CN117580888A - Epoxy resin composition, film, method for producing film, and cured product - Google Patents
Epoxy resin composition, film, method for producing film, and cured product Download PDFInfo
- Publication number
- CN117580888A CN117580888A CN202280046138.8A CN202280046138A CN117580888A CN 117580888 A CN117580888 A CN 117580888A CN 202280046138 A CN202280046138 A CN 202280046138A CN 117580888 A CN117580888 A CN 117580888A
- Authority
- CN
- China
- Prior art keywords
- epoxy resin
- resin composition
- component
- film
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 322
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 322
- 239000000203 mixture Substances 0.000 title claims abstract description 179
- 238000004519 manufacturing process Methods 0.000 title claims description 32
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 144
- 150000001875 compounds Chemical class 0.000 claims abstract description 111
- 125000001424 substituent group Chemical group 0.000 claims abstract description 49
- 239000003085 diluting agent Substances 0.000 claims abstract description 45
- 125000003118 aryl group Chemical group 0.000 claims abstract description 40
- 125000005843 halogen group Chemical group 0.000 claims abstract description 27
- 239000001257 hydrogen Substances 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 20
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 16
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 14
- 239000003094 microcapsule Substances 0.000 claims abstract description 12
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 10
- 239000010408 film Substances 0.000 claims description 151
- 239000011342 resin composition Substances 0.000 claims description 25
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 20
- 239000010410 layer Substances 0.000 claims description 20
- 125000003700 epoxy group Chemical group 0.000 claims description 16
- 239000003960 organic solvent Substances 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 11
- 239000011259 mixed solution Substances 0.000 claims description 6
- 150000002009 diols Chemical group 0.000 claims description 5
- 239000011229 interlayer Substances 0.000 claims description 5
- 238000007789 sealing Methods 0.000 claims description 5
- 229910000679 solder Inorganic materials 0.000 claims description 5
- 239000012789 electroconductive film Substances 0.000 claims 2
- 238000001723 curing Methods 0.000 description 158
- 239000000306 component Substances 0.000 description 131
- -1 amine compounds Chemical class 0.000 description 80
- 238000003860 storage Methods 0.000 description 62
- 238000000034 method Methods 0.000 description 51
- 239000002245 particle Substances 0.000 description 43
- 239000004593 Epoxy Substances 0.000 description 40
- 239000002904 solvent Substances 0.000 description 40
- 239000000047 product Substances 0.000 description 26
- 229920005989 resin Polymers 0.000 description 26
- 239000011347 resin Substances 0.000 description 26
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 24
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 24
- 239000000463 material Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 20
- 238000010438 heat treatment Methods 0.000 description 18
- 230000000694 effects Effects 0.000 description 17
- 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 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 150000001412 amines Chemical class 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 16
- 229910052801 chlorine Inorganic materials 0.000 description 16
- 238000002156 mixing Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 239000002612 dispersion medium Substances 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 14
- 230000009257 reactivity Effects 0.000 description 14
- 238000001035 drying Methods 0.000 description 13
- 238000011156 evaluation Methods 0.000 description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 238000010298 pulverizing process Methods 0.000 description 12
- 229930185605 Bisphenol Natural products 0.000 description 11
- 239000002775 capsule Substances 0.000 description 11
- 239000005056 polyisocyanate Substances 0.000 description 11
- 229920001228 polyisocyanate Polymers 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 239000012948 isocyanate Substances 0.000 description 10
- 125000005647 linker group Chemical group 0.000 description 10
- 239000004014 plasticizer Substances 0.000 description 10
- 239000002562 thickening agent Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000006872 improvement Effects 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 239000004065 semiconductor Substances 0.000 description 9
- 229920003986 novolac Polymers 0.000 description 8
- 229920000768 polyamine Polymers 0.000 description 8
- 239000011241 protective layer Substances 0.000 description 8
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 239000004202 carbamide Substances 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 239000008358 core component Substances 0.000 description 7
- 229930003836 cresol Natural products 0.000 description 7
- 239000010419 fine particle Substances 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 239000005011 phenolic resin Substances 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 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 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 239000003063 flame retardant Substances 0.000 description 6
- 239000011256 inorganic filler Substances 0.000 description 6
- 229910003475 inorganic filler Inorganic materials 0.000 description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 125000001302 tertiary amino group Chemical group 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 5
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 5
- 230000002776 aggregation Effects 0.000 description 5
- 238000004220 aggregation Methods 0.000 description 5
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 230000001747 exhibiting effect Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 230000007246 mechanism Effects 0.000 description 5
- 239000012766 organic filler Substances 0.000 description 5
- 229920006287 phenoxy resin Polymers 0.000 description 5
- 239000013034 phenoxy resin Substances 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- 229960004063 propylene glycol Drugs 0.000 description 5
- 235000013772 propylene glycol Nutrition 0.000 description 5
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 5
- 238000004448 titration Methods 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 229920002430 Fibre-reinforced plastic Polymers 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
- 238000013329 compounding Methods 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- 239000008393 encapsulating agent Substances 0.000 description 4
- 239000011151 fibre-reinforced plastic Substances 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 150000002483 hydrogen compounds Chemical class 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 239000003566 sealing material Substances 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 229920003002 synthetic resin Polymers 0.000 description 4
- 239000000057 synthetic resin Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 3
- YFBMUIMQJYESPZ-UHFFFAOYSA-N 3-phenoxy-1,2-propanediol Natural products C1C(OC(C)=O)CCC2(C)C3=CCC4(C)C(C(C)CCC(CC)C(C)C)CCC4(C)C3CCC21 YFBMUIMQJYESPZ-UHFFFAOYSA-N 0.000 description 3
- AWVDYRFLCAZENH-UHFFFAOYSA-N 3-phenoxypropan-1-ol Chemical compound OCCCOC1=CC=CC=C1 AWVDYRFLCAZENH-UHFFFAOYSA-N 0.000 description 3
- FNQIYTUXOKTMDM-UHFFFAOYSA-N 3-phenoxypropane-1,2-diol Chemical compound OCC(O)COC1=CC=CC=C1 FNQIYTUXOKTMDM-UHFFFAOYSA-N 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- HSRJKNPTNIJEKV-UHFFFAOYSA-N Guaifenesin Chemical compound COC1=CC=CC=C1OCC(O)CO HSRJKNPTNIJEKV-UHFFFAOYSA-N 0.000 description 3
- 239000004594 Masterbatch (MB) Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004146 Propane-1,2-diol Substances 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- JHWQMXKQJVAWKI-UHFFFAOYSA-N UNPD187286 Natural products OCC(O)CC1=CC=CC=C1 JHWQMXKQJVAWKI-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 3
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- RBNPOMFGQQGHHO-UHFFFAOYSA-N glyceric acid Chemical compound OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 229910052809 inorganic oxide Inorganic materials 0.000 description 3
- 239000011810 insulating material Substances 0.000 description 3
- 230000001788 irregular Effects 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 229920001568 phenolic resin Polymers 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 239000011295 pitch Substances 0.000 description 3
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 235000013824 polyphenols Nutrition 0.000 description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 229920002050 silicone resin Polymers 0.000 description 3
- 238000013112 stability test Methods 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-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
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 2
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- KFUSXMDYOPXKKT-UHFFFAOYSA-N 2-[(2-methylphenoxy)methyl]oxirane Chemical compound CC1=CC=CC=C1OCC1OC1 KFUSXMDYOPXKKT-UHFFFAOYSA-N 0.000 description 2
- HHRACYLRBOUBKM-UHFFFAOYSA-N 2-[(4-tert-butylphenoxy)methyl]oxirane Chemical compound C1=CC(C(C)(C)C)=CC=C1OCC1OC1 HHRACYLRBOUBKM-UHFFFAOYSA-N 0.000 description 2
- FUIQBJHUESBZNU-UHFFFAOYSA-N 2-[(dimethylazaniumyl)methyl]phenolate Chemical compound CN(C)CC1=CC=CC=C1O FUIQBJHUESBZNU-UHFFFAOYSA-N 0.000 description 2
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 description 2
- NBLIPZBCGXIEFO-UHFFFAOYSA-N 3-(4-(1-(4-(2,3-Epoxypropoxy)phenyl)-1-methylethyl)phenoxy)propane-1,2-diol Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C1=CC=C(OCC(O)CO)C=C1 NBLIPZBCGXIEFO-UHFFFAOYSA-N 0.000 description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 2
- GVBRFUJHRRZUHG-UHFFFAOYSA-N 3-(oxiran-2-ylmethoxy)propan-1-ol Chemical compound OCCCOCC1CO1 GVBRFUJHRRZUHG-UHFFFAOYSA-N 0.000 description 2
- 229910052582 BN Inorganic materials 0.000 description 2
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000011354 acetal resin Substances 0.000 description 2
- BQRYJKYDROZAMA-UHFFFAOYSA-N acetic acid;2-ethoxy-1-methoxypropane Chemical compound CC(O)=O.CCOC(C)COC BQRYJKYDROZAMA-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 229920006243 acrylic copolymer Polymers 0.000 description 2
- 229920000800 acrylic rubber Polymers 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052810 boron oxide Inorganic materials 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000010668 complexation reaction Methods 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 239000011258 core-shell material Substances 0.000 description 2
- 229910002026 crystalline silica Inorganic materials 0.000 description 2
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-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
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 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
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 2
- 239000005350 fused silica glass Substances 0.000 description 2
- 229960002146 guaifenesin Drugs 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 239000000347 magnesium hydroxide Substances 0.000 description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 239000004584 polyacrylic acid Substances 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920013716 polyethylene resin Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000009719 polyimide resin Substances 0.000 description 2
- 229920006324 polyoxymethylene Polymers 0.000 description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920005990 polystyrene resin Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 229910001961 silver nitrate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 235000015096 spirit Nutrition 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 150000004992 toluidines Chemical class 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- LTVUCOSIZFEASK-MPXCPUAZSA-N (3ar,4s,7r,7as)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methano-2-benzofuran-1,3-dione Chemical compound C([C@H]1C=C2)[C@H]2[C@H]2[C@]1(C)C(=O)OC2=O LTVUCOSIZFEASK-MPXCPUAZSA-N 0.000 description 1
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- OLRBYEHWZZSYQQ-VVDZMTNVSA-N (e)-4-hydroxypent-3-en-2-one;propan-2-ol;titanium Chemical compound [Ti].CC(C)O.CC(C)O.C\C(O)=C/C(C)=O.C\C(O)=C/C(C)=O OLRBYEHWZZSYQQ-VVDZMTNVSA-N 0.000 description 1
- OTJFQRMIRKXXRS-UHFFFAOYSA-N (hydroxymethylamino)methanol Chemical compound OCNCO OTJFQRMIRKXXRS-UHFFFAOYSA-N 0.000 description 1
- YOBOXHGSEJBUPB-MTOQALJVSA-N (z)-4-hydroxypent-3-en-2-one;zirconium Chemical compound [Zr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O YOBOXHGSEJBUPB-MTOQALJVSA-N 0.000 description 1
- SNVRDQORMVVQBI-UPHRSURJSA-N (z)-but-2-enedihydrazide Chemical compound NNC(=O)\C=C/C(=O)NN SNVRDQORMVVQBI-UPHRSURJSA-N 0.000 description 1
- NQOFYFRKWDXGJP-UHFFFAOYSA-N 1,1,2-trimethylguanidine Chemical compound CN=C(N)N(C)C NQOFYFRKWDXGJP-UHFFFAOYSA-N 0.000 description 1
- KGSFMPRFQVLGTJ-UHFFFAOYSA-N 1,1,2-triphenylethylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 KGSFMPRFQVLGTJ-UHFFFAOYSA-N 0.000 description 1
- NYSAPLQZKHQBSO-UHFFFAOYSA-N 1,2,3,4-tetrabromo-5-phenylbenzene Chemical group BrC1=C(Br)C(Br)=CC(C=2C=CC=CC=2)=C1Br NYSAPLQZKHQBSO-UHFFFAOYSA-N 0.000 description 1
- WBODDOZXDKQEFS-UHFFFAOYSA-N 1,2,3,4-tetramethyl-5-phenylbenzene Chemical group CC1=C(C)C(C)=CC(C=2C=CC=CC=2)=C1C WBODDOZXDKQEFS-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- ZGDSDWSIFQBAJS-UHFFFAOYSA-N 1,2-diisocyanatopropane Chemical compound O=C=NC(C)CN=C=O ZGDSDWSIFQBAJS-UHFFFAOYSA-N 0.000 description 1
- LINDOXZENKYESA-UHFFFAOYSA-N 1,2-dimethylguanidine Chemical compound CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- IBUMKDUXDJHRGB-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)cyclohexane Chemical compound O=C=NC(C)(C)C1CCCC(C(C)(C)N=C=O)C1 IBUMKDUXDJHRGB-UHFFFAOYSA-N 0.000 description 1
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- RHNNQENFSNOGAM-UHFFFAOYSA-N 1,8-diisocyanato-4-(isocyanatomethyl)octane Chemical compound O=C=NCCCCC(CN=C=O)CCCN=C=O RHNNQENFSNOGAM-UHFFFAOYSA-N 0.000 description 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- ASWPBPHMBJLXOE-UHFFFAOYSA-N 1-(2-ethyl-4-methylimidazol-1-yl)-3-phenoxypropan-2-ol Chemical compound CCC1=NC(C)=CN1CC(O)COC1=CC=CC=C1 ASWPBPHMBJLXOE-UHFFFAOYSA-N 0.000 description 1
- CESWUCNPXCPODN-UHFFFAOYSA-N 1-(2-methylphenoxy)propane-1,2-diol Chemical compound CC(O)C(O)OC1=CC=CC=C1C CESWUCNPXCPODN-UHFFFAOYSA-N 0.000 description 1
- IMJCKVKBXYZZGJ-UHFFFAOYSA-N 1-(dimethylamino)-3-phenoxypropan-2-ol Chemical compound CN(C)CC(O)COC1=CC=CC=C1 IMJCKVKBXYZZGJ-UHFFFAOYSA-N 0.000 description 1
- NCXUNZWLEYGQAH-UHFFFAOYSA-N 1-(dimethylamino)propan-2-ol Chemical compound CC(O)CN(C)C NCXUNZWLEYGQAH-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- DPVAXLIXQRRYKZ-UHFFFAOYSA-N 1-[2-(4,5-dihydroimidazol-1-yl)phenyl]-4,5-dihydroimidazole Chemical compound C1=NCCN1C1=CC=CC=C1N1C=NCC1 DPVAXLIXQRRYKZ-UHFFFAOYSA-N 0.000 description 1
- AHTPZXAPHHTTFU-UHFFFAOYSA-N 1-[3-(4,5-dihydroimidazol-1-yl)phenyl]-4,5-dihydroimidazole Chemical compound C1=NCCN1C1=CC=CC(N2C=NCC2)=C1 AHTPZXAPHHTTFU-UHFFFAOYSA-N 0.000 description 1
- FVUYJAGLGSXVEI-UHFFFAOYSA-N 1-[4-(4,5-dihydroimidazol-1-yl)butyl]-4,5-dihydroimidazole Chemical compound C1CN=CN1CCCCN1CCN=C1 FVUYJAGLGSXVEI-UHFFFAOYSA-N 0.000 description 1
- LOCJFVVULRDEEL-UHFFFAOYSA-N 1-[4-(4,5-dihydroimidazol-1-yl)phenyl]-4,5-dihydroimidazole Chemical compound C1=NCCN1C1=CC=C(N2C=NCC2)C=C1 LOCJFVVULRDEEL-UHFFFAOYSA-N 0.000 description 1
- YQMXOIAIYXXXEE-UHFFFAOYSA-N 1-benzylpyrrolidin-3-ol Chemical compound C1C(O)CCN1CC1=CC=CC=C1 YQMXOIAIYXXXEE-UHFFFAOYSA-N 0.000 description 1
- IFLCSHCQLDMGJB-UHFFFAOYSA-N 1-butoxy-3-(2-ethyl-4-methylimidazol-1-yl)propan-2-ol Chemical compound CCCCOCC(O)CN1C=C(C)N=C1CC IFLCSHCQLDMGJB-UHFFFAOYSA-N 0.000 description 1
- NWHBCDGVHNXUPQ-UHFFFAOYSA-N 1-butoxy-3-(2-methyl-4,5-dihydroimidazol-1-yl)propan-2-ol Chemical compound CCCCOCC(O)CN1CCN=C1C NWHBCDGVHNXUPQ-UHFFFAOYSA-N 0.000 description 1
- PZAHYZLSKYNENE-UHFFFAOYSA-N 1-butoxy-3-(2-methylimidazol-1-yl)propan-2-ol Chemical compound CCCCOCC(O)CN1C=CN=C1C PZAHYZLSKYNENE-UHFFFAOYSA-N 0.000 description 1
- SDWZQKKODUFTEY-UHFFFAOYSA-N 1-butoxy-3-(dimethylamino)propan-2-ol Chemical compound CCCCOCC(O)CN(C)C SDWZQKKODUFTEY-UHFFFAOYSA-N 0.000 description 1
- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- LYUVLUOMAJAVPI-UHFFFAOYSA-N 1-phenoxy-3-(2-phenyl-4,5-dihydroimidazol-1-yl)propan-2-ol Chemical compound C1CN=C(C=2C=CC=CC=2)N1CC(O)COC1=CC=CC=C1 LYUVLUOMAJAVPI-UHFFFAOYSA-N 0.000 description 1
- XBPWJDSOUOAUQN-UHFFFAOYSA-N 1-phenoxypropane-1,3-diol Chemical compound OCCC(O)OC1=CC=CC=C1 XBPWJDSOUOAUQN-UHFFFAOYSA-N 0.000 description 1
- FHTDDANQIMVWKZ-UHFFFAOYSA-N 1h-pyridine-4-thione Chemical compound SC1=CC=NC=C1 FHTDDANQIMVWKZ-UHFFFAOYSA-N 0.000 description 1
- ZUZAETTVAMCNTO-UHFFFAOYSA-N 2,3-dibutylbenzene-1,4-diol Chemical compound CCCCC1=C(O)C=CC(O)=C1CCCC ZUZAETTVAMCNTO-UHFFFAOYSA-N 0.000 description 1
- DGXAGETVRDOQFP-UHFFFAOYSA-N 2,6-dihydroxybenzaldehyde Chemical compound OC1=CC=CC(O)=C1C=O DGXAGETVRDOQFP-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 description 1
- QKVROWZQJVDFSO-UHFFFAOYSA-N 2-(2-methylimidazol-1-yl)ethanamine Chemical compound CC1=NC=CN1CCN QKVROWZQJVDFSO-UHFFFAOYSA-N 0.000 description 1
- ZNWOXGIEIAGCQA-UHFFFAOYSA-N 2-(2-methylphenyl)-4,5-dihydro-1h-imidazole Chemical compound CC1=CC=CC=C1C1=NCCN1 ZNWOXGIEIAGCQA-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- DALNXMAZDJRTPB-UHFFFAOYSA-N 2-(dimethylamino)acetohydrazide Chemical compound CN(C)CC(=O)NN DALNXMAZDJRTPB-UHFFFAOYSA-N 0.000 description 1
- DVVXXHVHGGWWPE-UHFFFAOYSA-N 2-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=CC=C1C(O)=O DVVXXHVHGGWWPE-UHFFFAOYSA-N 0.000 description 1
- DENMGZODXQRYAR-UHFFFAOYSA-N 2-(dimethylamino)ethanethiol Chemical compound CN(C)CCS DENMGZODXQRYAR-UHFFFAOYSA-N 0.000 description 1
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 description 1
- XWKAVQKJQBISOL-UHFFFAOYSA-N 2-(phenylazaniumyl)propanoate Chemical compound OC(=O)C(C)NC1=CC=CC=C1 XWKAVQKJQBISOL-UHFFFAOYSA-N 0.000 description 1
- WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- SFJRUJUEMVAZLM-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxymethyl]oxirane Chemical compound CC(C)(C)OCC1CO1 SFJRUJUEMVAZLM-UHFFFAOYSA-N 0.000 description 1
- GQTBMBMBWQJACJ-UHFFFAOYSA-N 2-[(4-butan-2-ylphenoxy)methyl]oxirane Chemical compound C1=CC(C(C)CC)=CC=C1OCC1OC1 GQTBMBMBWQJACJ-UHFFFAOYSA-N 0.000 description 1
- SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 description 1
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 description 1
- SEFYJVFBMNOLBK-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxymethyl]oxirane Chemical compound C1OC1COCCOCCOCC1CO1 SEFYJVFBMNOLBK-UHFFFAOYSA-N 0.000 description 1
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 1
- RMKLXHFCAADUQT-UHFFFAOYSA-N 2-[[3-(oxiran-2-ylmethoxymethyl)cyclohexyl]methoxymethyl]oxirane Chemical compound C1OC1COCC(C1)CCCC1COCC1CO1 RMKLXHFCAADUQT-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- MEVBAGCIOOTPLF-UHFFFAOYSA-N 2-[[5-(oxiran-2-ylmethoxy)naphthalen-2-yl]oxymethyl]oxirane Chemical compound C1OC1COC(C=C1C=CC=2)=CC=C1C=2OCC1CO1 MEVBAGCIOOTPLF-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- CGWBIHLHAGNJCX-UHFFFAOYSA-N 2-butylguanidine Chemical compound CCCCNC(N)=N CGWBIHLHAGNJCX-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- 229940013085 2-diethylaminoethanol Drugs 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- QUPKCFBHJFNUEW-UHFFFAOYSA-N 2-ethyl-4,5-dihydro-1h-imidazole Chemical compound CCC1=NCCN1 QUPKCFBHJFNUEW-UHFFFAOYSA-N 0.000 description 1
- SHYARJUKNREDGB-UHFFFAOYSA-N 2-ethyl-5-methyl-4,5-dihydro-1h-imidazole Chemical compound CCC1=NCC(C)N1 SHYARJUKNREDGB-UHFFFAOYSA-N 0.000 description 1
- KEWLVUBYGUZFKX-UHFFFAOYSA-N 2-ethylguanidine Chemical compound CCNC(N)=N KEWLVUBYGUZFKX-UHFFFAOYSA-N 0.000 description 1
- YTWBFUCJVWKCCK-UHFFFAOYSA-N 2-heptadecyl-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCC1=NC=CN1 YTWBFUCJVWKCCK-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- OVEUFHOBGCSKSH-UHFFFAOYSA-N 2-methyl-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound CC1=CC=CC=C1N(CC1OC1)CC1OC1 OVEUFHOBGCSKSH-UHFFFAOYSA-N 0.000 description 1
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 1
- GSKNLOOGBYYDHV-UHFFFAOYSA-N 2-methylphenol;naphthalen-1-ol Chemical compound CC1=CC=CC=C1O.C1=CC=C2C(O)=CC=CC2=C1 GSKNLOOGBYYDHV-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
- BKCCAYLNRIRKDJ-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1h-imidazole Chemical compound N1CCN=C1C1=CC=CC=C1 BKCCAYLNRIRKDJ-UHFFFAOYSA-N 0.000 description 1
- QRJZGVVKGFIGLI-UHFFFAOYSA-N 2-phenylguanidine Chemical compound NC(=N)NC1=CC=CC=C1 QRJZGVVKGFIGLI-UHFFFAOYSA-N 0.000 description 1
- BWMDMTSNSXYYSP-UHFFFAOYSA-N 2-propylguanidine Chemical compound CCCNC(N)=N BWMDMTSNSXYYSP-UHFFFAOYSA-N 0.000 description 1
- LLEASVZEQBICSN-UHFFFAOYSA-N 2-undecyl-1h-imidazole Chemical compound CCCCCCCCCCCC1=NC=CN1 LLEASVZEQBICSN-UHFFFAOYSA-N 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- ZRYCRPNCXLQHPN-UHFFFAOYSA-N 3-hydroxy-2-methylbenzaldehyde Chemical compound CC1=C(O)C=CC=C1C=O ZRYCRPNCXLQHPN-UHFFFAOYSA-N 0.000 description 1
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AHIPJALLQVEEQF-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1COC(C=C1)=CC=C1N(CC1OC1)CC1CO1 AHIPJALLQVEEQF-UHFFFAOYSA-N 0.000 description 1
- PVFQHGDIOXNKIC-UHFFFAOYSA-N 4-[2-[3-[2-(4-hydroxyphenyl)propan-2-yl]phenyl]propan-2-yl]phenol Chemical compound C=1C=CC(C(C)(C)C=2C=CC(O)=CC=2)=CC=1C(C)(C)C1=CC=C(O)C=C1 PVFQHGDIOXNKIC-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- UFFRSDWQMJYQNE-UHFFFAOYSA-N 6-azaniumylhexylazanium;hexanedioate Chemical compound [NH3+]CCCCCC[NH3+].[O-]C(=O)CCCCC([O-])=O UFFRSDWQMJYQNE-UHFFFAOYSA-N 0.000 description 1
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 1
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 description 1
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- GIXXQTYGFOHYPT-UHFFFAOYSA-N Bisphenol P Chemical compound C=1C=C(C(C)(C)C=2C=CC(O)=CC=2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 GIXXQTYGFOHYPT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- JJHHIJFTHRNPIK-UHFFFAOYSA-N Diphenyl sulfoxide Chemical compound C=1C=CC=CC=1S(=O)C1=CC=CC=C1 JJHHIJFTHRNPIK-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- RYECOJGRJDOGPP-UHFFFAOYSA-N Ethylurea Chemical compound CCNC(N)=O RYECOJGRJDOGPP-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004609 Impact Modifier Substances 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 229920001410 Microfiber Polymers 0.000 description 1
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 1
- 229930182559 Natural dye Natural products 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 241000123069 Ocyurus chrysurus Species 0.000 description 1
- QSBINWBNXWAVAK-PSXMRANNSA-N PE-NMe(16:0/16:0) Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCCNC)OC(=O)CCCCCCCCCCCCCCC QSBINWBNXWAVAK-PSXMRANNSA-N 0.000 description 1
- 241000382362 Persicaria tinctoria Species 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- OJMOMXZKOWKUTA-UHFFFAOYSA-N aluminum;borate Chemical compound [Al+3].[O-]B([O-])[O-] OJMOMXZKOWKUTA-UHFFFAOYSA-N 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 125000005365 aminothiol group Chemical group 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QBLDFAIABQKINO-UHFFFAOYSA-N barium borate Chemical compound [Ba+2].[O-]B=O.[O-]B=O QBLDFAIABQKINO-UHFFFAOYSA-N 0.000 description 1
- 239000010428 baryte Substances 0.000 description 1
- 229910052601 baryte Inorganic materials 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- IKWQWOFXRCUIFT-UHFFFAOYSA-N benzene-1,2-dicarbohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C(=O)NN IKWQWOFXRCUIFT-UHFFFAOYSA-N 0.000 description 1
- ALHNLFMSAXZKRC-UHFFFAOYSA-N benzene-1,4-dicarbohydrazide Chemical compound NNC(=O)C1=CC=C(C(=O)NN)C=C1 ALHNLFMSAXZKRC-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- JGCWKVKYRNXTMD-UHFFFAOYSA-N bicyclo[2.2.1]heptane;isocyanic acid Chemical compound N=C=O.N=C=O.C1CC2CCC1C2 JGCWKVKYRNXTMD-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- SAOKZLXYCUGLFA-UHFFFAOYSA-N bis(2-ethylhexyl) adipate Chemical compound CCCCC(CC)COC(=O)CCCCC(=O)OCC(CC)CCCC SAOKZLXYCUGLFA-UHFFFAOYSA-N 0.000 description 1
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- PLOYJEGLPVCRAJ-UHFFFAOYSA-N buta-1,3-diene;prop-2-enoic acid;styrene Chemical compound C=CC=C.OC(=O)C=C.C=CC1=CC=CC=C1 PLOYJEGLPVCRAJ-UHFFFAOYSA-N 0.000 description 1
- BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 description 1
- LBQQZNWFBQNKCL-UHFFFAOYSA-N butane-1,1-diol;ethane-1,2-diol;terephthalic acid Chemical compound OCCO.CCCC(O)O.OC(=O)C1=CC=C(C(O)=O)C=C1 LBQQZNWFBQNKCL-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- HCOMFAYPHBFMKU-UHFFFAOYSA-N butanedihydrazide Chemical compound NNC(=O)CCC(=O)NN HCOMFAYPHBFMKU-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- KUUHZZOPGUKSPX-UHFFFAOYSA-N calcium dioxosilane oxygen(2-) Chemical compound [O-2].[Ca+2].[Si](=O)=O KUUHZZOPGUKSPX-UHFFFAOYSA-N 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- GBAOBIBJACZTNA-UHFFFAOYSA-L calcium sulfite Chemical compound [Ca+2].[O-]S([O-])=O GBAOBIBJACZTNA-UHFFFAOYSA-L 0.000 description 1
- 235000010261 calcium sulphite Nutrition 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- HHTWOMMSBMNRKP-UHFFFAOYSA-N carvacrol Natural products CC(=C)C1=CC=C(C)C(O)=C1 HHTWOMMSBMNRKP-UHFFFAOYSA-N 0.000 description 1
- RECUKUPTGUEGMW-UHFFFAOYSA-N carvacrol Chemical compound CC(C)C1=CC=C(C)C(O)=C1 RECUKUPTGUEGMW-UHFFFAOYSA-N 0.000 description 1
- 235000007746 carvacrol Nutrition 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 239000012792 core layer Substances 0.000 description 1
- KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- YWJUZWOHLHBWQY-UHFFFAOYSA-N decanedioic acid;hexane-1,6-diamine Chemical compound NCCCCCCN.OC(=O)CCCCCCCCC(O)=O YWJUZWOHLHBWQY-UHFFFAOYSA-N 0.000 description 1
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000010332 dry classification Methods 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000005007 epoxy-phenolic resin Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- UNKQPEQSAGXBEV-UHFFFAOYSA-N formaldehyde;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound O=C.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 UNKQPEQSAGXBEV-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- WCASXYBKJHWFMY-UHFFFAOYSA-N gamma-methylallyl alcohol Natural products CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 229910001701 hydrotalcite Inorganic materials 0.000 description 1
- 229960001545 hydrotalcite Drugs 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000003703 image analysis method Methods 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- WYXXLXHHWYNKJF-UHFFFAOYSA-N isocarvacrol Natural products CC(C)C1=CC=C(O)C(C)=C1 WYXXLXHHWYNKJF-UHFFFAOYSA-N 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
- 238000010902 jet-milling Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000004658 ketimines Chemical class 0.000 description 1
- 229910001710 laterite Inorganic materials 0.000 description 1
- 239000011504 laterite Substances 0.000 description 1
- 230000033001 locomotion Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- ASHGTJPOSUFTGB-UHFFFAOYSA-N methyl resorcinol Natural products COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000003658 microfiber Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- KYCGURZGBKFEQB-UHFFFAOYSA-N n',n'-dibutylpropane-1,3-diamine Chemical compound CCCCN(CCCC)CCCN KYCGURZGBKFEQB-UHFFFAOYSA-N 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- DMDXQHYISPCTGF-UHFFFAOYSA-N n',n'-dipropylethane-1,2-diamine Chemical compound CCCN(CCC)CCN DMDXQHYISPCTGF-UHFFFAOYSA-N 0.000 description 1
- GZUCMODGDIGMBI-UHFFFAOYSA-N n',n'-dipropylpropane-1,3-diamine Chemical compound CCCN(CCC)CCCN GZUCMODGDIGMBI-UHFFFAOYSA-N 0.000 description 1
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 description 1
- PVYBFVZRZWESQN-UHFFFAOYSA-N n,n-diethyl-2-piperazin-1-ylethanamine Chemical compound CCN(CC)CCN1CCNCC1 PVYBFVZRZWESQN-UHFFFAOYSA-N 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- VSWALKINGSNVAR-UHFFFAOYSA-N naphthalen-1-ol;phenol Chemical compound OC1=CC=CC=C1.C1=CC=C2C(O)=CC=CC2=C1 VSWALKINGSNVAR-UHFFFAOYSA-N 0.000 description 1
- 239000000978 natural dye Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000005026 oriented polypropylene Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- IGALFTFNPPBUDN-UHFFFAOYSA-N phenyl-[2,3,4,5-tetrakis(oxiran-2-ylmethyl)phenyl]methanediamine Chemical compound C=1C(CC2OC2)=C(CC2OC2)C(CC2OC2)=C(CC2OC2)C=1C(N)(N)C1=CC=CC=C1 IGALFTFNPPBUDN-UHFFFAOYSA-N 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229940081066 picolinic acid Drugs 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 229920000962 poly(amidoamine) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
- KFUSANSHCADHNJ-UHFFFAOYSA-N pyridine-3-carbohydrazide Chemical compound NNC(=O)C1=CC=CN=C1 KFUSANSHCADHNJ-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000979 synthetic dye Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 1
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 1
- JLEHSYHLHLHPAL-UHFFFAOYSA-N tert-butylurea Chemical compound CC(C)(C)NC(N)=O JLEHSYHLHLHPAL-UHFFFAOYSA-N 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- JIVZKJJQOZQXQB-UHFFFAOYSA-N tolazoline Chemical compound C=1C=CC=CC=1CC1=NCCN1 JIVZKJJQOZQXQB-UHFFFAOYSA-N 0.000 description 1
- VLCLHFYFMCKBRP-UHFFFAOYSA-N tricalcium;diborate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]B([O-])[O-].[O-]B([O-])[O-] VLCLHFYFMCKBRP-UHFFFAOYSA-N 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 229940057402 undecyl alcohol Drugs 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- DIHAURBCYGTGCV-UHFFFAOYSA-N xi-4,5-Dihydro-2,4(5)-dimethyl-1H-imidazole Chemical compound CC1CN=C(C)N1 DIHAURBCYGTGCV-UHFFFAOYSA-N 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
Abstract
An epoxy resin composition comprising: component (A): epoxy resin, component (B): microcapsule curing agent, component (C): reactive diluent and component (D): a compound represented by the following formula (1). (in the formula (1), X 1 Having more than 2 and less than 5 continuous carbon-carbon bonds, X 1 Substituents of carbon contained in (a) and R 1 ~R 5 Each is one selected from the group consisting of hydrogen, an alkyl group, an unsaturated aliphatic group, an aromatic group, a substituent containing a hetero atom, a substituent containing a halogen atom, and a halogen atom. X is X 1 Substituents of carbon contained in (a) and R 1 ~R 5 Optionally the same or different from each other. And the compound of formula (1) is optionally selected from R 1 ~R 5 Any of which are fused ring compounds present in the same ring. )
Description
Technical Field
The present invention relates to an epoxy resin composition, a film, a method for producing the film, and a cured product.
Background
Conventionally, epoxy resins have been widely used as insulating materials for electric and electronic components, sealing materials, adhesives, conductive materials, matrix resins for fiber reinforced plastics, impregnating and fixing agents for motor coils, and the like.
Recently, demands for electronic equipment have been made to be small, high-functional, light-weight, multifunctional, and the like, and in the mounting technology of semiconductor chips, further miniaturization, and high-density have been performed by the small pitch between electrode pads and pad pitches, and the semiconductor chips have also been large. In the gap between the semiconductor chip and the substrate, there is an underfill material for protecting the bump connection portion and the circuit surface of the chip, and an epoxy resin composition can be used as the underfill material.
As an epoxy resin composition applicable to an underfill material, for example, a one-part epoxy resin composition is disclosed which contains microencapsulated amine/epoxy adduct particles and a reactive diluent and is excellent in storage stability, curing characteristics, cured product physical properties and low viscosity (for example, refer to patent document 1).
Further, for example, a one-pack type epoxy resin composition is disclosed which comprises a microcapsule type curing agent having a curing agent for epoxy resin containing 2 or more amine compounds as a core and a thermosetting liquid resin having a viscosity of 0.03pa·s or more and less than 3pa·s at 25 ℃ and which is excellent in storage stability, low-temperature curability and gap penetrability (for example, refer to patent document 2).
Prior art literature
Patent literature
Patent document 1: japanese patent No. 3454437
Patent document 2: japanese patent No. 6085130
Disclosure of Invention
Problems to be solved by the invention
In recent years, as a countermeasure against an increase in area due to an increase in size of the semiconductor chip, and a countermeasure against a narrow gap accompanied by a decrease in pitch of the semiconductor chip, an underfill material for a gap between the semiconductor chip and the substrate as described above is required to have low viscosity for sufficiently penetrating in a short time. In addition, in order to reduce the influence of the underfill material on the constituent members of the semiconductor chip, the underfill material is required to have sufficient curability at low temperatures, for example, in the vicinity of 100 ℃.
Further, from the viewpoint of improving productivity, the underfill material is required to be a one-part type epoxy resin composition capable of omitting a mixing step at the time of use, but since the epoxy resin and the curing agent in the one-part type epoxy resin composition are integrated, high storage stability is required.
That is, a one-part type epoxy resin composition having both low viscosity, sufficient curability at around 100 ℃ and high storage stability at a high level is demanded.
In addition, in recent years, along with miniaturization and thinning of electronic materials, importance of a film obtained by using an epoxy resin composition is increasing for the purpose of thinning an adhesive layer and an insulating layer. In order to obtain the film, a coating liquid is prepared by dissolving components such as an epoxy resin, a curing agent, a curing accelerator, and a film-forming polymer in a solvent, and the coating liquid is applied to a predetermined support, followed by drying treatment, thereby preparing a film. Therefore, the above-mentioned coating liquids are strongly required to have storage stability as a coating liquid, stability in a thin film manufacturing process in which the coating liquid is applied and dried, and stability in a thin film state.
In response to the various requirements for the epoxy resin composition described above, the one-part epoxy resin compositions disclosed in patent documents 1 and 2 have the following problems: there is room for improvement in terms of both curability and storage stability, and there is room for improvement in terms of stability in the production process and stability in the film state of films obtained using these epoxy resin compositions.
In view of the above problems of the prior art, an object of the present invention is to provide an epoxy resin composition which exhibits both low viscosity, sufficient curability at around 100 ℃ and excellent storage stability, and to provide an epoxy resin composition which is excellent in stability in a film production process and in stability in a film state of a film obtained using the epoxy resin composition.
Solution for solving the problem
The inventors have found as a result of intensive studies that: the above object can be achieved by the following means, and the present invention has been completed.
Namely, the present invention is as follows.
[ 1 ] an epoxy resin composition comprising:
component (A): an epoxy resin,
Component (B): a microcapsule curing agent,
Component (C): reactive diluent, and method for producing the same
Component (D): a compound represented by the following formula (1).
(in the formula (1), X 1 Having more than 2 and less than 5 continuous carbon-carbon bonds, X 1 Substituents of carbon contained in (a) and R 1 ~R 5 Respectively selected from hydrogen, alkyl, unsaturated aliphatic group, aromatic group, substituent containing hetero atom, substituent containing halogen atom and halogenA member of the group consisting of elemental atoms. X is X 1 Substituents of carbon contained in (a) and R 1 ~R 5 Optionally the same or different from each other. And the compound of formula (1) is optionally selected from R 1 ~R 5 Any of which are fused ring compounds present in the same ring. )
The epoxy resin composition according to the above [ 1 ], wherein the component (D) is a compound represented by the following formula (2).
(in the formula (2), X 2 Having more than 2 and less than 4 consecutive carbon-carbon bonds, X 2 Substituents of carbon contained in (a) and R 1 ~R 5 Each is one selected from the group consisting of hydrogen, an alkyl group, an unsaturated aliphatic group, an aromatic group, a substituent containing a hetero atom, a substituent containing a halogen atom, and a halogen atom. X is X 2 Substituents of carbon contained in (a) and R 1 ~R 5 Optionally the same or different from each other. And the compound represented by formula (2) is optionally selected from R 1 ~R 5 Any of which are fused ring compounds present in the same ring. )
The epoxy resin composition according to the above [ 1 ] or [ 2 ], wherein the component (D) is a compound represented by the following formula (3).
(in the formula (3), R 1 ~R 9 Each is one selected from the group consisting of hydrogen, an alkyl group, an unsaturated aliphatic group, an aromatic group, a substituent containing a hetero atom, a substituent containing a halogen atom, and a halogen atom.
R 1 ~R 9 Optionally the same or different from each other. And the compound represented by formula (3) is optionally selected from R 1 ~R 5 Any of which are fused ring compounds present in the same ring. )
The epoxy resin composition according to any one of the above [ 1 ] to [ 3 ], wherein the component (D) is a compound represented by the following formula (4).
(in the formula (4), R 1 ~R 8 Each is one selected from the group consisting of hydrogen, an alkyl group, an unsaturated aliphatic group, an aromatic group, a substituent containing a hetero atom, a substituent containing a halogen atom, and a halogen atom.
R 1 ~R 8 Optionally the same or different from each other. And the compound represented by formula (4) is optionally selected from R 1 ~R 5 Any of which are fused ring compounds present in the same ring. )
The epoxy resin composition according to any one of the above [ 1 ] to [ 4 ], wherein the epoxy resin of the component (A) contains at least bisphenol F-type epoxy resin.
The epoxy resin composition according to any one of the above [ 1 ] to [ 5 ], wherein the core of the microcapsule-type curing agent of the component (B) has a circularity of 0.93 or more.
The epoxy resin composition according to any one of the above [ 1 ] to [ 6 ], wherein the component (C) reactive diluent is a compound having an aromatic ring.
The epoxy resin composition according to any one of the above [ 1 ] to [ 7 ], wherein the component (C) reactive diluent is a monofunctional compound in which the aromatic ring is a single ring.
The epoxy resin composition according to any one of the above [ 1 ] to [ 8 ], wherein the content of the reactive diluent of the component (C) is 1% by mass or more and 20% by mass or less in the epoxy resin composition.
The epoxy resin composition according to any one of the above [ 1 ] to [ 9 ], wherein the content of the component (D) in the epoxy resin composition is 0.001% by mass or more and 5% by mass or less.
The epoxy resin composition according to any one of the above [ 1 ] to [ 10 ], wherein R is as defined in the above 1 ~R 5 Does not contain an epoxy group and a structure (terminal diol) of the following formula (5).
[ 12 ] a film, which has:
a support body; and
a resin composition layer formed on the support and containing the epoxy resin composition according to any one of [ 1 ] to [ 11 ].
The film according to [ 13 ] above, wherein the resin composition layer further comprises component (E): film-forming polymer.
The film according to [ 12 ] or [ 13 ], wherein the film is any one selected from the group consisting of an interlayer insulating film, a film-type solder resist, a sealing sheet, an electrically conductive film, an anisotropically electrically conductive film, and a thermally conductive film.
[ 15 ] A method for producing the film according to any one of the above [ 12 ] to [ 14 ], comprising the steps of:
after the supporting body is coated with a mixed solution containing at least the epoxy resin composition of any one of [ 1 ] to [ 11 ] and the component (F) organic solvent, the component (F) organic solvent is dried at a temperature of 50 to 160 ℃ for a period of 1 to 30 minutes.
[ 16 ] a cured product of the epoxy resin composition according to any one of the above [ 1 ] to [ 11 ].
A cured product of the film according to any one of [ 12 ] to [ 14 ].
ADVANTAGEOUS EFFECTS OF INVENTION
According to the present invention, an epoxy resin composition having low viscosity, sufficient curability at around 100 ℃, excellent storage stability, and excellent stability in a film production process and in a film state when applied to a film can be provided.
Detailed Description
Hereinafter, embodiments for carrying out the present invention (hereinafter referred to as "the present embodiment") will be described in detail.
The present embodiment is an example for explaining the present invention, and the present invention is not limited to the following. The present invention can be implemented by appropriately modifying the scope of the gist thereof.
[ epoxy resin composition ]
The epoxy resin composition of the present embodiment includes:
component (A): an epoxy resin,
Component (B): a microcapsule curing agent,
Component (C): reactive diluent, and method for producing the same
Component (D): a compound represented by the following formula (1).
In the formula (1), X 1 Having more than 2 and less than 5 continuous carbon-carbon bonds, X 1 Substituents of carbon contained in (a) and R 1 ~R 5 Each is one selected from the group consisting of hydrogen, an alkyl group, an unsaturated aliphatic group, an aromatic group, a substituent containing a hetero atom, a substituent containing a halogen atom, and a halogen atom. X is X 1 Substituents of carbon contained in (a) and R 1 ~R 5 Optionally the same or different from each other. And the compound of formula (1) is optionally selected from R 1 ~R 5 Any of which are fused ring compounds present in the same ring.
Component (A) epoxy resin
The epoxy resin composition of the present embodiment contains component (a): the epoxy resin (hereinafter, may be referred to as (a) epoxy resin or (a) component).
Examples of the epoxy resin (a) include, but are not limited to, difunctional epoxy resins such as bisphenol a type epoxy resin, bisphenol F type epoxy resin, bisphenol AD type epoxy resin, bisphenol M type epoxy resin, bisphenol P type epoxy resin, tetrabromobisphenol a type epoxy resin, biphenyl type epoxy resin, tetramethylbiphenyl type epoxy resin, tetrabromobiphenyl type epoxy resin, diphenyl ether type epoxy resin, benzophenone type epoxy resin, phenyl benzoate type epoxy resin, diphenyl sulfide type epoxy resin, diphenyl sulfoxide type epoxy resin, diphenyl sulfone type epoxy resin, diphenyl disulfide type epoxy resin, naphthalene type epoxy resin, anthracene type epoxy resin, hydroquinone type epoxy resin, methylhydroquinone type epoxy resin, dibutyl hydroquinone type epoxy resin, resorcinol type epoxy resin, methylresorcinol type epoxy resin, catechol type epoxy resin, and the like; trifunctional epoxy resins such as N, N-diglycidyl aminobenzene type epoxy resin and triazine type epoxy resin; tetrafunctional epoxy resins such as tetraglycidyl diaminodiphenylmethane type epoxy resin and diaminobenzene type epoxy resin; a multifunctional epoxy resin such as a phenol novolac type epoxy resin, a cresol novolac type epoxy resin, a triphenylmethane type epoxy resin, a tetraphenylethane type epoxy resin, a dicyclopentadiene type epoxy resin, a naphthol aralkyl type epoxy resin, and a brominated phenol novolac type epoxy resin; alicyclic epoxy resins.
The number of these may be 1 alone or 2 or more. Furthermore, an epoxy resin obtained by modifying them with isocyanate or the like may be used in combination.
The epoxy resin composition of the present embodiment preferably contains a bisphenol type epoxy resin from the viewpoint of handling properties and heat resistance, more preferably contains a bisphenol F type epoxy resin from the viewpoint of imparting storage stability and good reactivity, and further preferably contains a bisphenol a type epoxy resin from the viewpoint of imparting sufficient mechanical properties.
In addition, by further including bisphenol a type epoxy resin in addition to bisphenol F type epoxy resin, more excellent storage stability and good reactivity are exhibited. The mechanism is not limited to this, but may be considered as follows. Since the bisphenol a type epoxy resin is contained, aggregation of bisphenol F type epoxy resins is suppressed, uniformity of the epoxy resin composition of the present embodiment is improved, storage stability is improved, and molecular diffusivity after the start of curing is improved, thereby improving reactivity.
When the bisphenol F-type epoxy resin and the bisphenol a-type epoxy resin are used in combination, the amount of bisphenol F-type epoxy resin added is preferably 5 parts by mass or more, more preferably 15 parts by mass or more, still more preferably 25 parts by mass or more, still more preferably 30 parts by mass or more, still more preferably 40 parts by mass or more, relative to 100 parts by mass of the total of the bisphenol F-type epoxy resin and the bisphenol a-type epoxy resin, from the viewpoint of sufficiently exhibiting the above-mentioned effects. In addition, from the viewpoint of adding the bisphenol a-type epoxy resin in order to exhibit sufficient mechanical properties, the amount of bisphenol F-type epoxy resin added is preferably 90 parts by mass or less, more preferably 85 parts by mass or less, and still more preferably 80 parts by mass or less.
From the viewpoint of obtaining an epoxy resin composition having excellent electrical characteristics and excellent balance between curability and storage stability, the total chlorine content in the epoxy resin (a) is preferably 2500ppm or less, more preferably 2000ppm or less, further preferably 1500ppm or less, and still further preferably 900ppm or less.
From the viewpoint of achieving a predetermined technical significance, the total chlorine content in the epoxy resin (a) is preferably 0.01ppm or more, more preferably 0.02ppm or more, still more preferably 0.05ppm or more, still more preferably 0.1ppm or more, still more preferably 0.2ppm or more, and particularly preferably 0.5ppm or more.
Here, the total chlorine amount contained in the (a) epoxy resin means the total amount of organic chlorine and inorganic chlorine contained in the (a) epoxy resin, and is a value based on the mass of the (a) epoxy resin.
(A) The total chlorine content of the epoxy resin was measured by the following method.
The epoxy resin (a) was washed with xylene, and washing and filtration were repeated until no epoxy resin was present in the xylene as a washing liquid. Then, the filtrate was distilled off under reduced pressure at 100℃or lower to obtain an epoxy resin. 1 to 10g of the obtained epoxy resin sample was precisely weighed so that the titration amount became 3 to 7mL, dissolved in 25mL of ethylene glycol monobutyl ether, 25mL of a propylene glycol solution of 1 equivalent KOH was added thereto, and after boiling for 20 minutes, titration was performed with a silver nitrate aqueous solution, and the titration amount thus obtained was calculated.
Among the total chlorine, the chlorine contained in the 1, 2-chlorohydrin group is generally referred to herein as hydrolyzable chlorine. (A) The amount of hydrolyzable chlorine in the epoxy resin is preferably 100ppm or less, more preferably 50ppm or less, still more preferably 0.01ppm or more and 20ppm or less, still more preferably 0.05ppm or more and 10ppm or less. When the amount of hydrolyzable chlorine in the epoxy resin (a) is 100ppm or less, the epoxy resin composition of the present embodiment is advantageous from the viewpoint of achieving both high curability and storage stability, and the cured product of the epoxy resin composition of the present embodiment tends to exhibit excellent electrical characteristics.
The hydrolyzable chlorine in the epoxy resin (a) was measured by the following method.
3g of the sample was dissolved in 50mL of toluene, 20mL of a methanol solution of 0.1 equivalent KOH was added thereto, and after boiling for 15 minutes, titration was performed with a silver nitrate aqueous solution, and the amount of titration thus obtained was calculated.
Component (B) microcapsule type curing agent
The epoxy resin composition of the present embodiment contains component (B): a microcapsule-type curing agent (hereinafter, sometimes referred to as (B) a microcapsule-type curing agent, component (B)).
(B) The microcapsule-type curing agent is a curing agent having at least a core containing a curing agent component and a shell covering the core. By forming the component (B) as a microcapsule, the curing agent component is mixed with the epoxy resin (a) and the component (C) described below: reactive diluents, the following components (D): since the predetermined compound is physically isolated via the capsule film, the storage stability tends to be excellent.
< core >
The core constituting the microcapsule-type curing agent (B) is not particularly limited as long as it is a curing agent used in an epoxy resin, and examples thereof include amine-type curing agents, amide-type curing agents, phenol-type curing agents, acid anhydride-type curing agents, catalyst-type curing agents, modified products thereof, and the like. The number of these may be 1 alone or 2 or more.
The amine-based curing agent is not limited to the following, and examples thereof include amine adducts, modified polyamines, aliphatic polyamines, heterocyclic polyamines, alicyclic polyamines, aromatic amines, polyamidoamines, ketimines, and urethane amines.
The amide-based curing agent is not limited to the following, and examples thereof include dicyandiamide and guanidine compounds as derivatives thereof, compounds obtained by adding an acid anhydride to an amine-based compound, and hydrazide-based compounds.
The hydrazide-based compound is not limited to the following, and examples thereof include succinic dihydrazide, adipic dihydrazide, phthalic dihydrazide, isophthalic dihydrazide, terephthalic dihydrazide, parahydroxybenzoic acid dihydrazide, salicylic acid dihydrazide, phenylaminopropionic acid dihydrazide, maleic dihydrazide, and the like.
The guanidine compound is not limited to the following, and examples thereof include dicyandiamide, methyl guanidine, ethyl guanidine, propyl guanidine, butyl guanidine, dimethyl guanidine, trimethyl guanidine, phenyl guanidine, diphenyl guanidine, and toluyl guanidine.
The phenolic curing agent is not limited to the following, and examples thereof include phenol novolac resins, cresol novolac resins, phenol aralkyl resins, cresol aralkyl resins, naphthol aralkyl resins, biphenyl modified phenol aralkyl resins, dicyclopentadiene modified phenol resins, aminotriazine modified phenol resins, naphthol novolac resins, naphthol-phenol co-condensed novolac resins, naphthol-cresol co-condensed novolac resins, allylacrylic phenol resins, and the like.
The acid anhydride-based curing agent is not limited to the following, and examples thereof include phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, maleic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylnadic anhydride, hexahydrophthalic anhydride, and methylhexahydrophthalic anhydride.
The catalyst-based curing agent is not limited to the following, and examples thereof include a cationic heat curing catalyst and BF 3 Amine complexes, and the like.
Among the above-mentioned various curing agents constituting the core, an amine-based curing agent comprising a low-molecular amine compound (a 1) and an amine adduct is preferable from the viewpoint of having moderate reactivity.
Examples of the low molecular amine compound (a 1) constituting the amine-based curing agent include a compound having at least 1 primary amino group and/or secondary amino group and no tertiary amino group, a compound having at least 1 tertiary amino group and at least 1 active hydrogen group, and the like.
The "compound having at least 1 primary amino group and/or secondary amino group and having no tertiary amino group" is not limited to, and examples thereof include primary amines having no tertiary amino group such as methylamine, ethylamine, propylamine, butylamine, ethylenediamine, propylenediamine, hexamethylenediamine, diethylenetriamine, triethylenetetramine, ethanolamine, propanolamine, cyclohexylamine, isophoronediamine, aniline, toluidine, diaminodiphenylmethane, diaminodiphenylsulfone, and the like; secondary amines having no tertiary amino group such as dimethylamine, diethylamine, dipropylamine, dibutylamine, dipentamine, dihexylamine, dimethanolamine, diethanolamine, dipropanolamine, dicyclohexylamine, piperidine, piperidone, diphenylamine, phenylmethylamine, and phenylethylamine, and the like.
The "compound having at least 1 tertiary amino group and at least 1 active hydrogen group" is not limited to the following, and examples thereof include amino alcohols such as 2-dimethylaminoethanol, 1-methyl-2-dimethylaminoethanol, 1-phenoxymethyl-2-dimethylaminoethanol, 2-diethylaminoethanol, 1-butoxymethyl-2-dimethylaminoethanol, methyldiethanolamine, triethanolamine, and N-. Beta. -hydroxyethylmorpholine; aminophenols such as 2- (dimethylaminomethyl) phenol and 2,4, 6-tris (dimethylaminomethyl) phenol; imidazoles such as 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-phenylimidazole, 1-aminoethyl-2-methylimidazole, 1- (2-hydroxy-3-phenoxypropyl) -2-ethyl-4-methylimidazole, 1- (2-hydroxy-3-butoxypropyl) -2-methylimidazole, and 1- (2-hydroxy-3-butoxypropyl) -2-ethyl-4-methylimidazole; 1- (2-hydroxy-3-phenoxypropyl) -2-phenylimidazoline, 1- (2-hydroxy-3-butoxypropyl) -2-methylimidazoline, 2, 4-dimethylimidazoline, 2-ethylimidazoline, 2-ethyl-4-methylimidazoline, 2-benzylimidazoline, 2-phenylimidazoline, 2- (o-tolyl) -imidazoline, tetramethylene-bisimidazoline, 1, 3-trimethyl-1, 4-tetramethylene-bisimidazoline imidazolines such as 1, 3-trimethyl-1, 4-tetramethylene-bisimidazoline, 1, 3-trimethyl-1, 4-tetramethylene-bis-4-methylimidazoline, 1, 3-trimethyl-1, 4-tetramethylene-bis-4-methylimidazoline, 1, 2-phenylene-bisimidazoline, 1, 3-phenylene-bisimidazoline, 1, 4-phenylene-bisimidazoline, and 1, 4-phenylene-bis-4-methylimidazoline; tertiary amino amines such as dimethylaminopropylamine, diethylaminopropylamine, dipropylaminopropylamine, dibutylaminopropylamine, dimethylaminoethylamine, diethylaminoethylamine, dipropylaminoethylamine, dibutylaminoethylamine, N-methylpiperazine, N-aminoethylpiperazine, diethylaminoethylpiperazine and the like; aminothiols such as 2-dimethylaminoethanethiol, 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-mercaptopyridine, and 4-mercaptopyridine; aminocarboxylic acids such as N, N-dimethylaminobenzoic acid, N-dimethylglycine, nicotinic acid, isonicotinic acid, picolinic acid, and the like; amino hydrazides such as N, N-dimethylglycine hydrazide, nicotinic acid hydrazide and isonicotinic acid hydrazide.
Among these low-molecular amine compounds (a 1), imidazoles are preferable from the viewpoint of having moderate reactivity.
Next, examples of the amine adduct constituting the amine-based curing agent include compounds having an amino group obtained by reacting each of the carboxylic acid compound, the sulfonic acid compound, the urea compound, the isocyanate compound, and the epoxy resin (e 1) with the amine compound (a 2).
The carboxylic acid compound is not limited to the following, and examples thereof include succinic acid, adipic acid, sebacic acid, phthalic acid, dimer acid, and the like.
The sulfonic acid compound is not limited to the following, and examples thereof include ethanesulfonic acid, p-toluenesulfonic acid, and the like.
The urea compound is not limited to the following, and examples thereof include urea, methyl urea, dimethyl urea, ethyl urea, t-butyl urea, and the like.
The isocyanate compound is not limited to the following, and examples thereof include aliphatic diisocyanate, alicyclic diisocyanate, aromatic diisocyanate, aliphatic triisocyanate, polyisocyanate and the like.
The aliphatic diisocyanate is not limited to the following, and examples thereof include ethylene diisocyanate, propylene diisocyanate, butylene diisocyanate, hexamethylene diisocyanate, and trimethylhexamethylene diisocyanate.
The alicyclic diisocyanate is not limited to the following, and examples thereof include isophorone diisocyanate, 4' -dicyclohexylmethane diisocyanate, norbornane diisocyanate, 1, 4-isocyanatocyclohexane, 1, 3-bis (isocyanatomethyl) cyclohexane, and 1, 3-bis (2-isocyanatoprop-2-yl) cyclohexane.
The aromatic diisocyanate is not limited to the following, and examples thereof include toluene diisocyanate, 4' -diphenylmethane diisocyanate, xylene diisocyanate, and 1, 5-naphthalene diisocyanate.
The aliphatic triisocyanate is not limited to the following, and examples thereof include 1,6, 11-undecane triisocyanate, 1, 8-diisocyanate-4-isocyanatomethyl octane, and 1,3, 6-triisocyanatomethyl hexane.
The polyisocyanate is not limited to the following, and examples thereof include polymethylene polyphenyl polyisocyanates, polyisocyanates derived from the aforementioned diisocyanate compounds, and the like. Examples of the polyisocyanate derived from the diisocyanate compound include isocyanurate type polyisocyanates, biuret type polyisocyanates, urethane type polyisocyanates, allophanate type polyisocyanates, and carbodiimide type polyisocyanates.
The epoxy resin (e 1) may be a compound described in the above ((a) epoxy resin).
As the amine compound (a 2), an amine compound exemplified as an example of the low molecular amine compound (a 1) constituting the amine-based curing agent can be used.
Among these amine adducts, those obtained by the reaction of the epoxy resin (e 1) with the amine compound (a 2) are particularly preferable. The amine adduct obtained by the reaction of the epoxy resin (e 1) and the amine compound (a 2) is also preferable from the viewpoint that the unreacted amine compound (a 2) can be used as the low-molecular amine compound (a 1).
From the viewpoint of storage stability, the core component of the (B) microcapsule-type curing agent preferably contains a curing agent that is solid at 25℃under 1013 hPa. Thus, even if the capsule is damaged when the components are mixed, the dissolution of the core component out of the capsule can be suppressed, and the storage stability can be maintained.
The average particle diameter of the core constituting the microcapsule-type curing agent (B) is preferably more than 0.3 μm and not more than 12. Mu.m. By making the average particle diameter of the core larger than 0.3 μm, the following effects are obtained: the aggregation of the cores can be further prevented, and the microcapsule-type curing agent (B) can be more easily formed, and the storage stability of the epoxy resin composition of the present embodiment is practically sufficient. When the average particle diameter of the core is 12 μm or less, a homogeneous cured product can be obtained when the epoxy resin composition of the present embodiment is cured. Further, by making the average particle diameter of the core 12 μm or less, the epoxy resin composition of the present embodiment can be mixed with a diluent, a filler, a pigment, a dye, a flow regulator, a thickener, a reinforcing agent, a mold release agent, a wetting agent, a stabilizer, a flame retardant, a surfactant, an organic solvent, conductive fine particles, crystalline alcohol, other resins, and the like, so that the formation of aggregates having a large particle diameter can be prevented, and sufficient long-term reliability of the cured product can be obtained. The average particle diameter of the core is preferably larger than 0.3 μm, more preferably 0.4 μm or more, and even more preferably 0.5 μm or more as the lower limit value. The upper limit is preferably 12 μm or less, more preferably 10 μm or less, and even more preferably 9 μm or less.
The average particle diameter of the core means an average particle diameter defined by a median particle diameter. More specifically, it means: stokes particle diameter was measured by a particle size distribution analyzer (HORIBA LA-920, manufactured by HORIBA, ltd.) using a laser diffraction/light scattering method.
The method for controlling the average particle diameter of the core to the above numerical range is not limited to the following method, and examples thereof include: a method of precisely controlling the pulverizing process of the block-shaped curing agent; a method of obtaining a substance having a desired average particle diameter by performing a coarse pulverizing step and a fine pulverizing step as a pulverizing step of a lump-shaped curing agent, and further classifying the resultant substance using a precise classifying device; and a method in which a solution obtained by dissolving a bulk curing agent in a solvent is spray-dried.
As a device used for pulverization, for example, a ball mill, an attritor, a bead mill, a jet mill, or the like can be used as needed, and an impact pulverizing device is preferably used. Examples of the impact mill include a rotary fluid powder impact jet mill, a powder impact type reverse jet mill, and the like. Jet milling is a device that uses high-speed jet streams with air or the like as a medium to impact solid materials with each other and to atomize them. As a method of precisely controlling the pulverization step, there are a method of controlling the temperature, humidity, pulverization amount per unit time, and the like at the time of pulverization. Examples of the method for classifying the material having a desired average particle diameter after the pulverizing step using a precise classifying device include: a method of classifying the powder particles by using a sieve (for example, a standard sieve of 325 mesh, 250 mesh, or the like) or a classifier to obtain a powder particle having a predetermined average particle diameter after pulverization; a method of classifying by wind force according to the specific gravity of the particles, and the like. Examples of the classifier used include a wet classifier and a dry classifier, and a dry classifier is generally preferred. As a result of this type of Classifier, examples thereof include "Elbow-Jet" manufactured by the japanese iron industry company, "Fine Sharp Separator" manufactured by the Hosokawa Micron company, "Variable Impactor" manufactured by the Sanyoshi electric industry company, "Spedic Classifier" manufactured by the Sai Xin corporation, "donalsec" manufactured by the japan DONALDSON company, "YM Microcassette" manufactured by the An Chuan business company, "Turbo classification" manufactured by the japanese engineering company, "and other various gas separators, micron separators, dry classification devices such as MICROPLEX, ACCU-CUT, but is not limited to where they are located.
As a method of directly granulating the particles of the curing agent constituting the core without pulverization, there is a method of spray-drying a solution obtained by dissolving a bulk curing agent in a solvent. Specifically, there may be mentioned: and a method in which the curing agent constituting the core is uniformly dissolved in an appropriate organic solvent, sprayed in the form of fine droplets in a solution state, and then dried by hot air or the like. The drying apparatus in this case may be a conventional spray drying apparatus.
Further, as a method of granulating the granules of the curing agent, there are: the curing agent constituting the core is uniformly dissolved in an appropriate organic solvent, and thereafter, a poor solvent for the curing agent constituting the core is added while the solution is strongly stirred uniformly, whereby the curing agent constituting the core is precipitated in the form of fine particles. Then, the precipitated particles are separated by filtration, and then the solution is dried and removed at a low temperature equal to or lower than the melting point of the solidifying agent constituting the core.
As a method of adjusting the average particle diameter of the curing agent constituting the core in the particle state by a method other than classification, for example, a method of adjusting the average particle diameter by mixing a plurality of kinds of particles having different average particle diameters, and the like can be cited. For example, in the case of a large-particle-diameter curing agent which is difficult to crush and classify, a curing agent having an average particle diameter in the above range can be produced by adding and mixing a small-particle-diameter curing agent different from the large-particle-diameter curing agent.
The curing agent thus obtained may be further classified as required. Examples of mixers used for the purpose of mixing such powders include: a container rotary mixer for rotating a container body containing powder to be mixed; a container-fixing mixer for mixing by mechanical stirring and air flow stirring without rotating a container body containing powder; a composite mixer in which a container containing powder is rotated and mixed by other external force is also used.
The shape of the core constituting the microcapsule-type curing agent (B) is not limited to the following shape, and may be any of, for example, a granular shape, a powdery shape, an irregular shape, a shape with a curvature at the corners of the irregular shape, and the like.
The shape of the core constituting the microcapsule-type curing agent (B) is preferably closer to a positive sphere. The closer the core is to a positive sphere, the more uniformly a capsule film is formed as a shell described later, and the component (B) tends to exhibit low aggregation, excellent storage stability and excellent solvent resistance. The degree of approach to a positive sphere is expressed in terms of circularity, and the circularity of the positive sphere is 1. The circularity of the core of the component (B) is preferably 0.93 or more, more preferably 0.95 or more, and still more preferably 0.98 or more.
The circularity of the core constituting the microcapsule-type curing agent (B) can be measured by a flow-type particle image analysis method. More specifically, the particle diameter can be obtained by flowing the measurement sample in a liquid, photographing particles, obtaining the particle diameter from the particle projection area, and calculating the ratio of the circumference of the particle projection image to the circumference of the particle diameter equivalent circle.
The method of controlling the circularity of the core is not particularly limited, but a method of performing surface modification of a curing agent constituting the core is effective. Examples of the method include mechanically rounding the particles and subjecting the particles to hot air treatment.
< Shell >
(B) The microcapsule-type curing agent preferably has a structure in which the surface of the core is covered with a shell containing a synthetic resin and/or an inorganic oxide. Among these, the shell constituting the (B) microcapsule-type curing agent preferably contains a synthetic resin from the viewpoints of the stability of the film constituting the shell, the ease of breakage upon heating, and the uniformity of the cured product of the epoxy resin composition of the present embodiment.
The synthetic resin contained in the shell is not limited to the following, and examples thereof include epoxy resins, phenol resins, polyester resins, polyethylene resins, nylon resins, polystyrene resins, and urethane resins. Among these, the synthetic resin is preferably an epoxy resin, a phenol resin, or a urethane resin from the viewpoint of a balance between stability of a film constituting the shell and destructiveness upon heating.
The epoxy resin used in the shell is not limited to the following, and examples thereof include an epoxy resin having 2 or more epoxy groups, a resin produced by a reaction between an epoxy resin having 2 or more epoxy groups and a compound having 2 or more active hydrogens, a reaction product of a compound having 2 or more epoxy groups and a compound having a carbon-carbon double bond and 1 active hydrogen, and the like. Among these, from the viewpoint of stability, a resin produced by the reaction of a compound having 2 or more epoxy groups and a compound having 2 or more active hydrogens is preferable, and particularly, a reaction product of an amine-based curing agent and an epoxy resin having 2 or more epoxy groups is more preferable.
The phenol resin is not limited to the following, and examples thereof include phenol-formaldehyde polycondensates, cresol-formaldehyde polycondensates, resorcinol-formaldehyde polycondensates, bisphenol a-formaldehyde polycondensates, polyethylene polyamine modified products of phenol-formaldehyde polycondensates, and the like.
The polyester resin is not limited to the following, and examples thereof include ethylene glycol-terephthalic acid-polypropylene glycol polycondensate, ethylene glycol-butanediol-terephthalic acid polycondensate, terephthalic acid-ethylene glycol-polyethylene glycol polycondensate, and the like.
The polyethylene resin is not limited to the following, and examples thereof include ethylene-propylene-vinyl alcohol copolymer, ethylene-vinyl acetate-acrylic acid copolymer, and the like.
The nylon-based resin is not limited to the following, and examples thereof include adipic acid-hexamethylenediamine polycondensate, sebacic acid-hexamethylenediamine polycondensate, and p-phenylenediamine-terephthalic acid polycondensate.
The polystyrene resin is not limited to the following, and examples thereof include styrene-butadiene copolymer, styrene-butadiene-acrylonitrile copolymer, acrylonitrile-styrene-divinylbenzene copolymer, and styrene-propenyl alcohol copolymer.
Examples of the urethane resin include, but are not limited to, butyl isocyanate, cyclohexyl isocyanate, octadecyl isocyanate, phenyl isocyanate, toluene diisocyanate, diphenylmethane diisocyanate, xylylene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, tolidine diisocyanate, naphthalene diisocyanate, triphenylmethane triisocyanate, and the like, and condensates thereof, and polycondensates of polymers thereof with monohydric alcohols and polyhydric alcohols. Among these, urethane resins which are addition polymers of a monohydric alcohol or a polyhydric alcohol with a monoisocyanate or a polyisocyanate are preferable.
The inorganic oxide is not limited to the following, and examples thereof include boron compounds such as boron oxide and boric acid esters; silicon dioxide calcium oxide, and the like. Among these, boron oxide is preferable from the viewpoints of stability of the film constituting the shell and easiness of breakage upon heating.
In addition, from the viewpoint of balance between storage stability and curability of the epoxy resin composition of the present embodiment, the shell preferably contains 1 or 2 or more reaction products selected from the group consisting of isocyanate compounds, active hydrogen compounds, curing agents for epoxy resins, and amine compounds.
As the isocyanate compound, an isocyanate compound exemplified as a raw material of the amine adduct contained in the core can be used.
The active hydrogen compound is not limited to the following, and examples thereof include water, a compound having at least 1 primary amino group and/or secondary amino group, a compound having at least 1 hydroxyl group, and the like. These active hydrogen compounds may be used alone or in combination of 1 or more than 2.
The compound having at least 1 primary amino group and/or secondary amino group is not limited to the following, and examples thereof include aliphatic amines, alicyclic amines, and aromatic amines.
The aliphatic amine is not limited to the following, and examples thereof include alkylamines such as methylamine, ethylamine, propylamine, butylamine, dibutylamine, and the like; alkylene diamines such as ethylenediamine, propylenediamine, butylenediamine, hexamethylenediamine, and the like; polyalkylene polyamines such as diethylenetriamine, triethylenetetramine and tetraethylenepentamine; and polyoxyalkylene polyamines such as polyoxypropylene diamine and polyoxyethylene diamine.
The alicyclic amine is not limited to the following, and examples thereof include cyclopropylamine, cyclobutylamine, cyclopentylamine, cyclohexylamine, isophoronediamine, and the like.
The aromatic amine is not limited to the following, and examples thereof include aniline, toluidine, benzylamine, naphthylamine, diaminodiphenylmethane, and diaminodiphenylsulfone.
Examples of the compound having at least 1 hydroxyl group include alcohol compounds and phenol compounds.
Examples of the alcohol compound include, but are not limited to, monohydric alcohols such as methanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecyl alcohol, lauryl alcohol, dodecyl alcohol, stearyl alcohol, eicosanol, allyl alcohol, crotyl alcohol, propargyl alcohol, cyclopentanol, cyclohexanol, benzyl alcohol, cinnamyl alcohol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, and diethylene glycol monobutyl ether; polyhydric alcohols such as ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, 1, 3-butanediol, 1, 4-butanediol, hydrogenated bisphenol A, neopentyl glycol, glycerol, trimethylolpropane, pentaerythritol, etc.; polyols such as compounds having 2 or more secondary hydroxyl groups in 1 molecule obtained by reacting a compound having at least 1 epoxy group with a compound having at least 1 hydroxyl group, carboxyl group, primary amino group, secondary amino group or thiol group.
These alcohol compounds may be any of primary alcohols, secondary alcohols, tertiary alcohols.
The phenol compounds are not limited to the following, and examples thereof include monophenols such as phenol, cresol, xylenol, carvacrol, thymol, and naphthol; polyphenols such as catechol, resorcinol, hydroquinone, bisphenol A, bisphenol F, pyrogallol, phloroglucinol, 2- (dimethylaminomethyl) phenol, and 2,4, 6-tris (dimethylaminomethyl) phenol.
These compounds having at least 1 hydroxyl group are preferably polyols and polyphenols, more preferably polyols, from the viewpoints of potential and solvent resistance.
The reaction conditions for preparing 1 or 2 or more reaction products selected from the group consisting of isocyanate compounds, active hydrogen compounds, curing agents for epoxy resins, epoxy resins and amine compounds contained in the shell constituting the microcapsule-type curing agent (B) as described above are not particularly limited, and the reaction time is usually in the temperature range of-10 to 150 ℃ and 10 minutes to 12 hours.
The compounding ratio when the isocyanate compound and the active hydrogen compound are used for preparing the reaction product contained in the shell is preferably in the range of 1:0.1 to 1:1000 in terms of (isocyanate group in isocyanate compound): (active hydrogen in active hydrogen compound) (equivalent ratio).
The reaction may be carried out in a predetermined dispersion medium as required.
Examples of the dispersion medium include solvents, plasticizers, resins, and the like.
The solvent is not limited to the following, and examples thereof include hydrocarbons such as benzene, toluene, xylene, cyclohexane, mineral spirits, and naphtha; ketones such as acetone, methyl Ethyl Ketone (MEK), and methyl isobutyl ketone (MIBK); esters such as ethyl acetate, n-butyl acetate, propylene glycol monomethyl ethyl ether acetate, and the like; alcohols such as methanol, isopropanol, n-butanol, butyl cellosolve, butyl carbitol, and the like; water, and the like.
The plasticizer is not limited to the following, and examples thereof include phthalic acid diester plasticizers such as dibutyl phthalate and di (2-ethylhexyl) phthalate; aliphatic dibasic acid ester plasticizers such as di (2-ethylhexyl) adipate; triester-based plasticizers such as tricresyl phosphate; glycol ester plasticizers such as polyethylene glycol esters, and the like.
The resins are not limited to the following, and examples thereof include silicone resins, epoxy resins, and phenolic resins.
Among the above, the reaction of the epoxy resin with the curing agent for epoxy resin is usually carried out at a temperature ranging from-10℃to 150℃and preferably from 0℃to 100℃for a reaction time ranging from 1 hour to 168 hours and preferably from 2 hours to 72 hours. The dispersion medium is preferably a solvent or a plasticizer.
The reaction product contained in the above-described shell is usually 1 mass% or more, preferably 50 mass% or more, and may be 100 mass% or more based on the mass% of the shell.
In the microcapsule-type curing agent (B), as a method of forming a shell covering the surface of the core, for example, the following methods (1) to (3) are mentioned.
(1): and a method in which the capsule component and the particles of the curing agent are dissolved/dispersed in a solvent as a dispersion medium, and then the solubility of the capsule component in the dispersion medium is reduced to precipitate the capsules on the particle surfaces of the curing agent for epoxy resin.
(2): and a method in which particles of a curing agent are dispersed in a dispersion medium, and a material forming the capsule is added to the dispersion medium and precipitated onto the particles of the curing agent.
(3): a method of adding a raw material component for forming a capsule to a dispersion medium, and forming a shell-forming material with the particle surface of a curing agent as a reaction site.
The methods (2) and (3) are preferable because they allow simultaneous reaction and coverage.
In the methods (1) to (3), the dispersion medium may be a solvent, a plasticizer, a resin, or the like. As the solvent, plasticizer, and resin, those exemplified as solvents, plasticizers, and resins that can be used in preparing a reaction product of 1 or 2 or more selected from the group consisting of the above-mentioned isocyanate compounds, active hydrogen compounds, curing agents for epoxy resins, and amine compounds can be used.
After the shell is formed by the methods (2) and (3), the method of separating the microcapsule-type curing agent (B) from the dispersion medium is not particularly limited, and the unreacted raw material after the shell is formed is preferably separated and removed together with the dispersion medium. As such a method, a method of removing the dispersion medium and unreacted shell-forming material by filtration is exemplified.
Preferably, the microcapsule-type curing agent is washed after the dispersion medium is removed. By washing with the microcapsule-type curing agent, unreacted shell-forming material adhering to the surface can be removed.
The cleaning method is not particularly limited, and in the case of filtering the residue, the cleaning may be performed using a dispersion medium or a solvent in which the microcapsule-type curing agent is not dissolved. The microcapsule-type curing agent can be obtained in a powdery form by drying the microcapsule-type curing agent after filtration and washing. The drying method is not particularly limited, and drying is preferably performed at a temperature equal to or lower than the melting point or softening point of the curing agent, and examples thereof include drying under reduced pressure. The microcapsule-type curing agent can be easily compounded with the epoxy resin (a) by being powdered. In addition, when an epoxy resin is used as the dispersion medium, a masterbatch of a microcapsule-type curing agent integrated with the epoxy resin can be obtained at the same time as the shell is formed, and thus it is preferable.
The shell-forming reaction is usually carried out at a temperature ranging from-10 ℃ to 150 ℃, preferably from 0 ℃ to 100 ℃ for a reaction time ranging from 10 minutes to 72 hours, preferably from 30 minutes to 24 hours.
In addition, from the viewpoint of balance between storage stability and reactivity, the shell constituting the (B) microcapsule-type curing agent preferably has an absorption wave number of 1630 to 1680cm -1 Is an infrared urea-binding group having an absorption wave number of 1680 to 1725cm -1 The infrared biuret bonding groups and the absorption wave numbers of 1730-1755 cm -1 An infrared urethane linkage group of (a).
The urea bonding group, the biuret bonding group, and the urethane bonding group can be detected by measurement using a fourier transform infrared spectrophotometer (hereinafter, sometimes referred to as "FT-IR"), and the shell having the urea bonding group, the biuret bonding group, and the urethane bonding group can be confirmed by microscopic FT-IR.
Specifically, the modified aliphatic polyamine curing agent was added to the epoxy resin composition of the present embodiment, and it took 12 hours to cure the composition at 40 ℃, and thereafter, it took 24 hours to further partially and completely cure the epoxy resin at 120 ℃. Thereafter, a sample having a thickness of 5 to 20 μm was prepared from the obtained cured product by using a microtome, and the depth direction of the shell was analyzed by using a microscopic FT-IR. The presence of urea bonding groups, biuret bonding groups, urethane bonding groups can be observed by observation in the vicinity of the shell surface.
The thickness of the shell constituting the microcapsule-type curing agent (B) is preferably 5nm to 1000nm, more preferably 10nm to 100 nm. The storage stability of the epoxy resin composition of the present embodiment can be further improved by setting the thickness of the shell to 5nm or more. In addition, the curability can be further improved by setting the thickness of the shell to 1000nm or less. The thickness mentioned here is an average layer thickness, and can be measured by a transmission electron microscope.
When the amount of the (a) epoxy resin is 100 parts by mass, the amount of the (B) microcapsule-type curing agent in the epoxy resin composition of the present embodiment is preferably 1 part by mass or more, more preferably 5 parts by mass or more, still more preferably 10 parts by mass or more, still more preferably 20 parts by mass or more, still more preferably 30 parts by mass or more, from the viewpoint of imparting sufficient reactivity.
Further, from the viewpoint of suppressing aggregation of the (B) microcapsule-type curing agents with each other, from the viewpoint of imparting sufficient mechanical strength to the cured product, and from the viewpoint of imparting sufficient storage stability to the epoxy resin composition, it is preferably 100 parts by mass or less, more preferably 90 parts by mass or less, further preferably 80 parts by mass or less, further preferably 75 parts by mass or less, further preferably 70 parts by mass or less.
Component (C) reactive diluent
The epoxy resin composition of the present embodiment contains component (C): reactive diluents (hereinafter sometimes referred to as (C) reactive diluents, component (C)).
The reactive diluent is a compound having an epoxy group or an acryl group capable of being incorporated into a cured structure, and has an effect of reducing the viscosity of the epoxy resin composition by being contained in the epoxy resin composition of the present embodiment.
The reactive diluent (C) is not limited to the following, and examples thereof include (meth) acrylate compounds and epoxy compounds that can achieve low viscosity without impairing reactivity.
In the present specification, a compound having a viscosity of 1mpa·s or more and less than 3pa·s at 25 ℃ other than the compound exemplified in the epoxy resin (a) above is used as a reactive diluent.
In the epoxy resin composition of the present embodiment, the reactive diluent (C) is preferably an epoxy compound from the viewpoints of good compatibility with the epoxy resin (a) and the microcapsule curing agent (B) and incorporation into the cured structure after the reaction.
The (meth) acrylate compound used as the (C) reactive diluent is not limited to the following, and examples thereof include compounds having (meth) acryloyl groups at both ends of a polyalkylene oxide, polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, polybutylene glycol di (meth) acrylate, trimethylolpropane type polyfunctional (meth) acrylate, pentaerythritol type polyfunctional (meth) acrylate, dipentaerythritol type polyfunctional (meth) acrylate, and the like. Specifically, examples of the difunctional (meth) acrylate compound having 2 or more aromatic rings include compounds having a (meth) acrylate structure at both ends by adding polyalkylene oxide to bisphenol a, and examples of the monofunctional (meth) acrylate compound having 1 aromatic ring include phenyl (meth) acrylate and ethylene glycol monophenyl ether (meth) acrylate.
The epoxy compound used as the reactive diluent (C) is not limited to the following, and examples thereof include epoxy compounds having no aromatic ring and epoxy compounds having an aromatic ring.
Examples of the monofunctional epoxy compound having no aromatic ring include compounds such as n-butyl glycidyl ether, t-butyl glycidyl ether, allyl glycidyl ether, and 2-ethylhexyl glycidyl ether.
Examples of the monofunctional epoxy compound having 1 or more aromatic rings include styrene oxide, phenyl glycidyl ether, tolyl glycidyl ether, p-sec-butylphenyl glycidyl ether, t-butylphenyl glycidyl ether, trade names manufactured by sakazapresent pharmaceutical industry company: SY-OPG and the like.
Examples of the difunctional epoxy compound having no aromatic ring include 1, 4-cyclohexanedimethanol diglycidyl ether, 1, 3-cyclohexanedimethanol diglycidyl ether, (3, 4-epoxycyclohexyl) methyl-3, 4-epoxycyclohexyl carboxylate, ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1, 6-hexanediol diglycidyl ether, neopentyl glycol diglycidyl ether, dicyclopentadiene dimethanol diglycidyl ether, and trade names of mitsubishi chemical company: trade name of YX-8000, manufactured by sakazakii pharmaceutical industry company: SR-8EGS and the like.
Examples of the difunctional epoxy compound having 1 or more aromatic rings include compounds such as diglycidyl ether of hexahydrophthalic acid, diglycidyl ether of resorcinol, diglycidyl ether of tert-butylhydroquinone, diglycidyl ether of polyoxyalkylene bisphenol a, N-diglycidyl aniline, and N, N-diglycidyl o-toluidine.
Examples of the trifunctional epoxy compound include trimethylolpropane triglycidyl ether, glycerol triglycidyl ether, and N, N-bis (2, 3-epoxypropyl) -4- (2, 3-epoxypropoxy) aniline.
In the epoxy resin composition of the present embodiment, (C) the reactive diluent preferably has an aromatic ring from the viewpoint of improving solvent resistance. Further, from the viewpoint of further improving solvent resistance, the reactive diluent (C) is more preferably a monofunctional compound having a single aromatic ring and having a monofunctional functional group, particularly preferably an epoxy group or an acryl group. Further, the monofunctional group is more preferably an epoxy group from the viewpoint of exhibiting sufficient mechanical strength by incorporation of the component (C) into the cured product of the epoxy resin composition of the present embodiment after the reaction. As will be described later, the number of carbon atoms of each substituent of the aromatic ring is particularly preferably 3 or less from the viewpoint of improving the invasiveness of the component (B) into the capsule film and improving the solvent resistance.
On the other hand, from the viewpoint of suppressing the reaction of (C) the reactive diluent with (A) the epoxy resin and improving the storage stability, the (C) reactive diluent preferably contains no nitrogen atom.
The mechanism of improving the solvent resistance of the epoxy resin composition of the present embodiment by using the above-described structure for the (C) reactive diluent is not limited to this, but may be considered as follows.
In the case where the reactive diluent (C) has an aromatic ring, the aromatic rings of the reactive diluent incorporated in the shell of the microcapsule-type curing agent (B) exhibit a stacking effect with each other to form a network, and thus the aggregation force of the shell can be improved. Therefore, a shell that is not easily swelled even with a solvent can be constructed, and the solvent resistance of the epoxy resin composition of the present embodiment can be improved.
In addition, since the reactive diluent (C) is a monofunctional compound in which the aromatic ring is a single ring, the steric hindrance is reduced, and thus the reactive diluent (C) is liable to intrude into the shell, and a stacked network of aromatic rings can be formed in a more dense and wide region. Here, by setting the number of carbon atoms of each substituent of the aromatic ring to 3 or less, steric hindrance can be further reduced, invasion into the interior of the shell can be improved, and solvent resistance can be further improved.
The amount of the reactive diluent (C) to be added is preferably 1% by mass or more, more preferably 3% by mass or more, further preferably 4% by mass or more, further preferably 5% by mass or more, further preferably 6% by mass or more, relative to the entire epoxy resin composition of the present embodiment, from the viewpoint of imparting sufficient solvent resistance. In addition, from the viewpoint of suppressing excessive lowering of viscosity, deterioration of storage stability, and reduction of mechanical strength of the cured product, it is preferably 20% by mass or less, more preferably 15% by mass or less, further preferably 13% by mass or less, further preferably 12% by mass or less, further preferably 11% by mass or less.
Component (D) A compound represented by the formula (1)
The epoxy resin composition of the present embodiment contains, as the component (D), a compound represented by the following formula (1) (hereinafter, sometimes referred to as the component (D)).
By containing the component (D), the epoxy resin composition of the present embodiment can improve low viscosity and low-temperature curability while maintaining high storage stability, and can ensure a sufficiently cured region when the heat conduction system is not uniform.
In the formula (1), X 1 Having more than 2 and less than 5 consecutive carbon-carbon bonds. X is X 1 Substituents of carbon contained in (a) and R 1 ~R 5 Each is one selected from the group consisting of hydrogen, an alkyl group, an unsaturated aliphatic group, an aromatic group, a substituent containing a hetero atom, a substituent containing a halogen atom, and a halogen atom. X is X 1 Substituents of carbon contained in (a) and R 1 ~R 5 Optionally the same or different from each other. And the compound of formula (1) is optionally selected from R 1 ~R 5 Any of which are fused ring compounds present in the same ring.
The compound represented by the above formula (1) is not limited to the following, and examples thereof include 3-phenoxy-1-propanol, 3-phenoxy-1, 2-propanediol, 3-phenoxy-1, 3-propanediol, cresol glycerol ether (3- (o-tolyloxy-1, 2-propanediol), guaifenesin (3- (2-methoxyphenoxy) propane-1, 2-diol), bisphenol a (3-hydroxypropyl) glycidyl ether, bisphenol a (2, 3-dihydroxypropyl) glycidyl ether, the following compound 1, compound 2, and compound 3.
3- (4- (2- (2-hydroxy-3- (4- (2- (4- (ethylene oxide-2-ylmethoxy) phenyl) propan-2-yl) phenoxy) propoxy) -3- (4- (2- (4- (ethylene oxide-2-ylmethoxy) phenyl) propan-2-yl) phenoxy) propoxy) phenyl) propan-2-yl) phenoxy) propane-1, 2-diol
3- (4- (2- (4- (3- ((1, 3-bis) (4- (2- (4- (oxiran-2-ylmethoxy) phenyl) propan-2-yl)) phenoxy)
Propan-2-yl) oxy) -2-hydroxypropoxy) phenyl) propan-2-yl) phenoxy) propane-1, 2-diol
3- (4- (2- (4- (2-hydroxy-3- (4- (2- (4- (ethylene oxide-2-ylmethoxy) phenyl) propan-2-yl) phenoxy) propoxy) phenyl) propan-2-yl) phenoxy) propane-1, 2-diol
The mechanism by which the low viscosity property and the low temperature curability of the epoxy resin composition of the present embodiment are improved and the effect of improving the cured region is exhibited as the component (D) is not limited to this, but may be considered as follows.
(A) The interaction such as stacking of aromatic rings and hydrogen bonding between the epoxy resins is replaced with the interaction between the epoxy resin (a) and the component (D) by the aromatic group or hydroxyl group of the component (D), and the interaction between the epoxy resins (a) is eliminated, so that the entire epoxy resin composition is liable to undergo molecular movement, and thus the viscosity is reduced. In addition, when curing, a coordinate bond is formed between the hydroxyl group of the component (D) and the curing agent component in the microcapsule-type curing agent (B), so that the compatibility between the curing agent component and the epoxy resin (a) is improved, the diffusivity of the curing agent in the epoxy resin composition is improved, and a rapid reaction at a lower temperature can be realized. Further, it can be considered that: since the epoxy resin composition of the present embodiment contains the reactive diluent (C), the epoxy resin composition is further reduced in viscosity, and the above-mentioned diffusivity is markedly improved. Further, it can be considered that the above mechanism: particularly excellent improvement in reactivity is exhibited when the compatibility of the components (D), (a) epoxy resin and (C) reactive diluent is good.
In addition, in this mechanism, the component (D) plays a catalytic role in the reaction of the curing agent and the epoxy group until incorporated into the polymer.
The improvement of the cured region contributes to the improvement of the compatibility of the curing agent after the coordination of the component (D) with the epoxy resin (A) and the reactive diluent (C) and the improvement of the component diffusivity. The interaction, effect on complexation, compatibility is significantly affected by the molecular structure. Therefore, in the epoxy resin composition of the present embodiment, the component (D) contains the compound represented by the above formula (1).
The component (D) is preferably a compound represented by the following formula (2) from the viewpoint of suppressing steric hindrance when forming a coordinate bond with the curing agent component in the microcapsule-type curing agent (B) and exhibiting good curing characteristics.
In the formula (2), X 2 Having more than 2 and less than 4 consecutive carbon-carbon bonds, X 2 Substituents of carbon contained in (a) and R 1 ~R 5 Each is one selected from the group consisting of hydrogen, an alkyl group, an unsaturated aliphatic group, an aromatic group, a substituent containing a hetero atom, a substituent containing a halogen atom, and a halogen atom. X is X 2 Substituents of carbon contained in (a) and R 1 ~R 5 Optionally the same or different from each other. And the compound represented by formula (2) is optionally selected from R 1 ~R 5 Any of which is presentFused ring compounds in the same ring.
From the viewpoint of good dispersibility in epoxy resins after formation of coordination bonds with the curing agent component in the microcapsule-type curing agent (B), the component (D) is more preferably a compound having 2 continuous carbon-carbon bonds represented by the following formula (3).
In the formula (3), R 1 ~R 9 Each is one selected from the group consisting of hydrogen, an alkyl group, an unsaturated aliphatic group, an aromatic group, a substituent containing a hetero atom, a substituent containing a halogen atom, and a halogen atom.
R 1 ~R 9 Optionally the same or different from each other. And the compound represented by formula (3) is optionally selected from R 1 ~R 5 Any of which are fused ring compounds present in the same ring.
From the viewpoints of improving the solvent resistance stability, the stability at the time of producing a film, and the storage stability of a film, the component (D) is more preferably R in the above formula (3) shown by the following formula (4) 9 A compound which is a hydroxyl group.
In the formula (4), R 1 ~R 8 Each is one selected from the group consisting of hydrogen, an alkyl group, an unsaturated aliphatic group, an aromatic group, a substituent containing a hetero atom, a substituent containing a halogen atom, and a halogen atom.
R 1 ~R 8 Optionally the same or different from each other. And the compound represented by formula (4) is optionally selected from R 1 ~R 5 Any of which are fused ring compounds present in the same ring.
In addition, R of the compounds represented by the above formulas (3) and (4) as the component (D) is selected from the viewpoint of reducing steric hindrance for improving the complexation in the hardener component 6 、R 7 、R 8 Preferably a hydrogen atom.
From the viewpoint of effectively acting component (D), R in the compounds represented by the above formulas (1) to (4) of component D 1 ~R 5 Preferably contains no epoxy group and a structure of the following formula (5) (terminal diol structure).
The compounds represented by the above formulas (1) to (4) as the component (D) are produced by reacting R 1 ~R 5 The epoxy group is not contained, so that the epoxy group is not incorporated into a curing reaction system and can play a role for a long time.
In addition, R 1 ~R 5 The structure of the above formula (5) is provided, and the compound of the above formulae (1) to (4) has 2 or more functional groups capable of coordinate bonding with the curing agent in a positional relationship in which the steric hindrance effect is small, and as a result, coordinate bonds are formed between a plurality of molecules, whereby the molecular mobility is reduced. Accordingly, R in the compounds of the formulae (1) to (4) 1 ~R 5 Preferably, the structure of the aforementioned formula (5) (terminal diol structure) is not contained.
As an index of compatibility, there is an sp value (δ), and when the difference between sp values of the compounds is small, good compatibility is exhibited.
Since the component (D) has excellent compatibility with respect to the epoxy resin (a) and the reactive diluent (C), and the complex compound formed by the component (D) being coordinated with the curing agent has excellent compatibility with respect to the epoxy resin (a) and the reactive diluent (C), the epoxy resin composition of the present embodiment further exhibits the effects of reducing the viscosity, improving the low-temperature curability, and improving the cured region, and therefore the sp value of the component (D) preferably has a value similar to the sp value of the epoxy resin (a) and the reactive diluent (C).
The values described in polymeresinering AND SCIENCE, FEBRUARY,1974,Vol.14,No.2 by ROBERT f.fedors are used to determine the sp values of the respective compounds at 25 ℃ by the calculation method of Fedors (formula (i)).
In the following formula, δ represents an sp value.
δ=(ΣΔe/ΣΔv) 1/2 … math (i)
Δe represents cohesive energy of each substituent, and Δv represents molar molecular volume.
[ component (A) ]
Bisphenol a epoxy resin (n=0 body) … δ=10.9 (cal/cm) 3 ) 1/2
Bisphenol F type epoxy resin (n=0 body) … δ=12.1 (cal/cm) 3 ) 1/2
1, 6-bis (2, 3-epoxypropoxy) naphthalene … δ=13.1 (cal/cm) 3 ) 1/2
[ component (C) ]
Phenyl glycidyl ether … delta=10.6 (cal/cm 3 ) 1/2
O-tolylglycidyl ether … delta=9.7 (cal/cm 3 ) 1/2
1, 6-hexanediol diglycidyl ether … delta=9.8 (cal/cm 3 ) 1/2
[ component (D) ]
3-phenoxy-1-propanol … delta=12.0 (cal/cm) 3 ) 1/2
3-phenoxy-1, 2-propanediol … δ=14.3 (cal/cm) 3 ) 1/2
Cresol glycerol ether … delta=13.0 (cal/cm) 3 ) 1/2
Guaifenesin … delta=13.0 (cal/cm) 3 ) 1/2
Bisphenol a (3-hydroxypropyl) glycidyl ether … δ=11.6 (cal/cm) 3 ) 1/2
Bisphenol a (2, 3-dihydroxypropyl) glycidyl ether … δ=12.9 (cal/cm) 3 ) 1/2
Compound 1 … δ=12.0 (cal/cm 3 ) 1/2
Compound 2 … δ=12.0 (cal/cm 3 ) 1/2
Compound 3 … δ=12.6 (cal/cm 3 ) 1/2
From the viewpoint of further exhibiting the effects of lowering the viscosity, improving the low-temperature curability, and improving the cured region of the epoxy resin composition of the present embodiment, the epoxy resin (A) and/or the reactive diluent (C) contain an sp value of 9 to 14 (cal/cm 3 ) 1/2 In the case of the epoxy resin of (C), the sp value of the component (D) is preferably 7 (cal/cm) 3 ) 1/2 Above, more preferably 8 (cal/cm 3 ) 1/2 Above, it is more preferably 9 (cal/cm 3 ) 1/2 The above is more preferably 10 (cal/cm 3 ) 1/2 As described above, it is still more preferably 11 (cal/cm 3 ) 1/2 The above. As the upper limit value, it is preferably less than 20 (cal/cm 3 ) 1/2 More preferably 18 (cal/cm) 3 ) 1/2 Hereinafter, it is more preferably 16 (cal/cm 3 ) 1/2 The following is given.
The amount of the component (D) to be added is preferably 0.001 mass% or more, more preferably 0.005 mass% or more, still more preferably 0.01 mass% or more, and still more preferably 0.012 mass% or more, based on the entire epoxy resin composition, from the viewpoint of sufficiently exhibiting the effects of reducing the viscosity and improving the reactivity of the catalytic properties of the epoxy resin composition of the present embodiment. From the viewpoint of suppressing deterioration of storage stability due to excessive addition, it is preferably 5% by mass or less, more preferably 3% by mass or less, further preferably 2.5% by mass or less, and further preferably 2% by mass or less.
The component (D) may be added at the time of mixing with other components, may be produced in a system after mixing, and may be produced in a system at the time of producing the epoxy resin (A), the microcapsule-type curing agent (B) and the reactive diluent (C).
(other additives)
The epoxy resin composition of the present embodiment may further contain, as a curing agent and an additive other than the microcapsule-type curing agent (B), an organic filler, an inorganic filler, a pigment, a dye, a flow regulator, a thickener, a release agent, a wetting agent, a flame retardant, a surfactant, a resin, and the like, as required, in addition to the above-described components.
Examples of the curing agent other than the microcapsule-type curing agent (B) include curing agents and active ester compounds listed in the core component of the microcapsule-type curing agent.
The organic filler has a function as an impact modifier capable of relaxing stress generated by an impact.
The epoxy resin composition of the present embodiment can further improve adhesion to various connecting members by containing an organic filler. In addition, the occurrence and the progress of the fillet crack tend to be suppressed.
Examples of the organic filler include, but are not limited to, organic fine particles of acrylic resins, silicone resins, butadiene rubbers, polyesters, polyurethanes, polyvinyl butyrals, polyarylates, polymethyl methacrylates, acrylic rubbers, polystyrene, NBR, SBR, silicone-modified resins, and copolymers containing these as components.
From the viewpoint of improving the adhesion, examples of the organic fine particles include alkyl (meth) acrylate-butadiene-styrene copolymer, alkyl (meth) acrylate-silicone copolymer, silicone- (meth) acrylic copolymer, a composite of silicone and (meth) acrylic acid, a composite of alkyl (meth) acrylate-butadiene-styrene and silicone, and a composite of alkyl (meth) acrylate and silicone.
As the organic fine particles, organic fine particles having a core-shell structure and having a core layer and a shell layer having different compositions may be used. Examples of the core-shell type organic fine particles include particles having an acrylic resin grafted thereto with a silicone-acrylic rubber as a core, and particles obtained by grafting an acrylic resin to an acrylic copolymer.
These organic fillers may be used alone or in combination of 1 or more than 2.
Since the inorganic filler can adjust the thermal expansion coefficient of the epoxy resin composition of the present embodiment, the inclusion of the inorganic filler tends to improve the heat resistance and moisture resistance when the epoxy resin composition of the present embodiment is used as an underfill material.
Examples of the inorganic filler include, but are not limited to, silicates such as talc, calcined clay, uncalcined clay, mica, and glass; oxides such as titanium oxide, aluminum oxide (alumina), fused silica (e.g., fused spherical silica and fused crushed silica), synthetic silica, and crystalline silica; carbonates such as calcium carbonate, magnesium carbonate, hydrotalcite, etc.; hydroxides such as aluminum hydroxide, magnesium hydroxide, and calcium hydroxide; sulfates such as barium sulfate and calcium sulfate; sulfite such as calcium sulfite; borates such as zinc borate, barium metaborate, aluminum borate, calcium borate, sodium borate, and the like; nitride such as aluminum nitride, boron nitride, and silicon nitride.
Among these, fused silica, crystalline silica and synthetic silica powder are preferable from the viewpoint of improving heat resistance, moisture resistance and strength, and either of alumina and boron nitride is preferable. By using these, the coefficient of thermal expansion can be suppressed, and thus improvement in the cold and hot cycle test and the like can be expected.
The shape of the inorganic filler is not particularly limited, and may be any of irregular shape, spherical shape, and flake shape, for example.
These inorganic fillers may be used alone or in combination of 1 or more than 2.
Examples of pigments include, but are not limited to, kaolin, alumina trihydrate, aluminum hydroxide, chalk powder, gypsum, calcium carbonate, antimony trioxide, pantone, silica, aerosols, lithopone, barite, and titanium dioxide.
The dye is not limited to the following, and examples thereof include dyes derived from plants such as madder, polygonum tinctorium, and the like; natural dyes such as dyes derived from minerals such as loess and laterite; alizarin, indigo and other synthetic dyes; fluorescent dyes, and the like.
The flow control agent is not limited to the following, and examples thereof include organosilane compounds such as silane coupling agents; titanium tetraisopropoxide, titanium diisopropoxide bis (acetylacetonate) and other organic titanium compounds; zirconium tetra-n-butoxide, zirconium tetra-acetylacetonate, and other organozirconium compounds.
The thickener is not limited to the following, and examples thereof include animal thickeners such as gelatin; vegetable thickeners such as polysaccharides and cellulose; and a chemically synthesized thickener such as a polyacrylic acid thickener, a modified polyacrylic acid thickener, a polyether thickener, a urethane modified polyether thickener, and carboxymethyl cellulose.
The release agent is not limited to the following, and examples thereof include a fluorine-based release agent, a silicone-based release agent, and an acrylic release agent formed from a copolymer of glycidyl (meth) acrylate and a linear alkyl (meth) acrylate having 16 to 22 carbon atoms.
Examples of the wetting agent include, but are not limited to, unsaturated polyester copolymer-based wetting agents having an acidic group such as acrylic polyphosphates.
The flame retardant is not limited to the following materials, and examples thereof include metal hydroxides such as aluminum hydroxide and magnesium hydroxide; halogen flame retardants such as chlorine compounds and bromine compounds; phosphorus flame retardants such as condensed phosphoric acid esters; antimony-based flame retardants such as antimony trioxide and antimony pentoxide; inorganic oxides such as silica fillers, and the like.
The surfactant is not limited to the following, and examples thereof include anionic surfactants such as alkylbenzene sulfonate and alkylpolyoxyethylene sulfate; cationic surfactants such as alkyl dimethyl ammonium salts; amphoteric surfactants such as alkyl dimethyl amine oxide and alkyl carboxyl betaine; nonionic surfactants such as linear alcohols having 25 or more carbon atoms and fatty acid esters.
The resins are not limited to the following, and examples thereof include silicone resins, phenol resins, phenoxy resins, polyvinyl butyral resins, polyvinyl acetal resins, polyacrylic resins, and polyimide resins; and elastomers having functional groups such as carboxyl, hydroxyl, vinyl, and amino groups.
[ method for producing epoxy resin composition ]
The method for producing an epoxy resin composition according to the present embodiment includes a step of mixing the epoxy resin (a), the microcapsule-type curing agent (B), the reactive diluent (C), and the compound of the component (D) to obtain an epoxy resin composition.
The method for producing the epoxy resin composition of the present embodiment includes: mixing (A) epoxy resin, (C) reactive diluent and compound of component (D) in advance, and then adding (B) microcapsule curing agent; mixing the microcapsule curing agent (B), the reactive diluent (C) and the compound of the component (D), and then adding the epoxy resin (A); further, to a master batch in which (a) an epoxy resin and (B) a microcapsule-type curing agent are integrally formed, a compound of (a) an epoxy resin, (B) a microcapsule-type curing agent, (C) a reactive diluent, and component (D) and the like are added. The mixing method is not particularly limited either, and may be appropriately selected from, for example, a method using a planetary mixer, a method using a three-roll mill, and the like. The microcapsule-type curing agent (B) can be produced by any of the methods described above.
[ method for producing curable resin composition ]
The epoxy resin composition of the present embodiment can also be used as a master batch type epoxy resin curing agent to produce a curable resin composition. That is, the curable resin composition of the present embodiment can be produced by adding an epoxy resin, another curing agent, and the like to the epoxy resin composition. In this case, the curable resin composition is also included in the embodiment of the present invention.
The curable resin composition can be obtained by sufficiently mixing the epoxy resin composition of the present embodiment, (a) the epoxy resin, the curing agent listed as the core component of the (B) microcapsule-type curing agent, the substances listed as other additives, and the like to uniformity using an open roll such as a three-roll mill, a disperser, a planetary mixer, a kneader, an extruder, and the like.
The epoxy resin composition, the curable resin composition, and the epoxy resin composition blend liquid for films described later of the present embodiment may be subjected to a heat treatment at a temperature of 30 to 80 ℃ for 1 to 168 hours. The heating method is not particularly limited, and examples thereof include a method of heating by an oven, an incubator, a water bath, an oil bath, or the like. The temperature history is not particularly limited, and may be raised in stages, or may be raised at once, for example.
By the heat treatment, the reaction of the residual functional groups that react at a low temperature can be converged.
[ concrete modes of epoxy resin composition and curable resin composition ]
The epoxy resin composition and the curable resin composition using the same according to the present embodiment are not limited to the following compositions, and are suitable for use in sealing materials for electrical and electronic components such as underfill materials and relay sealing materials, insulating materials, adhesives, conductive materials, matrix resins for fiber reinforced plastics, impregnating and fixing materials for motor coils, and the like.
For example, the underfill material is required to have low viscosity for rapid penetration between the semiconductor chip and the substrate, stability against heat during penetration, and excellent curability at 100 ℃ or higher, and the epoxy resin composition of the present embodiment has all of these characteristics. Further, the epoxy resin composition of the present embodiment is suitable for the large-area semiconductor chip from the viewpoint of ensuring a sufficient curing area even when the heat conduction system is not uniform.
The matrix resin of the fiber-reinforced plastic and the impregnating and fixing material for the motor coil are suitable because they require permeability into the gaps between the microfibers and the coil, stability during permeation, and curability, and the epoxy resin composition of the present embodiment has all of these characteristics.
The curable resin composition obtained by using the epoxy resin composition of the present embodiment also has similar characteristics, and is therefore suitable for the above-described embodiment.
(film comprising the epoxy resin composition of the present embodiment)
The film of the present embodiment has a resin composition layer containing the epoxy resin composition of the present embodiment.
In this case, the epoxy resin composition may also function as an epoxy resin curing agent or a curing accelerator. The epoxy resin composition of the present embodiment is excellent in low viscosity, solvent resistance, storage stability, and curability, and is suitable for a film.
The film of the present embodiment includes, for example, a predetermined support and a resin composition layer formed on the support from an epoxy resin composition blend liquid described later, and may have a protective layer on a surface of the resin composition layer opposite to the support, if necessary.
< preparation method of epoxy resin composition blend solution for film >
Examples of the method for producing the epoxy resin composition blend liquid for forming the resin composition layer of the film include a method for producing the epoxy resin composition blend liquid by mixing the epoxy resin composition of the present embodiment, (a) an epoxy resin, a curing agent exemplified as a core component of the microcapsule-type curing agent (B), other additives, and component (E): a film-forming polymer, and the like, and further added with component (F): and mixing the organic solvents by a planetary mixer or the like.
As the polymer for forming a thin film of the above (E), all polymers having the following effects can be used: when the organic solvent is dried to form a film after the epoxy resin composition blend is applied, the effects of suppressing cracks, dents, and excessive flow are achieved, and the effect of maintaining the shape of the film is maintained. The component (E) is not limited to the following, and examples thereof include phenoxy resins, polyvinyl butyral resins, polyvinyl acetal resins, polyacrylic resins, and polyimide resins; and elastomers having functional groups such as carboxyl, hydroxyl, vinyl, and amino groups.
(E) The film-forming polymer is also sometimes referred to as a binder polymer.
The organic solvent (F) is not particularly limited, and a known solvent may be used. The solvent is not limited to the following solvents, and examples thereof include hydrocarbons such as toluene, xylene, cyclohexane, mineral spirits, and solvent naphtha; ketones such as acetone, methyl Ethyl Ketone (MEK), and methyl isobutyl ketone (MIBK); esters such as ethyl acetate, n-butyl acetate, propylene glycol monomethyl ethyl ether acetate, and the like; alcohols such as methanol, isopropanol, n-butanol, butyl cellosolve, butyl carbitol, and the like; amide solvents such as dimethylformamide, dimethylacetamide, and N-methylpyrrolidone.
< support body >
The support is preferably a material that can withstand the temperature at which the organic solvent dries. Examples of such a support include, but are not limited to, polyethylene terephthalate films, polyvinyl alcohol films, polyvinyl chloride films, vinyl chloride copolymer films, polyvinylidene chloride films, vinylidene chloride copolymer films, polymethyl methacrylate copolymer films, polystyrene films, polyacrylonitrile films, styrene copolymer films, polyamide films, cellulose derivative films, and the like.
As these films, films stretched as needed may be used.
< protective layer >
The protective layer is preferably a material capable of sufficiently maintaining the smoothness of the surface of the resin composition layer. Such a protective layer is not limited to the following protective layer, and a polyethylene film, a polypropylene film, a polyethylene terephthalate film which is easily peeled off, an oriented polypropylene film, or the like can be preferably used.
< method for producing thin film >
The film of the present embodiment can be produced by sequentially laminating a support, a resin composition layer, and a protective layer as needed.
As a method for laminating the support, the resin composition layer and the protective layer, a known method can be used.
For example, a mixed solution containing the epoxy resin composition of the present embodiment and (F) an organic solvent is prepared, and first, the mixed solution is applied to a support by a known method such as an applicator or a bar coater, and dried to form a resin composition layer on the support. The drying method is not particularly limited, and examples thereof include an oven, blowing hot air, and the like. The drying temperature and time are not particularly limited, and from the viewpoint of sufficiently removing the solvent and suppressing deformation of the support due to excessive heating and residual reaction of the resin composition layer during drying, drying is preferably performed at a temperature ranging from 50 to 160 ℃ for a drying time ranging from 1 to 30 minutes, and more preferably from 80 to 150 ℃ for 3 to 25 minutes. The drying temperature may be a constant temperature or a temperature gradient may be applied. Next, a protective layer is laminated on the formed resin composition layer as needed, whereby a film can be produced.
< specific modes of film >
The film of the present embodiment is not limited to the following film, and may be used as, for example, an interlayer insulating film, a film type solder resist, a sealing sheet, an electrically conductive film, an anisotropically electrically conductive film, a thermally conductive film, or the like.
The epoxy resin composition of the present embodiment is excellent in solvent resistance and storage stability, and therefore, the coatable time of the epoxy resin composition formulation for a film containing the same can be prolonged, and the storable time of the obtained film can be prolonged. In particular, films that have been conventionally generally subjected to freeze storage can be stored in the vicinity of cold storage to normal temperature.
Further, since the epoxy resin composition of the present embodiment has low viscosity, it is easy to control the viscosity of the mixed solution containing the same, and the coating property on the support is also excellent.
Further, the resin composition layer containing the epoxy resin composition of the present embodiment is sufficiently reduced in viscosity by heating at the time of film adhesion, and is excellent in stability in film production steps and storage, so that the reaction of the epoxy compound after film production is suppressed, and low viscosity can be maintained for a long period of time. By these characteristics, the film of the present embodiment is excellent in the following property of the irregularities, and can be adhered to a substrate without any void.
In addition, the epoxy resin composition of the present embodiment has excellent curability in the vicinity of 100 ℃, and therefore the film of the present embodiment also has excellent curability.
The above-described characteristics are required in common for an interlayer insulating film, a film type solder resist, a sealing sheet, an electrically conductive film, an anisotropically electrically conductive film, and a thermally conductive film, and therefore the film of the present embodiment is suitable for these modes.
[ cured product ]
The cured product of the present embodiment is the cured product of the epoxy resin composition of the present embodiment and the film of the present embodiment.
The cured product of the present embodiment can be produced by subjecting the epoxy resin composition and the film of the present embodiment to a heat treatment.
The heat treatment may be performed by, for example, heat treatment in a heating furnace such as an oven, thermocompression bonding, or the like. The heating conditions are not particularly limited, and may be appropriately selected depending on the composition of the epoxy resin composition and the heat treatment apparatus.
The cured product of this embodiment has excellent mechanical strength.
Examples
Specific examples and comparative examples are described below with respect to the present embodiment, but the present embodiment is not limited to the following examples and comparative examples.
The "parts" and "%" hereinafter are mass references unless otherwise specified.
[ method for producing microcapsule-type curing agent ]
Production example 1
50 parts by mass of bisphenol A type epoxy resin A-1 (the epoxy equivalent is 186g/eq, the total chlorine amount is 600ppm, the hydrolyzable chlorine amount is 50ppm, hereinafter referred to as "epoxy resin A-1"), 50 parts by mass of bisphenol F type epoxy resin A-2 (the epoxy equivalent is 172g/eq, the total chlorine amount is 500ppm, the hydrolyzable chlorine amount is 100ppm, hereinafter referred to as "epoxy resin A-2"), 100 parts by mass of a solid amine adduct of a curing agent core component B-1 (manufactured by Asahi chemical Co., ltd., having a circularity of 0.93, hereinafter referred to as "core B-1") and 10 parts by mass of a encapsulant c-1 (manufactured by Japanese polyurethane Co., ltd.: MR-400) were added, dispersed and mixed, and then reacted at 55℃for 5 hours to obtain a microcapsule type curing agent B-1 dispersed in the epoxy resin.
Production example 2
50 parts by mass of "epoxy resin A-1", "50 parts by mass of" epoxy resin A-2"," core B-1"100 parts by mass and 10 parts by mass of an encapsulating agent c-2 (T-80, manufactured by Tosoh Co., ltd.) were added, dispersed and mixed, and reacted at 55℃for 5 hours to obtain a microcapsule-type curing agent B-2 dispersed in the epoxy resin.
Production example 3
50 parts by mass of "epoxy resin A-1", "50 parts by mass of" epoxy resin A-2"," core component B-1"100 parts by mass, 7 parts by mass of an encapsulating agent c-3 (CORONATE 1391, manufactured by Tosoh corporation) and 3 parts by mass of an encapsulating agent c-4 (DURANATE TUL-100, manufactured by Asahi chemical Co., ltd.) were added, dispersed and mixed, and then reacted at 55℃for 5 hours to obtain a microcapsule-type curing agent B-3 dispersed in an epoxy resin.
[ preparation of epoxy resin composition ]
The epoxy resin (a), the microcapsule curing agent (B), the reactive diluent (C), and the component (D) were measured so as to be the compounding parts shown in the following component tables of tables 1 to 3: the compound represented by the formula (1) was mixed and then filtered at 55℃for 48 hours to obtain an epoxy resin composition.
The parts of the epoxy resin (a) described in tables 1 to 3 below are the amounts of the epoxy resins in the entire epoxy resin composition including the epoxy resins that were simultaneously compounded when "the microcapsule-type curing agent dispersed in the epoxy resin" produced in production examples 1, 2 and 3 was added. Therefore, the compounding ratio of "(B) a microcapsule-type curing agent" described in tables 1 to 3 below is the compounding ratio of the microcapsule-type curing agent itself composed of a core and a shell.
[ method for measuring and evaluating Properties ]
(initial viscosity measurement of epoxy resin composition)
The viscosity (initial viscosity) immediately after the preparation of the epoxy resin composition was measured at room temperature (25 ℃) using an E-type viscometer (TVE-35H, manufactured by east machine industries Co.).
From the viewpoints of sufficient gap permeability and manufacturing suitability of the resin composition layer constituting the film, the following evaluation was made: the initial viscosity is preferably 4500mpa·s or less, more preferably 3500mpa·s or less, and even more preferably 3000mpa·s or less.
(storage stability: storage stability viscosity magnification)
The initial viscosity immediately after the preparation of the epoxy resin composition and the viscosity after the lapse of 7 days at 40℃were measured at room temperature (25 ℃) using an E-type viscometer, and the storage stability viscosity magnification was calculated by the following equation (1).
Storage stability viscosity ratio = viscosity over time after 7 days at 40 ℃ initial viscosity … mathematical formula (1)
The following evaluation was made: the storage stability viscosity ratio is preferably 1.2 or less, more preferably 1.1 or less, and further preferably 1.0.
(temperature at which dynamic viscosity reaches a predetermined viscosity (curability at around 100 ℃ C.) as measured by rheometer)
The epoxy resin composition was heated from 25℃to 200℃by a rheometer (manufactured by HAAKE MARS, thermo scientific Co.) at a heating rate of 5℃per minute in a swinging mode (f=1 Hz), and a dynamic viscosity η' -temperature curve was obtained at this time.
From the obtained dynamic viscosity-temperature curve, it was confirmed that the dynamic viscosity reached 10 5 Temperature of mpa·s: t (. Degree. C.).
Depending on the temperature: t (. Degree. C.) was evaluated as follows.
T≤95℃…◎
95℃<T≤105℃…〇
105℃<T≤110℃…△
110℃<T…×
(curing zone)
The epoxy resin composition was sufficiently poured into a mold made of teflon (registered trademark) having a length of 550mm×a width of 350mm and a thickness of 2mm until the opening was reached, and the mold was heated by a heating furnace at a set temperature of 100℃for 25 minutes.
The volume of the cured product taken out of the teflon (registered trademark) mold after the completion of heating was set to Vc, the inflow volume of the epoxy resin composition was set to V0, and the curing region was calculated by the following equation (2).
Cured area (%) =100×vc/V0 … mathematical formula (2)
The evaluation was performed according to the following criteria based on the proportion (%) of the cured region.
The following (b) curing area: 100 percent of
And (c) a curing area: 80% or more and less than 100%
Delta cure zone: more than 50 percent and less than 80 percent
X cured area: less than 50%
The larger the curing area when the epoxy resin composition is cured, the more sufficient curing area can be ensured even when the heat conduction system in the curing area is insufficient, and from this point of view, it is evaluated as excellent.
That is, from the side of good evaluation, the sequences of good, [ delta ], [ x ] are shown in the table.
(solvent resistance stability)
To 80 parts by mass of the epoxy resin compositions of examples 1 to 19 and comparative example 2, 20 parts by mass of MEK (methyl ethyl ketone) as a solvent was mixed to prepare samples.
The resulting sample was heated at 50℃and the time (h) until the fluidity disappeared was measured.
The following evaluation was made: the time until the fluidity disappears is preferably 0.5 hour (h) or more, more preferably 1 hour (h) or more, and still more preferably 2 hours (h) or more.
(stability when an epoxy resin composition is used for producing a film)
A mixed solution of 50 parts by mass of a phenoxy resin (product name "PKHB" manufactured by InChem Co., ltd.), 50 parts by mass of a bisphenol A type liquid epoxy resin (product name "jER828" manufactured by Mitsubishi chemical Co., ltd.) and 100 parts by mass of MEK was prepared, and 20 parts by mass of any of the epoxy resin compositions of examples 1 to 19 and comparative example 2 was mixed with 100 parts by mass of the solution to prepare a blend solution for a film epoxy resin composition.
The blend was applied to a polyethylene terephthalate film (thickness: 50 μm) as a support so that the dry film thickness became 40 μm, and then heated and dried by an oven preheated to 120℃for 5 minutes, and then the surface opposite to the support was protected with a polyethylene terephthalate film subjected to an easy-to-peel treatment, to obtain a film. These films were used as films in examples 20 to 38 and comparative example 4, respectively.
The obtained film was subjected to measurement of FT-IR spectrum by a Fourier transform infrared spectrophotometer (FT/IR-6600, manufactured by Japanese spectroscopy Co., ltd.).
2920cm of methylene source of epoxy resin and phenoxy resin which does not undergo strength change due to heat drying -1 The absorption P1 in the vicinity was used as a reference and was 915cm from the epoxy group source -1 The strength ratio P2/P1 of the nearby absorption P2 was equal to the strength ratio P20/P10 (P10: 2920cm when a film was produced in the same manner as the composition after the removal of the microcapsule-type curing agent component in the epoxy resin composition as the curing agent component -1 Nearby absorption, P20 is 915cm of epoxy origin -1 Nearby absorption), the epoxy consumption rate was calculated using the following equation (3).
Epoxy consumption rate=100- [ (P2/P1)/(P20/P10) ] x 100 … (3)
The epoxy consumption rate was evaluated according to the following criteria.
Epoxy consumption rate of less than or equal to 0 percent and less than 10 percent …%
An epoxy consumption rate of less than or equal to 10% and less than 15% … well
An epoxy consumption rate of less than or equal to 15% and less than 20% … delta
Epoxy consumption rate … X of 20 percent or less
The table shows the order of good, delta, and x from the side of good evaluation.
(storage stability of film obtained by using epoxy resin composition)
Films were produced using any of the epoxy resin compositions of examples 1 to 19 and comparative example 2 in the same manner as described above (stability in producing films). Thereafter, the film was stored in an oven at 40℃for 7 days. The FT-IR spectrum was measured on the film after storage by the same method as described above (stability in film production), and the value of P2/P1 in the formula (3) was used as the value after storage, and the epoxy consumption rate after storage was calculated.
The epoxy consumption rate after storage was evaluated according to the following criteria.
Epoxy consumption rate of less than or equal to 0 percent and less than 10 percent …%
An epoxy consumption rate of less than or equal to 10% and less than 15% … well
An epoxy consumption rate of less than or equal to 15% and less than 20% … delta
Epoxy consumption rate … X of 20 percent or less
The table shows the order of good, delta, and x from the side of good evaluation.
(stability when an epoxy resin composition is used as a curing accelerator to prepare a film)
A solution was prepared by mixing 50 parts by mass of a phenoxy resin (product name "PKHB" manufactured by InChem Co., ltd.), 50 parts by mass of a bisphenol A type liquid epoxy resin (product name "jER828" manufactured by Mitsubishi chemical Co., ltd.) and 100 parts by mass of MEK to obtain a solution, and 2.5 parts by mass of Dicyandiamide (DICY) as a curing agent component and 2 parts by mass of the epoxy resin composition of examples 1, 5, 10 and 15 as a curing accelerator were mixed into the 100 parts by mass of the solution to prepare a solution for an epoxy resin material for a film.
When a film for obtaining the above-mentioned P20/P10 was produced using this blend solution, films of examples 39 to 42 were produced in the same manner as described above (stability in producing a film) except that a composition from which dicyandiamide as a curing agent and a microcapsule-type curing agent were removed was used, and the epoxy consumption rate was measured and evaluated.
The epoxy consumption rate was evaluated according to the following criteria.
Epoxy consumption rate of less than or equal to 0 percent and less than 10 percent …%
An epoxy consumption rate of less than or equal to 10% and less than 15% … well
An epoxy consumption rate of less than or equal to 15% and less than 20% … delta
Epoxy consumption rate … X of 20 percent or less
The table shows the order of good, delta, and x from the side of good evaluation.
(storage stability of film when epoxy resin composition is used as curing accelerator)
Using the epoxy resin compositions of examples 1, 5, 10 and 15, films were produced in the same manner as described above (stability in film production when the epoxy resin composition was used as a curing accelerator).
Thereafter, the film was stored in an oven at 40℃for 7 days. The FT-IR spectrum of the film after storage was measured by the same method as described above (stability when the epoxy resin composition was used as a curing accelerator to prepare a film), and the value of P2/P1 in the formula (3) was used as the value after storage, and the epoxy consumption rate after storage was calculated.
The epoxy consumption rate after storage was evaluated according to the following criteria.
Epoxy consumption rate of less than or equal to 0 percent and less than 10 percent …%
An epoxy consumption rate of less than or equal to 10% and less than 15% … well
An epoxy consumption rate of less than or equal to 15% and less than 20% … delta
Epoxy consumption rate … X of 20 percent or less
The table shows the order of good, delta, and x from the side of good evaluation.
(curability of film)
The film was produced by the method described above (stability when the epoxy resin composition was used to produce a film) and (stability when the epoxy resin composition was used as a curing accelerator to produce a film). Thereafter, the epoxy resin composition layer was transferred to an aluminum foil, and cured in an oven at 180 ℃ for 1 hour.
The appearance and cross section of the obtained cured product were observed, and whether curing was possible was judged.
[ description of the Components ]
The following shows the components (C) and (D) in tables 1 to 3.
The viscosity of the component (C) was measured by the same method as the initial viscosity measurement of the epoxy resin composition.
Component (C):
PGE: phenyl glycidyl ether (viscosity 6 mPas at 25 ℃ C.) (manufactured by Tokyo chemical industry Co., ltd.)
o-CGE: o-tolyl glycidyl ether (viscosity: 7 mPas at 25 ℃ C.) (Sigma-Aldrich Japan Co., ltd.)
tBPGE: tert-butylphenyl glycidyl ether (viscosity 20 mPas at 25 ℃ C.) (manufactured by Tokyo chemical industry Co., ltd.)
YED216D:1, 6-hexanediol diglycidyl ether (viscosity 121 mPa.s at 25 ℃ C.) (trade name manufactured by Mitsubishi chemical Co., ltd.)
Component (D):
3-phenoxy-1, 2-propanediol (manufactured by tokyo chemical industry Co., ltd.)
Cresol glycerol ether (Tokyo chemical industry Co., ltd.)
3-phenoxy-1-propanol (manufactured by Tokyo chemical industry Co., ltd.)
Other components:
NEWPOL BPE-20: polyol compound (trade name manufactured by Sanyo chemical industry Co., ltd.) obtained by adding ethylene oxide to bisphenol A
Examples 1 to 19 and comparative examples 1 to 3
The epoxy resin compositions were prepared by blending the components in the proportions shown in tables 1 to 3 and using the above-described method.
The characteristics of the prepared epoxy resin composition were measured by the above-described method.
TABLE 1
/>
TABLE 2
TABLE 3
When comparing examples with comparative examples 1 and 2, it is clear that: by adding the component (C) and the component (D), the epoxy resin composition having an excellent balance of properties can be obtained while maintaining excellent storage stability and achieving a reduction in viscosity and an improvement in reactivity.
When comparing example 1 with comparative example 3, it is clear that: the compound having the structure of the component (D) is effective in all of storage stability, reduction in viscosity and improvement in reactivity.
When comparing examples 1 and 4, it is clear that: when component (C) is PGE, a more excellent balance of properties is exhibited in terms of low viscosity and reactivity.
When examples 5, 10 and 11 were compared, the following tendencies were found: the more the amount of the component (D), the more excellent the low viscosity, and the less the amount of the component (D), the more excellent the storage stability.
When comparing examples 10, 15, 16, it is clear that: the more the amount of component (C) increases, the more excellent the curability and storage stability. On the other hand, when comparing example 1 with example 5, it is seen that: the more component (C) increases, the more storage stability decreases, because: since the amount of component (D) contained in examples 10, 15 and 16 is more appropriate, the effect of component (D) on the storage stability is small, and the effect of improving the storage stability can be imparted by stacking component (C) in the case. Further, since the viscosity decreases with an increase in the component (C), the dispersibility of the component (D) and the substance obtained by coordinating the component (D) with the curing agent increases during the curing reaction, and excellent curability is exhibited. When example 15 was compared with comparative example 1, it was found that: even if the component (D) is small, the effect of improving the reactivity is exhibited, and it is known that: component (D) plays a catalytic role.
When comparing examples 5, 13, 14, it is clear that: even when the ratio of the bisphenol A type epoxy resin to the bisphenol F type epoxy resin in the component (A) is changed, an epoxy resin composition having an excellent balance of properties can be obtained. It is also known that: the more the proportion of bisphenol F type epoxy resin in the component (A) increases, the more excellent the low viscosity and storage stability are.
The evaluation results of the cured area test are shown in table 4.
TABLE 4
It can be seen that: the addition of component (C) and component (D) improves the cured region. The evaluation results of the solvent resistance test are shown in tables 5 and 6.
TABLE 5
TABLE 6
When comparing the examples with comparative example 2, it is clear that: by adding component (C), the solvent resistance is improved.
When comparing example 1 with example 5, it is clear that: by increasing the amount of component (C), the solvent resistance is improved.
In addition, when comparing examples 5, 6, and 7 with example 18, it is seen that: when the component (C) is a compound having an aromatic ring, the solvent resistance is excellent. Further, when comparing examples 5 and 6 with example 7, it is clear that: in the case where component (C) is PGE and/or omicron-CGE, excellent solvent resistance is exhibited compared to tBPGE. This is considered to be because: the steric hindrance of the substituent of the aromatic ring is small, so that the substituent is easy to invade into the capsule membrane to form a denser aromatic ring stacking network.
In addition, when comparing examples 5 and 12 with example 19, it is clear that: the compound having a diol structure at the end of the component (D) is excellent in solvent resistance.
The results of the stability test of the films of examples 20 to 38 and comparative example 4 obtained by using the epoxy resin compositions of examples 1 to 19 and comparative example 2 when the films were produced and the storage stability test of the films are shown in tables 7 and 8.
TABLE 7
TABLE 8
When comparing examples 20 to 38 with comparative example 4, it is clear that: the addition of component (C) provides excellent stability in film production and excellent storage stability of the film.
When comparing example 20 with example 24, it is clear that: by increasing the amount of component (C), the stability of the film when it is produced and the storage stability of the film are improved.
When comparing examples 24, 25, 26 with example 37, it is clear that: when the component (C) is a compound having an aromatic ring, the stability in producing a film is excellent. In addition, when comparing examples 24 and 25 with example 26, it is clear that: when component (C) is PGE and/or omicron-CGE, both the stability when a film is produced and the storage stability of the film are superior to those of tBPGE.
When comparing examples 24, 32, 33, it is clear that: the more bisphenol F-type epoxy resin, the more excellent the stability in film production and the more excellent the storage stability of the film tend to be.
Table 9 shows the evaluation results of the stability at the time of film production and the storage stability test of the films of examples 39 to 42 using the epoxy resin compositions of examples 1, 5, 10 and 15 as curing accelerators.
TABLE 9
Examples 39 to 42 show excellent stability in film formation and film storage stability.
The evaluation results of the curability test of the films of examples 20 to 42 are shown in tables 10 and 11.
TABLE 10
TABLE 11
Any of the films of examples 20 to 42 exhibited excellent curability.
The present invention has been described above with reference to the embodiments, but the present invention is not limited to this, and may be modified as appropriate without departing from the scope of the invention.
The present application is based on Japanese patent applications (Japanese patent application No. 2021-114776) filed by No. 2021, no. 7, no. 12 and Japanese patent application No. 2021, no. 8, no. 18 filed by No. 2021-133229), the contents of which are incorporated herein by reference.
Industrial applicability
The epoxy resin composition of the present invention is industrially applicable to insulating materials, sealing materials, adhesives, conductive materials, matrix resins of fiber reinforced plastics, impregnating and fixing agents for motor coils, and the like for electric and electronic components such as underfills, and is industrially applicable to interlayer insulating films, film type solder resists, sealing sheets, conductive films, anisotropic conductive films, thermal conductive films, and other films obtained by using the epoxy resin composition of the present invention as a curing agent or a curing accelerator, and to various paste materials, various coating materials, paints, and the like for insulating adhesive pastes, conductive pastes, anisotropic conductive pastes, thermal conductive pastes, and the like that can use excellent solvent resistance.
Claims (17)
1. An epoxy resin composition comprising:
component (A): an epoxy resin,
Component (B): a microcapsule curing agent,
Component (C): reactive diluent, and method for producing the same
Component (D): a compound represented by the following formula (1),
in the formula (1), X 1 Having more than 2 and less than 5 continuous carbon-carbon bonds, X 1 Substituents of carbon contained in (a) and R 1 ~R 5 Each is one selected from the group consisting of hydrogen, an alkyl group, an unsaturated aliphatic group, an aromatic group, a substituent containing a hetero atom, a substituent containing a halogen atom, and a halogen atom, X 1 Substituents of carbon contained in (a) and R 1 ~R 5 Are optionally the same or different from each other, and the compound represented by formula (1) is optionally selected from R 1 ~R 5 Any of which are fused ring compounds present in the same ring.
2. The epoxy resin composition according to claim 1, wherein the component (D) is a compound represented by the following formula (2),
in the formula (2), X 2 Having more than 2 and less than 4 consecutive carbon-carbon bonds, X 2 Substituents of carbon contained in (a) and R 1 ~R 5 Each is one selected from the group consisting of hydrogen, an alkyl group, an unsaturated aliphatic group, an aromatic group, a substituent containing a hetero atom, a substituent containing a halogen atom, and a halogen atom, X 2 Substituents of carbon contained in (a) and R 1 ~R 5 Are optionally the same or different from each other, and the compound represented by formula (2) is optionally selected from R 1 ~R 5 Condensed rings of any of which are present in the same ringA compound.
3. The epoxy resin composition according to claim 1 or 2, wherein the component (D) is a compound represented by the following formula (3),
in the formula (3), R 1 ~R 9 Each of which is one selected from the group consisting of hydrogen, an alkyl group, an unsaturated aliphatic group, an aromatic group, a substituent containing a hetero atom, a substituent containing a halogen atom and a halogen atom,
R 1 ~R 9 are optionally identical or different from each other, and the compound of formula (3) is optionally selected from R 1 ~R 5 Any of which are fused ring compounds present in the same ring.
4. The epoxy resin composition according to any one of claims 1 to 3, wherein the component (D) is a compound represented by the following formula (4),
in the formula (4), R 1 ~R 8 Each of which is one selected from the group consisting of hydrogen, an alkyl group, an unsaturated aliphatic group, an aromatic group, a substituent containing a hetero atom, a substituent containing a halogen atom and a halogen atom,
R 1 ~R 8 are optionally the same or different from each other, and the compound represented by formula (4) is optionally selected from R 1 ~R 5 Any of which are fused ring compounds present in the same ring.
5. The epoxy resin composition according to any one of claims 1 to 4, wherein the component (a) epoxy resin comprises at least bisphenol F type epoxy resin.
6. The epoxy resin composition according to any one of claims 1 to 5, wherein the component (B) has a core circularity of 0.93 or more.
7. The epoxy resin composition according to any one of claims 1 to 6, wherein the component (C) reactive diluent is a compound having an aromatic ring.
8. The epoxy resin composition according to any one of claims 1 to 7, wherein the component (C) reactive diluent is a compound in which the aromatic ring is a single ring and is monofunctional.
9. The epoxy resin composition according to any one of claims 1 to 8, wherein the content of the component (C) reactive diluent is 1 mass% or more and 20 mass% or less in the epoxy resin composition.
10. The epoxy resin composition according to any one of claims 1 to 9, wherein the content of the component (D) in the epoxy resin composition is 0.001 mass% or more and 5 mass% or less.
11. The epoxy resin composition according to any one of claims 1 to 10, wherein the R 1 ~R 5 Does not contain an epoxy group and a structure (terminal diol) of the following formula (5),
12. a film, comprising:
a support body; and
a resin composition layer formed on the support and comprising the epoxy resin composition according to any one of claims 1 to 11.
13. The film according to claim 12, wherein the resin composition layer further comprises component (E): film-forming polymer.
14. The film according to claim 12 or 13, wherein the film is any one selected from the group consisting of an interlayer insulating film, a film type solder resist, a sealing sheet, an electroconductive film, an anisotropic electroconductive film, and a heat conductive film.
15. A method for producing the film according to any one of claims 12 to 14, comprising the steps of:
after the supporting body is coated with a mixed solution comprising at least the epoxy resin composition according to any one of claims 1 to 11 and the component (F) organic solvent, the component (F) organic solvent is dried at a temperature ranging from 50 to 160 ℃ for a time ranging from 1 to 30 minutes.
16. A cured product of the epoxy resin composition according to any one of claims 1 to 11.
17. A cured product of the film according to any one of claims 12 to 14.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2021-114776 | 2021-07-12 | ||
JP2021-133229 | 2021-08-18 | ||
JP2021133229 | 2021-08-18 | ||
PCT/JP2022/023186 WO2023286499A1 (en) | 2021-07-12 | 2022-06-08 | Epoxy resin composition, film, film production method, and cured product |
Publications (1)
Publication Number | Publication Date |
---|---|
CN117580888A true CN117580888A (en) | 2024-02-20 |
Family
ID=89862998
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202280046138.8A Pending CN117580888A (en) | 2021-07-12 | 2022-06-08 | Epoxy resin composition, film, method for producing film, and cured product |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN117580888A (en) |
-
2022
- 2022-06-08 CN CN202280046138.8A patent/CN117580888A/en active Pending
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR100938523B1 (en) | Latent hardener for epoxy resin and epoxy resin composition | |
JP5148292B2 (en) | Microcapsule type epoxy resin curing agent, master-batch type epoxy resin curing agent composition, one-part epoxy resin composition, and processed product | |
JP4326524B2 (en) | Capsule type curing agent and composition | |
KR100961417B1 (en) | High-stability microencapsulated hardener for epoxy resin and epoxy resin composition | |
JP5158088B2 (en) | Microcapsule type latent curing agent for epoxy resin and method for producing the same, and one-part epoxy resin composition and cured product thereof | |
JP6484446B2 (en) | Curing agent for epoxy resin, epoxy resin composition and material containing the same | |
JP5763527B2 (en) | Imidazole compound-containing microencapsulated composition, curable composition using the same, and masterbatch type curing agent | |
JP2007204669A (en) | Curing agent for epoxy resin, having specific small particle diameter particle size distribution and epoxy resin composition | |
JP2010053353A (en) | Microcapsule type latent curing agent for epoxy resin and method for producing the same, one-part epoxy resin composition, cured product of epoxy resin, adhesive, film for bonding, conductive material, and anisotropically conductive material | |
JP4877716B2 (en) | Curing agent for fast-curing epoxy resin and epoxy resin composition | |
JP5228644B2 (en) | Microcapsule type latent curing agent for epoxy resin and method for producing the same, one-pack epoxy resin composition and cured epoxy resin | |
JP5266936B2 (en) | Microcapsule type latent curing agent for epoxy resin, one-part epoxy resin composition, and epoxy resin cured product | |
CN117580888A (en) | Epoxy resin composition, film, method for producing film, and cured product | |
JP5245790B2 (en) | One-part epoxy resin composition | |
JP2021038314A (en) | Epoxy resin composition | |
WO2023286499A1 (en) | Epoxy resin composition, film, film production method, and cured product | |
JP6909281B2 (en) | Thermosetting resin composition | |
JP2022178390A (en) | Epoxy resin composition, epoxy resin adhesive and epoxy resin cured product | |
JP2020152818A (en) | Epoxy resin composition | |
JP2023137042A (en) | Masterbatch type curing agent for one-pack epoxy resin composition, and epoxy resin composition | |
JP2019189834A (en) | Curing agent for epoxy resin, curing agent composition for master batch type epoxy resin, one-component epoxy resin composition, and processed article |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination |