TWI621637B - Method for producing epoxy compound - Google Patents
Method for producing epoxy compound Download PDFInfo
- Publication number
- TWI621637B TWI621637B TW101112328A TW101112328A TWI621637B TW I621637 B TWI621637 B TW I621637B TW 101112328 A TW101112328 A TW 101112328A TW 101112328 A TW101112328 A TW 101112328A TW I621637 B TWI621637 B TW I621637B
- Authority
- TW
- Taiwan
- Prior art keywords
- epoxy compound
- component
- peak
- substituent
- resin composition
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 87
- 239000004593 Epoxy Substances 0.000 title claims abstract description 53
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 27
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- 125000001424 substituent group Chemical group 0.000 claims abstract description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 15
- 238000004817 gas chromatography Methods 0.000 claims abstract description 13
- 125000005843 halogen group Chemical group 0.000 claims abstract description 13
- 238000004458 analytical method Methods 0.000 claims abstract description 10
- 230000014759 maintenance of location Effects 0.000 claims abstract description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 16
- 238000000746 purification Methods 0.000 claims description 12
- 230000003647 oxidation Effects 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000011342 resin composition Substances 0.000 abstract description 43
- 150000008065 acid anhydrides Chemical class 0.000 abstract description 6
- 238000002156 mixing Methods 0.000 abstract description 6
- 238000002834 transmittance Methods 0.000 description 21
- 229920005989 resin Polymers 0.000 description 18
- 239000011347 resin Substances 0.000 description 18
- 238000004821 distillation Methods 0.000 description 14
- 230000003287 optical effect Effects 0.000 description 12
- 229920000647 polyepoxide Polymers 0.000 description 12
- 239000004065 semiconductor Substances 0.000 description 12
- 239000003822 epoxy resin Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- -1 dicyclic epoxide Chemical class 0.000 description 9
- 125000002723 alicyclic group Chemical group 0.000 description 8
- 239000003963 antioxidant agent Substances 0.000 description 8
- 230000003078 antioxidant effect Effects 0.000 description 8
- 125000003700 epoxy group Chemical group 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 125000001153 fluoro group Chemical group F* 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- PUNXVEAWLAVABA-UHFFFAOYSA-N 1,2,3,4-tetrahydroanthracene;1,2,5,6-tetrahydroanthracene Chemical compound C1=CC=C2C=C(CCCC3)C3=CC2=C1.C1=CCCC2=C1C=C1CCC=CC1=C2 PUNXVEAWLAVABA-UHFFFAOYSA-N 0.000 description 7
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 description 6
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 5
- 238000007789 sealing Methods 0.000 description 5
- 239000003566 sealing material Substances 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 4
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000013065 commercial product Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- 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 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- LLPKQRMDOFYSGZ-UHFFFAOYSA-N 2-methyl-4-methylimidazole Natural products CC1=CN=C(C)N1 LLPKQRMDOFYSGZ-UHFFFAOYSA-N 0.000 description 2
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 2
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Inorganic materials O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 238000009616 inductively coupled plasma Methods 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- QLWFRFCRJULPCK-UHFFFAOYSA-N methylantimony Chemical compound [Sb]C QLWFRFCRJULPCK-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- 125000005654 1,2-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([*:2])C([H])([*:1])C1([H])[H] 0.000 description 1
- 125000005837 1,2-cyclopentylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([*:2])C1([H])[H] 0.000 description 1
- ALTXUIJFJAHUPS-UHFFFAOYSA-N 1,2-epoxy-1,2-dihydrophenanthrene Chemical class C1=CC=C2C(C=CC3OC43)=C4C=CC2=C1 ALTXUIJFJAHUPS-UHFFFAOYSA-N 0.000 description 1
- 125000005655 1,3-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([*:2])C1([H])[H] 0.000 description 1
- 125000005838 1,3-cyclopentylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:2])C([H])([H])C1([H])[*:1] 0.000 description 1
- VOYADQIFGGIKAT-UHFFFAOYSA-N 1,3-dibutyl-4-hydroxy-2,6-dioxopyrimidine-5-carboximidamide Chemical compound CCCCn1c(O)c(C(N)=N)c(=O)n(CCCC)c1=O VOYADQIFGGIKAT-UHFFFAOYSA-N 0.000 description 1
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- STHGLRYNMROMHZ-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)-11-methyl-3-(8-methylnonyl)dodecane-1,3-diol Chemical compound C(CCCCCCC(C)C)C(O)(C(CO)(CO)CO)CCCCCCCC(C)C STHGLRYNMROMHZ-UHFFFAOYSA-N 0.000 description 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- BGCSUUSPRCDKBQ-UHFFFAOYSA-N 2,4,8,10-tetraoxaspiro[5.5]undecane Chemical compound C1OCOCC21COCOC2 BGCSUUSPRCDKBQ-UHFFFAOYSA-N 0.000 description 1
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- DGQFNPWGWSSTMN-UHFFFAOYSA-N 2-tert-butyl-4-[4-(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1CCCCC1=CC(C(C)(C)C)=C(O)C=C1C DGQFNPWGWSSTMN-UHFFFAOYSA-N 0.000 description 1
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 1
- GPNYZBKIGXGYNU-UHFFFAOYSA-N 2-tert-butyl-6-[(3-tert-butyl-5-ethyl-2-hydroxyphenyl)methyl]-4-ethylphenol Chemical compound CC(C)(C)C1=CC(CC)=CC(CC=2C(=C(C=C(CC)C=2)C(C)(C)C)O)=C1O GPNYZBKIGXGYNU-UHFFFAOYSA-N 0.000 description 1
- GRWFFFOEIHGUBG-UHFFFAOYSA-N 3,4-Epoxy-6-methylcyclohexylmethyl-3,4-epoxy-6-methylcyclo-hexanecarboxylate Chemical compound C1C2OC2CC(C)C1C(=O)OCC1CC2OC2CC1C GRWFFFOEIHGUBG-UHFFFAOYSA-N 0.000 description 1
- WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 description 1
- XDILCINHTMZTGG-UHFFFAOYSA-N 3-(3-dodecoxy-3-oxopropyl)sulfanylpropanoic acid Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(O)=O XDILCINHTMZTGG-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- PBEHQFUSQJKBAS-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol;phenol Chemical compound OC1=CC=CC=C1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 PBEHQFUSQJKBAS-UHFFFAOYSA-N 0.000 description 1
- PRWJPWSKLXYEPD-UHFFFAOYSA-N 4-[4,4-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butan-2-yl]-2-tert-butyl-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(C)CC(C=1C(=CC(O)=C(C=1)C(C)(C)C)C)C1=CC(C(C)(C)C)=C(O)C=C1C PRWJPWSKLXYEPD-UHFFFAOYSA-N 0.000 description 1
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RBHIUNHSNSQJNG-UHFFFAOYSA-N 6-methyl-3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2(C)OC2CC1C1(C)CO1 RBHIUNHSNSQJNG-UHFFFAOYSA-N 0.000 description 1
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 1
- NIJZFHNDUJXJMR-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethanol Chemical compound C1C(CO)CCC2OC21 NIJZFHNDUJXJMR-UHFFFAOYSA-N 0.000 description 1
- OXQXGKNECHBVMO-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptane-4-carboxylic acid Chemical compound C1C(C(=O)O)CCC2OC21 OXQXGKNECHBVMO-UHFFFAOYSA-N 0.000 description 1
- ADRNSOYXKABLGT-UHFFFAOYSA-N 8-methylnonyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCC(C)C)OC1=CC=CC=C1 ADRNSOYXKABLGT-UHFFFAOYSA-N 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- VPLKXGORNUYFBO-UHFFFAOYSA-N C1(CC2C(CC1)O2)CCC(C(OC)(OC)OC)CCCCCCCC Chemical compound C1(CC2C(CC1)O2)CCC(C(OC)(OC)OC)CCCCCCCC VPLKXGORNUYFBO-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001336 alkenes Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- VBQRUYIOTHNGOP-UHFFFAOYSA-N benzo[c][2,1]benzoxaphosphinine 6-oxide Chemical compound C1=CC=C2P(=O)OC3=CC=CC=C3C2=C1 VBQRUYIOTHNGOP-UHFFFAOYSA-N 0.000 description 1
- IDSLNGDJQFVDPQ-UHFFFAOYSA-N bis(7-oxabicyclo[4.1.0]heptan-4-yl) hexanedioate Chemical compound C1CC2OC2CC1OC(=O)CCCCC(=O)OC1CC2OC2CC1 IDSLNGDJQFVDPQ-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- DCZFGQYXRKMVFG-UHFFFAOYSA-N cyclohexane-1,4-dione Chemical compound O=C1CCC(=O)CC1 DCZFGQYXRKMVFG-UHFFFAOYSA-N 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- 125000004979 cyclopentylene group Chemical group 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- BQQUFAMSJAKLNB-UHFFFAOYSA-N dicyclopentadiene diepoxide Chemical compound C12C(C3OC33)CC3C2CC2C1O2 BQQUFAMSJAKLNB-UHFFFAOYSA-N 0.000 description 1
- IRDLUHRVLVEUHA-UHFFFAOYSA-N diethyl dithiophosphate Chemical compound CCOP(S)(=S)OCC IRDLUHRVLVEUHA-UHFFFAOYSA-N 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000000752 ionisation method Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- DHFYLDMPSGAGTP-UHFFFAOYSA-N phenoxymethanol Chemical class OCOC1=CC=CC=C1 DHFYLDMPSGAGTP-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- SUXIKHBBPQWLHO-UHFFFAOYSA-N trihydroxy-(8-methylnonyl)-(8-methyl-1-phenylnonyl)-lambda5-phosphane Chemical compound CC(C)CCCCCCCP(O)(O)(O)C(CCCCCCC(C)C)C1=CC=CC=C1 SUXIKHBBPQWLHO-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing Methods 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
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- 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
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/022—Polycondensates containing more than one epoxy group per molecule characterised by the preparation process or apparatus 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
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/027—Polycondensates containing more than one epoxy group per molecule obtained by epoxidation of unsaturated precursor, e.g. polymer or monomer
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
-
- 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
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4071—Curing agents not provided for by the groups C08G59/42 - C08G59/66 phosphorus containing compounds
-
- 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
- C08K5/00—Use of organic ingredients
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1535—Five-membered rings
- C08K5/1539—Cyclic anhydrides
-
- 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
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
- H01L23/296—Organo-silicon compounds
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/0001—Technical content checked by a classifier
- H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Epoxy Resins (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Led Device Packages (AREA)
Abstract
本發明提供一種樹脂組合物,其係調配下述式(1)所示之環氧化合物、酸酐及硬化促進劑而成者,且上述環氧化合物係經純化為以於利用氣相層析法分析而獲得之層析圖中,源自滯留時間較上述環氧化合物長之重質量分之峰的峰面積B相對於源自上述環氧化合物之峰的峰面積A之比B/A成為2.0×10-3以下者。
Description
本發明係關於一種含有環氧化合物之樹脂組合物、其硬化物及使用其之光半導體裝置。
近年來,於各種顯示板、圖像讀取用光源、交通信號、大型顯示器用單元等中得以實用之發光二極體(LED,light-emitting diode)等之發光元件或受光元件等光半導體裝置大部分係使用密封樹脂而製造。作為此種密封用樹脂,由於耐熱性、接著性、耐濕性、機械強度及電性特性等優異,故而通常使用環氧樹脂。
先前,作為密封材料,通常使用雙酚系二縮水甘油醚或酚系酚醛清漆型環氧樹脂(例如,專利文獻1)。然而,於利用該等先前之環氧樹脂對近年來得以實用之具有自藍色至近紫外線區域之發光波長的氮化物系LED進行密封之情形時,會產生環氧樹脂之芳香環因吸收短波長光而黃變,LED之發光強度明顯下降之問題。
此處,先前,已知於藉由環戊二烯與1,3-丁二烯之反應而合成乙烯降烯時,會副生四氫茚。並且近年來,要求有該四氫茚之有效之利用方法。
例如,於專利文獻2中,揭示有由四氫茚製造於分子內具有2個脂環骨架之環氧化合物、即四氫茚之二環氧化物之方法。
於專利文獻3中,揭示有使用調配規定量之(A)非酯型脂
環環氧化合物、(B)與上述(A)不同之環氧化合物及(C)陽離子聚合起始劑而成的熱固型樹脂組合物作為玻璃基板之替代品,作為(A)非酯型脂環環氧化合物,例示有四氫茚之二環氧化物。
[專利文獻1]日本專利特開2005-298616號公報
[專利文獻2]日本專利特開2004-182648號公報
[專利文獻3]日本專利特開2005-68303號公報
本發明之目的在於提供一種不僅對可見光而且對紫外線光亦具有充分之透光性之脂環式環氧樹脂硬化物、用以獲得該樹脂硬化物之樹脂組合物、及使用該樹脂組合物密封之光半導體裝置。
本發明係關於一種樹脂組合物,其係調配下述式(1)所示之環氧化合物、酸酐及硬化促進劑而成者,且以於利用氣相層析法分析而獲得之層析圖中,源自滯留時間較上述環氧化合物長之重質量分之峰的峰面積B相對於源自上述環氧化合物之峰的峰面積A之比B/A成為2.0×10-3以下之方式,對上述環氧化合物進行純化。
藉由此種樹脂組合物,可獲得不僅對可見光而且對紫外線光亦具有充分之透光性之樹脂硬化物。因此,上述樹脂組合物可較佳地用於用以密封光半導體元件之密封材料等用途中。
此外,專利文獻3所記載者係作為液晶面板等中所使用之玻璃基板之替代品而使用之熱固型樹脂組合物,於此種領域中未必需要對於可見光以外之光(例如UV-A(315~400 nm)等之紫外線光)之透過性。因此,於專利文獻3中,未對可見光以外之光之透光性進行評價,亦無用以獲得對於紫外線光之透過性之暗示等。進而,於專利文獻3中,記載有使用四氫茚之二環氧化物之實施例,與其他實施例相比,該實施例成為透光性較差者。
於本發明之樹脂組合物中,上述環氧化合物較佳為下述式(1-1)所示之化合物。
本發明之樹脂組合物亦可為進而調配有抗氧化劑者。
又,本發明之樹脂組合物亦可為進而調配有下述式(5)所示之化合物者。
本發明亦提供一種使上述樹脂組合物硬化而獲得之樹脂硬化物。本發明之樹脂硬化物對於可見光以外之光亦具有充分之透光性。
本發明亦提供一種使用上述樹脂組合物密封之光半導體裝置。
本發明亦關於一種環氧化合物之製造方法,其包括以下步驟:藉由下述式(2)所示之化合物之氧化反應而獲得下述式(1)所示之環氧化合物之氧化步驟;以及以於利用氣相層析法分析而獲得之層析圖中,源自滯留時間較上述環氧化合物長之重質量分之峰的峰面積B相對於源自上述環氧化合物之峰的峰面積A之比B/A成為2.0×10-3以下之方式,對上述氧化步驟中所獲得之上述環氧化合物進行純化之純化步驟。
於本發明之環氧化合物之製造方法中,較佳為上述式(2)所示之化合物為下述式(2-1)所示之化合物,上述式(1)所示之環氧化合物為下述式(1-1)所示之化合物。
本發明提供一種不僅對可見光而且對紫外線光亦具有充分之透光性之脂環式環氧樹脂硬化物、用以獲得該樹脂硬
化物之樹脂組合物、及使用該樹脂組合物密封之光半導體裝置。
以下,對於本發明之樹脂組合物之較佳之實施形態進行說明。
本實施形態之樹脂組合物係調配下述式(1)所示之環氧化合物(以下,有時稱為「(A)成分」)、酸酐(以下,有時稱為「(B)成分」)及硬化促進劑(以下,有時稱為「(C)成分」)而成者,且對(A)成分進行純化至於利用氣相層析法分析而獲得之層析圖中,源自滯留時間較(A)成分長之重質量分之峰的峰面積B相對於源自(A)成分之峰的峰面積A之比B/A成為2.0×10-3以下(較佳為1.3×10-3以下)。
根據本實施形態之樹脂組合物,可獲得不僅對可見光而且對紫外線光亦具有充分之透光性之樹脂硬化物。
又,就專利文獻1所記載之脂環式環氧樹脂而言,因於分子內具有酯基而具有水解性,存在因於高溫高濕下之使
用、於產生強酸之條件下之使用等而引起硬化物之物性降低之情況。對此,上述樹脂組合物之硬化物,耐熱性、耐濕性及耐酸性優異。
又,專利文獻3所記載者係作為液晶面板等所使用之玻璃基板之替代品而使用之熱固型樹脂組合物,於此種領域中未必需要對於可見光以外之光(例如UV-A(315~400 nm)等之紫外線光)之透過性。因此,於專利文獻3中,未對可見光以外之光之透光性進行評價,亦無用以獲得對於紫外線光之透過性之暗示等。進而,於專利文獻3中,記載有使用四氫茚之二環氧化物之實施例,但與其他實施例相比較,該實施例成為透光性較差者。
於(A)成分之比B/A超過2.0×10-3之情形時,例如對於樹脂硬化物之800 nm附近之光的透光性良好,但對於UV-A(315~400 nm)之透光性明顯變低。相對於此,藉由上述樹脂組合物,可獲得不僅對可見光而且對紫外線光(例如UV-A)亦具有充分之透光性之樹脂硬化物。
式(1)之R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11及R12分別獨立表示氫原子、鹵素原子、可具有取代基之烷基或可具有取代基之烷氧基。
作為烷基,較佳為碳數1~10之烷基,更佳為碳數1~4之烷基。於烷基具有取代基時,作為該取代基,可列舉鹵素原子、烷氧基等。
作為烷氧基,較佳為碳數1~10之烷氧基,更佳為碳數1~4之烷氧基。於烷氧基具有取代基時,作為該取代基,
可列舉鹵素原子、烷氧基等。
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11及R12較佳為分別獨立為氫原子、氟原子、烷基或烷氧基,更佳為分別獨立為氫原子或氟原子,進而較佳為分別獨立為氫原子。
即,作為(A)成分,可尤其較佳地使用下述式(1-1)所示之化合物。
氣相層析法分析可於以下之條件下進行。
.使用設備:安捷倫科技公司製造之6850系列
.管柱:Agilent 19091Z-413E(HP-1二甲基聚矽氧烷,毛細管30.0 m×320 μm×0.25 μm)
.入口(Inlet):250℃
.偵測器(Detector):250℃
.烘箱(Oven):50℃(10 min)、250℃(5℃/min)、250℃(20 min)
(A)成分亦可為立體異構物之混合物。於(A)成分為立體異構物之混合物時,峰面積A表示源自各立體異構物之峰之總面積。又,於(A)成分為立體異構物之混合物時,「滯留時間較(A)成分長」係表示滯留時間較(A)成分之立體異構物中之滯留時間最長者長。
圖1及圖2係表示於下述合成例1中獲得之環氧化合物之
藉由氣相層析法分析所獲得的層析圖之圖,但於圖1及圖2中,以a-1、a-2、a-3及a-4表示之峰為源自(A)成分者,以b表示之範圍之峰為源自重質量分者。
此外,各峰之分析可藉由下述條件下之氣相層析質譜分析而進行。
(a)氣相層析部
.使用設備:安捷倫科技公司製造之7890A
.管柱:Agilent 19091S-936(HP-1MS二甲基聚矽氧烷,毛
細管60.0 m×250 μm×0.25 μm)
.入口(Inlet):250℃
.烘箱(Oven):40℃(10 min)、300℃(5℃/min)、300℃(18 min)
(b)質譜分析部
.使用設備:安捷倫科技公司製造之5975C VL MSD
.離子化法:電子衝擊電離方式
.離子源溫度:230℃
.MS(Mass Spectrometer,質譜儀)四極溫度:150℃
例如,若對下述合成例1之環氧化合物進行氣相層析質譜分析,則作為相當於圖1及圖2之a-1、a-2、a-3及a-4所表示之峰者,觀察到源自分子量152之化合物之峰。因此,可確認a-1、a-2、a-3及a-4所表示之峰為源自(A)成分者。又,作為相當於圖1及圖2之b所表示之範圍之峰者,觀察到源自分子量155~168之重質量分之化合物之峰。
(A)成分可藉由包括下述氧化步驟與純化步驟之製造方
法而製造。
於氧化步驟中,藉由下述式(2)所示之化合物之氧化反應而合成(A)成分。
氧化反應之方法並無特別限制,例如可藉由日本專利特開2004-182648號公報所記載之方法而進行。
又,氧化反應可藉由先前習知之由烯烴化合物製造環氧化合物之方法而進行。作為此種方法,例如可列舉J.Org.Chem.2000,65,8651所記載之方法、Organic Syntheses,1997,74,91所記載之方法、Organic Syntheses,Coll.1998,9,288所記載之方法等。
又,作為氧化反應之具體例,可列舉於含有式(2)所示之化合物、吡啶、3-氰基吡啶及甲基三氧化錸之二氯甲烷溶液中添加30%之過氧化氫,於室溫(25℃)下使其反應之方法。
於純化步驟中,以於利用氣相層析法分析而獲得之層析圖中,源自滯留時間較(A)成分長之重質量分之峰的峰面積B相對於源自(A)成分之峰的峰面積A之比B/A成為2.0×10-3以下之方式,對上述氧化步驟中所獲得之(A)成分進行純化。
作為(A)成分之純化方法,只要為可使比B/A成為2.0×10-3以下之方法,則無特別限制,例如可列舉蒸餾純化。
(A)成分為對於熱不穩定之化合物,故若蒸餾純化中之溫度過高或滯留時間過長,則存在(A)成分之一部分分解,或產生重質量分之情況。因此,較佳為於蒸餾純化中將溫度設為20~150℃,將滯留時間設為0.01~60分鐘。作為蒸餾裝置,例如可列舉批次式精密蒸餾裝置、離心式分子蒸餾裝置、薄膜蒸餾裝置等。
更具體而言,蒸餾純化可於例如600 Pa、塔底溫度30~80℃之範圍內進行,可依序區分流出之餾分,將比B/A成為2.0×10-3以下之餾分取出而進行。
就樹脂硬化物之耐濕可靠性進一步提高,更適合於光半導體密封用途之方面而言,(A)成分之氯含量較佳為100 ppm以下,更佳為10 ppm以下。此外,氯含量係依據JIS規格K-7243-3而測定之值,具體而言,係藉由如下方式測定之值:使(A)成分溶解於二乙二醇單丁醚,並利用氫氧化鉀醇溶液於加熱回流下使其皂化,進行硝酸銀溶液之電位差滴定。
(A)成分之氯含量可藉由上述蒸餾純化而減少,亦可藉由鹼性水溶液清洗、吸附劑處理等方法而減少。
就樹脂硬化物之機械特性或電性特性進一步提高,更適合於光半導體密封用途之方面而言,(A)成分之金屬含量較佳為100 ppm以下,更佳為10 ppm以下。再者,金屬含量可藉由對(A)成分之10%甲苯溶液進行感應耦合電漿發光
(ICP(Inductively coupled plasma)發光)分析而測定。測定裝置例如可使用Perkin Elmer公司之Optima 4300DV等。該測定中,對於定性分析中所檢測出之金屬種類,可分別利用使用市售之金屬標準溶液而製成之校準曲線進行定量分析。
(A)成分之金屬含量可藉由上述蒸餾純化而減少,亦可藉由鹼性水溶液清洗、吸附劑處理等方法而減少。
(A)成分之調配量於樹脂組合物之總量基準中較佳為12~45質量%,更佳為14~38質量%。
(B)成分之酸酐係與樹脂組合物中之環氧化合物進行反應而使樹脂組合物硬化之成分。作為(B)成分,可列舉鄰苯二甲酸酐、順丁烯二酸酐、偏苯三甲酸酐、均苯四甲酸二酐、六氫鄰苯二甲酸酐、甲基六氫鄰苯二甲酸酐、四氫鄰苯二甲酸酐、甲基四氫鄰苯二甲酸酐、甲基內伸乙基四氫鄰苯二甲酸酐、三烷基四氫鄰苯二甲酸酐、甲基耐地酸酐、耐地酸酐、戊二酸酐等。
(B)成分之調配量相對於樹脂組合物中之環氧化合物之調配量100質量份,較佳為45~320質量份,更佳為70~250質量份。更詳細而言,相對於可發揮作為硬化劑之效果之有效量、即樹脂組合物中之環氧化合物之環氧基1當量,較佳為0.6~1.5當量,更佳為0.8~1.2當量。
(C)成分之硬化促進劑係促進樹脂組合物中之環氧化合物與(B)成分之反應,且促進樹脂組合物之硬化之成分。作為(C)成分,可列舉三級胺、咪唑類、羧酸金屬鹽、磷
化合物等。
作為三級胺,可列舉苄基二甲胺、2,4,6-三(二甲胺基甲基)苯酚、1,8-二氮雜雙環[5.4.0]十一碳烯-7、1,5-二氮雜雙環[4.3.0]壬烯-5等。又,作為咪唑類,可列舉2-甲基咪唑、2-甲基-4-甲基咪唑等。
作為羧酸金屬鹽,可列舉辛酸鋅、辛酸錫等。又,作為磷化合物,可列舉四苯基溴化鏻、o,o-二乙基二硫代磷酸四正丁基鏻等。
(C)成分之調配量相對於樹脂組合物中之環氧化合物之調配量100質量份,較佳為0.1~5質量份,更佳為0.2~2質量份。
樹脂組合物亦可調配除上述以外之成分。例如,樹脂組合物亦可進一步調配抗氧化劑(以下,有時稱為「(D)成分」)。
作為(D)成分,可列舉酚系抗氧化劑、硫系抗氧化劑、磷系抗氧化劑等。
作為酚系抗氧化劑,例如可列舉:2,6-二-第三丁基對甲酚(BHT,2,6-Di-tert-butyl-p-cresol)、丁基化羥基甲氧苯、2,6-二-第三丁基對乙基苯酚、β-(3,5-二-第三丁基-4-羥基苯基)丙酸硬脂酯等單酚類;2,2'-亞甲基雙(4-甲基-6-第三丁基苯酚)、2,2'-亞甲基雙(4-乙基-6-第三丁基苯酚)、4,4'-硫代雙(3-甲基-6-第三丁基苯酚)、4,4'-亞丁基雙(6-第三丁基-3-甲基苯酚)、3,9-雙[1,1-二甲基-2-{β-(3-第三丁基-4-羥基-5-甲苯基)丙醯氧基}乙基]2,4,8,10-四氧雜螺
[5.5]十一烷等雙酚類;1,1,3-三(2-甲基-4-羥基-5-第三丁基苯基)丁烷、1,3,5-三甲基-2,4,6-三(3,5-二-第三丁基-4-羥基苄基)苯、四[亞甲基-3-(3',5'-二-第三丁基-4'-羥基苯基)丙酸酯]甲烷、雙[3,3'-雙-(4'-羥基-3'-第三丁基苯基)丁酸]二醇酯、1,3,5-三(3',5'-二-第三丁基-4'-羥基苄基)-均三-2,4,6-(1H,3H,5H)三酮、生育酚等。
作為硫系抗氧化劑,可列舉3,3'-硫代二丙酸雙十二烷酯、3,3'-硫代二丙酸二硬脂醇酯等。
作為磷系抗氧化劑,可列舉:三苯基亞磷酸酯、十三烷基亞磷酸酯、二苯基異癸基亞磷酸酯、苯基二異癸基亞磷酸酯、三(壬基苯基)亞磷酸酯、二異癸基季戊四醇亞磷酸酯、三(2,4-二-第三丁基苯基)亞磷酸酯、環狀新戊烷四基雙(十八烷基)亞磷酸酯、環狀新戊烷四基雙(2,4-二-第三丁基苯基)亞磷酸酯、環狀新戊烷四基雙(2,4-二-第三丁基-4-甲苯基)亞磷酸酯、雙[2-第三丁基-6-甲基-4-{2-(十八烷氧基羰基)乙基}苯基]羥亞磷酸酯等亞磷酸酯類;9,10-二氫-9-氧雜-10-磷雜菲-10-氧化物、10-(3,5-二-第三丁基-4-羥基苄基)-9,10-二氫-9-氧雜-10-磷雜菲-10-氧化物等氧雜磷雜菲氧化物類;等。
(D)成分之調配量相對於樹脂組合物中之環氧化合物之調配量100質量份,較佳為0.01~5質量份,更佳為0.1~4質量份。
又,於樹脂組合物中,亦可進一步調配除(A)成分以外之環氧化合物(以下,有時稱為「(A')成分」)。
作為(A')成分,例如可列舉具有環脂族環氧基之化合物。作為具有環脂族環氧基之化合物,例如可列舉下述式(3)所示之化合物、下述式(4)所示之化合物及下述式(5)所示之化合物。
式(3)中,Ra表示氫原子、鹵素原子、可具有取代基之烷基或可具有取代基之烷氧基,複數之Ra彼此可相同,亦可不同。Ra較佳為氫原子、氟原子、烷基或烷氧基,更佳為氫原子或氟原子,進而較佳為氫原子。此外,作為Ra中之烷基及烷氧基,可例示與R1~R12中之烷基及烷氧基相同之基。
式(4)中,Rb表示氫原子、鹵素原子、可具有取代基之
烷基或可具有取代基之烷氧基,複數之Rb彼此可相同,亦可不同。Rb較佳為氫原子、氟原子、烷基或烷氧基,更佳為氫原子或氟原子,進而較佳為氫原子。此外,作為Rb中之烷基及烷氧基,可例示與R1~R12中之烷基及烷氧基相同之基。
式(5)中,Rc表示氫原子、鹵素原子、可具有取代基之烷基或可具有取代基之烷氧基,Z表示連結基。又,複數之Rc彼此可相同,亦可不同。Rc較佳為氫原子、氟原子、烷基或烷氧基,更佳為氫原子或氟原子,進而較佳為氫原子。此外,作為Rc中之烷基及烷氧基,可例示與R1~R12中之烷基及烷氧基相同之基。
作為連結基,例如可列舉:單鍵、二價烴基、羰基(-CO-)、醚鍵(-O-)、酯鍵(-COO-)、醯胺鍵(-CONH-)、碳酸鍵(-OCOO-)、及該等複數個連結而成之基。
上述二價烴基之碳數較佳為1~18。又,作為上述二價烴基,較佳為直鏈狀或支鏈狀之伸烷基、二價脂環式烴基(尤其是環伸烷基)等。作為伸烷基,可列舉亞甲基、甲基亞甲基、二甲基亞甲基、伸乙基、伸丙基、三亞甲基等。又,作為二價脂環式烴基,可列舉1,2-亞環戊基、1,3-亞環戊基、亞環戊基、1,2-亞環己基、1,3-亞環己基、1,4-亞環己基、亞環己基等。
作為式(5)所示之化合物之具體例,可列舉下述式(5-1)~(5-7)所示之化合物。
又,作為具有環脂族環氧基之化合物,亦可例示:二環戊二烯二氧化物、檸檬烯二氧化物、二(3,4-環氧基環己基)己二酸酯、3,4-環氧基環己基甲基-3',4'-環氧環己烷甲酸酯(作為市售品,有Celloxide2021P(Daicel化學工業製造)等)、(3,4-環氧基-6-甲基環己基)甲基-3,4-環氧基-6-甲基環己烷甲酸酯、伸乙基-1,2-二(3,4-環氧環己烷甲酸)酯等。
作為具有環脂族環氧基之化合物,可較佳地使用上述中之式(3)所示之化合物、式(4)所示之化合物、式(5)所示之
化合物(尤其是3,4-環氧基環己基甲基-3',4'-環氧環己烷甲酸酯)、3,4-環氧基環己基甲醇及3,4-環氧基環己基乙基三甲氧基矽烷。
又,作為(A')成分,亦可使用具有除環脂族環氧基以外之環氧基之化合物。作為此種化合物,可列舉:以雙酚A型及雙酚F型為代表之各種雙酚型二縮水甘油醚(作為市售品,有Epikote828、806(Japan Epoxy Resins公司製造),YD-128(東都化成製造)等);雙酚型環氧樹脂之核氫化產品(作為市售品,有HBE-100(新日本理化製造),YX-4000、YX-8000(Japan Epoxy Resins公司製造)等);環己烷二甲醇之二縮水甘油醚等具有環狀脂肪族骨架之縮水甘油醚(作為市售品,有DME-100(新日本理化製造)等);酚醛清漆型苯酚樹脂之縮水甘油醚;使DCPD(dicyclopentadiene,二環戊二烯)等共聚合而成之酚醛清漆型苯酚樹脂之縮水甘油醚;萘基等多環芳香族之縮水甘油醚;於脂環骨架上具有封端環氧基之環氧樹脂(作為市售品,有EHPE-3150、EHPE-3150CE(Daicel化學工業製造)等);具有環氧基之矽樹脂(作為市售品,有A-186(日本Unicar製造),KBM303、KBM403、KBM42(信越化學工業製造)等);等。
(A')成分可單獨使用1種或組合2種以上使用。
於調配(A')成分時,(A')成分之調配量A'相對於(A)成分之調配量A之比A'/A(質量比)可設為1/99~99/1,亦可設為1/99~90/10。
進而,於樹脂組合物中,作為除上述以外之成分,亦可
進一步調配紫外線吸收劑等添加劑。
本實施形態之樹脂組合物係藉由加熱而硬化,從而形成樹脂硬化物。以此種方式形成之樹脂硬化物不僅對於可見光具有透光性,而且對於可見光以外之光(例如UV-A(315~400 nm)等之紫外線)亦具有充分之透光性。因此,本實施形態之樹脂組合物可較佳地用於用以密封光半導體元件之密封材料等需要硬化物之透光性之用途。
又,將本實施形態之樹脂組合物注入特定之成型塊內,於特定之條件下進行加熱硬化而將光半導體元件密封,藉此可獲得光半導體裝置。此種光半導體裝置係將本實施形態之樹脂組合物作為密封材料來保護發光體之周邊,故而不存在由黃變所導致的亮度降低或變色等問題,作為可靠性較高之光半導體裝置而有用。
以上,對本發明之較佳之實施形態進行說明,但本發明並不限定於上述實施形態。
以下,根據實施例更具體地說明本發明,但本發明並不限定於實施例。
於設置有攪拌裝置之反應槽中,依序裝入四氫茚120 g、吡啶15.8 g、3-氰基吡啶20.8 g、甲基三氧化錸2.49 g、二氯甲烷440 g、30%之過氧化氫450 g。於室溫下攪拌2小時後,將油相與水相分離。於水相中加入二氯甲烷200 g並攪拌,清洗水相。將藉由清洗操作而產生之油相與先前
之油相混合,使用旋轉蒸發器蒸餾去除溶劑而獲得粗產物。
於0℃、220 Pa之條件下對所獲得之粗產物進行蒸餾,獲得上述式(1)所示之環氧化合物143 g。對所獲得之環氧化合物進行氣相層析法分析,結果源自滯留時間較環氧化合物長之重質量分之峰的峰面積B相對於源自環氧化合物之峰的峰面積A之比B/A為5.7×10-3。將該環氧化合物設為(A-5)成分。
其次,將(A-5)成分100 g裝入精密蒸餾器中,於600 Pa、塔底溫度30~80℃之範圍內進行精密蒸餾,依序區分流出之餾分。對區分之4個餾分進行氣相層析法分析,結果比B/A分別為1.0×10-3、1.1×10-3、1.6×10-3、3.0×10-3。將該等4個餾分分別設為(A-1)成分、(A-2)成分、(A-3)成分、(A-4)成分。相對於(A-5)成分100 g,(A-1)成分之蒸餾產量為20 g,(A-2)成分之蒸餾產量為20 g,(A-3)成分之蒸餾產量為20 g,(A-4)成分之蒸餾產量為35 g。將該等結果示於表1。
此外,氣相層析法分析係於以下所示之條件下進行。
.使用設備:安捷倫科技公司製造之6850系列
.管柱:Agilent 19091Z-413E(HP-1二甲基聚矽氧烷,毛細管30.0 m×320 μm×0.25 μm)
.入口(Inlet):250℃
.偵測器(Detector):250℃
.烘箱(Oven):50℃(10 min)、250℃(5℃/min)、250℃(20
min)
圖1係表示(A-1)成分之利用氣相層析法分析所獲得之層析圖之圖,圖2係表示(A-5)成分之利用氣相層析法分析所獲得之層析圖之圖。
利用分光光度計(日本分光製造:V-570)測定(A-1)~(A-5)成分之350 nm、400 nm、800 nm之波長之透光率(%)。測定結果如表2所示。
以表3及表4所示之份數(質量份)調配各原料,於室溫下進行攪拌,藉此獲得液狀樹脂組合物。作為(A')成分,使用Celloxide2021P(Daicel化學工業製造,3,4-環氧基環己基甲基-3',4'-環氧環己烷甲酸酯),作為酸酐使用RIKACID MH-700(新日本理化股份有限公司製造,4-甲基六氫鄰苯二甲酸酐/六氫鄰苯二甲酸酐=70/30),作為硬化促進劑,使用Hishicolin PX-4ET(日本化學工業股份有限公司製
造,四正丁基鏻o,o-二乙基二硫代磷酸酯),作為抗氧化劑,使用2,6-二-第三丁基對甲酚(於表3及4中,記作「BHT」)及三苯基亞磷酸酯(於表3及4中,記作「TPP」)。
其次,將所獲得之樹脂組合物澆鑄於60 mm×1 mm之鋁模中,藉由110℃×2小時之加熱與120℃×5小時之加熱而使其硬化,從而獲得包含樹脂硬化物之試樣。
將所獲得之試樣設置於分光光度計(日本分光製造:V-570)上,測定350 nm、400 nm、800 nm之波長之透光率(%)。測定結果如表5及表6所示。
如表2及表5所示,(A-1)~(A-5)成分之透光率根據比B/A而幾乎無變化,但就使用該等而製造之樹脂硬化物而言,對於UV-A之透光率產生明顯之差。
即,如表5及表6所示,實施例之由樹脂組合物所獲得之樹脂硬化物係350 nm之透光率為70%以上,400 nm之透光率為80%以上,透光率足夠高,與比較例之樹脂硬化物相比,具有優異之透光率。因此,可確認本發明之樹脂組合物作為用以密封光半導體元件之密封材料而有用。
a-1‧‧‧源自(A)成分之峰
a-2‧‧‧源自(A)成分之峰
a-3‧‧‧源自(A)成分之峰
a-4‧‧‧源自(A)成分之峰
b‧‧‧源自重質量分之峰
圖1係表示於合成例1中獲得之(A-1)成分之藉由氣相層析法分析所獲得的層析圖之圖。
圖2係表示於合成例1中獲得之(A-5)成分之藉由氣相層析法分析所獲得的層析圖之圖。
Claims (4)
- 一種環氧化合物之製造方法,其包括:利用下述式(2)所示之化合物之氧化反應而獲得下述式(1)所示之環氧化合物之氧化步驟;以於利用氣相層析法分析而獲得之層析圖中,源自滯留時間較上述環氧化合物長之重質量分之峰的峰面積B相對於源自上述環氧化合物之峰的峰面積A之比B/A成為2.0×10-3以下之方式,對上述氧化步驟中所獲得之上述環氧化合物進行純化之純化步驟,
- 如請求項1之環氧化合物之製造方法,其中上述式(2)所示之化合物為下述式(2-1)所示之化合物,上述式(1)所示之環氧化合物為下述式(1-1)所示之化合物,
- 一種環氧化合物之製造方法,其係下述式(1)所示之環氧化合物之製造方法,包括:將利用氣相層析法分析而獲得之層析圖中,源自滯留時間較上述環氧化合物長之重質量分之峰的峰面積B相對於源自上述環氧化合物之峰的峰面積A之比設定為比B/A,利用下述式(2)所示之化合物之氧化反應而獲得上述比B/A超過2.0×10-3之環氧化合物之氧化步驟;蒸餾利用上述氧化步驟而獲得之上述環氧化合物,而獲得上述比B/A為2.0×10-3以下之環氧化合物之純化步驟,
- 如請求項1至3中任一項之環氧化合物之製造方法,其中於上述純化步驟中,係以溫度為20~150℃、滯留時間為0.01~60分鐘蒸餾上述環氧化合物。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2011086409 | 2011-04-08 |
Publications (2)
Publication Number | Publication Date |
---|---|
TW201249884A TW201249884A (en) | 2012-12-16 |
TWI621637B true TWI621637B (zh) | 2018-04-21 |
Family
ID=46969270
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
TW101112328A TWI621637B (zh) | 2011-04-08 | 2012-04-06 | Method for producing epoxy compound |
Country Status (6)
Country | Link |
---|---|
US (1) | US9464186B2 (zh) |
JP (1) | JP6005035B2 (zh) |
KR (1) | KR101899800B1 (zh) |
CN (1) | CN103459454B (zh) |
TW (1) | TWI621637B (zh) |
WO (1) | WO2012137880A1 (zh) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013028790A (ja) * | 2011-06-24 | 2013-02-07 | Nippon Zeon Co Ltd | 高純度脂環式ジエポキシ化合物、硬化性エポキシ樹脂組成物、硬化物、透明封止材料及び発光素子 |
JP6171284B2 (ja) * | 2012-08-23 | 2017-08-02 | 日本ゼオン株式会社 | 高純度脂環式ジエポキシ化合物、硬化性エポキシ樹脂組成物、硬化物、透明封止材料および発光素子 |
JP2016505674A (ja) * | 2012-12-14 | 2016-02-25 | ブルー キューブ アイピー エルエルシー | 高固体エポキシコーティング |
CN109311906B (zh) * | 2016-06-10 | 2021-08-03 | Jxtg能源株式会社 | 环氧化合物、包含该环氧化合物的固化性组合物以及使固化性组合物固化得到的固化物 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI298065B (zh) * | 2001-03-23 | 2008-06-21 | Daicel Chem | |
JP2010235649A (ja) * | 2009-03-30 | 2010-10-21 | Sanyo Chem Ind Ltd | 精製エポキシ樹脂の製造方法 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02115217A (ja) * | 1988-10-24 | 1990-04-27 | Tosoh Corp | 光学材料用樹脂組成物 |
JP2004182648A (ja) | 2002-12-03 | 2004-07-02 | Daicel Chem Ind Ltd | 脂環式ジエポキシ化合物の製造方法 |
JP3973611B2 (ja) | 2003-08-25 | 2007-09-12 | ダイセル化学工業株式会社 | 熱硬化型エポキシ樹脂組成物および透明材料 |
CN100513453C (zh) | 2003-09-22 | 2009-07-15 | 三菱化学株式会社 | 脂环式环氧树脂、其制造方法、其组合物、环氧树脂固化物以及脂环式环氧树脂组合物的用途 |
KR20110104099A (ko) | 2003-09-22 | 2011-09-21 | 미쓰비시 가가꾸 가부시키가이샤 | 지환식 에폭시 수지, 그의 조성물, 에폭시 수지 경화물 및 지환식 에폭시 수지 조성물의 용도 |
JP4553572B2 (ja) * | 2003-11-12 | 2010-09-29 | ダイセル化学工業株式会社 | 紫外線硬化型接着剤およびその接着体 |
JP4426324B2 (ja) | 2004-01-21 | 2010-03-03 | ダイセル化学工業株式会社 | 非エステル型エポキシ樹脂および樹脂組成物 |
KR101144420B1 (ko) * | 2004-03-18 | 2012-05-11 | 가부시끼가이샤 다이셀 | 고순도 지환식 에폭시 화합물, 그 제조 방법, 경화성에폭시 수지 조성물, 그 경화물, 및 용도 |
JP4473030B2 (ja) | 2004-04-09 | 2010-06-02 | 稲畑産業株式会社 | 光半導体封止用樹脂組成物及びこれを用いた光半導体装置 |
EP1829936A4 (en) | 2004-11-18 | 2008-08-27 | Konica Minolta Med & Graphic | ACTIALLY HARDENABLE COMPOSITION, ACTIALLY HARDENABLE INK AND IMAGING METHOD |
JP5354868B2 (ja) * | 2006-07-06 | 2013-11-27 | 株式会社ダイセル | 脂環式ジエポキシ化合物の製造方法、エポキシ樹脂組成物の製造方法、及び硬化物の製造方法 |
JP5289713B2 (ja) * | 2007-02-01 | 2013-09-11 | 株式会社ダイセル | 硬化性樹脂組成物及びその硬化物 |
JP5184179B2 (ja) | 2008-03-28 | 2013-04-17 | 京セラ株式会社 | 薄膜共振子、フィルタおよびデュプレクサ |
JP2009249569A (ja) * | 2008-04-09 | 2009-10-29 | Japan Epoxy Resin Kk | 光学素子封止材用エポキシ樹脂組成物 |
TWI491596B (zh) * | 2008-10-10 | 2015-07-11 | Sumitomo Bakelite Co | 脂環二環氧化物之製備技術 |
-
2012
- 2012-04-05 CN CN201280015297.8A patent/CN103459454B/zh not_active Expired - Fee Related
- 2012-04-05 WO PCT/JP2012/059394 patent/WO2012137880A1/ja active Application Filing
- 2012-04-05 JP JP2013508925A patent/JP6005035B2/ja active Active
- 2012-04-05 US US14/009,909 patent/US9464186B2/en active Active
- 2012-04-05 KR KR1020137024384A patent/KR101899800B1/ko active IP Right Grant
- 2012-04-06 TW TW101112328A patent/TWI621637B/zh not_active IP Right Cessation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI298065B (zh) * | 2001-03-23 | 2008-06-21 | Daicel Chem | |
JP2010235649A (ja) * | 2009-03-30 | 2010-10-21 | Sanyo Chem Ind Ltd | 精製エポキシ樹脂の製造方法 |
Also Published As
Publication number | Publication date |
---|---|
KR20140021564A (ko) | 2014-02-20 |
JPWO2012137880A1 (ja) | 2014-07-28 |
US9464186B2 (en) | 2016-10-11 |
CN103459454A (zh) | 2013-12-18 |
US20140128510A1 (en) | 2014-05-08 |
KR101899800B1 (ko) | 2018-09-20 |
WO2012137880A1 (ja) | 2012-10-11 |
JP6005035B2 (ja) | 2016-10-12 |
TW201249884A (en) | 2012-12-16 |
CN103459454B (zh) | 2016-01-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
TWI440631B (zh) | 脂環式二環氧化合物之製造方法、環氧樹脂組成物之製造方法及硬化物之製造方法 | |
TW201120000A (en) | Multivalent carboxylic acid composition, curable resin composition, cured article and method for producing multivalent carboxylic acid composition | |
TW202104199A (zh) | 脂環式環氧化合物製品 | |
TWI621637B (zh) | Method for producing epoxy compound | |
JP2007326988A (ja) | エポキシ樹脂組成物 | |
WO2017126568A1 (ja) | エポキシ樹脂組成物 | |
CN111587267B (zh) | 脂环式环氧化合物产品 | |
WO2014010420A1 (ja) | 樹脂組成物、その硬化物及びそれを用いた光半導体装置 | |
JP2018095765A (ja) | エポキシ樹脂組成物及びエポキシ薄膜硬化物 | |
TW200909423A (en) | Adamantane derivative, method for producing the same, resin composition containing the same, and use of the same | |
JP5842600B2 (ja) | エポキシ樹脂組成物、硬化物、透明封止材料及び光半導体装置 | |
JP5387638B2 (ja) | エポキシ樹脂組成物 | |
TWI654216B (zh) | 含茀骨架的環氧樹脂及其製造方法、環氧樹脂組成物及其應用、以及硬化物 | |
JP6171284B2 (ja) | 高純度脂環式ジエポキシ化合物、硬化性エポキシ樹脂組成物、硬化物、透明封止材料および発光素子 | |
KR102289998B1 (ko) | 플루오렌 골격 함유 에폭시 수지의 제조 방법, 에폭시 수지 조성물, 및 경화물 | |
JP2013028790A (ja) | 高純度脂環式ジエポキシ化合物、硬化性エポキシ樹脂組成物、硬化物、透明封止材料及び発光素子 | |
JP2006312702A (ja) | エポキシ樹脂用硬化剤、その製造方法、それを用いたエポキシ樹脂組成物、その硬化物及び光半導体 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM4A | Annulment or lapse of patent due to non-payment of fees |