CN103282440A - Curable composition, cured article, and method for using curable composition - Google Patents
Curable composition, cured article, and method for using curable composition Download PDFInfo
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- CN103282440A CN103282440A CN2011800575925A CN201180057592A CN103282440A CN 103282440 A CN103282440 A CN 103282440A CN 2011800575925 A CN2011800575925 A CN 2011800575925A CN 201180057592 A CN201180057592 A CN 201180057592A CN 103282440 A CN103282440 A CN 103282440A
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- Prior art keywords
- silane
- compound
- expression
- silane compound
- composition
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- 239000000203 mixture Substances 0.000 title claims abstract description 73
- 238000000034 method Methods 0.000 title claims abstract description 25
- -1 silane compound Chemical class 0.000 claims abstract description 145
- 229910000077 silane Inorganic materials 0.000 claims abstract description 98
- 229920005604 random copolymer Polymers 0.000 claims abstract description 52
- 230000003287 optical effect Effects 0.000 claims abstract description 50
- 239000000463 material Substances 0.000 claims abstract description 37
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 32
- 150000004292 cyclic ethers Chemical group 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 105
- 238000007711 solidification Methods 0.000 claims description 89
- 230000008023 solidification Effects 0.000 claims description 89
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 48
- 229910052799 carbon Inorganic materials 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 239000003795 chemical substances by application Substances 0.000 claims description 24
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 20
- 150000008065 acid anhydrides Chemical class 0.000 claims description 19
- 229910052782 aluminium Inorganic materials 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 239000004411 aluminium Substances 0.000 claims description 16
- 150000002148 esters Chemical group 0.000 claims description 15
- 238000007789 sealing Methods 0.000 claims description 15
- 150000004696 coordination complex Chemical class 0.000 claims description 13
- 125000000962 organic group Chemical group 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 238000009833 condensation Methods 0.000 claims description 7
- 230000005494 condensation Effects 0.000 claims description 7
- 229910052719 titanium Inorganic materials 0.000 claims description 7
- 239000010936 titanium Substances 0.000 claims description 7
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 claims description 6
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims description 6
- 229910052726 zirconium Inorganic materials 0.000 claims description 5
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 4
- 239000000853 adhesive Substances 0.000 abstract 3
- 230000001070 adhesive effect Effects 0.000 abstract 3
- 150000004756 silanes Chemical class 0.000 description 31
- 239000002253 acid Substances 0.000 description 20
- 238000010438 heat treatment Methods 0.000 description 19
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 125000001118 alkylidene group Chemical group 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 239000003963 antioxidant agent Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 230000003078 antioxidant effect Effects 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 10
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 8
- 125000004450 alkenylene group Chemical group 0.000 description 8
- 125000004419 alkynylene group Chemical group 0.000 description 8
- 230000005540 biological transmission Effects 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- 239000006096 absorbing agent Substances 0.000 description 5
- 125000003968 arylidene group Chemical group [H]C(c)=* 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 230000006866 deterioration Effects 0.000 description 5
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 5
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 5
- 239000006200 vaporizer Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 3
- KVUMYOWDFZAGPN-UHFFFAOYSA-N 3-trimethoxysilylpropanenitrile Chemical compound CO[Si](OC)(OC)CCC#N KVUMYOWDFZAGPN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910018557 Si O Inorganic materials 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000002788 crimping Methods 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 125000003566 oxetanyl group Chemical group 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 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
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- ANVIGMZAHFUKDP-UHFFFAOYSA-N 1-chloropropane dimethoxysilane Chemical compound CO[SiH2]OC.C(CC)Cl ANVIGMZAHFUKDP-UHFFFAOYSA-N 0.000 description 2
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 235000002597 Solanum melongena Nutrition 0.000 description 2
- 244000061458 Solanum melongena Species 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- IFIGQJHXPCWXOR-UHFFFAOYSA-N butanoic acid;zirconium Chemical group [Zr].CCCC(O)=O IFIGQJHXPCWXOR-UHFFFAOYSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- QXIVZVJNWUUBRZ-UHFFFAOYSA-N dichloro-methoxy-methylsilane Chemical compound CO[Si](C)(Cl)Cl QXIVZVJNWUUBRZ-UHFFFAOYSA-N 0.000 description 2
- GAURFLBIDLSLQU-UHFFFAOYSA-N diethoxy(methyl)silicon Chemical compound CCO[Si](C)OCC GAURFLBIDLSLQU-UHFFFAOYSA-N 0.000 description 2
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229960005082 etohexadiol Drugs 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 2
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 230000000176 photostabilization Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000734 polysilsesquioxane polymer Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 description 2
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 description 2
- DOEHJNBEOVLHGL-UHFFFAOYSA-N trichloro(propyl)silane Chemical compound CCC[Si](Cl)(Cl)Cl DOEHJNBEOVLHGL-UHFFFAOYSA-N 0.000 description 2
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 2
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 2
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- IKVTWJDRWCUYRZ-UHFFFAOYSA-N (2-chlorophenyl)-trimethoxysilane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1Cl IKVTWJDRWCUYRZ-UHFFFAOYSA-N 0.000 description 1
- CVBWTNHDKVVFMI-LBPRGKRZSA-N (2s)-1-[4-[2-[6-amino-8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]purin-9-yl]ethyl]piperidin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCC1CCN1C2=NC=NC(N)=C2N=C1SC(C(=C1)Br)=CC2=C1OCO2 CVBWTNHDKVVFMI-LBPRGKRZSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- SEQRDAAUNCRFIT-UHFFFAOYSA-N 1,1-dichlorobutane Chemical compound CCCC(Cl)Cl SEQRDAAUNCRFIT-UHFFFAOYSA-N 0.000 description 1
- WIHMGGWNMISDNJ-UHFFFAOYSA-N 1,1-dichloropropane Chemical compound CCC(Cl)Cl WIHMGGWNMISDNJ-UHFFFAOYSA-N 0.000 description 1
- QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 description 1
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 description 1
- UXMYUFHUUYBDLL-UHFFFAOYSA-N 2,2-dimethyl-3-(oxiran-2-ylmethoxy)propan-1-ol Chemical compound OCC(C)(C)COCC1CO1 UXMYUFHUUYBDLL-UHFFFAOYSA-N 0.000 description 1
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- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 239000011116 polymethylpentene Substances 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- KVENDAGPVNAYLY-UHFFFAOYSA-N tribromo(ethyl)silane Chemical compound CC[Si](Br)(Br)Br KVENDAGPVNAYLY-UHFFFAOYSA-N 0.000 description 1
- KBSUPJLTDMARAI-UHFFFAOYSA-N tribromo(methyl)silane Chemical compound C[Si](Br)(Br)Br KBSUPJLTDMARAI-UHFFFAOYSA-N 0.000 description 1
- HPTIEXHGTPSFDC-UHFFFAOYSA-N tribromo(phenyl)silane Chemical compound Br[Si](Br)(Br)C1=CC=CC=C1 HPTIEXHGTPSFDC-UHFFFAOYSA-N 0.000 description 1
- IBOKZQNMFSHYNQ-UHFFFAOYSA-N tribromosilane Chemical compound Br[SiH](Br)Br IBOKZQNMFSHYNQ-UHFFFAOYSA-N 0.000 description 1
- NYQDBZQWFXNBRZ-UHFFFAOYSA-N trichloro-(2-chlorophenyl)silane Chemical compound ClC1=CC=CC=C1[Si](Cl)(Cl)Cl NYQDBZQWFXNBRZ-UHFFFAOYSA-N 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- HXOGQBSDPSMHJK-UHFFFAOYSA-N triethoxy(6-methylheptyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCCCC(C)C HXOGQBSDPSMHJK-UHFFFAOYSA-N 0.000 description 1
- FHVAUDREWWXPRW-UHFFFAOYSA-N triethoxy(pentyl)silane Chemical compound CCCCC[Si](OCC)(OCC)OCC FHVAUDREWWXPRW-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- XYJRNCYWTVGEEG-UHFFFAOYSA-N trimethoxy(2-methylpropyl)silane Chemical compound CO[Si](OC)(OC)CC(C)C XYJRNCYWTVGEEG-UHFFFAOYSA-N 0.000 description 1
- HILHCDFHSDUYNX-UHFFFAOYSA-N trimethoxy(pentyl)silane Chemical compound CCCCC[Si](OC)(OC)OC HILHCDFHSDUYNX-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- OZWKZRFXJPGDFM-UHFFFAOYSA-N tripropoxysilane Chemical compound CCCO[SiH](OCCC)OCCC OZWKZRFXJPGDFM-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- 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
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
- C09J183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/50—Assembly of semiconductor devices using processes or apparatus not provided for in a single one of the groups H01L21/18 - H01L21/326 or H10D48/04 - H10D48/07 e.g. sealing of a cap to a base of a container
- H01L21/52—Mounting semiconductor bodies in containers
-
- 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
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
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- 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
-
- 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
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- Chemical & Material Sciences (AREA)
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- Polymers & Plastics (AREA)
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- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
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- Computer Hardware Design (AREA)
- General Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Manufacturing & Machinery (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Silicon Polymers (AREA)
- Led Device Packages (AREA)
- Sealing Material Composition (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
- Die Bonding (AREA)
Abstract
The present invention is a curable composition containing: (A) a specific silane compound random copolymer and (B) a silane coupling agent having a reactive cyclic ether structure, the mass ratio of (A) and (B) being (A):(B) = 95:5 to 80:20. The present invention is also a cured article formed when the composition is cured, and a method for using the composition as an adhesive or the like for a material with which an optical element is fixed. The present invention provides a curable composition from which a cured article having superior heat resistance and transparency and having high adhesive strength is obtained, a cured article formed when the composition is cured, and a method for using the composition as an adhesive or the like for a material with which an optical element is fixed.
Description
Technical field
The solidification compound that the present invention relates to obtain the transparency and excellent heat resistance and have the cured article of high bonding force, make said composition solidify the cured article that forms, and the method for said composition being used sealing agent as the optical element immobilization material with caking agent or optical element immobilization material.
Background technology
Up to now, solidification compound has carried out various improvement according to purposes, in the industrial raw material that is widely used as optics and formed body, caking agent, coating agent etc.For example, the solidification compound that forms the excellent cured article of the transparency is preferably used as raw material, the coating agent of optics mostly, and in addition, the solidification compound that forms the cured article with high bonding force is preferably used as caking agent, coating agent mostly.
In addition, in recent years, when making the optical element sealing member, solidification compound also be used as the optical element immobilization material with caking agent and optical element immobilization material with optical element immobilization material compositions such as sealing agents.
Various laser apparatus, photodiode luminous elements such as (LED), photo detector, complex light element, optic integrated circuits etc. such as semiconductor laser (LD) are arranged in the optical element.In recent years, developed luminous spike length and be the blue light of shorter wavelength or the optical element of white light, and be widely used.The high brightnessization of the luminous element of this luminous spike length develops just tremendously, and the consequent is that the thermal value of optical element has the trend of further increase.
Yet, along with the high brightnessization of in recent years optical element, the optical element immobilization material with the cured article of composition be exposed to the light of high energy more for a long time, the heat of the more high temperature that produced by optical element, produce deterioration and the problem that ftractures or peel off.
In order to address this problem, having proposed in the patent documentation 1～3 with the polysilsesquioxane compound is the optical element immobilization material composition of principal constituent.
But, even in the patent documentation 1～3 record with the polysilsesquioxane compound be the optical element immobilization material of principal constituent with the cured article of composition, also be difficult to sometimes when keeping enough bonding force, obtain thermotolerance and the transparency.
In addition, compositions for use is used in sealing as optical element, has proposed to use the composition epoxy resin of alicyclic epoxy resin in the patent documentation 4, has proposed to contain the composition epoxy resin of poly-thiol compound in the patent documentation 5.
Yet, even using under the situation of these compositions, also can't make sometimes for through the time the sufficient fast light deterioration that changes satisfactory, bonding force reduces.
Therefore, urgent wish to develop can obtain that thermotolerance, the transparency are more excellent, the solidification compound of cured article with high bonding force.
The prior art document
Patent documentation
Patent documentation 1: TOHKEMY 2004-359933 communique
Patent documentation 2: TOHKEMY 2005-263869 communique
Patent documentation 3: TOHKEMY 2006-328231 communique
Patent documentation 4: Japanese kokai publication hei 7-309927 communique
Patent documentation 5: TOHKEMY 2009-001752 communique.
Summary of the invention
Invent problem to be solved
The present invention is the invention of finishing in view of the practical situation of above-mentioned prior art, its problem provides the solidification compound that can obtain the transparency and excellent heat resistance and have the cured article of high bonding force, make said composition solidify the cured article that forms, and the method for said composition being used sealing agent as the optical element immobilization material with caking agent or optical element immobilization material.
Be used for solving the means of problem
The inventor etc. have carried out conscientiously research repeatedly in order to solve above-mentioned problem, found that, with specific ratio contain (A) specific silane compound random copolymers and (B) composition of specific silane coupling agent can become long-term and keep the excellent transparency, the stable on heating while, even and at high temperature also have the cured article of high bonding force, thereby finished the present invention.
As mentioned above, a first aspect of the present invention provides the solidification compound of following (1)～(8).
(1) solidification compound, it contains: (A) weight-average molecular weight is 1000～30000 silane compound random copolymers, its intramolecularly has with (i) in the repeating unit of following formula (i), (ii) and (iii) expression and (ii), (i) and (iii), (ii) and (iii), perhaps (i), (ii) and repeating unit (iii); (B) has the silane coupling agent of reactive cyclic ether structure; Its ratio is counted (A) with (A) and mass ratio (B): (B)=and 95:5～80:20;
[Chemical formula 1]
In the formula, R
1The alkyl of expression hydrogen atom or carbon number 1～6, D represents that singly-bound maybe can have the divalent organic group of substituent carbon number 1～20, R
2The alkyl of expression carbon number 1～20 maybe can have substituent phenyl.
(2) according to (1) described solidification compound, wherein, described (A) silane compound random copolymers is with formula: R
1The amount ((R of the group that-CH (CN)-D-represents
1And R-CH (CN)-D))
2Amount ((R
2)) molar ratio computing (R
1-CH (CN)-D): (R
2The silane compound random copolymers of)=5:95～50:50.
(3) solidification compound, it contains: (A ') weight-average molecular weight is 1000～30000 silane compound random copolymers, and it is to make to comprise with formula (1): R
1-CH (CN)-D-Si (OR
3)
p(X
1)
3-pSilane compound (1) at least a of expression and with formula (2): R
2Si (OR
4)
q(X
2)
3-qThe mixture condensation of at least a silane compound of the silane compound (2) of expression obtains; (B) has the silane coupling agent of reactive cyclic ether structure; Its ratio is counted (A ') with (A ') and mass ratio (B): (B)=and 95:5～80:20;
In the formula (1), R
1The alkyl of expression hydrogen atom or carbon number 1～6, D represents that singly-bound maybe can have the divalent organic group of substituent carbon number 1～20, R
3The alkyl of expression carbon number 1～6, X
1The expression halogen atom, p represents 0～3 integer;
In the formula (2), R
2The alkyl of expression carbon number 1～20 maybe can have substituent phenyl, R
4The alkyl of expression carbon number 1～6, X
2The expression halogen atom, q represents 0～3 integer.
(4) according to (3) described solidification compound, wherein, described (A ') silane compound random copolymers is to make silane compound (1) and silane compound (2) be (silane compound (1)) with molar ratio computing: the silane compound random copolymers that the ratio condensation of (silane compound (2))=5:95～50:50 gets.
(5) according to each described solidification compound in (1)～(4), wherein, described (B) silane coupling agent is the silane coupling agent with cyclohexene oxide base.
(6) according to each described solidification compound in (1)～(5), wherein also containing (C) atoms metal is the metal complex of aluminium, zirconium or titanium, with respect to (A) composition or (A ') composition 100 mass parts, (C) content of composition is greater than 0 mass parts and below 10 mass parts.
(7) according to each described solidification compound in (1)～(5), wherein also contain the ester ring type acid anhydrides that (D) has carboxyl, with respect to (A) composition or (A ') composition 100 mass parts, (D) content of composition is greater than 0 mass parts and below 10 mass parts.
(8) according to each described solidification compound in (1)～(7), it is optical element immobilization material composition.
A second aspect of the present invention provides following (9), the cured article of (10).
(9) cured article, it is to make the cured article that each described solidification compound curing forms in (1)～(7).
(10) cured article, it is to make the cured article that each described solidification compound curing forms in (1)～(7).
A third aspect of the present invention provides following (11), the method for the use solidification compound of the present invention of (12).
(11) each described solidification compound in (1)～(7) is used as the method that the optical element immobilization material is used caking agent.
(12) each described solidification compound in (1)～(7) is used as the method that the optical element immobilization material is used sealing agent.
The effect of invention
Utilize solidification compound of the present invention, even can obtain under the situation of irradiation high energy light or painted and transparent reduction can not take place under the condition of high temperature yet, have an excellent transparency and have the cured article of high bonding force for a long time.
Solidification compound of the present invention can use when forming the optical element immobilization material, can be suitable as the optical element immobilization material especially with caking agent and optical element immobilization material sealing agent.
Embodiment
Below, be divided into 1) solidification compound, 2) cured article and 3) the present invention is described in detail for the using method of solidification compound.
1) solidification compound
Solidification compound of the present invention is characterised in that, contains:
(A) silane compound random copolymers, its intramolecularly have with (i) in the repeating unit of following formula (i), (ii) and (iii) expression and (ii), (i) and (iii), (ii) and (iii) or repeating unit (i), (ii) and (iii), weight-average molecular weight is 1000～30000; (B) has the silane coupling agent of reactive cyclic ether structure; Its ratio is counted (A) with (A) and mass ratio (B): (B)=and 95:5～80:20;
[Chemical formula 2]
In the formula, R
1The alkyl of expression hydrogen atom or carbon number 1～6, D represents that singly-bound maybe can have the divalent organic group of substituent carbon number 1～20; R
2The alkyl of expression carbon number 1～20 maybe can have substituent phenyl.
(A) silane compound random copolymers
Solidification compound of the present invention contains the silane compound random copolymers as (A) composition (below be sometimes referred to as " silane compound random copolymers (A) "), its have with (i) in the repeating unit of following formula (i), (ii) and (iii) expression and (ii), (i) and (iii), (ii) and (iii) or (i) with (ii) and repeating unit (iii), weight-average molecular weight is 1000～30000.
Silane compound random copolymers (A) both can have with (i), (ii), a kind of in the repeating unit of (iii) expression, also can have two or more.
In the formula (i)～(iii), R
1The alkyl of expression hydrogen atom or carbon number 1～6, preferred hydrogen atom.
As R
1The alkyl of carbon number 1～6 of expression, but exemplified by methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, the tertiary butyl, isobutyl-, sec-butyl, n-pentyl, n-hexyl etc.
D represents that singly-bound maybe can have the divalent organic group of substituent carbon number 1～20.
As this divalent organic group, can exemplify alkylidene group, the alkenylene that can have substituent carbon number 2～20, the alkynylene that can have substituent carbon number 2～20 that can have substituent carbon number 1～20, the arylidene that can have substituent carbon number 6～20, substituent by having (alkylidene group, alkenylene or alkynylene) and can have divalent organic group that can have substituent carbon number 7～20 that constitutes of substituent arylidene etc.
As the alkylidene group of described alkylidene group, can exemplify methylene radical, ethylidene, propylene, trimethylene, butylidene, pentylidene, hexylidene etc.
As the alkenylene of described alkenylene, but exemplified by vinyl, propenyl, butenyl, pentenyl etc.
As the alkynylene of described alkynylene, can exemplify ethynyl, proyl etc.
As the arylidene of described arylidene, can exemplify adjacent phenylene, metaphenylene, to phenylene, 2,6-naphthylidene etc.
As the substituting group of described alkylidene group, alkenylene and alkynylene, can exemplify halogen atoms such as fluorine atom, chlorine atom; Alkoxyl group such as methoxyl group, oxyethyl group; Alkylthio such as methylthio group, ethylmercapto group; Carbalkoxy such as methoxycarbonyl, ethoxycarbonyl; Deng.
As the substituting group of described arylidene, can exemplify cyano group; Nitro; Halogen atoms such as fluorine atom, chlorine atom, bromine atoms; Alkyl such as methyl, ethyl; Alkoxyl group such as methoxyl group, oxyethyl group; Alkylthio such as methylthio group, ethylmercapto group; Deng.
These substituting groups can be bonded in the optional position in the groups such as alkylidene group, alkenylene, alkynylene and arylidene, also can bonding have identical or different a plurality of.
As substituent by having (alkylidene group, alkenylene or alkynylene) with can have the divalent organic group that can have substituent carbon number 7～20 that constitutes of substituent arylidene, can exemplify the group that is formed by the described at least a and described at least a straight line bonding that can have substituent arylidene that can have substituent (alkylidene group, alkenylene or alkynylene).Specifically can exemplify the group of representing with following formula.
[chemical formula 3]
Wherein, as D, because can obtain having the cured article of high bonding force, so the alkylidene group of preferred carbon number 1～10, the more preferably alkylidene group of carbon number 1～6, the especially preferably alkylidene group of carbon number 1～3.
In the formula (i)～(iii), R
2The alkyl of expression carbon number 1～20 maybe can have substituent phenyl.
As R
2The alkyl of carbon number 1～20 of expression, but exemplified by methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, sec-butyl, isobutyl-, the tertiary butyl, n-pentyl, n-hexyl, n-octyl, iso-octyl, n-nonyl, positive decyl, dodecyl etc.
As R
2The substituting group that can have substituent phenyl of expression, but alkyl such as exemplified by methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, sec-butyl, isobutyl-, the tertiary butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, iso-octyl; Alkoxyl group such as methoxyl group, oxyethyl group; Halogen atoms such as fluorine atom, chlorine atom etc.
As R
2The concrete example that can have substituent phenyl of expression, but exemplified by phenyl, 2-chloro-phenyl-, 4-aminomethyl phenyl, 3-ethylphenyl, 2,4-3,5-dimethylphenyl, 2-p-methoxy-phenyl etc.
In the silane compound random copolymers (A), with formula: R
1The amount ((R of the group that-CH (CN)-D-represents
1And R-CH (CN)-D))
2Amount ((R
2)) mol ratio be preferably (R
1-CH (CN)-D): (R
2)=5:95～50:50, more preferably 10:90～40:60.By in this scope, the transparency of gained cured article and excellent in adhesion, and because excellent heat resistance, so even also can suppress the decline of these character after placing under the high temperature.
With formula: R
1Group and R that-CH (CN)-D-represents
2The amount NMR collection of illustrative plates that for example can measure silane compound random copolymers (A) come quantitatively.
The weight-average molecular weight (Mw) of silane compound random copolymers (A) is in 1000～30000 scope, preferably in 1500～6000 scope.By in this scope, the operability excellence of composition, and can obtain the cured article of cementability, excellent heat resistance.It is that the polystyrene standard scaled value that the gel permeation chromatography (GPC) of solvent obtains is tried to achieve that weight-average molecular weight (Mw) for example can be utilized with tetrahydrofuran (THF) (THF).
The molecular weight distribution (Mw/Mn) of silane compound random copolymers (A) does not have restriction especially, usually in 1.0～3.0 scope, preferably in 1.1～2.0 scope.By in this scope, can obtain the cured article of cementability, excellent heat resistance.
Silane compound random copolymers (A) can a kind of independent use, perhaps also can be used in combination.
In the solidification compound of the present invention, the silane compound random copolymers (A) of described (A) composition can be that (A ') makes and comprise with formula (1): R
1-CH (CN)-D-Si (OR
3)
p(X
1)
3-pSilane compound (1) at least a of expression and with formula (2): R
2Si (OR
4)
q(X
2)
3-qThe mixture condensation of at least a silane compound of the silane compound (2) of expression and weight-average molecular weight be 1000～30000 silane compound random copolymerss (below be sometimes referred to as " silane compound random copolymers (A ') "), preferred silane compound atactic copolymer (A) is silane compound random copolymers (A '); In the formula (1), R
1The alkyl of expression hydrogen atom or carbon number 1～6, D represents that singly-bound maybe can have the divalent organic group of substituent carbon number 1～20; R
3The alkyl of expression carbon number 1～6, X
1The expression halogen atom, p represents 0～3 integer; In the formula (2), R
2The alkyl of expression carbon number 1～20 maybe can have substituent phenyl, R
4The alkyl of expression carbon number 1～6, X
2The expression halogen atom, q represents 0～3 integer.
(silane compound (1))
Silane compound (1) is with formula (1): R
1-CH (CN)-D-Si (OR
3)
p(X
1)
3-pThe compound of expression.By using silane compound (1), even can obtain also good silane compound random copolymers of after the curing transparency, bonding force.
In the formula (1), R
1The alkyl of expression hydrogen atom or carbon number 1～6, preferred hydrogen atom.As concrete example, can exemplify as the R in the silane compound random copolymers (A)
1The group that exemplifies.
In the formula (1), D represents that singly-bound maybe can have the divalent organic group of substituent carbon number 1～20.As the concrete example of this divalent organic group, can exemplify the group that exemplifies as the D in the silane compound random copolymers (A).
R
3The alkyl of carbon numbers 1～6 such as expression methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, sec-butyl, isobutyl-, the tertiary butyl, n-pentyl, n-hexyl.
X
1Halogen atoms such as expression fluorine atom, chlorine atom, bromine atoms.
P represents 0～3 integer.
P is 2 when above, OR
3Can be the same or different each other.In addition, be 2 when above (3-p), X
1Can be the same or different each other.
As the concrete example of silane compound (1), can exemplify the cyano methyl Trimethoxy silane, the cyano methyl triethoxyl silane, 1-cyano ethyl Trimethoxy silane, 2-cyano ethyl Trimethoxy silane, 2-cyano ethyl triethoxyl silane, 2-cyano ethyl tripropoxy silane, 3-cyano group propyl trimethoxy silicane, 3-cyano group propyl-triethoxysilicane, 3-cyano group propyl group tripropoxy silane, 3-cyano group propyl group three butoxy silanes, 4-cyano group butyl trimethoxy silane, 5-cyano group amyltrimethoxysilane, 2-cyano group propyl trimethoxy silicane, 2-(cyano group methoxyl group) ethyl trimethoxy silane, 2-(2-cyano group oxyethyl group) ethyl trimethoxy silane, adjacent (cyano methyl) phenyl tripropoxy silane, between (cyano methyl) phenyltrimethoxysila,e, to (cyano methyl) phenyl triethoxysilane, to trialkoxy silane compounds such as (2-cyano ethyl) phenyltrimethoxysila,e;
The cyano methyl trichlorosilane, cyano methyl bromine dimethoxy silane, 2-cyano ethyl dichloromethane TMOS, 2-cyano ethyl dichloro Ethoxysilane, 3-cyano group propyltrichlorosilan, 3-cyano group propyl group tribromosilane, 3-cyano group propyl group dichloromethane TMOS, 3-cyano group propyl group dichloro Ethoxysilane, 3-cyano group propyl chloride dimethoxy silane, 3-cyano group propyl chloride diethoxy silane, 4-cyano group Butyryl Chloride diethoxy silane, 3-cyano group n-butyl chloride diethoxy silane, 2-(2-cyano group oxyethyl group) ethyl trichlorosilane, 2-(2-cyano group oxyethyl group) monobromoethane diethoxy silane, 2-(2-cyano group oxyethyl group) ethyl dichloro propoxy-silane, adjacent (2-cyano ethyl) phenyl-trichloro-silicane, between (2-cyano ethyl) phenyl methoxyl group two bromo-silicanes, to (2-cyano ethyl) phenyl dimethoxy chlorosilane, to halogenated silanes compounds such as (2-cyano ethyl) phenyl tribromosilanes; Deng.
These silane compounds (1) can a kind of independent use, perhaps also can be used in combination.
Wherein, as silane compound (1), because can obtain having the cured article of more excellent cementability, so preferred trialkoxy silane compounds more preferably has the trialkoxy silane compounds of 2-cyano ethyl or has the trialkoxy silane compounds of 3-cyano group propyl group.
(silane compound (2))
Silane compound (2) is with formula (2): R
2Si (OR
4)
q(X
2)
3-qThe compound of expression.
In the formula (2), R
2The alkyl of expression carbon number 1～20 maybe can have substituent phenyl.As concrete example, can exemplify as the R in the silane compound random copolymers (A)
2The group that exemplifies.
R
4Expression and above-mentioned R
3The alkyl of identical carbon number 1～6.
X
2Expression and above-mentioned X
1Identical halogen atom.
Q represents any integer of 0～3.
Q is 2 when above, OR
4Can be the same or different each other.In addition, be 2 when above (3-q), X
2Can be the same or different each other.
As the concrete example of silane compound (2), but alkyltrialkoxysilanecompounds compounds classes such as exemplified by methyl Trimethoxy silane, Union carbide A-162, ethyl trimethoxy silane, ethyl triethoxysilane, n-propyl Trimethoxy silane, ne-butyltriethoxysilaneand, isobutyl-Trimethoxy silane, n-pentyl triethoxyl silane, n-hexyl Trimethoxy silane, iso-octyl triethoxyl silane, dodecyl Trimethoxy silane, methyl dimethoxy oxygen base oxethyl silane, methyl diethoxy methoxy silane;
Halogenated alkyl alkoxysilane compound containing trialkylsilyl group in molecular structure classes such as methyl chloride dimethoxy silane, methyl dichloro methoxy silane, methyl dichloro methoxy silane, methyl chloride diethoxy silane, ethyl chloride dimethoxy silane, ethyl dichloromethane TMOS, normal propyl chloride dimethoxy silane, n-propyl dichloromethane TMOS;
Alkyl trihalosilane compounds such as METHYL TRICHLORO SILANE, methyl tribromosilane, ethyl trichlorosilane, ethyl tribromosilane, n-propyltrichlorosilan;
Phenyltrimethoxysila,e, 4-p-methoxy-phenyl Trimethoxy silane, 2-chloro-phenyl-Trimethoxy silane, phenyl triethoxysilane, 2-p-methoxy-phenyl triethoxyl silane, phenyl dimethoxy Ethoxysilane, diethylamino phenyl Oxymethoxy silane etc. can have substituent phenyl trialkoxy silane compounds;
Phenyl-chloride dimethoxy silane, phenyl dichloromethane TMOS, phenyl-chloride methoxy ethoxy silane, phenyl-chloride diethoxy silane, phenyl dichloro Ethoxysilane etc. can have substituent phenyl-halide for the alkoxysilane compound containing trialkylsilyl group in molecular structure class;
Phenyl-trichloro-silicane, phenyl tribromosilane, 4-p-methoxy-phenyl trichlorosilane, phenyl-trichloro-silicane, 2-ethoxyl phenenyl trichlorosilane, 2-chlorophenyl trichlorosilane etc. can have substituent phenyl trihalosilane compound.
These silane compounds (2) can a kind of independent use, perhaps also can be used in combination.
(mixture of silane compound)
The mixture of the silane compound that uses when making silane compound random copolymers (A '), it can be the mixture that is constituted by silane compound (1) and silane compound (2), in addition, in the scope of not damaging purpose of the present invention, can also be the mixture that comprises other silane compound, the preferred mixture that is constituted by silane compound (1) and silane compound (2).
The usage ratio of silane compound (1) and silane compound (2) is preferably (silane compound (1)) with molar ratio computing: (silane compound (2))=5:95～50:50, more preferably 10:90～40:60.
Method as the mixture condensation that makes described silane compound, there is not special restriction, other silane compound that can exemplify silane compound (1), silane compound (2) and use as required is dissolved in solvent, adds the catalyzer of specified amount, stirring method under specified temperature.
Used catalyzer can be any in acid catalyst and the alkaline catalysts.
As acid catalyst, can exemplify mineral acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid; Organic acids such as methylsulfonic acid, trifluoromethanesulfonic acid, Phenylsulfonic acid, tosic acid, acetic acid, trifluoroacetic acid; Deng.
As alkaline catalysts, can exemplify Trimethylamine 99, triethylamine, lithium diisopropylamine, two (TMS) Lithamide, pyridine, 1,8-diazabicyclo [5.4.0]-7-hendecene, aniline, picoline, 1, organic basess such as 4-diazabicyclo [2.2.2] octane, imidazoles; Organic salt such as Tetramethylammonium hydroxide, tetraethyl ammonium hydroxide oxyhydroxide; Metal alkoxides such as sodium methylate, sodium ethylate, sodium tert-butoxide, potassium tert.-butoxide; Metal hydride such as sodium hydride, hydrolith; Metal hydroxidess such as sodium hydroxide, potassium hydroxide, calcium hydroxide; Metal carbonates such as yellow soda ash, salt of wormwood, magnesiumcarbonate; Alkali metal bicarbonate salt such as sodium bicarbonate, saleratus; Deng.
Catalyst consumption is generally more than 0.1 mass parts below 10 mass parts with respect to 1 mole of the total amount of silane compound, is preferably below above 5 mass parts of 0.5 mass parts.
Used solvent can be according to the suitably selections such as kind of silane compound.Can exemplify for example water; Benzene,toluene,xylenes etc. are aromatic hydrocarbon based; Ester classes such as methyl acetate, ethyl acetate, propyl acetate, methyl propionate; Ketones such as acetone, methyl ethyl ketone, methyl iso-butyl ketone (MIBK), pimelinketone; Alcohols such as methyl alcohol, ethanol, n-propyl alcohol, Virahol, propyl carbinol, isopropylcarbinol, sec-butyl alcohol, the trimethyl carbinol; Deng.These solvents can a kind of independent use, perhaps also can two or more mixing use.
The consumption of solvent be in per 1 liter of solvent, the integral molar quantity of silane compound is generally 0.1mol～10mol, be preferably the amount of 0.5mol～10mol.
Temperature when making silane compound condensation (reaction) is usually in the temperature range of the boiling point of 0 ℃～used solvent, preferably in 20 ℃～100 ℃ scope.If temperature of reaction is too low, then condensation reaction has an inadequate situation.On the other hand, if temperature of reaction is too high, then be difficult to suppress gelation.Reaction finished in 30 minutes～20 hours usually.
After reaction finishes, use under the situation of acid catalyst, neutralize by in reaction soln, adding alkali aqueous solutions such as sodium bicarbonate, use under the situation of alkaline catalysts, neutralize by in reaction soln, adding acid such as hydrochloric acid, remove the salt that generate this moment by filtering separation or washing etc., thereby can obtain target silane compound random copolymers.
(B) has the silane coupling agent of reactive cyclic ether structure
Solidification compound of the present invention contain silane coupling agent with reactive cyclic ether structure (below be sometimes referred to as " silane coupling agent (B) ".) as (B) composition.Solidification compound of the present invention obtains the cured article that the transparency is excellent, have high bonding force because contain silane coupling agent (B) so can not be separated (gonorrhoea).
Reactive cyclic ether structure in the silane coupling agent (B) is the structure with reactive ring-type ether.As reactive ring-type ether, can exemplify for example epoxy group(ing); Cyclohexene oxide bases such as 3,4-epoxycyclohexyl; Oxetanyl; Tetrahydrofuran base; THP trtrahydropyranyl; Deng.Wherein, preferred epoxy group(ing), cyclohexene oxide base, oxetanyl, more preferably cyclohexene oxide base, preferred especially 3, the 4-epoxycyclohexyl.
As the concrete example of reactive cyclic ether structure, can exemplify the group with following formula (E1)～(E3) expression.
[chemical formula 4]
In the formula, h represents 1～10 integer ,-(CH
2)
h-in can contain ehter bond (O-).
Wherein, preferably with the group of formula (E2) expression, especially preferably be the group of 2～8 integer with formula (E2) expression and h.
As silane coupling agent (B), have reactive cyclic ether structure (E) and hydrolization group (OR simultaneously in the preferred molecule
b) the two silicoorganic compound, specifically can exemplify the compound with following formula (a) expression.
[chemical formula 5]
In the formula (a), E represents reactive cyclic ether structure, R
aThe alkyl of expression carbon number 1～6 maybe can have substituent phenyl, R
bThe alkyl of expression carbon number 1～6, i represents 1～3 integer, and j represents 0～2 integer, and k represents 1～3 integer, i+j+k=4.
In the formula (a), as with R
a, R
bThe alkyl of carbon number 1～6 of expression, can exemplify with as above-mentioned R
1The identical group of group that the alkyl of carbon number 1～6 of expression exemplifies hereinbefore is as with above-mentioned R
aThe expression can have substituent phenyl, can exemplify with as above-mentioned R
2That represents can have the identical group of group that substituent phenyl exemplifies hereinbefore.
Concrete example as with the silane coupling agent (B) of following formula (a) expression can exemplify 2-(3,4-epoxycyclohexyl) ethyl trimethoxy silane, 2-(3,4-epoxycyclohexyl) ethyl triethoxysilane etc. has the silane coupling agent of cyclohexene oxide base;
3-glycidoxypropyltrime,hoxysilane, 3-glycidoxy propyl-triethoxysilicane, 3-glycidoxy propyl group methyl dimethoxysilane, 3-glycidoxy propyl group methyldiethoxysilane etc. have the silane coupling agent of glycidoxy;
(trimethylene oxide-3-yl) methyltrimethoxy silane, (trimethylene oxide-3-yl) Union carbide A-162, (trimethylene oxide-3-yl) methyl dimethoxy silane, (trimethylene oxide-3-yl) methyl diethoxy silane, (trimethylene oxide-3-yl) methylethyl dimethoxy silane, (trimethylene oxide-3-yl) methylethyl diethoxy silane, (trimethylene oxide-3-yl) aminomethyl phenyl dimethoxy silane, (trimethylene oxide-3-yl) aminomethyl phenyl diethoxy silane, 2-(the ethyl trimethoxy silane of trimethylene oxide-3 '-yl), (trimethylene oxide-3 '-yl) ethyl triethoxysilane etc. has the silane coupling agent of oxetanyl to 2-; Deng.
Wherein, from the complexity that obtains with can obtain having the viewpoint of the cured article of higher bonding force, preferably with the compound of following formula (b) expression.
[chemical formula 6]
In the formula (b), E2, R
b, i, j, k represent implication same as described above.As R
b, preferable methyl, ethyl, propyl group, methoxymethyl etc. can have the alkyl of substituent carbon number 1～6.
Concrete example as the silane coupling agent of representing with formula (b) can exemplify 2-(3,4-epoxycyclohexyl) ethyl trimethoxy silane, 2-(3,4-epoxycyclohexyl) ethyl triethoxysilane etc.
Silane coupling agent (B) can a kind of independent use, perhaps also can be used in combination.
Solidification compound of the present invention is counted (A) with (A) and mass ratio (B): (B)=and the ratio of 95:5～80:20 contains above-mentioned (A) and (B) composition.
By using (A) and (B) composition with such ratio, though can obtain to obtain the transparency, excellent in adhesion and excellent heat resistance at high temperature bonding force also be difficult for the solidification compound of the cured article of reduction.From this viewpoint, preferred (A): (B)=ratio of 95:5～85:15, the ratio of preferred especially 92:8～87:13.
Solidification compound of the present invention is except (A) with (B) the composition, preferably also contain the metal complex that (C) atoms metal is aluminium, zirconium or titanium (below be sometimes referred to as " metal complex (C) ".)。By using metal complex (C), can promote curing reaction, can obtain the higher cured article of bonding force.
Be the metal complex (C) of aluminium as atoms metal, can exemplify the etheric acid complex compound of aluminium such as diisopropoxy list oil base etheric acid aluminium, the two oil base etheric acid aluminium of single isopropoxy, single isopropoxy list oleic acid list ethyl acetoacetic acid aluminium, diisopropoxy list lauryl etheric acid aluminium, diisopropoxy list stearyl etheric acid aluminium, diisopropoxy list iso stearyl etheric acid aluminium, the single lauryl etheric acid of single isopropoxy list-N-lauroyl-β-aluminum hydride aluminium, praseodynium aluminium; The acetylacetonate complex of aluminium such as two (isobutyl-etheric acid) aluminum chelates of single acetyl acetone, two (the 2-ethylhexyl etheric acid) aluminum chelates of single acetyl acetone, two (dodecyl etheric acid) aluminum chelates of single acetyl acetone, two (oil base etheric acid) aluminum chelates of single acetyl acetone; Deng.
Be the metal complex (C) of zirconium as atoms metal, can exemplify the acidylate complex compound of zirconiums such as secondary butyric acid zirconium, diethoxy uncle butyric acid zirconium; The acetylacetonate complex of zirconiums such as tetrem acyl acetone zirconium; The alkoxide complexes of zirconiums such as four zirconium iso-propoxides; Deng.
Be the metal complex (C) of titanium as atoms metal, can exemplify the acidylate complex compound of the titaniums such as ammonium salt of four propionic acid titaniums, four butanic acid titaniums, four-2 ethyl hexanoic acid titanium, trolamine dipropionic acid titanium, lactic acid titanium; The dibasic alkoxide complex compound of metatitanic acid four ethohexadiols (テ ト ラ オ Network チ レ Application グ リ コ ー Le チ タ ネ ー ト), two (ethohexadiol acid) titanium titaniums such as (チ タ ニ ウ system ジ オ Network チ ロ キ シ PVC ス (オ Network チ レ Application グ リ コ レ ー ト)) of two octyloxies.
Metal complex (C) can a kind of independent use, perhaps also can be used in combination.Use under the situation of metal complex (C), its content is with respect to (A) composition or (A ') composition 100 mass parts are preferably more than 0 mass parts and below 10 mass parts, more preferably greater than 0 mass parts and below 5 mass parts.
Solidification compound of the present invention is except (A) with (B) the composition, preferably also contain the ester ring type acid anhydrides that (D) have carboxyl (below be sometimes referred to as " ester ring type acid anhydrides (D) ".)。By using ester ring type acid anhydrides (D), can obtain the higher cured article of bonding force.
Ester ring type acid anhydrides (D) by at least one carboxyl substituted the ester ring type acid anhydrides.
Concrete example as the ester ring type acid anhydrides, can exemplify the 3-methyl isophthalic acid, 2,3,6-Tetra Hydro Phthalic Anhydride, 4-methyl isophthalic acid, 2,3,6-Tetra Hydro Phthalic Anhydride, Tetra Hydro Phthalic Anhydride, 3-methyl-hexahydrophthalic anhydride, 4-methyl-hexahydrophthalic anhydride, hexahydrophthalic anhydride, methyl norbornene dioic anhydride, 5-norbornylene-2,3-dicarboxylic anhydride, norbornane-2,3-dicarboxylic anhydride, methyl-5-norbornylene-2,3-dicarboxylic anhydride, methyl-norbornane-2,3-dicarboxylic anhydride etc.
Carboxyl can replace in the optional position of the ester ring type structure of ester ring type acid anhydrides, and the carboxyl quantity of the position of substitution and replacement does not have special restriction.
As ester ring type acid anhydrides (D), preferred hexahydrophthalic anhydride by carboxyl substituted and hexanaphthene-1,2,4-tricarboxylic acid-1,2 acid anhydride, hexanaphthene-1,2,3-tricarboxylic acid-1,2 acid anhydride, preferred especially hexanaphthene-1,2,4-tricarboxylic acid-1,2 acid anhydride.Can there be steric isomer in this compound, can be any isomer.
Ester ring type acid anhydrides (D) can a kind of independent use, perhaps also can be used in combination.When using ester ring type acid anhydrides (D), its content is with respect to (A) composition or (A ') composition 100 mass parts are preferably more than 0 mass parts and below 10 mass parts, more preferably greater than 0 mass parts and below 5 mass parts.
In the solidification compound of the present invention, except mentioned component, can also contain other composition in the scope of not damaging purpose of the present invention.
As other composition, can exemplify above-mentioned (B) in addition silane coupling agent, antioxidant, UV light absorber, photostabilizer, thinner etc.
As above-mentioned (B) silane coupling agent in addition, be silane coupling agent (B) silane coupling agent in addition, only otherwise damaging purpose of the present invention just is not particularly limited.Wherein, from obtaining the viewpoint of the higher cured article of bonding force, the preferred silane coupling agent with acid anhydride structure that uses.
As the concrete example of silane coupling agent, can exemplify 2-Trimethoxy silane base ethyl succinyl oxide, 3-tri-ethoxy silylpropyl succinyl oxide etc.
Silane coupling agent with acid anhydride structure can a kind of independent use, perhaps also can be used in combination.
When use had the silane coupling agent of acid anhydride structure, its consumption was generally below above 25 mass parts of 0.1 mass parts with respect to (A) composition or (A ') composition 100 mass parts, is preferably below above 15 mass parts of 0.5 mass parts.
The oxidative degradation of described antioxidant in order to prevent from heating adds.As antioxidant, can exemplify phosphorous antioxidant, phenol is that antioxidant, sulphur are antioxidant etc.
As phosphorous antioxidant, it is oxide-based etc. to exemplify phosphorous acid salt, oxa-phospho hetero phenanthrene.
Be antioxidant as phenol, can exemplify single phenols, bisphenols, polymer phenol etc.
Be antioxidant as sulphur, can exemplify 3,3 '-thio-2 acid, two lauryl alcohol esters, 3,3 '-thio-2 acid, two Semen Myristicae alcohol esters, 3,3 '-thio-2 acid 2 stearyl ester etc.
These antioxidants can a kind of independent use, perhaps also can be used in combination.The consumption of antioxidant is generally below 10 mass parts with respect to (A) composition or (A ') composition 100 mass parts.
The photostabilization that described UV light absorber improves the gained cured article is that purpose is added.
As UV light absorber, can exemplify salicylic acid, Benzophenones, benzotriazole category, hindered amines etc.
UV light absorber can a kind of independent use, perhaps also can be used in combination.
The consumption of UV light absorber is generally below 10 mass parts with respect to (A) composition or (A ') composition 100 mass parts.
The photostabilization that described photostabilizer improves the gained cured article is that purpose is added.
As photostabilizer, for example can exemplify that poly-[{ 6-(1,1,3,3,-tetramethyl butyl) amino-1,3,5-triazines-2,4-two bases } { (2,2,6,6-tetramethyl--4-piperidines) imino-} hexa-methylene { (2,2,6,6-tetramethyl--4-piperidines) imino-}] etc. hindered amines etc.
These photostabilizers can a kind of independent use, perhaps also can be used in combination.
The consumption of photostabilizer is generally below 10 mass parts with respect to (A) composition or (A ') composition 100 mass parts.
Described thinner adds for the viscosity of adjusting solidification compound.
As thinner, can exemplify for example glycerin diglycidyl ether, butanediol diglycidyl ether, diglycidylaniline, neopentyl glycol glycidyl ether, cyclohexanedimethanodiglycidyl diglycidyl ether, alkylidene group diglycidylether, polyethyleneglycol diglycidylether, polypropylene glycol diglycidyl ether, trihydroxymethylpropanyltri diglycidyl ether, T 55,4 vinyl cyclohexene list oxide compound, vinyl cyclohexene dioxide, the vinyl cyclohexene that methylates dioxide etc.
These thinners can a kind of independent use, perhaps also can be used in combination.
Solidification compound of the present invention for example can by with described (A), (B) composition and other composition of using is as required joined with the regulation ratio and, by known method mix, deaeration obtains.
Utilize the solidification compound of the present invention obtain as mentioned above, even can obtain under the situation of irradiation high energy light, painted and transparent reduction can not take place under the condition of high temperature yet, have an excellent transparency and have the cured article of high bonding force for a long time.
Therefore, solidification compound of the present invention is suitable as raw material, caking agent, coating agent of optics, formed body etc.Particularly because can solve the associated problem of the deterioration of the optical element immobilization material that produces along with the high brightnessization of optical element, so solidification compound of the present invention can be suitable as optical element immobilization material composition.
2) cured article
A second aspect of the present invention is to make solidification compound of the present invention solidify the cured article that forms.
As the method that solidification compound of the present invention is solidified, can exemplify and be heating and curing.Heating temperature when being cured is generally 100～200 ℃, is generally 10 minutes heat-up time～20 hours, is preferably 30 minutes～10 hours.
Even cured article of the present invention under the situation of irradiation high energy light, also painted and transparent reduction can not take place under the condition of high temperature, has the excellent transparency for a long time, and has high bonding force.
Therefore, cured article of the present invention can solve the associated problem of the deterioration of the optical element immobilization material that produces along with the high brightnessization of optical element, so can be suitable as the optical element immobilization material.For example be suitable as raw material, caking agent, coating agent of optics, formed body etc.
The cured article that solidification compound curing of the present invention is formed has this content of high bonding force and for example can confirm by mensuration bonding force as described below.That is, solidification compound is coated the minute surface of silicon, coated face is put on clung body its crimping, carry out heat treated and make its curing.Its mensuration platform at the bond testing machine that is heated to specified temperature (for example 23 ℃, 100 ℃) was in advance placed for 30 seconds, from the high position of distance clung body 50 μ m to bonding plane along continuous straight runs (shear direction) stress application, the bonding force of determination test sheet and clung body.
The bonding force of cured article is being preferably under 23 ℃ and 100 ℃ more than the 60N/2mm, more preferably more than the 80N/2mm.
The transparent excellent this point of described cured article can be confirmed by measuring transmittance.The transmittance of cured article is preferably more than 80% the light of wavelength 400nm, is preferably especially more than 86%, and the light of wavelength 450nm is preferably more than 87%.
Even the excellent heat resistance this point of described cured article can be confirmed according to the variation of bonding force after cured article being placed under the high temperature and the transparency is also little.About bonding force, after placing 30 seconds under 100 ℃, preferably keep the bonding force more than 50% of the bonding force under 23 ℃, more preferably keep the bonding force more than 65%.About the transparency, placement is after 500 hours down at 150 ℃, and the transmissivity of wavelength 400nm is preferably more than 80% of initial transmission.
3) using method of solidification compound
A third aspect of the present invention is to use solidification compound of the present invention to use the method for sealing agent with caking agent or optical element immobilization material as the optical element immobilization material.
As optical element, can exemplify luminous elements such as LED, LD, photo detector, complex light element, optic integrated circuit etc.
(optical element immobilization material caking agent)
Solidification compound of the present invention can be suitable as optical element immobilization material caking agent.
As using solidification compound of the present invention as the method for optical element immobilization material with caking agent, can exemplify said composition is coated on a side of the material (optical element and substrate thereof etc.) as adhering object or both sides' the bonding plane, after its crimping, it is heating and curing, makes as the material of adhering object bonding method securely each other.
Main baseplate material as being used for bonding optical element can exemplify category of glass such as soda-lime glass, thermotolerance hard glass; Pottery; The alloy of iron, copper, aluminium, gold and silver, platinum, chromium, titanium and these metals, stainless steel metal species such as (SUS302, SUS304, SUS304L, SUS309 etc.); Synthetic resins such as polyethylene terephthalate, polybutylene terephthalate, PEN, vinyl-vinyl acetate copolymer, polystyrene, polycarbonate, polymethylpentene, polysulfones, polyether-ether-ketone, polyethersulfone, polyphenylene sulfide, polyetherimide, polyimide, polymeric amide, acrylic resin, norbornene resin, cyclic olefin resins, glass epoxy resin; Deng.
Heating temperature when being heating and curing also depends on used solidification compound etc., is generally 100～200 ℃.Be generally 10 minutes heat-up time～20 hours, be preferably 30 minutes～10 hours.
(optical element immobilization material sealing agent)
Solidification compound of the present invention can be suitable as the sealing agent of optical element sealing member.
As the method for solidification compound of the present invention being used sealing agent as the optical element immobilization material, can exemplify and for example said composition is shaped to desired shape, after being surrounded by the formed body of optical element in obtaining, it is heating and curing, thus the method for manufacturing optical element sealing member etc.
Do not have special restriction as the method that solidification compound of the present invention is shaped to desired shape, can adopt known moulding method such as conventional transfer molding method, teeming practice.
Heating temperature when being heating and curing also depends on used solidification compound etc., is generally 100～200 ℃.Be generally 10 minutes heat-up time～20 hours, be preferably 30 minutes～10 hours.
The optical element sealing member of gained is because use solidification compound of the present invention, even be that short wavelength's the luminous element of 400～490nm is as optical element so use the luminous spike length such as LED send white or blue light, can be because of heat or the painted deterioration of light yet, the transparency, excellent heat resistance.
Embodiment
Then, the present invention will be described in more detail by embodiment and comparative example, but the present invention is not limited to following embodiment.
(weight-average molecular weight mensuration)
The weight-average molecular weight (Mw) of the silane compound random copolymers that obtains in the Production Example utilizes following device and condition to measure in the polystyrene standard scaled value.
Device name: HLC-8220GPC, East ソ ー corporate system
Post: TSKgelGMHXL → TSKgelGMHXL → TSKgel2000HXL
Solvent: tetrahydrofuran (THF)
Measure temperature: 40 ℃
Flow velocity: 1ml/ minute
Detector: differential refractometer.
(mensuration of IR collection of illustrative plates)
The IR collection of illustrative plates of the silane compound random copolymers that obtains in the Production Example uses and measures with lower device.
Fourier-transform infrared spectrophotometer (Spectrum100, パ ー キ Application エ ル マ ー corporate system).
(Production Example 1)
After in the eggplant type flask of 300ml, dropping into phenyltrimethoxysila,e (Tokyo changes into industrial's system) 20.2g (102mmol), 2-cyano ethyl Trimethoxy silane (ア ヅ マ ッ Network ス corporate system) 3.15g (18mmol), acetone 96ml, distilled water 24ml as solvent, while stirring phosphoric acid (the Northeast chemical company system) 0.15g (1.5mmol) that adds as catalyzer, at room temperature continue again to stir 16 hours.
Reaction is concentrated into 50ml with vaporizer after finishing, and adds ethyl acetate 100ml, neutralizes with saturated sodium bicarbonate aqueous solution.Leave standstill moments later, separate and take out organic layer.Then, behind organic layer usefulness distilled water wash 2 times, use anhydrous magnesium sulfate drying.Behind the filtering sal epsom, with vaporizer filtrate is concentrated into 50ml, it is dropped to make its precipitation in a large amount of normal hexanes, by the decant sediment separate out.The gained throw out is dissolved in methyl ethyl ketone (MEK) and reclaims, heat up in a steamer desolventizing with the vaporizer decompression, carry out vacuum-drying, thereby obtain silane compound random copolymers (A1) 13.5g.
The weight-average molecular weight (Mw) of silane compound random copolymers (A1) is 1900.
In addition, the IR spectrum data of silane compound random copolymers (A1) is as follows.
Si-Ph:698cm
-1、740cm
-1,Si-O:1132cm
-1,-CN:2259cm
-1。
(Production Example 2)
In the Production Example 1, except the consumption of phenyltrimethoxysila,e is that the consumption of 16.7g (84mmol), 2-cyano ethyl Trimethoxy silane is the 6.31g (36mmol), similarly operate with Production Example 1, obtain silane compound random copolymers (A2) 12.9g.
The weight-average molecular weight (Mw) of silane compound random copolymers (A2) is 2000.
In addition, the IR spectrum data of silane compound random copolymers (A2) is as follows.
Si-Ph:698cm
-1、740cm
-1,Si-O:1132cm
-1,-CN:2255cm
-1。
(Production Example 3)
After in the eggplant type flask of 300ml, dropping into phenyltrimethoxysila,e (Tokyo changes into industrial's system) 11.9g (60mmol), 3-glycidoxypropyltrime,hoxysilane (Tokyo changes into industrial's system) 14.2g (60mmol), toluene 60ml, distilled water 30ml as solvent, while stirring phosphoric acid (the Northeast chemical company system) 0.15g (1.5mmol) that adds as catalyzer, at room temperature continue again to stir 16 hours.
After reaction finishes, in reaction mixture, add ethyl acetate 100ml, neutralize with saturated sodium bicarbonate aqueous solution.Leave standstill moments later, separate and take out organic layer.Then, behind organic layer usefulness distilled water wash 2 times, use anhydrous magnesium sulfate drying.Behind the filtering sal epsom, with vaporizer filtrate is concentrated into 50ml, it is dropped to make its precipitation in a large amount of normal hexanes, by the decant sediment separate out.The gained throw out is dissolved in methyl ethyl ketone (MEK) and reclaims, heat up in a steamer desolventizing with the vaporizer decompression, carry out vacuum-drying, thereby obtain silane compound random copolymers (A3) 16.3g.
The weight-average molecular weight (Mw) of silane compound random copolymers (A3) is 2800.
In addition, the IR spectrum data of silane compound random copolymers (A3) is as follows.
Si-Ph:699cm
-1, 741cm
-1, Si-O:1132cm
-1, epoxy group(ing): 1254cm
-1
(embodiment 1)
Add the 2-(3 as silane coupling agent (B) among silane compound random copolymers (A1) 10g that in Production Example 1, obtains, the 4-epoxycyclohexyl) ethyl trimethoxy silane (Tokyo changes into industrial's system) 1.0g, with total material fully mix, deaeration, thereby obtain solidification compound (1).
(embodiment 2)
Among the embodiment 1, except the amount with 2-(3,4-epoxycyclohexyl) ethyl trimethoxy silane changes into beyond the 1.5g, operation obtains solidification compound (2) similarly to Example 1.
(embodiment 3)
Among the embodiment 1, silane compound random copolymers (A2) 10g that obtains in using Production Example 2 replaces the silane compound random copolymers (A1), and operation obtains solidification compound (3) similarly to Example 1.
(embodiment 4)
Among the embodiment 1, (note is made " C1 " in the following table 1 except also adding tetrem acyl acetone zirconium (Tokyo changes into industrial's system).) 0.01g as metal complex (C) in addition, similarly to Example 1 the operation, obtain solidification compound (4).
(embodiment 5)
Among the embodiment 4, except the amount with tetrem acyl acetone zirconium changed 0.05g into, operation obtained solidification compound (5) similarly to Example 4.
(embodiment 6)
Among the embodiment 4, except the amount with tetrem acyl acetone zirconium changed 0.1g into, operation obtained solidification compound (6) similarly to Example 4.
(embodiment 7)
Among the embodiment 4, except the amount with tetrem acyl acetone zirconium changed 1.0g into, operation obtained solidification compound (7) similarly to Example 4.
(embodiment 8)
Among the embodiment 1, (note is made " C2 " in the following table 1 except also adding praseodynium aluminium (Tokyo changes into industrial's system).) 0.05g as metal complex (C) in addition, similarly to Example 1 the operation, obtain solidification compound (8).
(embodiment 9)
Among the embodiment 1, (note is made " C3 " in the following table 1 except also adding two (ethohexadiol acid) titaniums (マ Star モ ト Off ァ イ Application ケ ミ カ Le corporate system, オ Le ガ チ ッ Network ス TC-200) of two octyloxies.) 0.05g as metal complex (C) in addition, similarly to Example 1 the operation, obtain solidification compound (9).
(embodiment 10)
Among the embodiment 1, except also adding hexanaphthene-1,2,4-tricarboxylic acid-1,2-acid anhydride (ガ ス chemical company of Mitsubishi system) 0.05g are operated as the ester ring type acid anhydrides (D) with carboxyl in addition similarly to Example 1, obtain solidification compound (10).
(embodiment 11)
Among the embodiment 10, except with hexanaphthene-1,2,4-tricarboxylic acid-1, the amount of 2-acid anhydride changes into beyond the 1.0g, and operation obtains solidification compound (11) similarly to Example 10.
(comparative example 1)
Among the embodiment 1, except the amount with 2-(3,4-epoxycyclohexyl) ethyl trimethoxy silane changes into beyond the 0.1g, operation obtains solidification compound (12) similarly to Example 1.
(comparative example 2)
Among the embodiment 1, except the amount with 2-(3,4-epoxycyclohexyl) ethyl trimethoxy silane changes into beyond the 3.0g, operation obtains solidification compound (13) similarly to Example 1.
(comparative example 3)
Among the embodiment 5, the silane compound random copolymers (A3) that obtains in using Production Example 3 replaces the silane compound random copolymers (A1), and operation obtains solidification compound (14) similarly to Example 5.
(comparative example 4)
Among the embodiment 10, the silane compound random copolymers (A3) that obtains in using Production Example 3 replaces the silane compound random copolymers (A1), and operation obtains solidification compound (15) similarly to Example 10.
[table 1]
For the cured article of the solidification compound 1～15 that obtains in embodiment 1～11 and the comparative example 1～4, transmissivity after mensuration bonding force as described below, initial transmission and the heating is estimated bonding thermotolerance, the initial transparency, thermotolerance (the heating back transparency).
Measurement result and evaluation are shown in following table 2.
(bonding force test)
On the minute surface of the square silicon of 2mm, be coated with each solidification compound 1～15 respectively, make thickness reach about 2 μ m, coated face is put in clung body (sheffield plate) go up its crimping.Then, 180 ℃ of following heat treated it is solidified, obtain the clung body of girdle tests sheet.The clung body of this girdle tests sheet was placed for 30 seconds at the mensuration platform that is heated to the bond testing machine (4000 series, デ イ ジ corporate system) of specified temperature (23 ℃, 100 ℃) in advance, from the high position of distance clung body 50 μ m with the speed of 200 μ m/s to bonding plane along continuous straight runs (shear direction) stress application, the test film under measuring 23 ℃ and 100 ℃ and the bonding force (N/2mm) of clung body.
(bonding thermotolerance)
In the test of bonding force under 100 ℃, bonding force is evaluated as " zero " when 80N/2mm is above, is evaluated as " △ " during more than 60N/2mm and less than 80N/2mm, is evaluated as during less than 60N/2mm " * ".
(mensuration of initial transmission)
Pour each solidification compound 1～15 into mould respectively, making length is that 25mm, width are that 20mm, thickness are 1mm, heats down at 140 ℃ to make its curing in 6 hours, makes test film respectively.For the gained test film, measure the initial transmission (%) of wavelength 400nm, 450nm with spectrophotometer (MPC-3100, Shimadzu Seisakusho Ltd.'s corporate system).
(the initial transparency)
During initial transmission was measured, the transmissivity of 400nm then had been evaluated as " zero " more than 80%, being evaluated as " △ " more than 70% and less than 80%, was evaluated as " * " less than 70%.
(mensuration of heating back transmissivity)
Each test film of having measured initial transmission dropped in 150 ℃ the baking oven 500 hours, and measured the transmissivity (%) of wavelength 400nm, 450nm again.With it as heating back transmissivity.
(thermotolerance (the heating back transparency))
During heating back transmissivity is measured, if the transmissivity of 400nm is then being evaluated as more than 80% of initial transmission " zero ", if be evaluated as " △ " more than 70% and less than 80%, if be evaluated as " * " less than 70%.
[table 2]
As shown in Table 2, the cured article of the solidification compound 1～11 of embodiment 1～11 is more than the 60N/2mm cementability and bonding excellent heat resistance under 23 ℃ and 100 ℃ of two kinds of conditions.In addition, the initial transmission of wavelength 400nm, 450nm, heating back transmissivity are all high, and the initial transparency, thermotolerance (the heating back transparency) are also excellent.
On the other hand, the cementability of comparative example 1,2 solidification compound 12,13 cured article is poor.In addition, the transmissivity of comparative example 3,4 solidification compound 14,15 cured article significantly reduces because of heating.
Claims (12)
1. solidification compound, it contains:
(A) weight-average molecular weight is 1000～30000 silane compound random copolymers, and its intramolecularly has with (i) in the repeating unit of following formula (i), (ii) and (iii) expression and (ii); (i) and (iii); (ii) and (iii); Perhaps (i), (ii) and repeating unit (iii),
[Chemical formula 1]
In the formula, R
1The alkyl of expression hydrogen atom or carbon number 1～6, D represents that singly-bound maybe can have the divalent organic group of substituent carbon number 1～20, R
2The alkyl of expression carbon number 1～20 maybe can have substituent phenyl; With
(B) has the silane coupling agent of reactive cyclic ether structure;
Its ratio is counted (A) with (A) and mass ratio (B): (B)=and 95:5～80:20.
2. solidification compound according to claim 1, wherein, described (A) silane compound random copolymers is with formula: R
1The amount ((R of the group that-CH (CN)-D-represents
1And R-CH (CN)-D))
2Amount ((R
2)) molar ratio computing (R
1-CH (CN)-D): (R
2The silane compound random copolymers of)=5:95～50:50.
3. solidification compound, it contains:
(A ') weight-average molecular weight is 1000～30000 silane compound random copolymers, and it is to make to comprise with formula (1): R
1-CH (CN)-D-Si (OR
3)
p(X
1)
3-pSilane compound (1) at least a of expression and with formula (2): R
2Si (OR
4)
q(X
2)
3-qThe mixture condensation of at least a silane compound of the silane compound (2) of expression obtains; With
(B) has the silane coupling agent of reactive cyclic ether structure;
Its ratio is counted (A ') with (A ') and mass ratio (B): (B)=and 95:5～80:20;
In the formula (1), R
1The alkyl of expression hydrogen atom or carbon number 1～6, D represents that singly-bound maybe can have the divalent organic group of substituent carbon number 1～20; R
3The alkyl of expression carbon number 1～6, X
1The expression halogen atom, p represents 0～3 integer;
In the formula (2), R
2The alkyl of expression carbon number 1～20 maybe can have substituent phenyl, R
4The alkyl of expression carbon number 1～6, X
2The expression halogen atom, q represents 0～3 integer.
4. solidification compound according to claim 3, wherein, described (A ') silane compound random copolymers is to make silane compound (1) and silane compound (2) be (silane compound (1)) with molar ratio computing: the silane compound random copolymers that the ratio condensation of (silane compound (2))=5:95～50:50 gets.
5. according to each described solidification compound in the claim 1～4, wherein, described (B) silane coupling agent is the silane coupling agent with cyclohexene oxide base.
6. according to each described solidification compound in the claim 1～5, wherein also containing (C) atoms metal is the metal complex of aluminium, zirconium or titanium, with respect to (A) composition or (A ') composition 100 mass parts, (C) content of composition is greater than 0 mass parts and below 10 mass parts.
7. according to each described solidification compound in the claim 1～5, wherein also contain the ester ring type acid anhydrides that (D) has carboxyl, with respect to (A) composition or (A ') composition 100 mass parts, (D) content of composition is greater than 0 mass parts and below 10 mass parts.
8. according to each described solidification compound in the claim 1～7, it is optical element immobilization material composition.
9. cured article, it makes in the claim 1～7 each described solidification compound solidify and forms.
10. cured article according to claim 9, it is the optical element immobilization material.
11. each described solidification compound in the claim 1～7 is used the method for caking agent as the optical element immobilization material.
12. each described solidification compound in the claim 1～7 is used the method for sealing agent as the optical element immobilization material.
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| CN106414558A (en) * | 2014-05-07 | 2017-02-15 | 琳得科株式会社 | Curable polysilsesquioxane compound, production method thereof, curable composition, cured product and use method of curable composition |
| CN106414559A (en) * | 2014-05-07 | 2017-02-15 | 琳得科株式会社 | Curable polysilsesquioxane compound, production method thereof, curable composition, cured product and use method of curable composition, etc. |
| CN106574117A (en) * | 2014-08-26 | 2017-04-19 | 琳得科株式会社 | Curable composition, method of producing curable composition, cured material, method of using curable composition, and optical device |
| CN113574117A (en) * | 2019-03-26 | 2021-10-29 | 琳得科株式会社 | Curable composition, cured product, and method of use of curable composition |
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| MY173820A (en) * | 2013-02-28 | 2020-02-24 | Lintec Corp | Curable composition, cured product, method for using curable composition, photoelement sealing body and method for producing photoelement sealing body |
| WO2015041339A1 (en) * | 2013-09-20 | 2015-03-26 | リンテック株式会社 | Curable composition, cured product, and method for using curable composition |
| MY175492A (en) * | 2013-09-20 | 2020-06-30 | Lintec Corp | Curable composition, curing product, and method for using curable composition |
| WO2015041344A1 (en) * | 2013-09-20 | 2015-03-26 | リンテック株式会社 | Curable composition, cured product, and method for using curable composition |
| CN106661330B (en) | 2014-07-23 | 2020-11-06 | 琳得科株式会社 | Curable composition, method for producing curable composition, cured product, method for using curable composition, and optical device |
| KR101887993B1 (en) | 2016-07-27 | 2018-08-13 | 주식회사 엘지화학 | Photo-curable resin composition and use of the same |
| TW201938648A (en) | 2018-03-12 | 2019-10-01 | 日商琳得科股份有限公司 | Curable composition, cured product, method for producing cured product, and method for using curable composition |
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| TWI504681B (en) * | 2010-03-08 | 2015-10-21 | Lintec Corp | A hardening composition, a hardened product, and a hardening composition |
| TWI509023B (en) * | 2010-03-09 | 2015-11-21 | Lintec Corp | A hardened composition, a hardened product, and a hardening composition |
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| CN106414558A (en) * | 2014-05-07 | 2017-02-15 | 琳得科株式会社 | Curable polysilsesquioxane compound, production method thereof, curable composition, cured product and use method of curable composition |
| CN106414559A (en) * | 2014-05-07 | 2017-02-15 | 琳得科株式会社 | Curable polysilsesquioxane compound, production method thereof, curable composition, cured product and use method of curable composition, etc. |
| CN106414558B (en) * | 2014-05-07 | 2019-09-20 | 琳得科株式会社 | Curable polysilsesquioxane compound, method for producing the same, curable composition, cured product, and method of using the curable composition |
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| CN106574117A (en) * | 2014-08-26 | 2017-04-19 | 琳得科株式会社 | Curable composition, method of producing curable composition, cured material, method of using curable composition, and optical device |
| CN106574117B (en) * | 2014-08-26 | 2020-07-14 | 琳得科株式会社 | Curable composition, preparation method of curable composition, cured product, method of using curable composition, and optical device |
| CN113574117A (en) * | 2019-03-26 | 2021-10-29 | 琳得科株式会社 | Curable composition, cured product, and method of use of curable composition |
| CN113574117B (en) * | 2019-03-26 | 2023-09-12 | 琳得科株式会社 | Curable composition, cured product, and method for using curable composition |
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