CN113631619B - Curable resin composition - Google Patents
Curable resin composition Download PDFInfo
- Publication number
- CN113631619B CN113631619B CN202080025042.4A CN202080025042A CN113631619B CN 113631619 B CN113631619 B CN 113631619B CN 202080025042 A CN202080025042 A CN 202080025042A CN 113631619 B CN113631619 B CN 113631619B
- Authority
- CN
- China
- Prior art keywords
- resin composition
- curable resin
- mass
- parts
- epoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000011342 resin composition Substances 0.000 title claims abstract description 93
- 239000003822 epoxy resin Substances 0.000 claims abstract description 58
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 58
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 56
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 52
- 229920005989 resin Polymers 0.000 claims abstract description 27
- 239000011347 resin Substances 0.000 claims abstract description 27
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 15
- 239000011256 inorganic filler Substances 0.000 claims abstract description 12
- 229910003475 inorganic filler Inorganic materials 0.000 claims abstract description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 27
- 125000002723 alicyclic group Chemical group 0.000 claims description 26
- 239000000945 filler Substances 0.000 claims description 26
- 239000011521 glass Substances 0.000 claims description 25
- 150000008065 acid anhydrides Chemical group 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 239000000377 silicon dioxide Substances 0.000 claims description 13
- FKIQSOGFDBALHA-UHFFFAOYSA-L aluminum trimagnesium potassium dioxido(oxo)silane oxygen(2-) difluoride Chemical compound [O--].[F-].[F-].[Mg++].[Mg++].[Mg++].[Al+3].[K+].[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O FKIQSOGFDBALHA-UHFFFAOYSA-L 0.000 claims description 12
- 150000003918 triazines Chemical class 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 21
- 239000001301 oxygen Substances 0.000 abstract description 21
- 229910052760 oxygen Inorganic materials 0.000 abstract description 21
- 230000004888 barrier function Effects 0.000 abstract description 16
- 238000001723 curing Methods 0.000 description 75
- -1 isocyanate compound Chemical class 0.000 description 64
- 239000002245 particle Substances 0.000 description 27
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 24
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 21
- 239000000126 substance Substances 0.000 description 19
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 16
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 11
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 11
- 229910052698 phosphorus Inorganic materials 0.000 description 11
- 239000011574 phosphorus Substances 0.000 description 11
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 10
- 239000004593 Epoxy Substances 0.000 description 10
- 229910052618 mica group Inorganic materials 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 239000010445 mica Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 229920003986 novolac Polymers 0.000 description 7
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 6
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000007822 coupling agent Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000011888 foil Substances 0.000 description 6
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 230000009257 reactivity Effects 0.000 description 6
- 229940014800 succinic anhydride Drugs 0.000 description 6
- 239000002966 varnish Substances 0.000 description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 5
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 5
- 229920000459 Nitrile rubber Polymers 0.000 description 5
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 5
- 239000005357 flat glass Substances 0.000 description 5
- 238000002834 transmittance Methods 0.000 description 5
- 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 4
- FKBMTBAXDISZGN-UHFFFAOYSA-N 5-methyl-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1C(C)CCC2C(=O)OC(=O)C12 FKBMTBAXDISZGN-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 4
- 125000004018 acid anhydride group Chemical group 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 230000003287 optical effect Effects 0.000 description 4
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 229910052604 silicate mineral Inorganic materials 0.000 description 4
- 229920002545 silicone oil Polymers 0.000 description 4
- 229910021647 smectite Inorganic materials 0.000 description 4
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 4
- 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 3
- KMOUUZVZFBCRAM-UHFFFAOYSA-N 1,2,3,6-tetrahydrophthalic anhydride Chemical compound C1C=CCC2C(=O)OC(=O)C21 KMOUUZVZFBCRAM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical class [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- 229910018557 Si O Inorganic materials 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
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- FLISWPFVWWWNNP-BQYQJAHWSA-N dihydro-3-(1-octenyl)-2,5-furandione Chemical compound CCCCCC\C=C\C1CC(=O)OC1=O FLISWPFVWWWNNP-BQYQJAHWSA-N 0.000 description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 230000035699 permeability Effects 0.000 description 3
- 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 3
- 229920001721 polyimide Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011164 primary particle Substances 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 3
- SSUJUUNLZQVZMO-UHFFFAOYSA-N 1,2,3,4,8,9,10,10a-octahydropyrimido[1,2-a]azepine Chemical compound C1CCC=CN2CCCNC21 SSUJUUNLZQVZMO-UHFFFAOYSA-N 0.000 description 2
- 150000000182 1,3,5-triazines Chemical class 0.000 description 2
- OEBXWWBYZJNKRK-UHFFFAOYSA-N 1-methyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound C1CCN=C2N(C)CCCN21 OEBXWWBYZJNKRK-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 2
- BVYPJEBKDLFIDL-UHFFFAOYSA-N 3-(2-phenylimidazol-1-yl)propanenitrile Chemical compound N#CCCN1C=CN=C1C1=CC=CC=C1 BVYPJEBKDLFIDL-UHFFFAOYSA-N 0.000 description 2
- AORTZIIKTZPIQU-UHFFFAOYSA-N 3-butyl-4-methyloxolane-2,5-dione Chemical compound CCCCC1C(C)C(=O)OC1=O AORTZIIKTZPIQU-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
- ZHBXLZQQVCDGPA-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)sulfonyl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(S(=O)(=O)C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 ZHBXLZQQVCDGPA-UHFFFAOYSA-N 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- 229920000089 Cyclic olefin copolymer Polymers 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical class [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- HPTYUNKZVDYXLP-UHFFFAOYSA-N aluminum;trihydroxy(trihydroxysilyloxy)silane;hydrate Chemical compound O.[Al].[Al].O[Si](O)(O)O[Si](O)(O)O HPTYUNKZVDYXLP-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000011889 copper foil Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- LSDYBCGXPCFFNM-UHFFFAOYSA-M dimethyl phosphate;tributyl(methyl)phosphanium Chemical compound COP([O-])(=O)OC.CCCC[P+](C)(CCCC)CCCC LSDYBCGXPCFFNM-UHFFFAOYSA-M 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229910052621 halloysite Inorganic materials 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 239000012948 isocyanate Substances 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
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 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
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000011112 polyethylene naphthalate Substances 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000000411 transmission spectrum Methods 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
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 2
- 239000013585 weight reducing agent Substances 0.000 description 2
- DEQUKPCANKRTPZ-UHFFFAOYSA-N (2,3-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1O DEQUKPCANKRTPZ-UHFFFAOYSA-N 0.000 description 1
- SDUWQMDIQSWWIE-UHFFFAOYSA-N (3-cyanato-5-methylidenecyclohexa-1,3-dien-1-yl) cyanate Chemical compound C=C1CC(OC#N)=CC(OC#N)=C1 SDUWQMDIQSWWIE-UHFFFAOYSA-N 0.000 description 1
- OLQWMCSSZKNOLQ-ZXZARUISSA-N (3s)-3-[(3r)-2,5-dioxooxolan-3-yl]oxolane-2,5-dione Chemical compound O=C1OC(=O)C[C@H]1[C@@H]1C(=O)OC(=O)C1 OLQWMCSSZKNOLQ-ZXZARUISSA-N 0.000 description 1
- RUEBPOOTFCZRBC-UHFFFAOYSA-N (5-methyl-2-phenyl-1h-imidazol-4-yl)methanol Chemical compound OCC1=C(C)NC(C=2C=CC=CC=2)=N1 RUEBPOOTFCZRBC-UHFFFAOYSA-N 0.000 description 1
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- DEKLIKGLDMCMJG-UHFFFAOYSA-M decanoate;tetrabutylphosphanium Chemical compound CCCCCCCCCC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC DEKLIKGLDMCMJG-UHFFFAOYSA-M 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-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
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical group [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- AQBLLJNPHDIAPN-LNTINUHCSA-K iron(3+);(z)-4-oxopent-2-en-2-olate Chemical compound [Fe+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O AQBLLJNPHDIAPN-LNTINUHCSA-K 0.000 description 1
- 150000002513 isocyanates Chemical class 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
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- ZQZQURFYFJBOCE-FDGPNNRMSA-L manganese(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Mn+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O ZQZQURFYFJBOCE-FDGPNNRMSA-L 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- KNRCVAANTQNTPT-UHFFFAOYSA-N methyl-5-norbornene-2,3-dicarboxylic anhydride Chemical compound O=C1OC(=O)C2C1C1(C)C=CC2C1 KNRCVAANTQNTPT-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- 239000005543 nano-size silicon particle Substances 0.000 description 1
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 description 1
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 1
- 229960002460 nitroprusside Drugs 0.000 description 1
- CHWKGJOTGCSFNF-UHFFFAOYSA-N norbornene anhydride Chemical compound C1CC2C3C(=O)OC(=O)C3=C1C2 CHWKGJOTGCSFNF-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- JFOJYGMDZRCSPA-UHFFFAOYSA-J octadecanoate;tin(4+) Chemical compound [Sn+4].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O JFOJYGMDZRCSPA-UHFFFAOYSA-J 0.000 description 1
- 238000010943 off-gassing Methods 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- PRCNQQRRDGMPKS-UHFFFAOYSA-N pentane-2,4-dione;zinc Chemical compound [Zn].CC(=O)CC(C)=O.CC(=O)CC(C)=O PRCNQQRRDGMPKS-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- CUQCMXFWIMOWRP-UHFFFAOYSA-N phenyl biguanide Chemical compound NC(N)=NC(N)=NC1=CC=CC=C1 CUQCMXFWIMOWRP-UHFFFAOYSA-N 0.000 description 1
- LYKRPDCJKSXAHS-UHFFFAOYSA-N phenyl-(2,3,4,5-tetrahydroxyphenyl)methanone Chemical compound OC1=C(O)C(O)=CC(C(=O)C=2C=CC=CC=2)=C1O LYKRPDCJKSXAHS-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
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920000734 polysilsesquioxane polymer Polymers 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000790 scattering method Methods 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 1
- GHPYAGKTTCKKDF-UHFFFAOYSA-M tetraphenylphosphanium;thiocyanate Chemical compound [S-]C#N.C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 GHPYAGKTTCKKDF-UHFFFAOYSA-M 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011701 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5435—Silicon-containing compounds containing oxygen containing oxygen in a ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/26—Di-epoxy compounds heterocyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/28—Di-epoxy compounds containing acyclic nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/40—Glass
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08L63/06—Triglycidylisocyanurates
Abstract
The present invention provides a curable resin composition which can form a cured body suitable for use in a resin member of an electronic device such as an organic EL, a high-brightness LED, a solar cell, etc., and which is excellent in heat resistance and oxygen barrier property. A curable resin composition comprising the following components (A) to (D): (A) an epoxy resin containing nitrogen atoms; (B) an epoxy group-containing silicone compound; (C) an inorganic filler; and (D) a curing agent.
Description
Technical Field
The present invention relates to a curable resin composition for a resin member, which is characterized by heat resistance and oxygen barrier property (OxygenBarrier) in electronic device applications such as organic EL, high-luminance LED, solar cell, and the like.
Background
In some cases, a resin member formed of a cured product of a resin composition or the like is used in sealing parts, bonding parts, light transmitting parts, and the like in electronic devices, particularly in optical devices such as organic EL, high-luminance LED, and solar cell. In such a resin member, oxygen barrier properties are sometimes required in order to suppress degradation of internal components of electronic devices and the like due to oxygen in the air. In addition, heat resistance is sometimes required in order to suppress degradation of internal elements and the like of electronic devices due to outgas (out gas) generated from the resin member by heat. For example, patent document 1 discloses a resin composition containing a blocked isocyanate obtained by blocking an isocyanate compound with an imidazole, an epoxy resin, and a phenoxy resin, but the heat resistance and the oxygen barrier property are not considered. As described above, the conventional resin member is not necessarily satisfactory in terms of heat resistance and oxygen barrier property, and a curable resin composition for a resin member satisfying these properties at the same time is required.
Prior art literature
Patent literature
Patent document 1: japanese patent application laid-open No. 2011-84667.
Disclosure of Invention
Problems to be solved by the invention
Accordingly, an object of the present invention is to provide a curable resin composition which is excellent in heat resistance and oxygen barrier properties and which can be formed into a cured product suitable for use in electronic devices such as organic EL, high-luminance LED, solar cell, and the like.
Means for solving the problems
The present inventors have made intensive studies to solve the above problems, and as a result, have found that the above problems can be solved by using a curable resin composition containing the following components (a) to (D), and have completed the present invention. Namely, the present invention includes the following.
[1] A curable resin composition comprising the following components (A) to (D):
(A) An epoxy resin containing nitrogen atoms;
(B) A silicone compound containing an epoxy group;
(C) An inorganic filler; and
(D) A curing agent;
[2] the curable resin composition according to [1], wherein (E) a curing accelerator is further contained;
[3] the curable resin composition according to [1] or [2], wherein (A) the nitrogen atom-containing epoxy resin comprises a glycidylamine-type epoxy resin and/or a triazine derivative epoxy resin;
[4] The curable resin composition according to any one of [1] to [3], wherein (B) the epoxy group-containing silicone compound comprises a cyclic siloxane skeleton;
[5] the curable resin composition according to any one of [1] to [4], wherein (B) the epoxy group-containing silicone compound contains an alicyclic epoxy group;
[6] the curable resin composition according to any one of [1] to [5], wherein (C) the inorganic filler comprises 1 or more selected from the group consisting of synthetic fluorophlogopite, plate-like glass filler and silica;
[7] the curable resin composition according to any one of [1] to [6], wherein (D) the curing agent is an acid anhydride;
[8] the curable resin composition according to any one of [1] to [7], which is used for a resin member of an electronic device;
[9] an electronic device comprising the cured product of the curable resin composition according to any one of [1] to [8] as a resin member.
ADVANTAGEOUS EFFECTS OF INVENTION
The cured product formed from the curable resin composition of the present invention has a small amount of outgassing (i.e., high heat resistance) and high oxygen barrier properties even when exposed to high temperatures. Therefore, the curable resin composition of the present invention is suitable for use in resin members of electronic devices such as organic EL, high-luminance LED, solar cell, and the like.
Detailed Description
The present invention will be described below in terms of preferred embodiments thereof.
[ curable resin composition ]
The curable resin composition of the present invention contains (A) an epoxy resin containing a nitrogen atom, (B) a silicone compound containing an epoxy group, (C) an inorganic filler, and (D) a curing agent as essential components.
(A) epoxy resin containing nitrogen atom
The epoxy resin containing a nitrogen atom (hereinafter, also referred to as component (a)) used in the present invention may be any epoxy resin containing a nitrogen atom in its skeleton, and is not particularly limited. From the viewpoint of achieving the object of the present invention (particularly oxygen barrier property) at a high level, the component (a) is preferably a glycidylamine-type epoxy resin and/or a triazine derivative epoxy resin.
(glycidylamine type epoxy resin)
The glycidylamine-type epoxy resin is an epoxy resin having a structure in which an amine group is glycidylated, and examples thereof include: glycidyl compounds of tetraglycidyl diaminodiphenylmethane, xylylenediamine, triglycidylaminophenol (triglycidyl para-aminophenol, triglycidyl meta-aminophenol, etc.), tetraglycidyl diaminodiphenylmethane, tetraglycidyl diaminodiphenylsulfone, tetraglycidyl diaminodiphenyl ether, tetraglycidyl diaminomethylcyclohexanone, diglycidyl toluidine, diglycidyl aniline, diglycidyl methoxyaniline, diglycidyl dimethylaniline, diglycidyl trifluoromethylaniline, etc.
Examples of the commercial products include: "630" (triglycidyl para-aminophenol; manufactured by Mitsubishi chemical corporation), "604" (tetraglycidyl diamino diphenyl methane; manufactured by Mitsubishi chemical corporation), "TETRAD-X" (glycidyl compound of xylylenediamine; manufactured by Mitsubishi gas chemical corporation), "TGDDS" (tetraglycidyl diamino diphenyl sulfone; manufactured by Mitsubishi chemical corporation), "EP-3980S" (diglycidyl aniline, manufactured by ADEKA corporation), "GAN", "GOT" (diglycidyl aniline, manufactured by Japanese chemical corporation), and the like. The epoxy group equivalent of the glycidylamine-type epoxy resin is preferably 50 to 1,000, more preferably 50 to 500, still more preferably 60 to 300, particularly preferably 80 to 200, from the viewpoint of reactivity and the like. The "epoxy equivalent" is the gram number (g/eq) of the resin containing 1 gram equivalent of epoxy group, and can be measured according to the method defined in JIS K7236.
(triazine derivative epoxy resin)
Examples of the triazine derivative epoxy resin include 1,3, 5-triazine derivative epoxy resins, and the 1,3, 5-triazine derivative epoxy resin is preferably an epoxy resin having an isocyanurate ring skeleton. In addition, the epoxy resin having an isocyanurate ring skeleton preferably has 2 or more epoxy groups, more preferably 3 epoxy groups, per 1 isocyanurate ring. Specific examples of the epoxy resin having an isocyanurate ring skeleton include, for example: 1,3, 5-triglycidyl isocyanurate, tris (2, 3-epoxypropyl) isocyanurate, tris (. Alpha. -methylglycidyl) isocyanurate, tris (1-methyl-2, 3-epoxypropyl) isocyanurate, 1,3, 5-tris (2, 3-epoxypropyl) -1,3, 5-triazine-2, 4,6 (1H, 3H, 5H) -trione, 1,3, 5-tris (3, 4-epoxybutyl) -1,3, 5-triazine-2, 4,6 (1H, 3H, 5H) -trione, 1,3, 5-tris (5, 6-epoxybutyl) -1,3, 5-triazine-2, 4,6 (1H, 3H, 5H) -trione, tris {2, 2-bis [ (oxetan-2-ylmethoxy) methyl ] butyl } -3,3' - [1,3, 5-triazine-2, 4,6 (1H, 3H, 5H) -trione-1, 5-trione-tripropionate, and the like.
Examples of commercial products of triazine derivative epoxy resins (epoxy resins having isocyanurate ring skeleton) include: TEPIC-G, TEPIC-S, TEPIC-SS, TEPIC-HP, TEPIC-L, TEPIC-PAS, TEPIC-VL, TEPIC-FL, TEPIC-3 ', 3' - [1,3, 5-triazin-2, 4,6 (1H, 3H, 5H) -trione, TEPIC-VL, TEPIC-3, 5-tris (5, 6-epoxybutyl) -1,3, 5-tris (1H, 3H, 5H) -trione, and TEPIC-FL, TEPIC, UC, 1, 3' - [1,3, 5-triazin-2, 4,6 (1H, 3H, 5H) -trione.
The epoxy group equivalent of the triazine derivative epoxy resin is preferably 50 to 1,000, more preferably 50 to 500, still more preferably 60 to 300, particularly preferably 80 to 200, from the viewpoint of reactivity and the like.
In the present invention, when the triazine derivative epoxy resin has a structure in which an amino group is glycidylated, the triazine derivative epoxy resin does not belong to the above-mentioned glycidylamine type epoxy resin. That is, in the present invention, the "glycidylamine-type epoxy resin" does not include a triazine derivative.
In the curable resin composition of the present invention, the nitrogen atom content in the component (a) is preferably 0.05 to 50%, more preferably 1 to 45%. By setting the nitrogen atom content within the above range, a cured product having sufficiently high transparency and oxygen barrier property can be easily obtained, and a curable resin composition having good reactivity in curing of the resin can be obtained. The "nitrogen atom content" can be calculated by the following formula (i).
Nitrogen atom content (%) = [ (average number of nitrogen atoms in 1 molecule×number of nitrogen atoms)/(molecular weight of epoxy resin) ]×100 (i).
In the curable resin composition of the present invention, the average number of epoxy groups in the molecule is preferably 2, 3 or 4 for component (a).
(A) The components may be used alone or in combination of 2 or more. The content of the component (a) in the curable resin composition is not particularly limited, but is preferably 1% by mass or more, more preferably 2% by mass or more, and even more preferably 3% by mass or more, based on 100% by mass of the nonvolatile component in the curable resin composition, from the viewpoint of oxygen barrier property. From the viewpoint of transparency, the amount of the nonvolatile component in the curable resin composition is preferably 60% by mass or less, more preferably 50% by mass or less, and still more preferably 40% by mass or less, based on 100% by mass of the nonvolatile component.
In one embodiment of the present invention, the content of the component (a) is preferably 3 mass% or more, more preferably 5 mass% or more, and even more preferably 8 mass% or more, based on the total amount of the epoxy resin (non-volatile component). The content of the epoxy resin is preferably 70 mass% or less, more preferably 60 mass% or less, and even more preferably 50 mass% or less, based on the total amount (non-volatile component) of the epoxy resin.
(B) epoxy group-containing Silicone Compound
The epoxy group-containing siloxane compound (hereinafter, also referred to as component (B)) used in the present invention is a compound having a skeleton containing an epoxy group in a molecule, which is based on a siloxane bond (si—o—si), and examples of the siloxane skeleton include a cyclic siloxane skeleton, a polysiloxane (silicone) skeleton, a polysilsesquioxane skeleton, and the like. From the viewpoint of achieving heat resistance at a higher level, the siloxane skeleton is preferably a cyclic siloxane skeleton, that is, a cyclic siloxane compound having an epoxy group is preferable as the component (B). The number of Si-O units forming the cyclic siloxane skeleton (the same as the number of silicon atoms forming the siloxane ring) is preferably 2 to 12, more preferably 4 to 8.
The epoxy group-containing siloxane compound preferably has 2 or more epoxy groups in 1 molecule. In addition, among the cyclic siloxane compounds having an epoxy group, the epoxy group is preferably 2 to 4.
(B) When the component (a) is used in a light transmitting portion or the like and transparency is required for a resin member, the epoxy group is preferably an alicyclic epoxy group having an epoxy group in an alicyclic skeleton, that is, the component (B) is preferably a silicone compound containing an alicyclic epoxy group, and more preferably a cyclic silicone compound containing an alicyclic epoxy group, from the viewpoint of making transparency excellent. Examples of the alicyclic skeleton include a cyclopropane skeleton, a cyclobutane skeleton, a cyclopentane skeleton, a cyclohexane skeleton, a cycloheptane skeleton, and a cyclooctane skeleton, and a cyclohexane skeleton is particularly preferable. That is, the alicyclic epoxy group is particularly preferably an oxycyclohexenyl group (Cyclohexene oxide group). (B) The components may be used alone or in combination of 2 or more.
Specific examples of the component (B) include: 2, 4-bis [2- (3- { oxabicyclo [4.1.0] heptyl }) ethyl ] -2,4,6,6,8,8-hexamethyl-cyclotetrasiloxane, 4, 8-bis [2- (3- { oxabicyclo [4.1.0] heptyl }) ethyl ] -2,2,4,6,6,8-hexamethyl-cyclotetrasiloxane, 2, 4-bis [2- (3- { oxabicyclo [4.1.0] heptyl }) ethyl ] -6, 8-dipropyl-2, 4,6, 8-tetramethyl-cyclotetrasiloxane, 4, 8-bis [2- (3- { oxabicyclo [4.1.0] heptyl }) ethyl ] -2, 6-dipropyl-2, 4,6, 8-tetramethyl-cyclotetrasiloxane, 2,4, 8-tris [2- (3- { oxabicyclo [4.1.0] heptyl }) ethyl ] -2,4,6,6,8-pentamethyl-cyclotetrasiloxane, 2,4, 8-tris [2- (3- { oxabicyclo [ 4.0.0 ] ethyl ] -6, 8-tetramethyl-cyclotetrasiloxane, 4, 6-dimethyl }) ethyl ] -2, 6-bis [2- (3- { oxabicyclo [4.1.0] heptyl }) ethyl ] -2,6, 8-tetramethyl-cyclotetrasiloxane.
The epoxy group equivalent of the epoxy group-containing silicone compound is preferably 50 to 6,000, more preferably 50 to 5,000, even more preferably 60 to 4,000, particularly preferably 80 to 4,000, from the viewpoint of reactivity and the like. The weight average molecular weight of the epoxy group-containing silicone compound is preferably 200 to 8,000, more preferably 200 to 6,000.
Examples of the commercial products of the epoxy group-containing siloxane compound include: an alicyclic epoxy-based cyclic polysiloxane oligomer (cyclic siloxane compound having an alicyclic epoxy group) "KR-470" (having an epoxy number of 4), "X-40-2670" (having an epoxy number of 4), "X-40-2678" (having an epoxy number of 2) (both are manufactured by Xinyue chemical Co., ltd.), modified silicone oils having alicyclic epoxy groups at both ends "X-22-169B", "X-22-169AS" (both are manufactured by Xinyue chemical Co., ltd.), modified silicone oils having epoxy groups at both ends "X-22-163", "KF-105", "X-22-163A", "X-22-163B", "X-22-163C", modified silicone oils having alicyclic epoxy groups at side chains "X-22-2046", "KF-102" (both are manufactured by Xinyue chemical Co., ltd.), modified silicone oils having epoxy groups at side chains "X-22-343", "KF-101", "KF-1001", "X-22-2000" (both are manufactured by Xinyue chemical Co., ltd.), and the like.
The content of the component (B) in the curable resin composition of the present invention is not particularly limited, but is preferably 10 mass% or more, more preferably 15 mass% or more, still more preferably 20 mass% or more, and particularly preferably 15 mass% or more, based on 100 mass% of the nonvolatile component of the curable resin composition, from the viewpoint of improving heat resistance. From the viewpoint of reducing the oxygen permeability, the content is preferably 90 mass% or less, more preferably 80 mass% or less, still more preferably 75 mass% or less, and particularly preferably 70 mass% or less, based on 100 mass% of the nonvolatile component of the curable resin composition.
In one embodiment of the present invention, the content of the component (B) is preferably 15 mass% or more, more preferably 20 mass% or more, and even more preferably 25 mass% or more, based on the total amount of the epoxy resin (non-volatile component). The content of the epoxy resin is preferably 70 mass% or less, more preferably 60 mass% or less, and even more preferably 50 mass% or less, based on the total amount (non-volatile component) of the epoxy resin.
Inorganic filler (C)
The inorganic filler (hereinafter, also referred to as component (C)) used in the present invention may be used without particular limitation. The inorganic filler may be used alone or in combination of 2 or more. The inorganic filler is preferably a plate filler or silica from the viewpoint of achieving oxygen barrier properties at a higher level. In addition, when the resin member is used in a light transmission portion or the like and transparency is required, plate-like glass, layered silicate minerals (in particular, smectite and synthetic fluorophlogopite) and nanosilica are preferable from the viewpoint of making transparency excellent. The plate glass and the layered silicate mineral (particularly, smectite and synthetic fluorophlogopite) are plate fillers. In one embodiment of the present invention, the inorganic filler preferably contains 1 or more selected from synthetic fluorophlogopite, plate-like glass filler and silica.
The plate-like filler is not particularly limited as long as the effect of the present invention can be exerted, and examples thereof include plate-like glass (a glass, C glass, E glass, etc.), and layered silicate minerals. Examples of the layered silicate mineral include kaolinite, halloysite (halloysite), talc, smectite, and mica. Among the mica, synthetic fluorophlogopite is preferred from the viewpoint of making transparency excellent. The plate-shaped filler is particularly preferably plate-shaped glass, smectite or synthetic fluorophlogopite from the viewpoint of excellent transparency. These plate-like fillers may be used alone in an amount of 1 or in an amount of 2 or more.
The synthetic fluorophlogopite is one of the synthetic micas, and is different from natural mica and other synthetic micas (K tetrasilicon mica, na-band mica, li-band mica) in that it is a large crystal with high transparency. On the other hand, as the plate glass filler, plate glass fillers having various glass compositions typified by a glass, C glass, E glass, and the like can be used.
The average particle diameter/thickness ratio (average particle diameter/average thickness) of the plate-like filler is preferably 1 or more, more preferably 1.5 or more, and still more preferably 2 or more. When the average particle diameter-thickness ratio is 1 or more, sufficient oxygen barrier properties tend to be easily obtained. The average particle diameter thickness ratio is preferably 1000 or less, more preferably 800 or less, and even more preferably 500 or less. When the average particle diameter-thickness ratio is 1000 or less, sufficient dispersibility tends to be easily obtained.
The average thickness of the plate-like filler is preferably 0.01 to 20. Mu.m, more preferably 0.05 to 10. Mu.m. The average thickness can be determined using the following method.
The thicknesses of 100 particles were measured using a Scanning Electron Microscope (SEM), and the measured values were averaged to obtain the respective thicknesses. In this case, each particle may be measured by observation with a scanning electron microscope, or may be measured by filling a resin with a filler (particle group) and molding the resin, breaking the molded article, and observing the broken surface. In all measurement methods, the sample stage of the scanning electron microscope was adjusted by the sample stage micro-motion device so that the cross section (thickness surface) of the particles was perpendicular to the irradiation electron beam axis of the scanning electron microscope.
The average particle diameter of the plate-like filler is preferably 0.5 μm or more, more preferably 1 μm or more, and even more preferably 2 μm or more from the viewpoint of improving the oxygen barrier property. From the viewpoint of transparency, it is preferably 2000 μm or less, more preferably 1500 μm or less, and even more preferably 1000 μm or less.
The average particle size can be determined using a laser diffraction-scattering method based on Mie scattering theory. Specifically, it can be determined by: the particle size distribution of the filler was prepared based on volume by using a laser diffraction type particle size distribution measuring apparatus, and the median particle size was used as the average particle size. For the measurement sample, a product obtained by dispersing a filler in water by ultrasonic waves can be preferably used. As the laser diffraction scattering particle size distribution measuring apparatus, LA-500 manufactured by horiba, inc. can be used.
The silica is preferably of primary particle sizeIs a so-called nano-silica of nano-scale. As for the silica, spherical silica can be generally used. Silica having a primary particle size of 1 to 100nm is preferable, and silica having a primary particle size of 1 to 50nm is more preferable. Since the measurement of the 1 st particle diameter of the nanosilica is difficult, a conversion value converted from the specific surface area measurement value (according to JIS Z8830) may be used. In the silica preferred in the present invention, the BET specific surface area is set to a predetermined value, whereby the silica more preferred in the present invention can be formed. Preferred BET specific surface area is 2720-27 m 2 Preferably 2720-54 m 2 /g。
In addition, the inorganic filler may be surface-treated with a surface treatment agent. Examples of the surface treating agent include an aminosilane-based coupling agent, an epoxy silane-based coupling agent, a mercapto silane-based coupling agent, a vinyl silane-based coupling agent, an imidazole silane-based coupling agent, an organosilane compound, and a titanate-based coupling agent. The surface treating agent may be used in an amount of 1 or in a combination of 2 or more.
The content of the component (C) in the curable resin composition of the present invention is not particularly limited, but is preferably 1% by mass or more, more preferably 2% by mass or more, still more preferably 3% by mass or more, and particularly preferably 5% by mass or more, based on 100% by mass of the nonvolatile component of the curable resin composition, from the viewpoint of improving the oxygen barrier property. From the viewpoint of transparency, the content is preferably 65 mass% or less, more preferably 60 mass% or less, still more preferably 55 mass% or less, and particularly preferably 50 mass% or less, based on 100 mass% of the nonvolatile component of the curable resin composition.
Curing agent (D)
The curing agent (hereinafter, also referred to as "component (D)") used in the present invention is not particularly limited as long as it has a function of curing the epoxy resin. Examples thereof include phenol-based curing agents, naphthol-based curing agents, acid anhydride-based curing agents, active ester-based curing agents, benzoxazine-based curing agents, cyanate-based curing agents, carbodiimide-based curing agents, imidazole-based curing agents, and the like. From the viewpoints of heat resistance and transparency, the component (D) is preferably an acid anhydride-based curing agent. The curing agent may be used alone or in combination of 1 or more than 2.
The acid anhydride-based curing agent may be a curing agent having 1 or more acid anhydride groups in 1 molecule. Examples of the acid anhydride-based curing agent include phthalic anhydride, succinic anhydride, maleic anhydride, trimellitic anhydride, norbornene anhydride, nitrile rubber (nitrile rubber) having an acid anhydride group, and the like. Examples of the phthalic acid anhydride include phthalic anhydride, 1,2,3, 6-tetrahydrophthalic anhydride, hexahydrophthalic anhydride, 4-methylhexahydrophthalic anhydride, and 3,3', 4' -diphenylsulfone tetracarboxylic dianhydride. Examples of the succinic anhydride include succinic anhydride, octenyl succinic anhydride, tetrapropenyl succinic anhydride, butane-1, 2,3, 4-tetracarboxylic dianhydride, and the like. Examples of the maleic anhydride include maleic anhydride. Examples of the trimellitic anhydride include ethylene glycol bis (trimellitic anhydride) ester and glycerol bis (trimellitic anhydride) monoacetate. Examples of the norbornene acid anhydride include methyl-5-norbornene-2, 3-dicarboxylic acid anhydride, bicyclo [2.2.1] heptane-2, 3-dicarboxylic acid anhydride, and methylcyclobicyclo [2.2.1] heptane-2, 3-dicarboxylic acid anhydride. Examples of the nitrile rubber having an acid anhydride group include a succinic anhydride-modified hydrogenated nitrile rubber, a maleic anhydride-modified hydrogenated nitrile rubber, and the like. The acid anhydride is particularly preferably a norbornene acid anhydride.
Examples of the commercially available acid anhydride-based curing agent include: rikacid TH (1, 2,3, 6-tetrahydrophthalic anhydride), rikacid HH (hexahydrophthalic anhydride), rikacid HNA-100 (methyl bicyclo [2.2.1] heptane-2, 3-dicarboxylic anhydride/bicyclo [2.2.1] heptane-2, 3-dicarboxylic anhydride), rikacid MH-700G (4-methyl hexahydrophthalic anhydride/hexahydrophthalic anhydride=70/30), rikacid MH (4-methyl hexahydrophthalic anhydride), rikacid TMEG-S, rikacid TMEG-100, rikacid TMEG-200, new Nippon chemical Co., ltd Rikacid TMEG-500, rikacid TMEG-600 (ethylene glycol bis-trimellitic anhydride ester), rikacid TMTA-C (glycerol bis (trimellitic anhydride ester) monoacetate), rikacid MTA-15 (a mixture of glycerol bis (trimellitic anhydride ester) monoacetate and alicyclic dicarboxylic anhydride), rikacid DDSA (tetrapropenyl succinic anhydride), rikacid OSA (octenyl succinic anhydride), rikacid HF-08 (an ester of alicyclic anhydride and polyalkylene glycol), rikacid SA (succinic anhydride), rikacid DSDA (3, 3',4,4' -diphenyl sulfone tetracarboxylic dianhydride), rikacidBT-100 (1, 2,3, 4-butane tetracarboxylic dianhydride), rikacid TBN series (nonvolatile acid anhydride), and the like.
The acid anhydride equivalent of the acid anhydride-based curing agent is preferably 70 to 1,000, more preferably 80 to 900, even more preferably 90 to 800, particularly preferably 100 to 700, from the viewpoint of reactivity and the like. The "acid anhydride equivalent" is the gram number (g/eq) of the acid anhydride-based curing agent containing 1 gram equivalent of acid anhydride groups, and can be measured by component analysis by Nuclear Magnetic Resonance (NMR) or Gas Chromatography (GC).
Examples of the phenol-based curing agent and the naphthol-based curing agent include a phenol-based curing agent having a phenol structure (novolac structure), a naphthol-based curing agent having a phenol structure, a phenol-based curing agent having a triazine skeleton, and a naphthol-based curing agent having a triazine skeleton.
As the active ester curing agent, there can be generally mentioned compounds having 2 or more ester groups having high reactivity in 1 molecule, such as phenol esters, thiophenol esters, N-hydroxylamine esters, esters of heterocyclic hydroxyl compounds, and the like. The active ester curing agent is preferably one obtained by condensation reaction of a carboxylic acid compound and/or a thiocarboxylic acid compound with a hydroxyl compound and/or a thiol compound. Examples of the carboxylic acid compound include benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, and pyromellitic acid. Examples of the phenol compound or the naphthol compound include hydroquinone, resorcinol, bisphenol a, bisphenol F, bisphenol S, phenolphthalein, methylated bisphenol a, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, α -naphthol, β -naphthol, 1, 5-dihydroxynaphthalene, 1, 6-dihydroxynaphthalene, 2, 6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucinol, dicyclopentadiene type diphenol compound, novolac (phenol novolac), and the like. The "dicyclopentadiene type phenol compound" herein means a phenol compound obtained by condensing 1 molecule of dicyclopentadiene with 2 molecules of phenol.
More specifically, an active ester compound containing a dicyclopentadiene type diphenol structure, an active ester compound containing a naphthalene structure, an active ester compound containing an acetylation compound of a novolac resin, an active ester compound containing a benzoyl compound of a novolac resin, and the like are exemplified.
Examples of the cyanate-based curing agent include bisphenol a dicyanate, polyphenol cyanate (oligo (3-methylene-1, 5-phenylene cyanate)), 2-functional cyanate resins such as 4,4 '-methylenebis (2, 6-dimethylphenyl cyanate), 4' -ethylenediphenyl dicyanate, hexafluorobisphenol a dicyanate, 2-bis (4-cyanate-yl) phenylpropane, 1-bis (4-cyanate-phenyl methane), bis (4-cyanate-3, 5-dimethylphenyl) methane, 1, 3-bis (4-cyanate-phenyl-1- (methylethylene)) benzene, bis (4-cyanate-phenyl) sulfide, and bis (4-cyanate-phenyl) ether, polyfunctional cyanate resins derived from phenol novolac resins and cresol novolac resins, and prepolymers obtained by partially triazinizing these cyanate resins.
Examples of the imidazole-based curing agent include 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 1, 2-dimethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-phenylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazolium trimellitate, 1-cyanoethyl-2-phenylimidazolium trimellitate, 2, 4-diamino-6- [2' -methylimidazole- (1 ') ] -ethyl-s triazine, 2, 4-diamino-6- [2' -undecylimidazole- (1 ') ] -ethyl-s triazine, 2, 4-diamino-6- [2' -methylethyl ] -2 ' -methylimidazole-ethyl-s triazine, 1-cyanoethyl-2 ' -cyanoethyl-4-methylimidazole, 1' -cyanoethyl-2-undecylium trimellitate, 1-cyanoethyl-2-phenylimidazole, 1' -cyanoethyl-4-diimine-2-cyanoethyl-2-methylimidazole and 2-d-2-methylimidazole-d 2, 4-diamino-6- [2 '-methylimidazolyl- (1') ] -ethyl-s-triazine isocyanurate adduct, 2-phenylimidazole isocyanurate adduct, 2-phenyl-4, 5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2, 3-dihydro-1H-pyrrolo [1,2-a ] benzimidazole, 1-dodecyl-2-methyl-3-benzylimidazolium chloride, 2-methylimidazoline, imidazole compounds such as 2-phenylimidazoline, and adducts of imidazole compounds with epoxy resins.
The content of the curing agent (D) in the curable resin composition of the present invention is not particularly limited as long as the effect of the present invention can be exerted, and from the viewpoint of optical characteristics such as total light transmittance and haze, the content is preferably 90 mass% or less, more preferably 85 mass% or less, still more preferably 80 mass% or less, and particularly preferably 75 mass% or less, relative to 100 mass% of the nonvolatile component of the curable resin composition. From the viewpoint of accelerating the curing of the curable resin composition, the content is preferably 2% by mass or more, more preferably 5% by mass or more, and even more preferably 7% by mass or more, relative to 100% by mass of the nonvolatile component of the curable resin composition.
In one embodiment of the present invention, the content of the component (D) is preferably 5 mass% or more, more preferably 7 mass% or more, and still more preferably 10 mass% or more, relative to the total amount (non-volatile component) of the epoxy resin. The content of the epoxy resin is preferably 150% by mass or less, more preferably 135% by mass or less, and even more preferably 120% by mass or less, based on the total amount of the epoxy resin (non-volatile component).
Curing accelerator (E)
The curable resin composition of the present invention may contain a curing accelerator (hereinafter, also referred to as "component (E)") for the purpose of improving curability and the like, in addition to the components (a) to (D). The curing accelerator is not particularly limited, and examples thereof include amine-based curing accelerators, imidazole-based curing accelerators, phosphorus-based curing accelerators, guanidine-based curing accelerators, metal-based curing accelerators, and the like. The curing accelerator may be used alone or in combination of 1 or more than 2.
Examples of the amine-based curing accelerator include triethylamine, tributylamine, 4-Dimethylaminopyridine (DMAP), benzyldimethylamine, 2,4, 6-tris (dimethylaminomethyl) phenol, and 1, 8-diazabicyclo [5.4.0] undecene, and examples of the amine-based curing accelerator include aliphatic amine-based curing agents such as 4-dimethylaminopyridine and 1, 8-diazabicyclo [5.4.0] undecene; benzidine, o-tolidine, 4 '-diaminodiphenylmethane, 4' -diamino-3, 3 '-dimethyldiphenylmethane, 4' -diamino-3, 3 '-diethyldiphenylmethane, 4' -diamino-3, 3',5,5' -tetramethyl diphenylmethane, 4 '-diamino-3, 3',5,5 '-tetraethyldiphenylmethane, 4' -diamino-3, 3 '-diethyl-5, 5' -dimethyldiphenylmethane, 4 '-diaminodiphenyl ether, 1, 3-bis (3-aminophenoxy) benzene, 1, 3-bis (4-aminophenoxy) benzene, 1, 4-bis (3-aminophenoxy) benzene, 1, 4-bis (4-aminophenoxy) benzene, 1, 3-bis (4-aminophenoxy) neopentane aromatic amine curing agents such as 4,4' - [1, 3-phenylenebis (1-methylethylene) ] diphenylamine, 4'- [1, 4-phenylenebis (1-methylethylene) ] diphenylamine, 2-bis [4- (4-aminophenoxy) phenyl ] propane, 2-bis [4- (4-aminophenoxy) phenyl ] hexafluoropropane, and 4,4' -bis (4-aminophenoxy) biphenyl.
Examples of the imidazole-based curing accelerator include those described in the above imidazole-based curing agents. When the imidazole-based curing agent is used together with other curing agents, the imidazole-based curing agent may function as a curing accelerator.
Examples of the phosphorus-based curing accelerator include triphenylphosphine, a phosphonium borate compound, tetraphenylphosphonium tetraphenylborate, n-butylphosphonium tetraphenylborate, tetrabutylphosphonium decanoate, (4-methylphenyl) triphenylphosphine thiocyanate, tetraphenylphosphonium thiocyanate, butyltriphenylphosphine thiocyanate, methyltributylphosphonium dimethylphosphate, tetraphenylphosphonium, and tetrabutylphosphonium.
Examples of the guanidine-based curing accelerator include dicyandiamide, 1-methylguanidine, 1-ethylguanidine, 1-cyclohexylguanidine, 1-phenylguanidine, 1- (o-tolylguanidine), dimethylguanidine, diphenylguanidine, trimethylguanidine, tetramethylguanidine, pentamethylguanidine, 1,5, 7-triazabicyclo [4.4.0] dec-5-ene, 7-methyl-1, 5, 7-triazabicyclo [4.4.0] dec-5-ene, 1-methylbiguanide, 1-ethylbiguanide, 1-n-butylbiguanide, 1-n-octadecylbiguanide, 1-dimethylbiguanide, 1-diethylbiguanide, 1-cyclohexylbiguanide, 1-allylbiguanide, 1-phenylbiguanide, and 1- (o-tolylguanide).
Examples of the metal curing accelerator include metal, organometallic complexes and organometallic salts of cobalt, copper, zinc, iron, nickel, manganese, tin, and the like. Specific examples of the organometallic complex include cobalt (II) acetylacetonate, organic cobalt complexes such as cobalt (III) acetylacetonate, organic copper complexes such as copper (II) acetylacetonate, organic zinc complexes such as zinc (II) acetylacetonate, organic iron complexes such as iron (III) acetylacetonate, organic nickel complexes such as nickel (II) acetylacetonate, and organic manganese complexes such as manganese (II) acetylacetonate. Examples of the organic metal salt include zinc octoate, tin octoate, zinc naphthenate, cobalt naphthenate, tin stearate, and zinc stearate.
In the curable resin composition of the present invention, the content of the curing accelerator in the case of using the curing accelerator is usually in the range of 0.05 to 5 mass% relative to the total amount (nonvolatile component) of the epoxy resin contained in the curable resin composition.
Additive (F)
The curable resin composition of the present invention may contain a radical polymerization initiator such as dimethyl 2,2' -azobis (isobutyric acid), an organic filler such as rubber particles, silicone powder, nylon powder, and fluororesin powder in a range that does not impair the effects of the present invention; silicone-based, fluorine-based, polymer-based defoamers or leveling agents; thickeners such as Orben, benton, etc.; an antioxidant; a heat stabilizer; additives such as light stabilizers.
< usage >
The curable resin composition of the present invention can be used as a resin member for sealing parts, adhesion parts, light transmission parts, etc. in electronic devices, especially in optical devices such as organic EL, high-luminance LED, solar cell, etc.
When the curable resin composition of the present invention is molded into a film, for example, a varnish (resin composition varnish) prepared by mixing components of the curable resin composition and an organic solvent using a kneading roll, a rotary mixer, or the like is applied to a support subjected to a mold release treatment, and the organic solvent is removed from the varnish applied to the support by heating (blowing hot air or the like) and/or a reduced pressure treatment using a known machine, whereby a resin composition molded into a film (hereinafter, also referred to as a "film-like resin composition") can be obtained.
As the support of the support subjected to the mold release treatment, for example, polyolefin such as polyethylene, polypropylene, polyvinyl chloride and the like can be used; polyesters such as cycloolefin polymers, polyethylene terephthalate (hereinafter, sometimes abbreviated as "PET"), and polyethylene naphthalate; a polycarbonate; plastic films such as polyimide (PET films are preferable), aluminum foils, stainless steel foils, copper foils, and other metal foils. The release treatment of the release-treated support may be, for example, a release treatment using a release agent such as a silicone resin release agent, an alkyd resin release agent, or a fluororesin release agent.
The solid content of the resin composition varnish is preferably 20 to 80 mass%, more preferably 30 to 70 mass%.
The heating conditions for removing the organic solvent from the varnish of the resin composition are not particularly limited, and generally, the heating is preferably performed at about 50 to 130℃for about 2 to 10 minutes.
Examples of the organic solvent include ketones such as acetone, methyl Ethyl Ketone (MEK), cyclohexanone, ethyl acetate, butyl acetate, cellosolve acetate, acetate such as propylene glycol monomethyl ether acetate and carbitol acetate, cellosolves such as cellosolve, carbitol such as butyl carbitol, aromatic hydrocarbons such as toluene and xylene, dimethylformamide, dimethylacetamide, and N-methylpyrrolidone. As the organic solvent, only 1 kind of the above-mentioned organic solvents may be used, or 2 or more kinds thereof may be used in combination.
The thickness of the film-like resin composition varies depending on the apparatus and the application location to which the film-like resin composition is applied, and is preferably in the range of 1 to 1000. Mu.m, more preferably 2 to 800. Mu.m.
In order to protect the film-like resin composition formed on the support before curing the resin composition, the resin composition is preferably protected with a protective film in advance, and for example, a known device can be used to laminate a release-treated protective film on the film-like resin composition formed on the support in advance. Examples of the machine for laminating the protective film include a roll laminator, a press machine, and a vacuum-pressurized laminator.
As the protective film subjected to the mold release treatment, for example, a polyolefin such as polyethylene, polypropylene, polyvinyl chloride, or the like; polyesters such as cycloolefin polymers, polyethylene terephthalate (hereinafter, sometimes abbreviated as "PET"), and polyethylene naphthalate; a polycarbonate; a plastic film (preferably a PET film) such as polyimide, or a support formed of a metal foil such as aluminum foil, stainless steel foil, or copper foil. Examples of the release treatment include release treatments using a release agent such as a silicone resin release agent, an alkyd resin release agent, and a fluororesin release agent.
< curing body >)
The cured product of the present invention is a product obtained by thermally curing the curable resin composition of the present invention, and can be a resin member of an electronic device. When the film-shaped resin composition is cured, a film-shaped cured product can be obtained, and a film-shaped resin member can be obtained.
The curing temperature for thermal curing is preferably 70℃or higher, more preferably 80℃or higher, from the viewpoint of sufficiently conducting the curing reaction. Further, from the viewpoint of preventing coloration of the cured product, it is preferably 180℃or lower, more preferably 165℃or lower. The heating time is preferably 10 minutes or longer, more preferably 20 minutes or longer. Further, it is preferably 150 minutes or less, more preferably 130 minutes or less.
Examples of the heating means include heating by pressure bonding with a hot air circulation oven, an infrared heater, a hot air heater (Heat gun), a high-frequency induction heating device, and a heating tool (Heat tool).
In the curable resin composition of the present invention, a liquid resin composition such as varnish may be applied to a desired position and a curing reaction may be performed to form a resin member having a desired shape.
Examples
The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples. In the following description, "parts" in the amounts of components means "parts by mass" unless otherwise specified. The materials used in the examples and comparative examples are shown below.
(A) Composition of the components
"TEPIC-VL" (manufactured by Nissan chemical industry Co., ltd.): epoxy resin having isocyanurate Ring skeleton, 1,3, 5-triglycidyl isocyanurate, having an epoxy equivalent of 135g/eq and a nitrogen content of 12%
"TEPIC-FL" (manufactured by Nissan chemical industry Co., ltd.): epoxy resin having isocyanurate Ring skeleton, 1,3, 5-triglycidyl isocyanurate, having an epoxy equivalent of 175g/eq and a nitrogen content of 9%
"EP3890S" (manufactured by ADEKA Co.): glycidylamine type epoxy resin, diglycidyl aniline, epoxy equivalent of 115g/eq, nitrogen content of 6%
"630" (Mitsubishi chemical corporation): para-aminophenol type epoxy resin, triglycidyl para-aminophenol, epoxy equivalent of 95g/eq, and nitrogen content of 5%.
(B) Composition of the components
"KR-470" (made by Xinyue chemical Co.): a cyclic siloxane compound having an alicyclic epoxy group, an epoxy group equivalent of 200g/eq, an epoxy group number of 4, and a Si-O unit number of 4
"X-40-2678" (manufactured by Xinyue chemical Co., ltd.): a cyclic siloxane compound having an alicyclic epoxy group, an epoxy group equivalent of 290g/eq, an epoxy group number of 2, and a Si-O unit number of 4.
(C) Composition of the components
"FTD010FY-F01" (manufactured by Nitro Corp.): plate-like glass filler having an average particle diameter of 10 μm and an average particle diameter-thickness ratio of 25
"MEG160FY" (manufactured by japan plate nitroprusside): plate-like glass filler having an average particle diameter of 160 μm and an average particle diameter-thickness ratio of 30
"PDM-20L" (manufactured by TOPY Industrial Co., ltd.): mica (synthetic fluorophlogopite) with an average particle size of 20 μm and an average particle size to thickness ratio of 70
"PDM-40L" (manufactured by TOPY Industrial Co., ltd.): mica (synthetic fluorophlogopite) with an average particle size of 40 μm and an average particle size to thickness ratio of 90
"Y10SV-AM1" (manufactured by Admatechs Co.): nano silicon dioxide (surface treatment of vinyl silane coupling agent), particle size of 10nm, specific surface area of 300m 2 /g。
(D) Composition of the components
"HNA-100" (manufactured by Nippon chemical Co., ltd.): norbornene-based acid anhydride (bicycloheptane dicarboxylic acid anhydride) having an acid anhydride equivalent of 184g/eq.
(E) Composition of the components
"PX-4MP" (manufactured by Japanese chemical industry Co., ltd.): phosphorus-based curing accelerator (methyltributylphosphonium dimethyl phosphate).
Example 1 >
10 parts of an epoxy resin having an isocyanurate ring skeleton (TEPIC-VL) manufactured by Nissan chemical industry Co., ltd., "KR-470" manufactured by Xinyue chemical Co., ltd.), 70 parts of a cyclic siloxane compound having an alicyclic epoxy group (X-40-2678 "manufactured by Xinyue chemical Co., ltd.), 20 parts of a norbornene-based acid anhydride (HNA-100" manufactured by Xinshi chemical Co., ltd.), 16 parts of a plate-shaped glass filler (FTD 010FY-F01 "manufactured by Nippon plate-Nitro chemical Co., ltd.), 4 parts of a plate-shaped glass filler (MEG 160FY" manufactured by Nitro chemical Co., ltd.) and 2.1 parts of a phosphorus-based curing accelerator (PX-4 MP "manufactured by Nitro chemical Co., ltd.) were mixed and uniformly dispersed by a high-speed rotary mixer to obtain a resin composition.
Example 2 >
A resin composition was obtained in the same manner as in example 1 except that 10 parts of "TEPIC-VL" was changed to 10 parts of "TEPIC-FL" and 91 parts of "HNA-100" was changed to 88 parts.
Example 3 >
A resin composition was obtained in the same manner as in example 1, except that 10 parts of "TEPIC-VL" was changed to 10 parts of a glycidylamine type epoxy resin "EP-3980s", 91 parts of "HNA-100" was changed to 93 parts, and 2.1 parts of "PX-4mp" was changed to 2.2 parts.
Example 4 >
A resin composition was obtained in the same manner as in example 3 except that 10 parts of "EP-3980S" was changed to 10 parts of "630" and 93 parts of "HNA-100" was changed to 95 parts.
Example 5 >
The materials used in example 1 were uniformly dispersed in the same manner as in example 1 except that the blending ratios shown in table 1 were changed to obtain a resin composition of example 5.
Example 6 >
30 parts of an epoxy resin having an isocyanurate ring skeleton (TEPIC-VL) manufactured by Nissan chemical industry Co., ltd., "KR-470" manufactured by Xinyue chemical Co., ltd.), 80 parts of a cyclic siloxane compound having an alicyclic epoxy group (X-40-2678 "manufactured by Xinyue chemical Co., ltd.), 20 parts of a norbornene-based acid anhydride (HNA-100" manufactured by Xin-Japanese chemical Co., ltd.), 16 parts of synthetic fluorophlogopite (PDM-20L "manufactured by TOPY industry Co., ltd.), 5 parts of synthetic fluorophlogopite (PDM-40L" manufactured by TOPY industry Co., ltd.) and 2.6 parts of a phosphorus-based curing accelerator (PX-4 MP "manufactured by Japanese chemical industry Co., ltd.) were mixed and then uniformly dispersed by a high-speed rotary mixer to obtain a resin composition.
Example 7 >
30 parts of an epoxy resin having an isocyanurate ring skeleton (TEPIC-FL manufactured by Nissan chemical industry Co., ltd.), 60 parts of a cyclic siloxane compound having an alicyclic epoxy group (KR-470 manufactured by Xinyue chemical Co., ltd.), 10 parts of a cyclic siloxane compound having an alicyclic epoxy group (X-40-2678 manufactured by Xinyue chemical Co., ltd.), 94 parts of norbornene-based acid anhydride (HNA-100 manufactured by Xin-Japanese chemical Co., ltd.), 20 parts of a plate-shaped glass filler (FTD 010FY-F01 manufactured by Nippon plate-Nitro Co., ltd.), 50 parts of nano silica (Y10 SV-AM1 manufactured by Admatechs Co., ltd.) and 2.7 parts of a phosphorus-based curing accelerator (PX-4 MP manufactured by Japan chemical industry Co., ltd.) were mixed and uniformly dispersed by a high-speed rotary mixer to obtain a resin composition.
Example 8 >
10 parts of an epoxy resin having an isocyanurate ring skeleton (TEPIC-VL, manufactured by Nissan chemical industry Co., ltd.), 90 parts of a cyclic siloxane compound having an alicyclic epoxy group (KR-470, manufactured by Xinyue chemical Co., ltd.), 96 parts of norbornene-based acid anhydride (HNA-100, manufactured by Xinshi chemical Co., ltd.), 20 parts of a plate-shaped glass filler (FTD 010FY-F01, manufactured by Nitro chemical Co., ltd.) and 2.2 parts of a phosphorus-based curing accelerator (PX-4 MP, manufactured by Nitro chemical industry Co., ltd.) were mixed and uniformly dispersed by a high-speed rotary mixer to obtain a resin composition.
Example 9 >
A resin composition was obtained in the same manner as in example 8, except that 90 parts of "KR-470" was changed to 90 parts of "X-40-2678", 96 parts of "HNA-100" was changed to 71 parts, and 2.2 parts of "PX-4mp" was changed to 1.9 parts.
Comparative example 1 >
70 parts of a cyclic siloxane compound having an alicyclic epoxy group (KR-470, made by Xinyue chemical Co., ltd.), 30 parts of a cyclic siloxane compound having an alicyclic epoxy group (X-40-2678, made by Xinyue chemical Co., ltd.), 83 parts of a norbornene-based acid anhydride (HNA-100, made by Xin-Kagaku chemical Co., ltd.), and 1.9 parts of a phosphorus-based curing accelerator (PX-4 MP, made by Japan chemical industry Co., ltd.) were mixed and then uniformly dispersed by a high-speed rotary mixer to obtain a resin composition.
Comparative example 2 >
70 parts of a cyclic siloxane compound having an alicyclic epoxy group (KR-470, made by Xinyue chemical Co., ltd.), 30 parts of a cyclic siloxane compound having an alicyclic epoxy group (X-40-2678, made by Xinyue chemical Co., ltd.), 83 parts of norbornene-based acid anhydride (HNA-100, made by Xinshi chemical Co., ltd.), 16 parts of a plate-shaped glass filler (FTD 010FY-F01, made by Nitro Japan Co., ltd.), 4 parts of a plate-shaped glass filler (MEG 160FY, made by Nitro Japan Co., ltd.) and 2.1 parts of a phosphorus-based curing accelerator (PX-4 MP, made by Nitro chemical Co., ltd.) were mixed and uniformly dispersed by a high-speed rotary mixer to obtain a resin composition.
Comparative example 3 >
100 parts of p-aminophenol type epoxy resin "630", 184 parts of norbornene type acid anhydride (HNA-100 ", manufactured by Nippon chemical Co., ltd.) and 16 parts of plate glass filler (FTD 010FY-F01", manufactured by Nitro Japan Co., ltd.) were mixed together, 4 parts of plate glass filler (MEG 160FY ", manufactured by Nitro Japan Co., ltd.) and 3.1 parts of phosphorus type curing accelerator (PX-4 MP", manufactured by Nitro chemical Co., ltd.) were uniformly dispersed by a high-speed rotary mixer to obtain a resin composition.
Comparative example 4 >
10 parts of an epoxy resin having an isocyanurate ring skeleton (TEPIC-FL, manufactured by Nissan chemical industry Co., ltd.), 70 parts of a cyclic siloxane compound having an alicyclic epoxy group (KR-470, manufactured by Xinyue chemical Co., ltd.), 20 parts of a cyclic siloxane compound having an alicyclic epoxy group (X-40-2678, manufactured by Xinyue chemical Co., ltd.), 88 parts of a norbornene-based acid anhydride (HNA-100, manufactured by Xin-Japanese chemical Co., ltd.), and 1.9 parts of a phosphorus-based curing accelerator (PX-4 MP, manufactured by Japan chemical industry Co., ltd.) were mixed, and then uniformly dispersed by a high-speed rotary mixer to obtain a resin composition.
< Heat resistance test >)
The resin compositions prepared in examples and comparative examples were heated at 90℃for 2 hours and then heated at 150℃for 2 hours, whereby a cured product was produced, and the thermal weight decrease (%) at 380℃upon heating was measured by a differential thermal weight simultaneous measurement apparatus (Hitachi High-Tech Science Corporation product "TG/DTA STA7200 RV"). The evaluation was performed by the following means: in an aluminum sample pan, 10mg of each cured product sample was weighed, and the sample was left open without covering, and the temperature was raised from 25 to 400 ℃ at a temperature-raising rate of 20 ℃/min under atmospheric conditions. The thermal weight reduction rate was calculated by the following formula (ii).
The thermal weight reduction rate (%) =100× (mass before heating (μg) -mass at a predetermined temperature (μg))/mass before heating (μg) (ii).
For the heat resistance test, the evaluation was performed using the following criteria:
good following: below 20%
Bad x: 20% or more.
< oxygen transmittance measurement >)
(1) On a polyimide film (UPILEX (manufactured by Yu Xing Co., ltd., thickness: 75 μm), a frame (planar shape of the frame: 10 cm. Times.10 cm, planar area: 100 cm) was formed with an adhesive tape of 200 μm thickness 2 ) The resin composition was poured into the frame, the bar coating was performed with a glass bar, and the resultant was heated at 90℃for 2 hours and then at 150℃for 2 hours in a heat-circulating oven, whereby a cured body (test piece) having a thickness of about 200 μm was obtained. The thickness of the obtained cured product was measured to 1 μm by a micrometer (manufactured by Mitutoyo Co.).
(2) The oxygen permeability (unit: ml. 200. Mu.m/m) of the test piece was measured in an atmosphere of 50% RH (relative humidity) at 23℃using an oxygen permeability measuring device (trade name "OX-TRAN 2/22L" manufactured by MOCON Co.) 2 Day atm), the evaluation was performed using the following criteria;
good following: less than 500 ml.200 μm/m 2 ·day·atm
Bad x: 500 ml.200 μm/m 2 Day atm or more.
< determination of total light transmittance >)
(1) After resin composition was poured into a frame of boat glass (boat glass having a length of 8mm, a width of 6mm and a thickness of 200 μm), the resin composition was heated at 90℃for 2 hours and then at 150℃for 2 hours in a thermal cycle oven, whereby the resin composition was cured to obtain a laminate (sample for evaluation, thickness of cured product: 200 μm) having a cured product of the resin composition.
(2) Evaluation of light absorption ability in short wavelength region (measurement of total light transmittance at 400 nm)
The light transmittance spectrum of the obtained evaluation sample was measured using a fiber-optic spectrophotometer (MCPD-7700, model 311C, manufactured by Otsuka electronics, inc., external light source unit: halogen lamp MC-2564 (24V, 150W specification)) equipped with an integrating sphere of phi 80mm (model SRS-99-010, reflectance 99%) at a distance of 0mm from the evaluation sample and a distance of 48mm from the light source. The reference object was set to the same glass as described above. The total light transmittance (%) at 400nm was obtained from the obtained light transmittance spectrum.
The composition and test results of the resin compositions of examples and comparative examples are shown in table 1 below. As is clear from table 1, the curable resin compositions of examples can form cured products having both high heat resistance and high oxygen barrier properties. Further, it was found that the curable resin composition of examples was also excellent in transparency.
TABLE 1
Industrial applicability
The cured product of the curable resin composition of the present invention has a small amount of outgas generation and excellent heat resistance even when exposed to high temperatures. The resin member is excellent in oxygen barrier property and is suitable for use in sealing parts, adhesion parts, light transmitting parts and the like in electronic devices, particularly in optical devices such as organic EL, high-luminance LED, solar cell and the like.
The present application is based on Japanese patent application No. 2019-068248, the entire contents of which are incorporated herein.
Claims (8)
1. A curable resin composition comprising the following components (A) to (D):
(A) An epoxy resin containing nitrogen atoms,
(B) A silicone compound having an epoxy group,
(C) Inorganic filler
(D) The curing agent is used for curing the resin,
the inorganic filler (C) comprises a material selected from the group consisting of synthetic fluorophlogopite, plate-like glass filler, and BET specific surface area of 2720-27 m 2 1 or more of silica per gram,
the content of the component (B) is 20 to 90 mass% based on 100 mass% of the nonvolatile component of the curable resin composition.
2. The curable resin composition according to claim 1, further comprising (E) a curing accelerator.
3. The curable resin composition according to claim 1 or 2, wherein (a) the nitrogen atom-containing epoxy resin comprises a glycidylamine-type epoxy resin and/or a triazine derivative epoxy resin.
4. The curable resin composition according to claim 1, wherein (B) the epoxy group-containing silicone compound comprises a cyclic siloxane skeleton.
5. The curable resin composition according to claim 1, wherein (B) the epoxy group-containing silicone compound contains an alicyclic epoxy group.
6. The curable resin composition according to claim 1, wherein (D) the curing agent is an acid anhydride.
7. The curable resin composition according to claim 1, which is used for a resin member of an electronic device.
8. An electronic device comprising the cured product of the curable resin composition according to claim 1 as a resin member.
Applications Claiming Priority (3)
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JP2019-068248 | 2019-03-29 | ||
JP2019068248A JP7215300B2 (en) | 2019-03-29 | 2019-03-29 | Curable resin composition |
PCT/JP2020/013979 WO2020203750A1 (en) | 2019-03-29 | 2020-03-27 | Curable resin composition |
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Citations (5)
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WO2008078662A1 (en) * | 2006-12-25 | 2008-07-03 | Dow Corning Toray Co., Ltd. | Curable silicone composition |
CN103154073A (en) * | 2011-01-07 | 2013-06-12 | 株式会社大赛璐 | Curable epoxy resin composition |
KR20140005100A (en) * | 2012-07-04 | 2014-01-14 | 아지노모토 가부시키가이샤 | Resin composition |
TW201418311A (en) * | 2012-09-07 | 2014-05-16 | Daicel Corp | Curable epoxy resin composition and cured product thereof, and optical semiconductor device |
JP2017155145A (en) * | 2016-03-02 | 2017-09-07 | 株式会社ダイセル | Curable epoxy resin composition for optical material |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH0797434A (en) * | 1993-09-29 | 1995-04-11 | Nissan Chem Ind Ltd | Epoxy resin composition |
JP5577667B2 (en) | 2009-10-16 | 2014-08-27 | 味の素株式会社 | Resin composition |
JP2018119032A (en) * | 2017-01-23 | 2018-08-02 | 株式会社ダイセル | Curable resin composition for light reflection and cured product thereof, and optical semiconductor device |
-
2019
- 2019-03-29 JP JP2019068248A patent/JP7215300B2/en active Active
-
2020
- 2020-03-27 WO PCT/JP2020/013979 patent/WO2020203750A1/en active Application Filing
- 2020-03-27 KR KR1020217035087A patent/KR20210148237A/en unknown
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008078662A1 (en) * | 2006-12-25 | 2008-07-03 | Dow Corning Toray Co., Ltd. | Curable silicone composition |
CN103154073A (en) * | 2011-01-07 | 2013-06-12 | 株式会社大赛璐 | Curable epoxy resin composition |
KR20140005100A (en) * | 2012-07-04 | 2014-01-14 | 아지노모토 가부시키가이샤 | Resin composition |
TW201418311A (en) * | 2012-09-07 | 2014-05-16 | Daicel Corp | Curable epoxy resin composition and cured product thereof, and optical semiconductor device |
JP2017155145A (en) * | 2016-03-02 | 2017-09-07 | 株式会社ダイセル | Curable epoxy resin composition for optical material |
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JP7215300B2 (en) | 2023-01-31 |
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