WO2024116571A1 - Composition d'adhésif - Google Patents
Composition d'adhésif Download PDFInfo
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- WO2024116571A1 WO2024116571A1 PCT/JP2023/034529 JP2023034529W WO2024116571A1 WO 2024116571 A1 WO2024116571 A1 WO 2024116571A1 JP 2023034529 W JP2023034529 W JP 2023034529W WO 2024116571 A1 WO2024116571 A1 WO 2024116571A1
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- WIPO (PCT)
- Prior art keywords
- adhesive composition
- acid
- adhesive
- composition according
- group
- Prior art date
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- 230000001070 adhesive effect Effects 0.000 title claims abstract description 109
- 239000000853 adhesive Substances 0.000 title claims abstract description 107
- 239000000203 mixture Substances 0.000 title claims abstract description 70
- 239000002253 acid Substances 0.000 claims abstract description 65
- 229920005989 resin Polymers 0.000 claims abstract description 65
- 239000011347 resin Substances 0.000 claims abstract description 65
- 239000003822 epoxy resin Substances 0.000 claims abstract description 61
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 61
- 125000005462 imide group Chemical group 0.000 claims abstract description 53
- -1 dianhydride compound Chemical class 0.000 claims abstract description 51
- 239000003063 flame retardant Substances 0.000 claims abstract description 36
- 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 claims abstract description 23
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 22
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000011574 phosphorus Substances 0.000 claims abstract description 21
- 239000000539 dimer Substances 0.000 claims abstract description 20
- 239000012787 coverlay film Substances 0.000 claims abstract description 13
- 125000004185 ester group Chemical group 0.000 claims abstract description 10
- 125000001033 ether group Chemical group 0.000 claims abstract description 10
- 239000010408 film Substances 0.000 claims description 15
- 239000002985 plastic film Substances 0.000 claims description 13
- 229920006255 plastic film Polymers 0.000 claims description 13
- 238000007334 copolymerization reaction Methods 0.000 claims description 12
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 11
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 10
- 239000012790 adhesive layer Substances 0.000 claims description 10
- 239000011889 copper foil Substances 0.000 claims description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- 230000001681 protective effect Effects 0.000 claims description 9
- MXPYJVUYLVNEBB-UHFFFAOYSA-N 2-[2-(2-carboxybenzoyl)oxycarbonylbenzoyl]oxycarbonylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1C(O)=O MXPYJVUYLVNEBB-UHFFFAOYSA-N 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 239000010410 layer Substances 0.000 claims description 3
- 238000010030 laminating Methods 0.000 claims 1
- 238000009413 insulation Methods 0.000 abstract description 25
- 239000000470 constituent Substances 0.000 abstract description 4
- 238000005476 soldering Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 description 27
- 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 24
- 239000012948 isocyanate Substances 0.000 description 20
- 238000000034 method Methods 0.000 description 20
- 229920001721 polyimide Polymers 0.000 description 20
- 238000001723 curing Methods 0.000 description 19
- 150000002513 isocyanates Chemical class 0.000 description 19
- 150000001412 amines Chemical class 0.000 description 18
- 238000011156 evaluation Methods 0.000 description 17
- 239000000047 product Substances 0.000 description 15
- 229910000679 solder Inorganic materials 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 12
- 239000009719 polyimide resin Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
- 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 10
- 125000000524 functional group Chemical group 0.000 description 10
- 229920000459 Nitrile rubber Polymers 0.000 description 9
- 239000004593 Epoxy Substances 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 230000007423 decrease Effects 0.000 description 7
- 230000001771 impaired effect Effects 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 125000003700 epoxy group Chemical group 0.000 description 6
- 229920003986 novolac Polymers 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000010959 steel Substances 0.000 description 6
- 229930185605 Bisphenol Natural products 0.000 description 5
- 239000004962 Polyamide-imide Substances 0.000 description 5
- 239000006087 Silane Coupling Agent Substances 0.000 description 5
- 229910010413 TiO 2 Inorganic materials 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 238000013007 heat curing Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 229920002312 polyamide-imide Polymers 0.000 description 5
- 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 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000004642 Polyimide Substances 0.000 description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 210000001787 dendrite Anatomy 0.000 description 4
- 239000011256 inorganic filler Substances 0.000 description 4
- 229910003475 inorganic filler Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 239000012766 organic filler Substances 0.000 description 4
- 239000011295 pitch Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine powder Natural products NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- 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 3
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 3
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 description 2
- KMRIWYPVRWEWRG-UHFFFAOYSA-N 2-(6-oxobenzo[c][2,1]benzoxaphosphinin-6-yl)benzene-1,4-diol Chemical compound OC1=CC=C(O)C(P2(=O)C3=CC=CC=C3C3=CC=CC=C3O2)=C1 KMRIWYPVRWEWRG-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- WXUAQHNMJWJLTG-UHFFFAOYSA-N 2-methylbutanedioic acid Chemical compound OC(=O)C(C)CC(O)=O WXUAQHNMJWJLTG-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- QNVNLUSHGRBCLO-UHFFFAOYSA-N 5-hydroxybenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(O)=CC(C(O)=O)=C1 QNVNLUSHGRBCLO-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920000106 Liquid crystal polymer Polymers 0.000 description 2
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 2
- 229920000877 Melamine resin Chemical class 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 229920001665 Poly-4-vinylphenol Polymers 0.000 description 2
- 239000004734 Polyphenylene sulfide Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 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
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 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
- 238000005516 engineering process Methods 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 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
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 150000004658 ketimines Chemical class 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- 229910052451 lead zirconate titanate Inorganic materials 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 229920000069 polyphenylene sulfide Polymers 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 2
- GGAUUQHSCNMCAU-ZXZARUISSA-N (2s,3r)-butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C[C@H](C(O)=O)[C@H](C(O)=O)CC(O)=O GGAUUQHSCNMCAU-ZXZARUISSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
- SCZNXLWKYFICFV-UHFFFAOYSA-N 1,2,3,4,5,7,8,9-octahydropyrido[1,2-b]diazepine Chemical compound C1CCCNN2CCCC=C21 SCZNXLWKYFICFV-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
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- JSKIRARMQDRGJZ-UHFFFAOYSA-N dimagnesium dioxido-bis[(1-oxido-3-oxo-2,4,6,8,9-pentaoxa-1,3-disila-5,7-dialuminabicyclo[3.3.1]nonan-7-yl)oxy]silane Chemical compound [Mg++].[Mg++].[O-][Si]([O-])(O[Al]1O[Al]2O[Si](=O)O[Si]([O-])(O1)O2)O[Al]1O[Al]2O[Si](=O)O[Si]([O-])(O1)O2 JSKIRARMQDRGJZ-UHFFFAOYSA-N 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- SLQTWNAJXFHMHM-UHFFFAOYSA-N dimethoxy-methyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](C)(OC)OC)CCC2OC21 SLQTWNAJXFHMHM-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- NKZSPGSOXYXWQA-UHFFFAOYSA-N dioxido(oxo)titanium;lead(2+) Chemical compound [Pb+2].[O-][Ti]([O-])=O NKZSPGSOXYXWQA-UHFFFAOYSA-N 0.000 description 1
- KZHJGOXRZJKJNY-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Si]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O KZHJGOXRZJKJNY-UHFFFAOYSA-N 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical class C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- HHBOIIOOTUCYQD-UHFFFAOYSA-N ethoxy-dimethyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(C)CCCOCC1CO1 HHBOIIOOTUCYQD-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229920006015 heat resistant resin Polymers 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- HFGPZNIAWCZYJU-UHFFFAOYSA-N lead zirconate titanate Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ti+4].[Zr+4].[Pb+2] HFGPZNIAWCZYJU-UHFFFAOYSA-N 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052863 mullite Inorganic materials 0.000 description 1
- INJVFBCDVXYHGQ-UHFFFAOYSA-N n'-(3-triethoxysilylpropyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCN INJVFBCDVXYHGQ-UHFFFAOYSA-N 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- UQKAOOAFEFCDGT-UHFFFAOYSA-N n,n-dimethyloctan-1-amine Chemical compound CCCCCCCCN(C)C UQKAOOAFEFCDGT-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 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
- 235000019198 oils Nutrition 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
- BUZHLYBJNNZTPL-UHFFFAOYSA-N pentane-1,2,4,5-tetracarboxylic acid Chemical compound OC(=O)CC(C(O)=O)CC(C(O)=O)CC(O)=O BUZHLYBJNNZTPL-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000768 polyamine Chemical class 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 239000011116 polymethylpentene Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- AABBHSMFGKYLKE-SNAWJCMRSA-N propan-2-yl (e)-but-2-enoate Chemical compound C\C=C\C(=O)OC(C)C AABBHSMFGKYLKE-SNAWJCMRSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 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
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 229910052596 spinel Inorganic materials 0.000 description 1
- 239000011029 spinel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BALCYVFFDOBQPW-UHFFFAOYSA-M tetraphenylazanium;chloride Chemical compound [Cl-].C1=CC=CC=C1[N+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BALCYVFFDOBQPW-UHFFFAOYSA-M 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- RKFCDGOVCBYSEW-AUUKWEANSA-N tmeg Chemical compound COC=1C(OC)=CC(C(OC(C=2OC)=C34)=O)=C3C=1OC(=O)C4=CC=2O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RKFCDGOVCBYSEW-AUUKWEANSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- NNENFOSYDBTCBO-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC NNENFOSYDBTCBO-UHFFFAOYSA-M 0.000 description 1
- GLSQMJPVEVGXMZ-UHFFFAOYSA-N tributyl-(2,5-dihydroxyphenyl)phosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)C1=CC(O)=CC=C1O GLSQMJPVEVGXMZ-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical group NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- RUDFQVOCFDJEEF-UHFFFAOYSA-N yttrium(III) oxide Inorganic materials [O-2].[O-2].[O-2].[Y+3].[Y+3] RUDFQVOCFDJEEF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
- C09J179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09J179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/35—Heat-activated
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
Definitions
- the present invention relates to an adhesive composition that combines a polyimide resin and a curing agent, and more specifically, to an adhesive composition that has excellent adhesion, insulation reliability, and solder heat resistance, and is suitable for flexible printed wiring board applications such as copper-clad laminates, coverlay films, and adhesive sheets.
- Flexible printed circuit boards are circuit boards that are widely used in electronic devices that require flexibility and space-saving features, such as smartphones, tablets, and digital cameras. As devices become smaller and more sophisticated, the number of components mounted on them increases, and flexible printed circuit boards are required to form wiring at a finer pitch than before.
- Polyimide resins are one of the materials used in flexible printed wiring boards. Polyimide resins are mainly synthesized from aromatic monomers, and because they exhibit high heat resistance, insulating reliability, and mechanical strength, they are used as base films for copper-clad laminates and coverlay films.
- adhesives are required for copper-clad laminates made by bonding a base film to copper foil for wiring, coverlay films to protect circuits, and adhesive sheets for bonding boards together, and the production process requires the use of heat-curing adhesives.
- polyimide resins made from aromatic monomers have a high glass transition temperature, making it difficult to bond them together using a normal heat press, and therefore difficult to use as adhesives.
- polyimide resins as adhesives while maintaining their characteristics such as heat resistance, insulating reliability, and mechanical strength
- methods are being investigated that involve copolymerizing long-chain monomers and oligomers such as aliphatic ones to impart fluidity and flexibility when bonding, and then combining them with a curing agent.
- Patent Document 1 proposes using modified polyamideimide, a polyimide resin in which siloxane containing an amine, a reactive functional group, has been introduced to the molecular chain end, as the main component of the adhesive.
- Patent Document 2 proposes using modified polyamideimide, a polyimide resin in which acrylonitrile-butadiene rubber containing a carboxylic acid, a reactive functional group, has been introduced to the molecular chain end, as the main component of the adhesive.
- the polyimide resin with the siloxane structure described in Patent Document 1 requires the use of a starting material with a very expensive siloxane bond to impart a level of flexibility that allows its use as an adhesive, and is therefore less economical. There was also concern that the adhesiveness of the resin would decrease as the amount of siloxane structure introduced increased. In addition, in order to achieve sufficient adhesiveness with the modified polyamideimide described in Patent Document 2, it is necessary to introduce a large amount of acrylonitrile-butadiene rubber, and as a result, insulation reliability decreases due to the influence of moisture absorption by the nitrile in the acrylonitrile-butadiene rubber, making it difficult to use for wiring with a narrow pitch. Therefore, in applications for flexible printed wiring boards, a polyimide resin that can be used as an adhesive is desired, but conventional technology has not been able to obtain a resin that satisfies both adhesiveness and insulation reliability at the same time.
- the present invention was made to solve the problems of the conventional technology described above, and its purpose is to provide an adhesive composition that is suitable for use in flexible printed wiring boards and that simultaneously satisfies the adhesive properties, insulation reliability, and solder heat resistance.
- the inventors conducted extensive research to achieve the above-mentioned objective, and discovered that introducing a dimer acid as a long-chain monomer constituting a polyimide resin and further introducing an acid dianhydride compound having an ester group or ether group can provide fluidity and flexibility during lamination without using a highly hygroscopic raw material such as acrylonitrile-butadiene rubber, and thus the present invention was completed.
- the present invention comprises the following configurations [1] to [9].
- An adhesive composition comprising an imide group-containing resin (A) and an epoxy resin (B), wherein the imide group-containing resin (A) has an acid dianhydride compound (C) having an ester group or an ether group, and a dimer acid (D) as structural units.
- the acid dianhydride compound (C) is an alkylene glycol bisanhydrotrimellitate.
- E phosphorus-based flame retardant
- a copper-clad laminate comprising an insulating plastic film and a copper foil laminated on at least one surface of the insulating plastic film via the adhesive composition according to any one of [1] to [3].
- a coverlay film comprising an adhesive layer made of the adhesive composition according to any one of [1] to [3] and an insulating plastic film laminated thereon.
- An adhesive sheet comprising an adhesive layer made of the adhesive composition according to any one of [1] to [3] and a peelable protective film laminated thereon.
- a flexible printed wiring board comprising a layer made of the adhesive composition according to any one of [1] to [3].
- the adhesive composition of the present invention can simultaneously exhibit excellent adhesion, high insulation reliability, and solder heat resistance. Therefore, the adhesive composition of the present invention can be suitably used as an adhesive for flexible printed wiring boards.
- the adhesive composition of the present invention since the adhesive composition of the present invention has high insulation reliability after curing and high fluidity before curing, it can be suitably used as a coverlay film and lamination adhesive film for flexible printed wiring boards for fine pitches with narrow wiring spacing between circuits and flexible printed wiring boards for coils that generate strong magnetic forces.
- the adhesive composition of the present invention contains an imide group-containing resin (A), an epoxy resin (B), and, if necessary, a flame retardant, and is characterized in that the imide group-containing resin (A) has, as structural units, an acid dianhydride compound (C) having an ester group or an ether group (hereinafter also referred to as the acid dianhydride compound (C) or simply as the (C) component), and a dimer acid (D).
- an imide group-containing resin (A) has, as structural units, an acid dianhydride compound (C) having an ester group or an ether group (hereinafter also referred to as the acid dianhydride compound (C) or simply as the (C) component), and a dimer acid (D).
- the imide group-containing resin (A) is a resin having imide groups as a repeating unit, and refers to a so-called polyimide resin.
- the resin may also have other bonds, such as amide groups, urethane groups, ester groups, and ether groups, as repeating units.
- the acid dianhydride compound (C) having an ester group or an ether group has the effect of enhancing the interaction between the adhesive and the surface of the adherend due to the polarity of the ester group or ether group when the resulting imide group-containing resin (A) is used as an adhesive composition, thereby enabling the adhesive to exhibit stronger adhesive strength. As a result, it also has the effect of making peeling and swelling less likely to occur in solder heat resistance evaluation.
- Examples of the acid dianhydride compound (C) having an ester group include alkylene glycol bisanhydrotrimellitates such as ethylene glycol bisanhydrotrimellitate, propylene glycol bisanhydrotrimellitate, 1,4-butanediol bisanhydrotrimellitate, hexamethylene glycol bisanhydrotrimellitate, polyethylene glycol bisanhydrotrimellitate, and polypropylene glycol bisanhydrotrimellitate.
- Examples of the acid dianhydride compound (C) having an ether group include 4,4'-(4,4'-isopropylidenediphenoxy)diphthalic dianhydride and oxydiphthalic dianhydride.
- the copolymerization amount of the (C) component is preferably 1 to 80 mol%, more preferably 10 to 60 mol%, and even more preferably 15 to 50 mol%, when the total amount of polycarboxylic acid components constituting the imide group-containing resin (A) is taken as 100 mol%. If the amount of copolymerization of component (C) is less than the lower limit, the adhesiveness may be poor, and if it is more than the upper limit, the raw material cost may become high, which may be industrially disadvantageous.
- Dimer acid (D) is a dicarboxylic acid having 36 carbon atoms produced by dimerization of an unsaturated fatty acid having 18 carbon atoms.
- dimer acid (D) one in which the unsaturated bond has been hydrogenated can also be used.
- Aromatic polyimide resins have poor fluidity and flexibility during the adhesive bonding process, making it difficult to obtain sufficient adhesive strength.
- the imide group-containing resin (A) used in the present invention is copolymerized with dimer acid (D) as a structural unit, and the aliphatic chain imparts fluidity and flexibility to the resin, allowing it to fill in unevenness on the adherend surface during thermocompression bonding, thereby improving adhesion.
- the copolymerization amount of dimer acid (D) is preferably 1 to 80 mol%, more preferably 10 to 70 mol%, and even more preferably 30 to 60 mol%, when the total amount of polycarboxylic acid components constituting the imide group-containing resin (A) is taken as 100 mol%. If the copolymerization amount of dimer acid (D) is less than the lower limit, adhesion may be poor, and if it is more than the upper limit, the imide group-containing resin may not have good heat resistance.
- the imide group-containing resin (A) may have a polycarboxylic acid component other than the above-mentioned (C) component and dimer acid (D).
- a polycarboxylic acid component it is preferable to use a polycarboxylic acid component having an aromatic ring from the viewpoint of improving the heat resistance of the obtained imide group-containing resin (A) and adhesive composition.
- polycarboxylic acid components having an aromatic ring examples include trimellitic anhydride, pyromellitic dianhydride, benzophenone tetracarboxylic dianhydride, biphenyl tetracarboxylic dianhydride, naphthalene tetracarboxylic dianhydride, diphenyl sulfone tetracarboxylic dianhydride, perylene tetracarboxylic dianhydride, (hexafluoroisopropylidene) diphthalic anhydride, terephthalic acid, isophthalic acid, orthophthalic acid, and naphthalenedicarboxylic acid. These may be used alone or in combination.
- the copolymerization amount of the polycarboxylic acid component having an aromatic ring is preferably 20 to 90 mol%, more preferably 30 to 80 mol%, and even more preferably 40 to 70 mol%, when the total amount of polycarboxylic acid components constituting the imide group-containing resin (A) is taken as 100 mol%. Note that if the acid dianhydride compound (C) has an aromatic ring, it is included in this calculation.
- polycarboxylic acid component In addition to the polycarboxylic acid components having an aromatic ring already described, aliphatic or alicyclic polycarboxylic acids or monoanhydrides or dianhydrides of polycarboxylic acids can be used as the polycarboxylic acid component to the extent that the effects of the present invention are not impaired.
- any of the above-mentioned polycarboxylic acid components having an aromatic ring may be hydrogenated, meso-butane-1,2,3,4-tetracarboxylic acid dianhydride, pentane-1,2,4,5-tetracarboxylic acid dianhydride, cyclobutane tetracarboxylic acid dianhydride, cyclopentane tetracarboxylic acid dianhydride, cyclohex-1-ene-2,3,5,6-tetracarboxylic acid dianhydride, cyclohexane dicarboxylic acid, succinic acid, glutaric acid, adipic acid, heptanedioic acid, octanedioic acid, azelaic acid, sebacic acid, undecadioic acid, dodecanedioic acid, 2-methylsuccinic acid, etc. may be used alone or in combination.
- the imide group-containing resin (A) can be obtained by polymerizing a polycarboxylic acid component and an amine component or an isocyanate component as the main raw materials.
- the amine component can be a compound with an amino group having two or more functionalities
- the isocyanate component can be a compound with an isocyanate group having two or more functionalities.
- the isocyanate component constituting the imide group-containing resin (A) one having an aromatic ring is preferable from the viewpoint of improving the heat resistance of the adhesive composition, and examples thereof include diphenylmethane-4,4'-diisocyanate and its structural isomers, as well as dimethyldiphenylmethane diisocyanate, diethyldiphenylmethane diisocyanate, dimethoxydiphenylmethane diisocyanate, diphenylether diisocyanate, benzophenone diisocyanate, diphenylsulfone diisocyanate, tolylene diisocyanate, xylylene diisocyanate, naphthalene diisocyanate, 4,4'-[2,2-bis(4-phenoxyphenyl)propane]diisocyanate, dimethylbiphenyl diisocyanate, diethylbiphenyl diisocyanate, dimethoxybiphenyl di
- an aliphatic or alicyclic isocyanate component or amine component can be used as the isocyanate component or amine component to the extent that the effect of the present invention is not impaired.
- any of the isocyanate components or amine components having an aromatic ring described above that have been hydrogenated isophorone diisocyanate, 1,4-cyclohexane diisocyanate, 1,3-cyclohexane diisocyanate, 4,4'-dicyclohexylmethane diisocyanate, ethylene diisocyanate, propylene diisocyanate, hexamethylene diisocyanate, etc.
- the amine component can be any of these isocyanate components in which the isocyanate group has been replaced with an amino group. These may be used alone or in combination. From the viewpoint of the heat resistance and flame retardancy of the resulting adhesive composition using the imide group-containing resin (A), the copolymerization amount of these components is preferably 50 mol% or less, and more preferably 20 mol% or less, when the total amount of isocyanate components and amine components is taken as 100 mol%.
- a compound having three or more functional groups with the imide group-containing resin (A).
- examples include polyfunctional carboxylic acids such as trimesic acid, dicarboxylic acids having a hydroxyl group such as 5-hydroxyisophthalic acid, dicarboxylic acids having an amino group such as 5-aminoisophthalic acid, compounds having three or more hydroxyl groups such as glycerin and polyglycerin, and compounds having three or more amino groups such as tris(2-aminoethyl)amine.
- the amount of copolymerization is preferably 20 mol% or less when the total amount of all polycarboxylic acid components, or the total amount of all isocyanate components and all amine components is taken as 100 mol%. If it exceeds 20 mol%, there is a risk of gelation or the generation of insoluble matter during resin polymerization.
- the imide group-containing resin (A) can be copolymerized with polyesters, polyethers, polycarbonates, polysiloxanes, etc., as components that impart flexibility to the resulting resin, to an extent that does not impair the effects of the present invention.
- the copolymerization amount of these components in the imide group-containing resin (A) is large, there is a risk that the heat resistance, insulation reliability, and economic efficiency will be impaired, so it is preferable that the copolymerization amount of these components is 10 mol % or less when the total amount of all polycarboxylic acid components, or the total amount of all isocyanate components, and the total amount of all amine components is taken as 100 mol %.
- the content of the imide group-containing resin (A) in the adhesive composition of the present invention is preferably 1 to 80 mass %, and more preferably 10 to 70 mass %, assuming that the entire non-volatile content of the adhesive composition is 100 mass %. If the content of the imide group-containing resin is too low, the adhesive composition will contain less high molecular weight components, which may make it brittle and difficult to handle. On the other hand, if the content of the imide group-containing resin is too high, the proportion of the epoxy resin, which is a thermosetting component, will decrease, which may result in insufficient curing and reduced heat resistance.
- the imide group-containing resin (A) can be produced by known methods such as a method of reacting a polycarboxylic acid component with an isocyanate component (isocyanate method), a method of reacting a polycarboxylic acid component with an amine component to form an amic acid and then ring-closing the amic acid (direct method), or a method of reacting a compound having a carboxylic acid anhydride and a carboxylic acid chloride with an amine component (acid chloride method).
- isocyanate method is advantageous in that the by-product carbon dioxide is removed from the system as a gas.
- imide group-containing resins typically using the isocyanate method
- imide group-containing resins can also be produced using the direct method and acid chloride method by using compounds that contain the corresponding amine components or carboxylic acid chlorides.
- the polymerization reaction of the imide group-containing resin (A) can be carried out by stirring the polycarboxylic acid component and the isocyanate component in a solvent while heating them to 60°C to 200°C.
- the molar ratio of the polycarboxylic acid component/isocyanate component is preferably in the range of 90/100 to 100/90.
- the content (copolymerization amount) of the polycarboxylic acid component and the isocyanate component in the imide group-containing resin is the same as the ratio of each component during polymerization.
- catalysts such as alkali metals such as sodium fluoride, potassium fluoride, and sodium methoxide, amines such as triethylenediamine, triethylamine, 1,8-diazabicyclo[5,4,0]-7-undecene, and 1,5-diazabicyclo[4,3,0]-5-nonene, and dibutyltin dilaurate can be used.
- the amount of these catalysts is too small, the desired catalytic effect will not be fully achieved, and if the amount is too large, side reactions may occur, so it is preferable to use 0.01 to 5 mol%, and more preferably 0.1 to 3 mol%, of the polycarboxylic acid component or the isocyanate component, whichever is larger, taken as 100 mol%.
- Solvents that can be used in the polymerization reaction of the imide group-containing resin (A) include, for example, N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, N-butyl-2-pyrrolidone, ⁇ -butyrolactone, dimethylimidazolidinone, dimethylsulfoxide, dimethylformamide, dimethylacetamide, cyclohexanone, and cyclopentanone.
- N-methyl-2-pyrrolidone or dimethylacetamide is preferred because of the solubility of the resulting imide group-containing resin and the efficiency of the polymerization reaction.
- the non-volatile content and solution viscosity can be adjusted by diluting with the solvent used in the polymerization reaction or another low-boiling point solvent. These may be used alone or in combination.
- Low boiling point solvents for dilution include aromatic solvents such as toluene and xylene, aliphatic solvents such as hexane, heptane, and octane, alcohol solvents such as methanol, ethanol, propanol, butanol, and isopropanol, ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, and cyclopentanone, ether solvents such as diethyl ether and tetrahydrofuran, and ester solvents such as ethyl acetate, butyl acetate, and isobutyl acetate.
- aromatic solvents such as toluene and xylene
- aliphatic solvents such as hexane, heptane, and octane
- alcohol solvents such as methanol, ethanol, propanol,
- the adhesive composition of the present invention contains an epoxy resin (B).
- an epoxy resin (B) By using a combination of the imide group-containing resin (A) and the epoxy resin (B), the state in which the imide group-containing resin (A), which has excellent heat resistance, is sufficiently adhered to a substrate can be strengthened by reaction with the epoxy resin (B), and excellent solder heat resistance is imparted, making the adhesive composition suitable as an adhesive for flexible printed wiring board applications.
- the epoxy resin (B) may be modified with silicone, urethane, polyimide, polyamide, etc., and may contain sulfur atoms, nitrogen atoms, etc. in the molecular skeleton.
- the epoxy resin (B) include bisphenol type epoxy resins such as bisphenol A type epoxy resin, bisphenol F type epoxy resin, and bisphenol S type epoxy resin, novolac type epoxy resins such as phenol novolac type epoxy resin and cresol novolac type epoxy resin, alicyclic epoxy resins such as hexahydrophthalic acid glycidyl ester, hydrogenated products of the bisphenol type epoxy resins, and hydrogenated products of the novolac type epoxy resins, linear aliphatic epoxy resins such as dimer acid glycidyl ester, epoxidized polybutadiene, and epoxidized soybean oil.
- the epoxy equivalent of the epoxy resin (B) is preferably 100 to 300 g/eq, and more preferably 150 to 200 g/eq.
- the type of epoxy resin (B) is preferably one having an aromatic ring, and bisphenol-type epoxy resins and novolac-type epoxy resins are more preferred.
- epoxy resins (B) include, for example, bisphenol A type epoxy resins such as jER828 and 1001 manufactured by Mitsubishi Chemical Corporation, hydrogenated bisphenol A type epoxy resins such as ST-2004 and 2007 manufactured by Nippon Steel Chemical & Material Co., Ltd., bisphenol F type epoxy resins such as EXA-9726 manufactured by DIC Corporation and YDF-170 and 2004 manufactured by Nippon Steel Chemical & Material Co., Ltd., phenolic resins such as jER152 and 154 manufactured by Mitsubishi Chemical Corporation and DEN-438 manufactured by The Dow Chemical Company.
- Volac type epoxy resins dicyclopentadiene type epoxy resins such as HP7200 and HP7200H manufactured by DIC Corporation, YDCN-700 series manufactured by Nippon Steel Chemical & Material Co., Ltd., cresol novolac type epoxy resins such as EOCN-125S, 103S, and 104S manufactured by Nippon Kayaku Co., Ltd., flexible epoxy resins such as YD-171 manufactured by Nippon Steel Chemical & Material Co., Ltd., Epon 1031S manufactured by Mitsubishi Chemical Corporation, Araldite 0163 manufactured by BASF Japan Ltd., Nagase Chemtec Co., Ltd.
- epoxy resins examples include polyfunctional epoxy resins such as DENACOL EX-611, EX-614, EX-622, EX-512, EX-521, EX-421, EX-411, and EX-321 manufactured by Nippon Steel Corporation; heterocycle-containing epoxy resins such as EPICOAT 604 manufactured by Mitsubishi Chemical Corporation, YH-434 manufactured by Nippon Steel Chemical & Material Co., Ltd., and Araldite PT810 manufactured by BASF Japan Ltd.; alicyclic epoxy resins such as CELLOXIDE 2021 and EHPE3150 manufactured by Daicel Chemical Industries, Ltd., and ERL4234 manufactured by UCC Corporation; Examples of such epoxy resins include bisphenol S type epoxy resins such as Epiclon EXA-1514 (trade name) manufactured by Nissan Chemical Industries, Ltd., triglycidyl isocyanurates such as TEPIC (trade name) manufactured by Nissan Chemical Industries, Ltd., bixylenol type epoxy resins such as YX-4000 (trade name)
- the content of the epoxy resin (B) in the adhesive composition of the present invention is preferably 1 to 50 mass %, and more preferably 10 to 40 mass %, assuming that the entire non-volatile content of the adhesive composition is 100 mass %. If the epoxy resin content is too low, sufficient thermosetting properties cannot be obtained, and as a result, the heat resistance of the adhesive composition may be poor. If the epoxy resin content is too high, the flexibility of the adhesive composition may be impaired, reducing the adhesive strength, or the insulation reliability may be reduced due to impurities contained in the epoxy resin.
- a flame retardant can be added to the adhesive composition of the present invention for the purpose of imparting flame retardancy.
- the flame retardant used in the present invention is not limited, but is preferably non-halogen-based from an environmental perspective.
- non-halogen flame retardants include nitrogen-based and metal hydroxide flame retardants
- phosphorus-based flame retardants (E) are preferred because of their excellent flame retardant effect.
- the phosphorus-based flame retardant (E) is not particularly limited as long as it contains a phosphorus atom in its structure, but phosphinic acid derivatives and phosphazene-based flame retardants are preferred from the standpoints of hydrolysis resistance, heat resistance, and low bleed-out properties.
- the content of the flame retardant in the adhesive composition of the present invention is preferably 1 to 50 mass% of the non-volatile content of the adhesive composition, and more preferably 10 to 40 mass%. If the content of the flame retardant is low, sufficient flame retardancy may not be obtained, and if the content of the flame retardant is high, the heat resistance, adhesion, and insulation reliability of the adhesive composition may be reduced.
- Phosphinic acid derivatives that are preferred are phenanthrene-type phosphinic acid derivatives, such as 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (manufactured by Sanko Co., Ltd., product name: HCA), 10-benzyl-10-hydro-9-oxa-10-phosphaphenanthrene-10-oxide (manufactured by Sanko Co., Ltd., product name: BCA), 10-(2,5-dihydroxyphenyl)-10H-9-oxa-10-phosphaphenanthrene-10-oxide (manufactured by Sanko Co., Ltd., product name: HCA-HQ), and XZ-92741 manufactured by Olin.
- phenanthrene-type phosphinic acid derivatives such as 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (manufactured by Sanko Co., Ltd., product name
- the phosphazene flame retardant is represented by the following general formula (1) or (2) (wherein X may be the same or different and is hydrogen, a hydroxyl group, an amino group, an alkyl group, an aryl group, a phenoxy group, an allyl group, a cyanophenoxy group, a hydroxyphenoxy group, or the like, and n is an integer of 3 to 25).
- phosphazene flame retardants include, for example, cyclic phenoxyphosphazene (manufactured by Otsuka Chemical Co., Ltd., product names: SPB-100, SPE-100), cyclic cyanophenoxyphosphazene (manufactured by Fushimi Pharmaceutical Co., Ltd., product name: FP-300), and cyclic hydroxyphenoxyphosphazene (manufactured by Otsuka Chemical Co., Ltd., product name: SPH-100).
- cyclic phenoxyphosphazene manufactured by Otsuka Chemical Co., Ltd., product names: SPB-100, SPE-100
- cyclic cyanophenoxyphosphazene manufactured by Fushimi Pharmaceutical Co., Ltd., product name: FP-300
- cyclic hydroxyphenoxyphosphazene manufactured by Otsuka Chemical Co., Ltd., product name: SPH-100
- the phosphorus-based flame retardant (E) it is preferable to use in combination (i) a phosphorus-based flame retardant that does not have a functional group that reacts with an epoxy group, and (ii) a phosphorus-based flame retardant that has a functional group that reacts with an epoxy group, especially a phosphorus-based flame retardant that has two or more functional groups that react with an epoxy group.
- the ratio of the phosphorus-based flame retardants (i) and (ii) is preferably 1:9 to 9:1, more preferably 2:8 to 8:2, by mass. If there is too much phosphorus-based flame retardant (i), the insulation reliability may decrease, and if there is too much phosphorus-based flame retardant (ii), the adhesion may decrease.
- Phosphorus-based flame retardants that do not have a functional group that reacts with epoxy groups are not incorporated into the crosslinked structure during heat curing, and therefore play a role in imparting flexibility to the adhesive after heat curing.
- flame retardants include the aforementioned cyclic phenoxyphosphazene (manufactured by Otsuka Chemical Co., Ltd., product names: SPB-100, SPE-100), cyclic cyanophenoxyphosphazene (manufactured by Fushimi Pharmaceutical Co., Ltd., product name: FP-300), 10-benzyl-10-hydro-9-oxa-10-phosphaphenanthrene-10-oxide (manufactured by Sanko Co., Ltd., product name: BCA), and phosphate ester-based flame retardants (manufactured by Daihachi Chemical Co., Ltd., product name: PX-200).
- Phosphorus-based flame retardants that have a functional group that reacts with epoxy groups are incorporated into the crosslinked structure during heat curing, and thus play a role in suppressing bleed-out and preventing a decrease in heat resistance.
- the aforementioned cyclic hydroxyphenoxyphosphazene manufactured by Otsuka Chemical Co., Ltd., product name: SPH-100
- 10-(2,5-dihydroxyphenyl)-10-H-9-oxa-10-phosphaphenanthrene-10-oxide manufactured by Sanko Co., Ltd., product name HCA-HQ
- Olin's XZ-92741 fall into this category.
- there is only one functional group that reacts with epoxy it becomes the end of the crosslinked structure and cuts the network, so there is a possibility that the effect of not reducing heat resistance (ii) will be insufficient.
- phosphorus-based flame retardants may be used alone or in combination of two or more types as necessary, as long as the flame retardancy, solder heat resistance, and low bleed-out properties are not impaired.
- the adhesive composition of the present invention may contain an additional curing agent for curing the epoxy resin (B) or a curing catalyst for promoting the reaction between the epoxy resin (B) and the imide group-containing resin, as long as the properties are not impaired.
- a curing agent is not particularly limited as long as it is a compound that reacts with the epoxy resin (B), and examples thereof include amine-based curing agents, compounds having a phenolic hydroxyl group, compounds having a carboxylic acid, and compounds having an acid anhydride. These curing agents are used to adjust the functional group equivalent between the epoxy resin (B) and the imide group-containing resin.
- the curing catalyst is not particularly limited as long as it promotes the reaction between the epoxy resin (B) and the imide group-containing resin and the curing agent.
- imidazole derivatives such as 2MZ, 2E4MZ, C11Z, C17Z, 2PZ, 1B2MZ, 2MZ-CN, 2E4MZ-CN, C11Z-CN, 2PZ-CN, 2PHZ-CN, 2MZ-CNS, 2E4MZ-CNS, 2PZ-CNS, 2MZ-AZINE, 2E4MZ-AZINE, C11Z-AZINE, 2MA-OK, 2P4MHZ, 2PHZ, and 2P4BHZ manufactured by Shikoku Chemical Industry Co., Ltd.; guanamines such as acetoguanamine and benzoguanamine; diaminodiphenylmethane, m-phenylenediamine, m- Xylylenediamine, diaminodiphenylsulfone,
- curing agent and curing catalyst examples include quaternary ammonium salts such as tetraphenylammonium chloride, the polycarboxylic acid anhydrides, diphenyliodonium tetrafluoroborate, triphenylsulfonium hexafluoroantimonate, 2,4,6-triphenylthiopyrylium hexafluorophosphate, photocationic polymerization catalysts such as Irgacure 261 (manufactured by Ciba Specialty Chemicals Co., Ltd.) and Optomer SP-170 (manufactured by ADEKA Corporation), styrene-maleic anhydride resins, equimolar reactants of phenylisocyanate and dimethylamine, and equimolar reactants of organic polyisocyanates such as tolylene diisocyanate and isophorone diisocyanate and dimethylamine.
- quaternary ammonium salts such as t
- a silane coupling agent can be added to the adhesive composition of the present invention to improve adhesion.
- Specific examples include aminosilane, mercaptosilane, vinylsilane, epoxysilane, methacrylsilane, isocyanatesilane, ketiminesilane, or mixtures or reactants thereof, or compounds obtained by reacting these with polyisocyanates.
- silane coupling agents include aminosilanes such as 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropylmethyldimethoxysilane, 3-aminopropylethyldiethoxysilane, bistrimethoxysilylpropylamine, bistriethoxysilylpropylamine, bismethoxydimethoxysilylpropylamine, bisethoxydiethoxysilylpropylamine, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropyltriethoxysilane, and N-2-(aminoethyl)-3-aminopropylethyldiethoxysilane; mercapto
- silane coupling agent examples include methacrylsilanes such as epoxy silane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, and 3-methacryloxypropyltriethoxysilane; isocyanate silanes such as isocyanatepropyltriethoxysilane and isocyanatepropyltrimethoxysilane; and ketimine silanes such as ketimine propyltrimethoxysilane and ketimine propyltriethoxysilane. These may be used alone or in combination of two or more.
- methacrylsilanes such as epoxy silane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, and 3-methacryloxypropyltrieth
- epoxy silane has a reactive epoxy group and can react with an imide group-containing resin, so it is preferable in terms of improving heat resistance and moist heat resistance.
- the amount of the silane coupling agent is preferably 0 to 3 mass%, and more preferably 0 to 2 mass%, when the entire non-volatile content of the resin composition is 100 mass%. If the amount exceeds the above range, the heat resistance tends to decrease.
- the adhesive composition of the present invention may contain an organic or inorganic filler for the purpose of improving the solder heat resistance, as long as the effect of the present invention is not impaired.
- organic filler include powders of heat-resistant resins such as polyimide and polyamideimide.
- inorganic fillers examples include silica (SiO 2 ), alumina (Al 2 O 3 ), titania (TiO 2 ), tantalum oxide (Ta 2 O 5 ), zirconia (ZrO 2 ), silicon nitride (Si 3 N 4 ), barium titanate (BaO.TiO 2 ), barium carbonate (BaCO 3 ), lead titanate (PbO.TiO 2 ), lead zirconate titanate (PZT), lead lanthanum zirconate titanate (PLZT), gallium oxide (Ga 2 O 3 ), spinel (MgO.Al 2 O 3 ), mullite (3Al 2 O 3.2SiO 2 ), cordierite (2MgO.2Al 2 O 3.5SiO 2 ), talc (3MgO.4SiO 2.H 2 O), aluminum titanate (TiO 2 -Al 2 O 3 ), yttria-containing zirconia (Y 2 O
- silica is preferred because of its ease of dispersion and heat resistance improvement effect. These may be used alone or in combination of two or more.
- the amount of these organic fillers and inorganic fillers added is preferably 1 to 30 mass % and more preferably 3 to 15 mass % based on the non-volatile components of the adhesive composition. If the amount of organic filler or inorganic filler added is too large, the adhesive coating film may become embrittled, and if the amount added is too small, the effect of improving heat resistance may not be sufficient.
- the adhesive composition of the present invention is suitable for use in flexible printed wiring boards.
- the adhesive composition of the present invention can be used for copper-clad laminates, coverlay films, and adhesive sheets.
- the copper-clad laminate of the present invention has a structure in which copper foil is bonded to at least one side of an insulating plastic film using the adhesive composition of the present invention.
- the copper foil is not particularly limited, but rolled copper foil or electrolytic copper foil that is conventionally used in flexible printed wiring boards can be used.
- the coverlay film of the present invention has a structure in which an adhesive layer made of the adhesive composition of the present invention and an insulating plastic film are laminated, and in particular has a structure of insulating plastic film/adhesive layer or insulating plastic film/adhesive layer/protective film.
- the insulating plastic film is a film made of plastic such as polyimide, polyamideimide, polyethylene terephthalate, polyethylene naphthalate, liquid crystal polymer (LCP), fluororesin, polyphenylene sulfide, polyethersulfone, polyetheretherketone, aramid, polycarbonate, polyarylate, etc., having a thickness of 1 to 200 ⁇ m, and a plurality of films selected from these may be laminated.
- plastic such as polyimide, polyamideimide, polyethylene terephthalate, polyethylene naphthalate, liquid crystal polymer (LCP), fluororesin, polyphenylene sulfide, polyethersulfone, polyetheretherketone, aramid, polycarbonate, polyarylate, etc.
- the protective film there are no particular restrictions on the protective film as long as it can be peeled off without impairing the properties of the adhesive, and examples of the protective film include plastic films such as polyethylene, polypropylene, polyolefin, polyester, polymethylpentene, polyvinyl chloride, polyvinylidene fluoride, polyphenylene sulfide, etc., films coated with silicone, fluoride, or other release agents, paper laminated with these, and paper impregnated or coated with peelable resin.
- plastic films such as polyethylene, polypropylene, polyolefin, polyester, polymethylpentene, polyvinyl chloride, polyvinylidene fluoride, polyphenylene sulfide, etc.
- films coated with silicone, fluoride, or other release agents paper laminated with these, and paper impregnated or coated with peelable resin.
- the adhesive sheet of the present invention has a structure in which an adhesive layer made of the adhesive composition of the present invention and a peelable protective film are laminated together, and in particular has a structure of protective film/adhesive layer or protective film/adhesive/protective film.
- An insulating plastic film layer may be provided within the adhesive layer.
- the adhesive sheet can also be used for multilayer printed circuit boards.
- a solution of the adhesive composition of the present invention is applied onto the insulating plastic film or copper foil substrate, the solvent is dried, and the adhesive is thermocompressed to the adherend and then thermoset before use.
- a heat treatment may be performed after the solvent is dried to cause a partial reaction between the imide group-containing resin and the curing agent. The state before thermocompression is called the B stage.
- coverlay films and adhesive sheets using the adhesive of the present invention have high fluidity in the B-stage state and high insulation after heat curing, and flexible printed wiring boards using them can accommodate fine pitch patterns with circuit widths and circuit spacings of several ⁇ m to 20 ⁇ m, and can also accommodate flexible printed wiring boards for coils with a large ratio of circuit height to circuit width (aspect ratio) and narrow circuit spacing.
- the solution of the adhesive composition was applied to a polyimide film (Apical 12.5NPI, manufactured by Kaneka) so that the thickness after drying was 20 ⁇ m, and dried in a hot air dryer at 140 ° C for 3 minutes to obtain a sample in a B-stage state.
- the adhesive-coated surface of this B-stage sample was overlapped with the glossy surface of a copper foil (BHY, manufactured by JX Nippon Oil & Gas Exploration Co., Ltd., thickness 18 ⁇ m), set in a press, heated from room temperature, and thermocompressed at 60 minutes x 30 kg / cm 2 after reaching 180 ° C.
- the polyimide film was peeled off in a 180 ° direction at a speed of 50 mm / min in an atmosphere of 25 ° C. using a tensile tester (Autograph AG-X plus, manufactured by Shimadzu), the adhesive strength was measured, and the adhesiveness was evaluated according to the following evaluation criteria.
- Evaluation criteria ⁇ : Adhesive strength is 0.7 N/mm or more.
- Adhesive strength is less than 0.5 N/mm.
- thermocompression-bonded sample was evaluated according to the following evaluation criteria in accordance with the UL-94VTM standard. (Evaluation criteria) ⁇ : VTM-0 is satisfied. ⁇ : VTM-0 is not satisfied.
- Insulation reliability-2 is an evaluation method in which the L/S of the comb-type circuit pattern is narrower than that in insulation reliability-1, making the conditions stricter.
- Trimellitic anhydride NBR HUNTSMAN CTBN1300x13NA, acrylonitrile-butadiene rubber having carboxy groups at both ends
- MDI Fujifilm Wako Pure Chemical Industries, Ltd.
- Diphenylmethane diisocyanate TDI Tokyo Chemical Industry Co., Ltd.
- Tolylene diisocyanate ToDI Nippon Soda Co., Ltd.
- o-Tolidine diisocyanate NMP Fujifilm Wako Pure Chemical Industries, Ltd.
- N-Methyl-2-pyrrolidone DMAc N,N-dimethylacetamide manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.
- Example 1 An adhesive composition was prepared by mixing 55 parts by mass of a solution of the imide group-containing resin (A1) as a solid content, 25 parts by mass of jER828 (epoxy resin (B)) as a solid content, 10 parts by mass of BCA (phosphorus-based flame retardant (E)) as a solid content, and 6 parts by mass of ZX-92741 (phosphorus-based flame retardant (E)) as a solid content.
- jER828, BCA, and ZX-92741 a dimethylacetamide solution with a solid content of 30% by mass was prepared in advance and used.
- the adhesive composition obtained was evaluated for adhesion, flame retardancy, insulation reliability, and solder heat resistance. The results are shown in Table 2.
- Adhesive compositions were prepared in the same manner as in Example 1, except that the types and amounts of the imide group-containing resin (A), the epoxy resin (B), and the phosphorus-based flame retardant (E) were changed to obtain the adhesive composition formulation shown in Table 2. Note that for the epoxy resin (B) and the phosphorus-based flame retardant (E), a dimethylacetamide solution with a solid content of 30 mass% was prepared in advance and used. The adhesive compositions obtained were evaluated for adhesion, flame retardancy, insulation reliability, and solder heat resistance. The results are shown in Table 2.
- jER828 Mitsubishi Chemical epoxy resin (bisphenol type epoxy resin, epoxy equivalent: 189 g/eq)
- jER152 Epoxy resin manufactured by Mitsubishi Chemical (phenol novolac type epoxy resin, epoxy equivalent: 177 g/eq)
- jER1001 Mitsubishi Chemical epoxy resin (bisphenol type epoxy resin, epoxy equivalent: 475 g/eq)
- BCA 10-benzyl-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide
- HCA 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide
- ZX-92741 Olin, phosphorus phenol compound having two phenolic hydroxyl groups
- the adhesive compositions of Examples 1 to 13, which satisfy the requirements of the present invention were able to simultaneously exhibit excellent adhesion, high insulation reliability, and solder heat resistance.
- the imide group-containing resin did not have dimer acid as a constituent unit, so the flexibility as an adhesive was insufficient and the adhesive properties could not be satisfied.
- the imide group-containing resin did not have an acid dianhydride compound having an ester group or ether group as a constituent unit, so the solder heat resistance was poor.
- the imide group-containing resin did not have dimer acid as a constituent unit, and instead acrylonitrile-butadiene rubber (NBR) was used as a raw material, so the insulation reliability was poor due to the influence of moisture absorption by the nitrile in the NBR.
- NBR acrylonitrile-butadiene rubber
- the adhesive composition of the present invention has excellent adhesion, insulation reliability, and solder heat resistance, making it suitable for use in coverlay films, adhesive sheets, copper-clad laminates, and the like. Therefore, the present invention is extremely useful in this industry.
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Abstract
L'invention fournit une composition d'adhésif qui est adaptée à une application à une carte de circuit imprimé souple, et qui satisfait simultanément de manière satisfaisante des propriétés d'adhérence, de fiabilité d'isolation et de résistance à la chaleur de soudage. Plus précisément, l'invention concerne une composition d'adhésif qui comprend une résine à teneur en groupe imide (A) et une résine époxy (B). Cette composition d'adhésif est caractéristique en ce que ladite résine à teneur en groupe imide (A) possède en tant qu'unités structurelles un composé dianhydride d'acide (C) possédant un groupe ester ou un groupe éther, et un acide dimérisé (D). La composition d'adhésif de l'invention peut également comprendre un agent ignifuge à base de phosphore (E). Enfin, cette composition d'adhésif peut être mise en œuvre de manière adaptée dans une application de carte de circuit imprimé souple, particulièrement un stratifié cuivré, un film protecteur, une feuille d'adhésif, ou similaire.
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Citations (2)
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JP2011042730A (ja) * | 2009-08-20 | 2011-03-03 | Hitachi Chem Co Ltd | 接着剤組成物、フィルム状接着剤、接着シート及び半導体装置 |
JP2022089494A (ja) * | 2020-12-04 | 2022-06-16 | 東洋インキScホールディングス株式会社 | 絶縁性組成物、熱硬化性接着シート、熱伝導性接着層および複合部材 |
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JP2011042730A (ja) * | 2009-08-20 | 2011-03-03 | Hitachi Chem Co Ltd | 接着剤組成物、フィルム状接着剤、接着シート及び半導体装置 |
JP2022089494A (ja) * | 2020-12-04 | 2022-06-16 | 東洋インキScホールディングス株式会社 | 絶縁性組成物、熱硬化性接着シート、熱伝導性接着層および複合部材 |
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