JP5736568B2 - 速硬化性に優れたエネルギー線硬化型エポキシ樹脂組成物 - Google Patents
速硬化性に優れたエネルギー線硬化型エポキシ樹脂組成物 Download PDFInfo
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- JP5736568B2 JP5736568B2 JP2011520897A JP2011520897A JP5736568B2 JP 5736568 B2 JP5736568 B2 JP 5736568B2 JP 2011520897 A JP2011520897 A JP 2011520897A JP 2011520897 A JP2011520897 A JP 2011520897A JP 5736568 B2 JP5736568 B2 JP 5736568B2
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- epoxy resin
- resin composition
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- curable epoxy
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- 239000003822 epoxy resin Substances 0.000 title claims description 81
- 229920000647 polyepoxide Polymers 0.000 title claims description 81
- 239000000203 mixture Substances 0.000 title claims description 47
- -1 oxetanyl silicate Chemical compound 0.000 claims description 39
- 230000003287 optical effect Effects 0.000 claims description 18
- 239000000945 filler Substances 0.000 claims description 16
- 239000000853 adhesive Substances 0.000 claims description 13
- 230000001070 adhesive effect Effects 0.000 claims description 13
- 150000002921 oxetanes Chemical class 0.000 claims 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 17
- 238000001723 curing Methods 0.000 description 15
- 125000002091 cationic group Chemical group 0.000 description 11
- 125000000524 functional group Chemical group 0.000 description 8
- 239000003504 photosensitizing agent Substances 0.000 description 8
- 125000002723 alicyclic group Chemical group 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 239000006087 Silane Coupling Agent Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 4
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 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
- 239000000047 product Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
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- FNYWFRSQRHGKJT-UHFFFAOYSA-N 3-ethyl-3-[(3-ethyloxetan-3-yl)methoxymethyl]oxetane Chemical compound C1OCC1(CC)COCC1(CC)COC1 FNYWFRSQRHGKJT-UHFFFAOYSA-N 0.000 description 2
- LMIOYAVXLAOXJI-UHFFFAOYSA-N 3-ethyl-3-[[4-[(3-ethyloxetan-3-yl)methoxymethyl]phenyl]methoxymethyl]oxetane Chemical compound C=1C=C(COCC2(CC)COC2)C=CC=1COCC1(CC)COC1 LMIOYAVXLAOXJI-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000004844 aliphatic epoxy resin Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000010227 cup method (microbiological evaluation) Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 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 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
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- 150000003839 salts Chemical class 0.000 description 2
- 150000004760 silicates Chemical class 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- CTLDMRCJDQGAQJ-UHFFFAOYSA-N (1,1-dimethoxy-2-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(OC)(OC)CC1=CC=CC=C1 CTLDMRCJDQGAQJ-UHFFFAOYSA-N 0.000 description 1
- VLTYTTRXESKBKI-UHFFFAOYSA-N (2,4-dichlorophenyl)-phenylmethanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 VLTYTTRXESKBKI-UHFFFAOYSA-N 0.000 description 1
- UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- QFDDZIRGHKFRMR-UHFFFAOYSA-N 10-butylacridin-9-one Chemical compound C1=CC=C2N(CCCC)C3=CC=CC=C3C(=O)C2=C1 QFDDZIRGHKFRMR-UHFFFAOYSA-N 0.000 description 1
- JTINZFQXZLCHNS-UHFFFAOYSA-N 2,2-bis(oxiran-2-ylmethoxymethyl)butan-1-ol Chemical compound C1OC1COCC(CO)(CC)COCC1CO1 JTINZFQXZLCHNS-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- LJWZDTGRJUXOCE-UHFFFAOYSA-N 2-(2-ethylhexyl)oxetane Chemical compound CCCCC(CC)CC1CCO1 LJWZDTGRJUXOCE-UHFFFAOYSA-N 0.000 description 1
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 description 1
- FVCHRIQAIOHAIC-UHFFFAOYSA-N 2-[1-[1-[1-(oxiran-2-ylmethoxy)propan-2-yloxy]propan-2-yloxy]propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COC(C)COC(C)COCC1CO1 FVCHRIQAIOHAIC-UHFFFAOYSA-N 0.000 description 1
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 1
- SEFYJVFBMNOLBK-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxymethyl]oxirane Chemical compound C1OC1COCCOCCOCC1CO1 SEFYJVFBMNOLBK-UHFFFAOYSA-N 0.000 description 1
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 1
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 description 1
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 1
- FPKCTSIVDAWGFA-UHFFFAOYSA-N 2-chloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 FPKCTSIVDAWGFA-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 1
- FGVKJYKWWJKWPD-UHFFFAOYSA-N 3-(4-methylphenyl)-2-propan-2-yl-1-sulfanylthioxanthen-9-one Chemical compound CC1=CC=C(C=C1)C2=CC3=C(C(=C2C(C)C)S)C(=O)C4=CC=CC=C4S3 FGVKJYKWWJKWPD-UHFFFAOYSA-N 0.000 description 1
- BIDWUUDRRVHZLQ-UHFFFAOYSA-N 3-ethyl-3-(2-ethylhexoxymethyl)oxetane Chemical compound CCCCC(CC)COCC1(CC)COC1 BIDWUUDRRVHZLQ-UHFFFAOYSA-N 0.000 description 1
- JUXZNIDKDPLYBY-UHFFFAOYSA-N 3-ethyl-3-(phenoxymethyl)oxetane Chemical compound C=1C=CC=CC=1OCC1(CC)COC1 JUXZNIDKDPLYBY-UHFFFAOYSA-N 0.000 description 1
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 description 1
- ABKAVCFPZAEGKI-UHFFFAOYSA-N 4-ethenyl-7-oxabicyclo[4.1.0]heptane;6-ethenyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C=C)CCC2OC21.C1CCCC2OC21C=C ABKAVCFPZAEGKI-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
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- MJROXKDHBUQFOF-UHFFFAOYSA-N C[Si](OC)(OC)C.C1(=CC=CC=C1)[Si](OC(C)C)(OC(C)C)OC(C)C Chemical compound C[Si](OC)(OC)C.C1(=CC=CC=C1)[Si](OC(C)C)(OC(C)C)OC(C)C MJROXKDHBUQFOF-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
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- NQSMEZJWJJVYOI-UHFFFAOYSA-N Methyl 2-benzoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 NQSMEZJWJJVYOI-UHFFFAOYSA-N 0.000 description 1
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- YFMXAWGLYRTAJH-UHFFFAOYSA-N anthracene-9,10-dione;2-methylanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1.C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 YFMXAWGLYRTAJH-UHFFFAOYSA-N 0.000 description 1
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
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- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- ZUEKXCXHTXJYAR-UHFFFAOYSA-N tetrapropan-2-yl silicate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)OC(C)C ZUEKXCXHTXJYAR-UHFFFAOYSA-N 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- GIHPVQDFBJMUAO-UHFFFAOYSA-N tributoxy(ethyl)silane Chemical compound CCCCO[Si](CC)(OCCCC)OCCCC GIHPVQDFBJMUAO-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 125000005289 uranyl group Chemical group 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on 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
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
- G03F7/0755—Non-macromolecular compounds containing Si-O, Si-C or Si-N bonds
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
エポキシ樹脂としては、特に限定されないが、例えば、ビスフェノールA型エポキシ樹脂、ビスフェノールF型エポキシ樹脂、ビフェニル型エポキシ樹脂、ナフタレン型エポキシ樹脂、フェノールノボラック型エポキシ樹脂、クレゾールノボラック型エポキシ樹脂、水添ビスフェノールA型エポキシ樹脂、水添ビスフェノールF型エポキシ樹脂、ポリブタジエン型エポキシ樹脂、ポリイソプレン型エポキシ樹脂、脂環式エポキシ樹脂、脂肪族系エポキシ樹脂などを例示することができる。これらの樹脂は、それぞれ単独で使用してもよいし、又は二種以上を組み合わせて使用してもよい。
カチオン硬化性官能基をもつシリケート化合物としては、カチオン硬化可能なシリケート化合物であれば特に限定されない。カチオン硬化性官能基もつシリケート化合物としては、例えば、グリシジルシリケート、脂環式エポキシシリケート、ビニルシリケート、オキセタニルシリケートが挙げられる。
光酸発生剤としては、エネルギー線の照射によりルイス酸又はブレンステッド酸を発生する化合物であれば限定されないが、例えばスルホニウム塩、ヨードニウム塩が挙げられる。光酸発生剤の使用量の範囲は、45重量部のエポキシ樹脂に対して、好ましくは0.5〜10重量部であり、より好ましくは1〜4重量部である。光酸発生剤は、4−ブチロラクトン等の溶剤に溶解又は分散して添加することもできる。
本発明のエネルギー線硬化型エポキシ樹脂組成物は、本発明の効果を奏する範囲内で、オキセタン化合物(オキセタニルシリケートを除く)、フィラー、光増感剤、シランカップリング剤などのその他の添加剤を含むことができる。
本発明のエネルギー線硬化型エポキシ樹脂組成物は、たとえば、LD(レーザーダイオード)、光検出器(PD:フォトディデクタ)、レンズ、プリズムなどの光学部品やレンズ等の光学部品を搭載する光学モジュール等を高い固定精度で迅速に固定できるので、光学装置組み立て用の接着剤として有用である。光学装置として、例えば、特許文献1、2や、特開2007−311006公報の段落0023に記載の光ピックアップ装置において、スキューネジでアクチュエータの傾きを調整した後の固定にも使用できる。また、その他に、ミラー等の光学部品の固定やサスペンションワイヤーの固定にも使用可能である。
表1に示した配合に基づき、光酸発生剤PI2074又はCPI−210Sを4−ブチロラクトンに溶かし、これをエピクロン850に加え、透明になるまで撹拌して、比較例1及び2のエネルギー線硬化型エポキシ樹脂組成物を調製した。
実施例1〜6及び比較例1〜2のエネルギー線硬化型エポキシ樹脂組成物の硬化性を試験した。硬化性は、それぞれのエネルギー線硬化型エポキシ樹脂組成物を1mm厚に塗布した後、浜松ホトニクス製UV照射機で500mW/cm2(365nm)を2.5秒間、5秒間、10秒間、15秒間、20秒間又は30秒間照射して硬化状態を指触で確認した。指触により、液状の場合は×、柔らかい硬化物の場合は△、固化している場合は○と評価した。結果を表2に示す。
表3に示した配合に基づき、実施例7〜11及び比較例3のエネルギー線硬化型エポキシ樹脂組成物を調製した。
実施例7〜11及び比較例3のエネルギー線硬化型エポキシ樹脂組成物のそれぞれの硬化性を試験例1と同様にして試験した。結果を表4に示す。
実施例7及び8並びに比較例3のエネルギー線硬化型エポキシ樹脂組成物のそれぞれの硬化収縮率及び弾性率を測定した。硬化収縮率は、JIS K 6833記載のカップ法に準じて測定した。弾性率は、SII社製 EXSTAR6000を使用して、平板引張法で測定した。結果を表5に示す。
表6に示した配合に基づき、実施例12〜14のエネルギー線硬化型エポキシ樹脂組成物を調製した。
実施例12〜14のエネルギー線硬化型エポキシ樹脂組成物のそれぞれの硬化性を試験例1と同様にして試験した。試験結果を表6に示す。
表7に示した配合に基づき、実施例15〜18のエネルギー線硬化型エポキシ樹脂組成物を調製した。
EXA-8067:ビスフェノールA型エポキシ樹脂(DIC社製:EXA-850CRPとビスフェノールAの反応品)
I-651:2,2−ジメトキシ−1,2−ジフェニルエタン(チバ社製増感剤)
実施例15及び16のエネルギー線硬化型エポキシ樹脂組成物のそれぞれのLED硬化性を試験した。LED硬化性は、アルミ板上にエネルギー線硬化型エポキシ樹脂組成物を一滴たらし、これを波長365nmのLED照射機により500mW/cm2の照度(照度計浜松ホトニクス製C6080−13)で10秒間照射して硬化し、硬化状態を指触にて確認した。LED硬化性の基準は、○:硬化(固体)、×印:未硬化(液状)であった。試験結果を表8に示す。
実施例15、17及び18のエネルギー線硬化型エポキシ樹脂組成物のそれぞれのハロゲン量をEN14582燃焼イオンクロマトグラフ法により測定した。測定結果を表9に示す。
実施例15、17及び18のエネルギー線硬化型エポキシ樹脂組成物のそれぞれの深部硬化性を測定した。紫外線ランプによる深部硬化性は、内径5mmφの長さ5mmの黒チューブにエネルギー線硬化型エポキシ樹脂組成物を充填し、紫外線照射機(浜松ホトニクス社製LC5)により上部から紫外線を照度500mW/cm2(365nm)(照度計:浜松ホトニクス製 C6080−13)で10秒間照射し、硬化したエネルギー線硬化型エポキシ樹脂組成物の長さを測定した。LEDによる深部硬化性は、内径5mmφの長さ5mmの黒チューブにエネルギー線硬化型エポキシ樹脂組成物を充填し、波長365nmのLED照射機により上部から照度500mW/cm2(照度計:浜松ホトニクス製 C6080−13)で10秒間照射し、硬化したエネルギー線硬化型エポキシ樹脂組成物の長さを測定した。測定結果を表10に示す。
実施例15及び17のエネルギー線硬化型エポキシ樹脂組成物のそれぞれの硬度、硬化収縮率、弾性率を測定した。硬度(D)は、JIS K 7215記載のデュロメータにより測定した。硬化収縮率は、JIS K 6833記載のカップ法に準じて測定した。Tanδと貯蔵弾性率は、SII社製 EXSTAR6000を使用して、平板引張法で測定した。
Claims (6)
- エポキシ樹脂とオキセタニルシリケートと光酸発生剤とを含む、光学装置組み立て用の接着剤であるエネルギー線硬化型エポキシ樹脂組成物であって、前記エポキシ樹脂45重量部に対して、前記オキセタニルシリケートを2.5〜10重量部及び前記光酸発生剤を1〜4重量部含有するエポキシ樹脂組成物。
- さらに、フィラーを含有する、請求項1記載の組成物。
- さらに、オキセタニルシリケート以外のオキセタン化合物を含有する、請求項1又は2記載の組成物。
- 光ピックアップ装置組み立て用の接着剤である、請求項1〜3のいずれか1項記載の組成物。
- 請求項1〜3のいずれか1項記載の組成物を使用して組み立てた光学装置。
- 請求項4記載の組成物を使用して組み立てた光ピックアップ装置。
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JP2009098187A (ja) * | 2007-10-12 | 2009-05-07 | Sekisui Chem Co Ltd | 光学部品用接着剤 |
JP2009298888A (ja) * | 2008-06-11 | 2009-12-24 | Sekisui Chem Co Ltd | 光後硬化性組成物 |
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CN102471456B (zh) | 2014-12-24 |
TW201116604A (en) | 2011-05-16 |
JPWO2011001911A1 (ja) | 2012-12-13 |
KR20120111955A (ko) | 2012-10-11 |
KR101671047B1 (ko) | 2016-10-31 |
WO2011001911A1 (ja) | 2011-01-06 |
CN102471456A (zh) | 2012-05-23 |
TWI481686B (zh) | 2015-04-21 |
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