.000 claims abstract description 37
- 239000011347 resin Substances 0.000 claims abstract description 37
- 229920006295 polythiol Polymers 0.000 claims abstract description 23
- 150000003553 thiiranes Chemical class 0.000 claims abstract description 18
- 239000004593 Epoxy Substances 0.000 claims abstract description 17
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 6
- -1 methylene, ethylidene Chemical group 0.000 claims description 60
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000002723 alicyclic group Chemical group 0.000 claims description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 3
- 230000008961 swelling Effects 0.000 abstract description 16
- 239000000853 adhesive Substances 0.000 abstract description 14
- 239000011248 coating agent Substances 0.000 abstract description 4
- 229910052751 metal Inorganic materials 0.000 abstract description 4
- 239000002184 metal Substances 0.000 abstract description 4
- 238000000576 coating method Methods 0.000 abstract description 2
- 239000010409 thin film Substances 0.000 abstract 1
- 238000001723 curing Methods 0.000 description 30
- 239000003795 chemical substances by application Substances 0.000 description 22
- 150000001412 amines Chemical class 0.000 description 14
- 230000001070 adhesive effect Effects 0.000 description 13
- 229920003986 novolac Polymers 0.000 description 12
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 11
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 238000011156 evaluation Methods 0.000 description 9
- 150000002989 phenols Chemical class 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- ITXACGPMGJCSKF-UHFFFAOYSA-N 1,3-dithietane Chemical compound C1SCS1 ITXACGPMGJCSKF-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 6
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000005011 phenolic resin Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 0 CC(*(*)C=C(*C(C=C1)=C*(*)C=C1N(CC1OC1)CC1OC1)C=C1)=C1N(CC1OC1)C1COC1 Chemical compound CC(*(*)C=C(*C(C=C1)=C*(*)C=C1N(CC1OC1)CC1OC1)C=C1)=C1N(CC1OC1)C1COC1 0.000 description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 239000006087 Silane Coupling Agent Substances 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
- 125000001931 aliphatic group Chemical group 0.000 description 4
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000012948 isocyanate Substances 0.000 description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 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
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 239000001993 wax Substances 0.000 description 4
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
- DQKFGBUUTSPTJB-UHFFFAOYSA-N CCCSCCC1[S+](CCSCC)S1 Chemical compound CCCSCCC1[S+](CCSCC)S1 DQKFGBUUTSPTJB-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 150000002513 isocyanates Chemical group 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 3
- 229960001755 resorcinol Drugs 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 2
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- CEUQYYYUSUCFKP-UHFFFAOYSA-N 2,3-bis(2-sulfanylethylsulfanyl)propane-1-thiol Chemical compound SCCSCC(CS)SCCS CEUQYYYUSUCFKP-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 2
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 2
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 2
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 2
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 241000705989 Tetrax Species 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 description 2
- YAAUVJUJVBJRSQ-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2-[[3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propoxy]methyl]-2-(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS YAAUVJUJVBJRSQ-UHFFFAOYSA-N 0.000 description 2
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 2
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- LMMDJMWIHPEQSJ-UHFFFAOYSA-N bis[(3-methyl-7-oxabicyclo[4.1.0]heptan-4-yl)methyl] hexanedioate Chemical compound C1C2OC2CC(C)C1COC(=O)CCCCC(=O)OCC1CC2OC2CC1C LMMDJMWIHPEQSJ-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-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
- 150000001993 dienes Chemical class 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
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- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
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- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- HVOYZOQVDYHUPF-UHFFFAOYSA-N n,n',n'-trimethylethane-1,2-diamine Chemical compound CNCCN(C)C HVOYZOQVDYHUPF-UHFFFAOYSA-N 0.000 description 2
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- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
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- 150000007519 polyprotic acids Polymers 0.000 description 2
- 239000007962 solid dispersion Substances 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 239000012970 tertiary amine catalyst Substances 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
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Abstract
Description
前記(A)エポキシ樹脂が、(A−1)エポキシ当量が110g/eq以下であってエポキシ基を3個以上有するポリエポキシ化合物を、少なくとも含有することを特徴とする樹脂組成物によって達成された。
本発明に使用される(A)成分であるエポキシ樹脂は、(A−1)エポキシ当量が110g/eq以下であってエポキシ基を3個以上有するポリエポキシ化合物を、少なくとも必須成分として含有するものである。このような分子量が小さく多官能である(A−1)成分を使用することによって、硬化後の耐熱性および耐薬品性に対して特に優れた向上効果がある。
の中から選ばれる基である。また、上記基において、*は結合手を表し、R10およびR11はそれぞれ独立に水素原子または非置換若しくはフッ素置換のメチルを表し、nは4〜12の整数を表す。
また、本発明において、(A)成分中、(a−2)成分であるポリエポキシ化合物を使用する場合のその含有量は、1〜20質量%であることが好ましく、2〜10質量%であることが特に好ましい。(a−2)成分の含有量が、1質量%未満では、作業性や密着性などの改善効果が十分に得られないおそれがあり、20質量%を超えて使用すると、耐熱性や耐薬品性が低下するおそれがある。
さらに、本発明において、(A)成分中、(a−3)成分であるポリエポキシ化合物を使用する場合のその含有量は、5〜80質量%であることが好ましく、10〜50質量%であることが特に好ましい。(a−3)成分を80質量%を超えて使用すると、粘度の上昇を生じて、作業性が低下するおそれがある。
本発明における(B)成分であるエピスルフィド樹脂は、エピスルフィド環を有する化合物であり、その製造方法は特に限定されるものではないが、エポキシ樹脂の酸素原子をチオシアン酸カリウム等の触媒を用いて硫黄原子で置き換えることによって容易に得られるものである。すなわち、本発明で使用される(B)成分であるエピスルフィド樹脂としては、上記エポキシ樹脂の酸素原子の一部または全部を硫黄原子に置き換えた化合物などが挙げられる。
本発明における(C)成分であるポリチオール化合物は、硬化剤として作用する化合物であり、例えば、脂肪族ポリチオール化合物、芳香族ポリチオール化合物、エーテル結合を有するポリチオール化合物、エステル結合を有するポリチオール化合物、その他特殊構造を有するポリチオール化合物などが挙げられ、これらのポリチオール化合物をエポキシ化合物で付加変性したものも使用することができる。
(C)成分の含有量は、(A)成分1当量に対し、0.2〜2.0当量とすることができ、0.8〜1.2当量が好ましく、0.9〜1.1当量がより好ましい。(C)成分の使用量が0.2当量未満の場合には、低温硬化性が得られないおそれがあり、(C)成分を2.0当量を超えて使用した場合には、耐熱性などの硬化物物性が低下するおそれがある。
(B)成分の含有量は、(A)成分および(C)成分の総量100質量部に対し、10〜300質量部とすることができ、20〜200質量部が好ましく、30〜150質量部がより好ましい。(B)成分の含有量が、10質量部より少ない場合には、耐膨潤性の改善効果が十分でないおそれがあり、300質量部を超えて使用した場合には、硬化物物性が低下するおそれがある。
さらにこれらのイソシアネート化合物は、カルボジイミド変性、イソシアヌレート変性、ビウレット変性等の形で用いてもよく、各種のブロッキング剤によってブロックされたブロックイソシアネートの形で用いてもよい。
SUS板に各樹脂組成物を厚み100μmで塗布した後、幅2.5mmの銅箔の半分を樹脂組成物に付着させ、90℃、1時間で樹脂組成物を硬化させた。その後、万能型ボンドテスター4000plus(ノードソン・アドバンスト・テクノロジー(株)製)を用いて、剥離速度0.2mm/sの条件で、90度ピール試験を行った。接着強度の値について、以下の指標に従い評価を行った。
A:接着強度が1.3N/mm以上
B:接着強度が1.1N/mm以上 1.3N/mm未満
C:接着強度が0.9N/mm以上 1.1N/mm未満
D:接着強度が0.9N/mm未満
実用レベルを考慮すると、AまたはBであれば評価は良好であり、CまたはDであれば評価は不良である。
得られた樹脂組成物を90℃で1時間硬化させ、10mm×10mm×1mmの寸法の評価試験片を作製した。試験片をN−メチルピロリドン/水=1/1の溶液に浸し、60℃で48日間膨潤させた。評価試験片の膨潤前後の重量を測定して、次式により膨潤率を求めた。膨張率の値について、以下の指標に従い評価を行った。
膨潤率=〔(膨潤後の重量−膨潤前の重量)/膨潤前の重量〕×100[%]
A:10%未満
B:10%以上15%未満
C:15%以上20%未満
D:20%以上
実用レベルを考慮すると、AまたはBであれば評価は良好であり、CまたはDであれば評価は不良である。
得られた樹脂組成物について、示差走査熱量計(DSC)を用いて、90℃で2時間維持したのち昇温し、残発熱量を測定した。低温硬化性は、下記式に従い、反応率として求めた。ここで、低温硬化が進んでいるものほど、90℃で2時間放置時に反応が進行しているため、残発熱量は小さくなる。
反応率=〔1−(90℃2時間後の発熱量/未硬化時の発熱量)〕×100(%)
A:10%未満
B:10%以上15%未満
C:15%以上20%未満
D:20%以上
実用レベルを考慮すると、AまたはBであれば評価は良好であり、CまたはDであれば評価は不良である。
EP2:EPPN−502H〔日本化薬(株)製 固形エポキシ樹脂(エポキシ当量158〜178g/eq)〕
EP3:EP−4088S〔(株)ADEKA製 ジシクロペンタジエンジメタノール型エポキシ樹脂(エポキシ当量165g/eq)〕
EP4:EP−3950S〔(株)ADEKA製 アミノフェノールエポキシ樹脂(エポキシ当量95g/eq)〕
EP5:MY721〔ハンツマン製 ジアミノジフェニルメタン型エポキシ樹脂(エポキシ当量110g/eq)〕
EPS1:水添ビスフェノールA−ビスエピスルフィド
T−1:ジペンタエリスリトールヘキサキス(3−メルカプトプロピオネート)
T−2:1,3,4,6−テトラキス(2−メルカプトエチル)グリコールウリル
IM−1:1−ベンジル−2−メチルイミダゾール
IM−2:四国化成工業(株)製;2MUSIZ
C−1:3−グリシドキシプロピルトリメトキシシラン
C−2:N−(2−アミノエチル)−3−アミノプロピルメチルトリメトキシシラン
C−3:3−メルカプトプロピルトリメトキシシラン
C−4:チタンエチルアセトアセテート
Claims (5)
- (A)エポキシ樹脂、(B)エピスルフィド樹脂、および、(C)ポリチオール化合物を含有する樹脂組成物であって、
前記(A)エポキシ樹脂が、(A−1)エポキシ当量が110g/eq以下であってエポキシ基を3個以上有するポリエポキシ化合物を、少なくとも含有することを特徴とする樹脂組成物。 - 前記(A−1)ポリエポキシ化合物が、下記式(a−1−1)〜(a−1−5)で表されるポリエポキシ化合物の中から選ばれる少なくとも一種である請求項1記載の樹脂組成物。
式(a−1−1)中、R1はメチル、エチル、プロピルまたはイソプロピルを表し、sは0〜4の整数を表す。
式(a−1−2)中、R2およびR3は、それぞれ独立してメチル、エチル、プロピルまたはイソプロピルを表し、R4はメチレン、エチリデンまたはイソプロピリデンを表し、tおよびuはそれぞれ独立して0〜4の整数を表す。
式(a−1−3)中、R5はメチル、エチル、プロピルまたはイソプロピルを表し、pは0〜4の整数を表す。
式(a−1−4)中、R6はメチル、エチル、プロピルまたはイソプロピルを表し、qは0〜4の整数を表す。
- 前記(B)エピスルフィド樹脂が、芳香環または脂環構造を有するエピスルフィド化合物である請求項1〜3のうちいずれか一項記載の樹脂組成物。
- 前記(C)ポリチオール化合物が、チオール基を4個以上有するポリチオール化合物である請求項1〜4のうちいずれか一項記載の樹脂組成物。
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