JP5568314B2 - ポリオルガノシロキサン化合物を主成分とする接着剤 - Google Patents
ポリオルガノシロキサン化合物を主成分とする接着剤 Download PDFInfo
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- JP5568314B2 JP5568314B2 JP2009554279A JP2009554279A JP5568314B2 JP 5568314 B2 JP5568314 B2 JP 5568314B2 JP 2009554279 A JP2009554279 A JP 2009554279A JP 2009554279 A JP2009554279 A JP 2009554279A JP 5568314 B2 JP5568314 B2 JP 5568314B2
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- silane compound
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- carbon atoms
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- 239000000853 adhesive Substances 0.000 title claims description 62
- 230000001070 adhesive effect Effects 0.000 title claims description 60
- 150000001875 compounds Chemical class 0.000 title claims description 59
- -1 1 Chemical class 0.000 claims description 190
- 229910000077 silane Inorganic materials 0.000 claims description 73
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 33
- 125000005843 halogen group Chemical group 0.000 claims description 29
- 229910052751 metal Inorganic materials 0.000 claims description 25
- 239000002184 metal Substances 0.000 claims description 25
- 229920003002 synthetic resin Polymers 0.000 claims description 15
- 239000000057 synthetic resin Substances 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 14
- 239000011521 glass Substances 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 239000000919 ceramic Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 239000003963 antioxidant agent Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 150000002739 metals Chemical class 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000004611 light stabiliser Substances 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
- 230000003078 antioxidant effect Effects 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 5
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 239000000956 alloy Substances 0.000 claims description 3
- 229910045601 alloy Inorganic materials 0.000 claims description 3
- 150000004982 aromatic amines Chemical class 0.000 claims description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052737 gold Inorganic materials 0.000 claims description 3
- 239000010931 gold Substances 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 239000005011 phenolic resin Substances 0.000 claims description 2
- 229920000734 polysilsesquioxane polymer Polymers 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000758 substrate Substances 0.000 description 16
- 238000000034 method Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 125000000732 arylene group Chemical group 0.000 description 8
- 125000006239 protecting group Chemical group 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 239000004020 conductor Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 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 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 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
- 229920001577 copolymer Polymers 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 3
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-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
- FZTPAOAMKBXNSH-UHFFFAOYSA-N 3-trimethoxysilylpropyl acetate Chemical compound CO[Si](OC)(OC)CCCOC(C)=O FZTPAOAMKBXNSH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-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
- 125000002252 acyl group Chemical group 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000011889 copper foil Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 125000003136 n-heptyl 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])* 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- HSOYYCLJBUIKMI-UHFFFAOYSA-N C[SiH2]OC(Cl)Cl Chemical compound C[SiH2]OC(Cl)Cl HSOYYCLJBUIKMI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 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
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- GSKJMEQNVZJJIL-UHFFFAOYSA-N dichloromethoxy(propyl)silane Chemical compound C(CC)[SiH2]OC(Cl)Cl GSKJMEQNVZJJIL-UHFFFAOYSA-N 0.000 description 2
- 238000007772 electroless plating Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 2
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000005416 organic matter Substances 0.000 description 2
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 2
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 2
- 239000005054 phenyltrichlorosilane Substances 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 229920002379 silicone rubber Polymers 0.000 description 2
- 239000004945 silicone rubber Substances 0.000 description 2
- 238000001542 size-exclusion chromatography Methods 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-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
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 2
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- QRVASEIATBVCRN-UHFFFAOYSA-N (2,4-ditert-butyl-4-methylcyclohexa-1,5-dien-1-yl) dihydrogen phosphite Chemical compound P(O)(O)OC1=C(CC(C=C1)(C)C(C)(C)C)C(C)(C)C QRVASEIATBVCRN-UHFFFAOYSA-N 0.000 description 1
- IKVTWJDRWCUYRZ-UHFFFAOYSA-N (2-chlorophenyl)-trimethoxysilane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1Cl IKVTWJDRWCUYRZ-UHFFFAOYSA-N 0.000 description 1
- 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 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
- ARVUDIQYNJVQIW-UHFFFAOYSA-N (4-dodecoxy-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(OCCCCCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 ARVUDIQYNJVQIW-UHFFFAOYSA-N 0.000 description 1
- VNFXPOAMRORRJJ-UHFFFAOYSA-N (4-octylphenyl) 2-hydroxybenzoate Chemical compound C1=CC(CCCCCCCC)=CC=C1OC(=O)C1=CC=CC=C1O VNFXPOAMRORRJJ-UHFFFAOYSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 1
- NHAZGSRLKBTDBF-UHFFFAOYSA-N 1,2,4-triazol-1-amine Chemical compound NN1C=NC=N1 NHAZGSRLKBTDBF-UHFFFAOYSA-N 0.000 description 1
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
- FWHUTKPMCKSUCV-UHFFFAOYSA-N 1,3-dioxo-3a,4,5,6,7,7a-hexahydro-2-benzofuran-5-carboxylic acid Chemical compound C1C(C(=O)O)CCC2C(=O)OC(=O)C12 FWHUTKPMCKSUCV-UHFFFAOYSA-N 0.000 description 1
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- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- OWNXEGRCIOMNSN-UHFFFAOYSA-N tribromo(3-bromopropyl)silane Chemical compound BrCCC[Si](Br)(Br)Br OWNXEGRCIOMNSN-UHFFFAOYSA-N 0.000 description 1
- AKZFRSVAIXEQQT-UHFFFAOYSA-N tribromo(3-chloropropyl)silane Chemical compound ClCCC[Si](Br)(Br)Br AKZFRSVAIXEQQT-UHFFFAOYSA-N 0.000 description 1
- GNFASNGPRPMXAG-UHFFFAOYSA-N tribromo(3-phenylmethoxypropyl)silane Chemical compound Br[Si](Br)(Br)CCCOCC1=CC=CC=C1 GNFASNGPRPMXAG-UHFFFAOYSA-N 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
- PQZRTKDQUBMHQJ-UHFFFAOYSA-N tribromo(oxiran-2-ylmethyl)silane Chemical compound Br[Si](Br)(Br)CC1CO1 PQZRTKDQUBMHQJ-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
- SSZIBXDZTVQYGY-UHFFFAOYSA-N tribromo-[3-(methoxymethoxy)propyl]silane Chemical compound COCOCCC[Si](Br)(Br)Br SSZIBXDZTVQYGY-UHFFFAOYSA-N 0.000 description 1
- BMJRPFUOHCHOOB-UHFFFAOYSA-N tribromo-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound Br[Si](Br)(Br)CCCOCC1CO1 BMJRPFUOHCHOOB-UHFFFAOYSA-N 0.000 description 1
- OOPKJVYUAXPGHS-UHFFFAOYSA-N tributoxy(3-chloropropyl)silane Chemical compound CCCCO[Si](CCCCl)(OCCCC)OCCCC OOPKJVYUAXPGHS-UHFFFAOYSA-N 0.000 description 1
- QPCISYCRQISSKN-UHFFFAOYSA-N tributoxy(3-fluoropropyl)silane Chemical compound CCCCO[Si](CCCF)(OCCCC)OCCCC QPCISYCRQISSKN-UHFFFAOYSA-N 0.000 description 1
- SGCFZHOZKKQIBU-UHFFFAOYSA-N tributoxy(ethenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C=C SGCFZHOZKKQIBU-UHFFFAOYSA-N 0.000 description 1
- GIHPVQDFBJMUAO-UHFFFAOYSA-N tributoxy(ethyl)silane Chemical compound CCCCO[Si](CC)(OCCCC)OCCCC GIHPVQDFBJMUAO-UHFFFAOYSA-N 0.000 description 1
- SILWZLRRQOSOQD-UHFFFAOYSA-N tributoxy(oxiran-2-ylmethyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)CC1CO1 SILWZLRRQOSOQD-UHFFFAOYSA-N 0.000 description 1
- WAAWAIHPWOJHJJ-UHFFFAOYSA-N tributoxy(propyl)silane Chemical compound CCCCO[Si](CCC)(OCCCC)OCCCC WAAWAIHPWOJHJJ-UHFFFAOYSA-N 0.000 description 1
- FQYWWLSIKWDAEC-UHFFFAOYSA-N tributoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)CCCOCC1CO1 FQYWWLSIKWDAEC-UHFFFAOYSA-N 0.000 description 1
- OOXSLJBUMMHDKW-UHFFFAOYSA-N trichloro(3-chloropropyl)silane Chemical compound ClCCC[Si](Cl)(Cl)Cl OOXSLJBUMMHDKW-UHFFFAOYSA-N 0.000 description 1
- OPMAXPVCTSDVDC-UHFFFAOYSA-N trichloro(3-fluoropropyl)silane Chemical compound FCCC[Si](Cl)(Cl)Cl OPMAXPVCTSDVDC-UHFFFAOYSA-N 0.000 description 1
- XXZCMCZRRPRXAM-UHFFFAOYSA-N trichloro(3-iodopropyl)silane Chemical compound Cl[Si](Cl)(Cl)CCCI XXZCMCZRRPRXAM-UHFFFAOYSA-N 0.000 description 1
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 description 1
- ISCVFOODKHAEBC-UHFFFAOYSA-N trichloro(oxiran-2-ylmethyl)silane Chemical compound Cl[Si](Cl)(Cl)CC1CO1 ISCVFOODKHAEBC-UHFFFAOYSA-N 0.000 description 1
- DOEHJNBEOVLHGL-UHFFFAOYSA-N trichloro(propyl)silane Chemical compound CCC[Si](Cl)(Cl)Cl DOEHJNBEOVLHGL-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
- QDGORAVIRGNDBW-UHFFFAOYSA-N trichloro-(2-ethoxyphenyl)silane Chemical compound CCOC1=CC=CC=C1[Si](Cl)(Cl)Cl QDGORAVIRGNDBW-UHFFFAOYSA-N 0.000 description 1
- NNWMTCDMYFZDHA-UHFFFAOYSA-N trichloro-(4-methoxyphenyl)silane Chemical compound COC1=CC=C([Si](Cl)(Cl)Cl)C=C1 NNWMTCDMYFZDHA-UHFFFAOYSA-N 0.000 description 1
- XBWRLPTYWJUPKS-UHFFFAOYSA-N trichloro-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound Cl[Si](Cl)(Cl)CCCOCC1CO1 XBWRLPTYWJUPKS-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
- UXRBHEQFVKYHRG-UHFFFAOYSA-N triethoxy(3-fluoropropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCF UXRBHEQFVKYHRG-UHFFFAOYSA-N 0.000 description 1
- PBCOGINAGIMDDC-UHFFFAOYSA-N triethoxy(3-phenylmethoxypropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1=CC=CC=C1 PBCOGINAGIMDDC-UHFFFAOYSA-N 0.000 description 1
- JZYKVBRBIWTMEB-UHFFFAOYSA-N triethoxy(3-triethylsilyloxypropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCO[Si](CC)(CC)CC JZYKVBRBIWTMEB-UHFFFAOYSA-N 0.000 description 1
- XFPXEXSXVSCKQC-UHFFFAOYSA-N triethoxy(3-trityloxypropyl)silane Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCCC[Si](OCC)(OCC)OCC)C1=CC=CC=C1 XFPXEXSXVSCKQC-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- OKDJUBJTKGOTCQ-UHFFFAOYSA-N triethoxy(oxiran-2-ylmethyl)silane Chemical compound CCO[Si](OCC)(OCC)CC1CO1 OKDJUBJTKGOTCQ-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
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- NNNBKZHPEASMSV-UHFFFAOYSA-N triethoxy-(2-methoxyphenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1OC NNNBKZHPEASMSV-UHFFFAOYSA-N 0.000 description 1
- PGBUIPONYKQQMF-UHFFFAOYSA-N triethoxy-[3-(2-methoxyethoxymethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCOCCOC PGBUIPONYKQQMF-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-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
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- YOGRNCSVLDKNCY-UHFFFAOYSA-N trimethoxy(2-trimethylsilyloxyethyl)silane Chemical compound CO[Si](OC)(OC)CCO[Si](C)(C)C YOGRNCSVLDKNCY-UHFFFAOYSA-N 0.000 description 1
- SEAZOECJMOZWTD-UHFFFAOYSA-N trimethoxy(oxiran-2-ylmethyl)silane Chemical compound CO[Si](OC)(OC)CC1CO1 SEAZOECJMOZWTD-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- ZESWBFKRPIRQCD-UHFFFAOYSA-N trimethoxy-(4-methoxyphenyl)silane Chemical compound COC1=CC=C([Si](OC)(OC)OC)C=C1 ZESWBFKRPIRQCD-UHFFFAOYSA-N 0.000 description 1
- YFFNIIAVGWYOQJ-UHFFFAOYSA-N trimethoxy-[3-(methoxymethoxy)propyl]silane Chemical compound COCOCCC[Si](OC)(OC)OC YFFNIIAVGWYOQJ-UHFFFAOYSA-N 0.000 description 1
- SAKLXMOLLSWVHU-UHFFFAOYSA-N trimethoxy-[3-[(2-methylpropan-2-yl)oxy]propyl]silane Chemical compound CO[Si](OC)(OC)CCCOC(C)(C)C SAKLXMOLLSWVHU-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 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
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- 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
-
- 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
- C09J183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Silicon Polymers (AREA)
- Adhesives Or Adhesive Processes (AREA)
Description
しかしながら、この方法によりより精細な回路パターンを形成する場合においては、高密度の極細回路線が、絶縁基板表面の凹凸の影響を受け、微細で高密度な導体回路を形成することが困難な場合があった。
しかしながら、特許文献2〜6には、ラダー型構造を有するポリオルガノシロキサン化合物が、金属や合成樹脂を強固に接着する接着剤となることは記載されていない。
(1)分子内に、式(I)
R2は、置換基を有していてもよいフェニル基、置換基(ハロゲン原子、前記式:OGで表される基、およびシアノ基を除く。)を有していてもよい炭素数1〜20のアルキル基、または炭素数2〜20のアルケニル基を表し、
l、m、nはそれぞれ独立して、0又は任意の自然数を表す。ただし、lおよびnがともに0である場合を除く。また、A同士、X0同士、R1同士およびR2同士は、互いに同一であっても相異なっていてもよく、l、mおよびnがそれぞれ2以上のとき、下記(i)、(ii)および(iii)
で表される繰り返し単位を有する、ラダー型構造のポリオルガノシロキサン化合物を主成分とする接着剤。
(4)前記Aが炭素数1〜10のアルキレン基であることを特徴とする(1)〜(3)のいずれかに記載の接着剤。
(5)前記X0が塩素原子、アセトキシ基、又はシアノ基であることを特徴とする(1)〜(4)のいずれかに記載の接着剤。
(7)前記金属が、銅、アルミニウム、金、白金及びこれらの金属の合金からなる群から選ばれる少なくとも一種である(6)に記載の接着剤。
1)接着剤
本発明の接着剤は、(i)分子内に、前記式(I)で示される繰り返し単位を有する、ラダー型構造のポリオルガノシロキサン化合物(以下、「ポリオルガノシロキサン化合物(I)」ということがある。)、又は(ii)触媒の存在下、式:X0−CH(R1)−A−Si(OR3)p(X1)3−p(式中、X0、R1およびAは前記と同じ意味を表し、R3は炭素数1〜6のアルキル基を表し、X1はハロゲン原子を表し、pは0〜3のいずれかの整数を表す。)で表されるシラン化合物(1)と、式:R2Si(OR4)q(X2)3−q(式中、R2は前記と同じ意味を表し、R4は炭素数1〜6のアルキル基を表し、X2はハロゲン原子を表し、qは0〜3のいずれかの整数を表す。)で表されるシラン化合物(2)を、シラン化合物(1)とシラン化合物(2)のモル比で、[シラン化合物(1)]:[シラン化合物(2)]=5:95〜100:0の割合で反応させて得られたポリオルガノシロキサン化合物(以下、「ポリオルガノシロキサン化合物(Ia)」ということがある。)を主成分とすることを特徴とする。
本発明の成形材料中におけるポリオルガノシロキサン化合物(I)又はポリオルガノシロキサン化合物(Ia)の含有量は、接着剤全体に対して、通常、70重量%以上、好ましくは80重量%以上、より好ましくは90重量%以上である。
連結基としては、例えば、置換基を有していてもよいアルキレン基、置換基を有していてもよいアリーレン基、置換基を有していてもよいアルキレン基と置換基を有していてもよいアリーレン基との組み合わせ等が挙げられる。
置換基を有していてもよいアリーレン基のアリーレン基としては、o−フェニレン基、m−フェニレン基、p−フェニレン基、2,6−ナフチレン基等が挙げられる。
これらの置換基は、アルキレン基又はアリーレン基の任意の位置に結合していてよく、同一若しくは相異なって複数個が結合していてもよい。
炭素数2〜20のアルケニル基としては、ビニル基、i−プロペニル基、アリル基等が挙げられる。
pは0〜3のいずれかの整数を表す。pが2以上のとき、複数の式:OR3で表される基同士は同一であっても相異なっていてもよく、(3−p)が2以上のとき、複数のX1同士は同一であっても相異なっていてもよい。
フェニルトリクロロシラン、フェニルクロロジメトキシシラン、フェニルジクロロメトキシシラン、フェニルトリブロモシラン、フェニルクロロメトキシエトキシシラン、4−メトキシフェニルトリクロロシラン、2−クロロフェニルトリクロロシラン、フェニルトリクロロシラン、2−エトキシフェニルトリクロロシラン;等の置換基を有していてもよいフェニルシラン化合物類;
メチルトリクロロシラン、メチルクロロジメトキシシラン、メチルジクロロメトキシシラン、メチルジクロロメトキシシラン、メチルトリブロモシラン、メチルクロロジエトキシシラン、エチルトリクロロシラン、エチルクロロジメトキシシラン、エチルジクロロメトキシシラン、エチルトリブロモシラン、n−プロピルトリクロロシラン、n−プロピルクロロジメトキシシラン、n−プロピルジクロロメトキシシラン等のアルキルシラン化合物類;
3−メタクリロキシプロピルトリメトキシシラン、3−メタクリロキシプロピルトリエトキシシラン、3−メタクリロキシプロピルトリプロポキシシラン、3−メタクリロキシプロピルトリブトキシシラン、3−メタクリロキシプロピルトリクロロシラン、3−メタクリロキシプロピルクロロジメトキシシラン、3−メタクリロキシプロピルジクロロメトキシシラン、3−メタクリロキシプロピルクロロジエトキシシラン、3−メタクリロキシプロピルジクロロエトキシシラン、3−メタクリロキシプロピルトリブロモシラン、
シラン化合物(2)は一種単独で、あるいは二種以上を組み合わせて用いることができる。
酸触媒としては、塩酸、硫酸、硝酸、りん酸等の無機酸;メタンスルホン酸、トリフルロロメタンスルホン酸、ベンゼンスルホン酸、p−トルエンスルホン酸、酢酸、トリフルオロ酢酸等の有機酸;が挙げられる。
酸化防止剤としては、例えば、フェノール系、硫黄系、リン系酸化防止剤等が挙げられる。
紫外線吸収剤としては、例えば、フェニルサリシレート、p−t−ブチルフェニルサリシレート、p−オクチルフェニルサリシレート等のサリチル酸類;2,4−ジヒドロキシベンゾフェノン、2−ヒドロキシ−4−メトキシベンゾフェノン、2−ヒドロキシ−4−オクトキシベンゾフェノン、2−ヒドロキシ−4−ドデシルオキシベンゾフェノン、2,2’−ジヒドロキシ−4−メトキシベンゾフェノン、2,2’−ジヒドロキシ−4,4’−ジメトキシベンゾフェノン、2−ヒドロキシ−4−メトキシ−5−スルホベンゾフェノン等のベンゾフェノン類;2−(2’−ヒドロキシ−5’−メチルフェニル)ベンゾトリアゾール、2−(2’−ヒドロキシ−5’−tert−ブチルフェニル)ベンゾトリアゾール、2−(2’−ヒドロキシ−3’,5’−ジ−tert−ブチルフェニル)ベンゾトリアゾール、2−(2’−ヒドロキシ−3’−tert−ブチル−5’−メチルフェニル)−5−クロロベンゾトリアゾール、2−(2’−ヒドロキシ−3’,5’−ジ−tert−ブチルフェニル)−5−クロロベンゾトリアゾール、2−(2’−ヒドロキシ−3’,5’−ジ−tert−アミルフェニル)ベンゾトリアゾール、2−{(2’−ヒドロキシ−3’,3’’,4’’,5’’,6’’−テトラヒドロフタルイミドメチル)−5’−メチルフェニル}ベンゾトリアゾール等のベンゾトリアゾール類;ビス(2,2,6,6−テトラメチル−4−ピペリジル)セバケート、ビス(1,2,2,6,6−ペンタメチル−4−ピペリジル)セバケート、ビス(1,2,2,6,6−ペンタメチル−4−ピペリジル)[{3,5−ビス(1,1−ジメチルエチル)−4−ヒドロキシフェニル}メチル]ブチルマロネート等のヒンダードアミン類;等が挙げられる。
光安定剤としては、例えば、ポリ[{6−(1,1,3,3,−テトラメチルブチル)アミノ−1,3,5−トリアジン−2,4−ジイル}{(2,2,6,6−テトラメチル−4−ピペリジン)イミノ}ヘキサメチレン{(2,2,6,6−テトラメチル−4−ピペリジン)イミノ}]等のヒンダードアミン類が挙げられる。
希釈剤としては、例えば、グリセリンジグリシジルエーテル、ブタンジオールジグリシジルエーテル、ジグリシジルアニリン、ネオペンチルグリコールグリシジルエーテル、シクロヘキサンジメタノールジグリシジルエーテル、アルキレンジグリシジルエーテル、ポリグリコールジグリシジルエーテル、ポリプロピレングリコールジグリシジルエーテル、トリメチロールプロパントリグリシジルエーテル、グリセリントリグリシジルエーテル、4−ビニルシクロヘキセンモノオキサイド、ビニルシクロヘキセンジオキサイド、メチル化ビニルシクロヘキセンジオキサイド等が挙げられる。これらの希釈剤は一種単独で、あるいは二種以上を組み合わせて使用することができる。
シランカップリング剤としては、例えば、3−グリシドキシプロピルトリメトキシシラン、3−グリシドキシプロピルトリエトキシシラン、2−(3,4−エポキシシクロヘキシル)エチルトリメトキシシラン、2−(3,4−エポキシシクロヘキシル)エチルトリエトキシシラン、ビニルトリメトキシシラン、ビニルトリエトキシシラン等が挙げられる。
酸無水物としては、テトラヒドロ無水フタル酸、メチルテトラヒドロ無水フタル酸、ヘキサヒドロ無水フタル酸、メチルヘキサヒドロ無水フタル酸、ノルボルナン−2,3−ジカルボン酸無水物、メチルノルボルナン−2,3−ジカルボン酸無水物、シクロヘキサン−1,2,4−トリカルボン酸、シクロヘキサン−1,3,5−トリカルボン酸、シクロヘキサン−1,3,4−トリカルボン酸−3,4−無水物、無水マレイン酸、無水フタル酸、無水コハク酸、無水ドデシルコハク酸、無水ピロメリット酸、無水トリメリット酸等が挙げられる。
ただし、本発明は以下の実施例によって何ら制限されるものではない。
(1)シラン化合物(1)
1A:3−クロロプロピルトリメトキシシラン(東京化成工業社製)
1B:3−アセトキシプロピルトリメトキシシラン(アヅマックス社製)
1C:2−シアノエチルトリメトキシシラン(アヅマックス社製)
(2)シラン化合物(2)
2A:フェニルトリメトキシシラン(東京化成工業社製)
以下に示す製造方法A又は製造方法Bにより、下記第1表に示すように、接着剤1〜8を製造した。
攪拌子を入れた200mlのナス型フラスコに、第1表に示す、シラン化合物(1)、シラン化合物(2)、溶媒としてトルエン20ml、及び蒸留水10mlを仕込んだ後、全容を室温で撹拌しながら、触媒としてリン酸(関東化学社製)0.10g(1mmol)を加え、同温度で16時間さらに撹拌を継続した。その後、反応混合物に飽和炭酸水素ナトリウム水溶液を加えて中和した。これに酢酸エチル100mlを加え有機物を分取した。
攪拌子を入れた200mlのナス型フラスコに、第1表に示す、シラン化合物(1)、シラン化合物(2)、トルエン20ml、蒸留水10mlを仕込んだ後、全容を室温で撹拌しながら、触媒としてリン酸(関東化学社製)0.10g(1mmol)を加え、同温度で16時間さらに撹拌を継続した。その後、反応混合物に飽和炭酸水素ナトリウム水溶液を加えて中和し、静置した後、トルエン及び水をデカンテーションにより除去した。
用いたシラン化合物(2)の種類及び使用量、並びに得られた第1表には、併せて、得られたポリオルガノシロキサン化合物の重量平均分子量(Mw)を第1表に示す。
20mlのガラス製サンプル管に、3,4−エポキシシクロヘキシルメチル 3,4−エポキシシクロヘキサンカルボキシレート(アルドリッチ社製)2g、2,2−ビス(4−グリシジルオキシフェニル)プロパン(東京化成工業社製)1g、4−メチルシクロヘキサン−1,2−ジカルボン酸無水物(東京化成工業社製)3g、及びトリフェニルホスフィン(関東化学社製)0.03gを添加し、全容を十分に混合して、エポキシ樹脂組成物を得た。このものを接着剤9とした。
各種被着体の上に、直径3mmの穴をあけた厚さ1mmのシリコーンゴムシートを固定した。この穴に、実施例1〜8及び比較例1で得られた接着剤1〜9をそれぞれ流し込んで、140℃で6時間加熱処理して硬化した。その後、シリコーンゴム製シートを剥離し、被着体と接着剤とのせん断接着力を、ボンドテスター(シリーズ4000、デイジ社製)により測定した。その結果を第3表に示す。
Claims (7)
- 分子内に、式(I)
R2は、アルキル基、アルコキシ基及びハロゲン原子からなる群から選ばれる置換基を有していてもよいフェニル基、または、炭素数1〜20のアルキル基を表し、
l、m、nはそれぞれ独立して、0又は任意の自然数を表す。ただし、lおよびnがともに0である場合を除く。また、A同士、X0同士、R1同士およびR2同士は、互いに同一であっても相異なっていてもよく、l、mおよびnがそれぞれ2以上のとき、下記(i)、(ii)および(iii)
で表される繰り返し単位を有するラダー型構造を有し、かつ、触媒の存在下、式:X 0 −CH(R 1 )−A−Si(OR 3 ) p (X 1 ) 3−p (式中、X 0 、R 1 およびAは前記と同じ意味を表し、R 3 は炭素数1〜6のアルキル基を表し、X 1 はハロゲン原子を表し、pは0〜3のいずれかの整数を表す。)で表されるシラン化合物(1)と、式:R 2 Si(OR 4 ) q (X 2 ) 3−q (式中、R 2 は前記と同じ意味を表し、R 4 は炭素数1〜6のアルキル基を表し、X 2 はハロゲン原子を表し、qは0〜3のいずれかの整数を表す。)で表されるシラン化合物(2)を、シラン化合物(1)とシラン化合物(2)のモル比で、[シラン化合物(1)]:[シラン化合物(2)]=10:90〜100:0の割合で反応させて得られたものであるポリシルセスキオキサン化合物を、接着剤全体に対し70重量%以上含有する接着剤。 - 触媒の存在下、式:X0−CH(R1)−A−Si(OR3)p(X1)3−p{式中、Aは炭素数1〜10のアルキレン基を表し、R 1 は水素原子または炭素数1〜6のアルキル基を表し、X 0 は、ハロゲン原子、式:OGで表される基〔式中、Gは、式:−C(=O)R 5 (R 5 は、炭素数1〜6のアルキル基;又は、アルキル基、ハロゲン原子及びアルコキシ基からなる群から選ばれる置換基を有していてもよいフェニル基を表す。)で表される基を表す。〕、またはシアノ基を表す。R3は炭素数1〜6のアルキル基を表し、X1はハロゲン原子を表し、pは0〜3のいずれかの整数を表す。}で表されるシラン化合物(1)と、式:R2Si(OR4)q(X2)3−q(式中、R2は、アルキル基、アルコキシ基及びハロゲン原子からなる群から選ばれる置換基を有していてもよいフェニル基、または、炭素数1〜20のアルキル基を表す。R4は炭素数1〜6のアルキル基を表し、X2はハロゲン原子を表し、qは0〜3のいずれかの整数を表す。)で表されるシラン化合物(2)を、シラン化合物(1)とシラン化合物(2)のモル比で、[シラン化合物(1)]:[シラン化合物(2)]=5:95〜100:0の割合で反応させて得られたポリオルガノシロキサン化合物を、接着剤全体に対し70重量%以上含有する接着剤。
- 前記X0が塩素原子、アセトキシ基、またはシアノ基であることを特徴とする請求項1または2に記載の接着剤。
- 硬化剤を含まないことを特徴とする請求項1〜3のいずれかに記載の接着剤。
- 酸化防止剤、紫外線吸収剤、光安定剤、希釈剤、シランカップリング剤、酸無水物、芳香族アミンおよびフェノール樹脂から選ばれる他の成分を含有する請求項1〜3のいずれかに記載の接着剤。
- 接着する材料が、ガラス、セラミックス、金属および合成樹脂からなる群から選ばれる少なくとも一種である請求項1〜5のいずれかに記載の接着剤。
- 前記金属が、銅、アルミニウム、金、白金およびこれらの金属の合金からなる群から選
ばれる少なくとも一種である請求項6に記載の接着剤。
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CN104212409B (zh) | 2016-08-24 |
TW200946627A (en) | 2009-11-16 |
CN101965387B (zh) | 2015-01-07 |
KR20150107888A (ko) | 2015-09-23 |
CN104232016A (zh) | 2014-12-24 |
CN101965387A (zh) | 2011-02-02 |
CN104212409A (zh) | 2014-12-17 |
US20110054139A1 (en) | 2011-03-03 |
WO2009104505A1 (ja) | 2009-08-27 |
KR20100120156A (ko) | 2010-11-12 |
KR101581974B1 (ko) | 2015-12-31 |
TWI443167B (zh) | 2014-07-01 |
US8357261B2 (en) | 2013-01-22 |
KR20170018490A (ko) | 2017-02-17 |
JPWO2009104505A1 (ja) | 2011-06-23 |
KR101732296B1 (ko) | 2017-05-02 |
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