JP2022522100A - 付加硬化性シリコーン接着剤組成物 - Google Patents
付加硬化性シリコーン接着剤組成物 Download PDFInfo
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- JP2022522100A JP2022522100A JP2021543201A JP2021543201A JP2022522100A JP 2022522100 A JP2022522100 A JP 2022522100A JP 2021543201 A JP2021543201 A JP 2021543201A JP 2021543201 A JP2021543201 A JP 2021543201A JP 2022522100 A JP2022522100 A JP 2022522100A
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- JP
- Japan
- Prior art keywords
- group
- sio
- silicone
- alkyl
- adhesion promoter
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000000203 mixture Substances 0.000 title claims abstract description 110
- 239000013464 silicone adhesive Substances 0.000 title abstract description 6
- 239000000654 additive Substances 0.000 title description 6
- 230000000996 additive effect Effects 0.000 title description 3
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 96
- 239000002318 adhesion promoter Substances 0.000 claims abstract description 70
- 125000003118 aryl group Chemical group 0.000 claims abstract description 41
- 239000000463 material Substances 0.000 claims abstract description 19
- 150000004678 hydrides Chemical class 0.000 claims abstract description 13
- 229910052751 metal Inorganic materials 0.000 claims abstract description 13
- 239000002184 metal Substances 0.000 claims abstract description 13
- 229920003023 plastic Polymers 0.000 claims abstract description 13
- 239000004033 plastic Substances 0.000 claims abstract description 13
- -1 C2-C8 Alkoxy Oxy Chemical group 0.000 claims description 49
- 150000002430 hydrocarbons Chemical class 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 41
- 229930195733 hydrocarbon Natural products 0.000 claims description 40
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 239000000758 substrate Substances 0.000 claims description 19
- 239000004215 Carbon black (E152) Substances 0.000 claims description 18
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 239000000945 filler Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 229910052710 silicon Inorganic materials 0.000 claims description 12
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 11
- 239000003112 inhibitor Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 10
- 230000001070 adhesive effect Effects 0.000 claims description 10
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
- 239000000853 adhesive Substances 0.000 claims description 9
- 229910000077 silane Inorganic materials 0.000 claims description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 229910004283 SiO 4 Inorganic materials 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 7
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 4
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims description 4
- 238000004132 cross linking Methods 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 229910001092 metal group alloy Inorganic materials 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 5
- 239000003431 cross linking reagent Substances 0.000 claims 2
- 150000002739 metals Chemical class 0.000 abstract description 7
- 238000010586 diagram Methods 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 239000011347 resin Substances 0.000 description 13
- 229920005989 resin Polymers 0.000 description 13
- 150000004756 silanes Chemical class 0.000 description 11
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 6
- 235000006708 antioxidants Nutrition 0.000 description 6
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 5
- 239000004734 Polyphenylene sulfide Substances 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 229920001707 polybutylene terephthalate Polymers 0.000 description 5
- 229920000069 polyphenylene sulfide Polymers 0.000 description 5
- 239000004971 Cross linker Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000006459 hydrosilylation reaction Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 239000004611 light stabiliser Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 3
- DTFQULSULHRJOA-UHFFFAOYSA-N 2,3,5,6-tetrabromobenzene-1,4-diol Chemical compound OC1=C(Br)C(Br)=C(O)C(Br)=C1Br DTFQULSULHRJOA-UHFFFAOYSA-N 0.000 description 2
- VJIDDJAKLVOBSE-UHFFFAOYSA-N 2-ethylbenzene-1,4-diol Chemical compound CCC1=CC(O)=CC=C1O VJIDDJAKLVOBSE-UHFFFAOYSA-N 0.000 description 2
- WPMYUUITDBHVQZ-UHFFFAOYSA-M 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=CC(CCC([O-])=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-M 0.000 description 2
- URFNSYWAGGETFK-UHFFFAOYSA-N 4,4'-Dihydroxybibenzyl Chemical compound C1=CC(O)=CC=C1CCC1=CC=C(O)C=C1 URFNSYWAGGETFK-UHFFFAOYSA-N 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- FLPKSBDJMLUTEX-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) 2-butyl-2-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]propanedioate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)C(C(=O)OC1CC(C)(C)N(C)C(C)(C)C1)(CCCC)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FLPKSBDJMLUTEX-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- FRNQLQRBNSSJBK-UHFFFAOYSA-N divarinol Chemical compound CCCC1=CC(O)=CC(O)=C1 FRNQLQRBNSSJBK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 description 2
- 239000002530 phenolic antioxidant Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 229920006380 polyphenylene oxide Polymers 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- 229910052990 silicon hydride Inorganic materials 0.000 description 2
- 239000002210 silicon-based material Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 2
- YEYCMBWKTZNPDH-UHFFFAOYSA-N (2,2,6,6-tetramethylpiperidin-4-yl) benzoate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)C1=CC=CC=C1 YEYCMBWKTZNPDH-UHFFFAOYSA-N 0.000 description 1
- KJYSXRBJOSZLEL-UHFFFAOYSA-N (2,4-ditert-butylphenyl) 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 KJYSXRBJOSZLEL-UHFFFAOYSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- ISNSMFRWEZSCRU-UHFFFAOYSA-N 1,6-bis(4-hydroxyphenyl)hexane-1,6-dione Chemical compound C1=CC(O)=CC=C1C(=O)CCCCC(=O)C1=CC=C(O)C=C1 ISNSMFRWEZSCRU-UHFFFAOYSA-N 0.000 description 1
- OTCWVYFQGYOYJO-UHFFFAOYSA-N 1-o-methyl 10-o-(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate Chemical compound COC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 OTCWVYFQGYOYJO-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
- UNIVUTHKVHUXCT-UHFFFAOYSA-N 2,2-bis(4-hydroxyphenyl)acetonitrile Chemical compound C1=CC(O)=CC=C1C(C#N)C1=CC=C(O)C=C1 UNIVUTHKVHUXCT-UHFFFAOYSA-N 0.000 description 1
- ZSDAMBJDFDRLSS-UHFFFAOYSA-N 2,3,5,6-tetrafluorobenzene-1,4-diol Chemical compound OC1=C(F)C(F)=C(O)C(F)=C1F ZSDAMBJDFDRLSS-UHFFFAOYSA-N 0.000 description 1
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical compound CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 1
- JGJKHOVONFSHBV-UHFFFAOYSA-N 2,4,5,6-tetrabromobenzene-1,3-diol Chemical compound OC1=C(Br)C(O)=C(Br)C(Br)=C1Br JGJKHOVONFSHBV-UHFFFAOYSA-N 0.000 description 1
- NLQBQVXMWOFCAU-UHFFFAOYSA-N 2,4,5,6-tetrafluorobenzene-1,3-diol Chemical compound OC1=C(F)C(O)=C(F)C(F)=C1F NLQBQVXMWOFCAU-UHFFFAOYSA-N 0.000 description 1
- WMVJWKURWRGJCI-UHFFFAOYSA-N 2,4-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC=C(O)C(C(C)(C)CC)=C1 WMVJWKURWRGJCI-UHFFFAOYSA-N 0.000 description 1
- GJDRKHHGPHLVNI-UHFFFAOYSA-N 2,6-ditert-butyl-4-(diethoxyphosphorylmethyl)phenol Chemical compound CCOP(=O)(OCC)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 GJDRKHHGPHLVNI-UHFFFAOYSA-N 0.000 description 1
- LUELYTMQTXRXOI-UHFFFAOYSA-N 2-(2-phenylpropan-2-yl)benzene-1,4-diol Chemical compound C=1C(O)=CC=C(O)C=1C(C)(C)C1=CC=CC=C1 LUELYTMQTXRXOI-UHFFFAOYSA-N 0.000 description 1
- LEVFXWNQQSSNAC-UHFFFAOYSA-N 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-hexoxyphenol Chemical compound OC1=CC(OCCCCCC)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 LEVFXWNQQSSNAC-UHFFFAOYSA-N 0.000 description 1
- IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 description 1
- VXLIZRNHJIWWGV-UHFFFAOYSA-N 2-[1-(2-hydroxyphenyl)cyclopentyl]phenol Chemical compound OC1=CC=CC=C1C1(C=2C(=CC=CC=2)O)CCCC1 VXLIZRNHJIWWGV-UHFFFAOYSA-N 0.000 description 1
- XCUMMFDPFFDQEX-UHFFFAOYSA-N 2-butan-2-yl-4-[2-(3-butan-2-yl-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C1=C(O)C(C(C)CC)=CC(C(C)(C)C=2C=C(C(O)=CC=2)C(C)CC)=C1 XCUMMFDPFFDQEX-UHFFFAOYSA-N 0.000 description 1
- XRCRJFOGPCJKPF-UHFFFAOYSA-N 2-butylbenzene-1,4-diol Chemical compound CCCCC1=CC(O)=CC=C1O XRCRJFOGPCJKPF-UHFFFAOYSA-N 0.000 description 1
- XQOAPEATHLRJMI-UHFFFAOYSA-N 2-ethyl-4-[2-(3-ethyl-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C1=C(O)C(CC)=CC(C(C)(C)C=2C=C(CC)C(O)=CC=2)=C1 XQOAPEATHLRJMI-UHFFFAOYSA-N 0.000 description 1
- TVWGHFVGFWIHFN-UHFFFAOYSA-N 2-hexadecan-2-yl-4,6-dimethylphenol Chemical compound CCCCCCCCCCCCCCC(C)C1=CC(C)=CC(C)=C1O TVWGHFVGFWIHFN-UHFFFAOYSA-N 0.000 description 1
- GAODDBNJCKQQDY-UHFFFAOYSA-N 2-methyl-4,6-bis(octylsulfanylmethyl)phenol Chemical compound CCCCCCCCSCC1=CC(C)=C(O)C(CSCCCCCCCC)=C1 GAODDBNJCKQQDY-UHFFFAOYSA-N 0.000 description 1
- XCZKKZXWDBOGPA-UHFFFAOYSA-N 2-phenylbenzene-1,4-diol Chemical compound OC1=CC=C(O)C(C=2C=CC=CC=2)=C1 XCZKKZXWDBOGPA-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- NJRNUAVVFBHIPT-UHFFFAOYSA-N 2-propylbenzene-1,4-diol Chemical compound CCCC1=CC(O)=CC=C1O NJRNUAVVFBHIPT-UHFFFAOYSA-N 0.000 description 1
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 1
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- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
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- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
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- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
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- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-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
- 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 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- WKEXHTMMGBYMTA-UHFFFAOYSA-N trimethyl propyl silicate Chemical compound CCCO[Si](OC)(OC)OC WKEXHTMMGBYMTA-UHFFFAOYSA-N 0.000 description 1
- OZWKZRFXJPGDFM-UHFFFAOYSA-N tripropoxysilane Chemical compound CCCO[SiH](OCCC)OCCC OZWKZRFXJPGDFM-UHFFFAOYSA-N 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
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- 125000005023 xylyl group Chemical group 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
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- 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
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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- 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
-
- 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
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- 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
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
-
- 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
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
- C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
-
- 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
- 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
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
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- 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
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Abstract
Description
Z1とZ2は独立して
または
であり、
ここでR3、R4、R5、R6、R7、R8、R9、およびR10は、H、C1-C10アルキル、または-OR11から独立して選択され、ここでR11はC1-C10アルキルであり、そしてR3、R4、R5、R6、R7、R8、R9、および/またはR10の少なくとも1つはHであり、
xは1から10であり;
yは2から10であり;そして
Arは芳香族基である。
ここでXは上記のとおりであり、そしてR14、R15、R16、R17、R18、R19、R20、およびR21は、水素、C1-C10アルキル、C3-C8シクロアルキル、またはC6-C10アリールから独立して選択される。
ここでR51、R52、およびR53は、H、C1-C10アルキル、または-OR54から独立して選択され、ここでR54はC1-C10アルキルであり、そしてR51、R52、およびR53の少なくとも1つはHであり;そして
R50は、ケイ素原子に結合した側鎖を有する有機ケイ素基であり、そして以下の式で表され、
Q1-C(O)-O-Q2
ここで
Q1は、ケイ素原子とエステル結合の間に2つ以上の炭素原子を有する炭素鎖を形成する直鎖または分岐のアルキレン基を表し、そして
Q2は、酸素原子と側鎖:SiR48 r(OR49)3-rにおけるケイ素原子の間に3つ以上の炭素原子を有する炭素鎖を形成する直鎖または分岐のアルキレン基を表す。
第2の接着促進剤(i)は、式R47-SiR48 r(OR49)3-rの1つまたは複数の化合物から選択され、ここでR47は水素またはヒドリド官能基であり;R48はC1-C10炭化水素基から独立して選択され;各R49は、C1-C10炭化水素から独立して選択され;そしてrは0であり;そして
第2の接着促進剤(ii)は、下記式の化合物から選択される。
ここでR51、R52、およびR53は、H、C1-C10アルキル、または-OR54から独立して選択され、ここでR54はC1-C10アルキルであり、そしてR51、R52、およびR53の少なくとも1つおよび少なくとも1つはHであり;そしてR50は、C1-C30炭化水素;C6-C30アリール基;アルキルアクリレート基;アルキルカルボキシレート基;またはエステル基である。
M1 aM2 bD1 cD2 dT1 eT2 fQg、ここで
M1=R23R24R25SiO1/2
M2=R26R27R28SiO1/2
D1=R29R30SiO2/2
D2=R31R32SiO2/2
T1=R33SiO3/2
T2=R34SiO3/2
Q=SiO4/2
ここでR23、R24、R25、R27、R28、R29、R30、R32、およびR33は、C1-C30炭化水素、C6-C30芳香族基、またはC1-C30アルコキシ基から独立して選択され、
R26、R31、およびR34は、C1-C30炭化水素、C6-C30芳香族基、C1-C30アルコキシ基、またはC2-C30アルケニル基から独立して選択され、但しR26、R31、および/またはR34のうちの1つまたは複数は、C2-C30アルケニル基から選択されるという条件であり、
下付き文字a、b、c、d、e、f、gは、ゼロまたは正であって、以下の制限:2<a+b+c+d+e+f+g<2000、b+d+f>0を受ける。
M3 hM4 iD3 jD4 kT3 mT4 nQo、ここで
M3=R35R36R37SiO1/2
M4=R38R39R40SiO1/2
D3=R41R42SiO2/2
D4=R43R44SiO2/2
T3=R45SiO3/2
T4=R46SiO3/2
Q=SiO4/2
ここでR35、R36、R37、R41、R42、R45は、C1-C30炭化水素、C6-C30芳香族基、またはC1-C30アルコキシ基から独立して選択され、
R38、R39、R40、R43、R44、およびR46は、水素、C1-C30炭化水素、C6-C30芳香族基、C1-C30アルコキシ基、またはC2-C30アルケニル基から独立して選択され、但しR38、R39、R40、R43、R44、および/またはR46の1つまたは複数が水素であるという条件であり、
下付き文字a、b、c、d、e、f、gはゼロまたは正であって、次の制限:1<h+i+j+k+m+n+o<100、i+k+n>0を受ける。
Z1-R1-O-Ar-O-R2-Z2
ここでR1およびR2は、C1-C30二価炭化水素;C2-C20二価炭化水素;C4-C10二価炭化水素;またはC1-C4二価炭化水素であり;
Z1およびZ2は、独立して
または
であり、
ここでR3、R4、R5、R6、R7、R8、R9、およびR10は、H、C1-C10アルキル、または-OR11から独立して選択され、ここでR11はC1-C10アルキルであり、そしてR3、R4、R5、R6、R7、R8、R9、および/またはR10の少なくとも1つはHであり、
Xは1から10であり;
Yは2から10であり;そして
Arは芳香族基である。
ここでXは上記のとおりであり、R12およびR13は、互いに同一または異なり、またはそれらが結合する環内にあり、そして、水素、C1-C10アルキル、C1-C10アルコキシ、C2-C8アルケニル、C2-C8アルケニルオキシ、C3-C8シクロアルキル、C3-C8シクロアルコキシ、C6-C10アリール、C6-C10アリールオキシ、C7-C10アラルコキシ、C7-C12アルキルアリール、またはC7-C12アルキルアリールオキシから選択され、そしてtおよびwは0-4であり、ここでtまたはwが4未満のとき、特定されていない1つまたは複数の原子価は水素によって占められている。
ここでXは上記のとおりであり、そしてR14、R15、R16、R17、R18、R19、R20、およびR21は、水素、C1-C10アルキル、C3-C8シクロアルキル、またはC6-C10アリールから独立して選択される。一実施形態では、Xは-C(R22)2-であり、ここでR22は、水素、C1-C10アルキル、C3-C8シクロアルキル、またはC6-C10アリールから独立して選択される。一実施形態では、化合物の-O-Ar-O-部分は、以下の式である。
M1 aM2 bD1 cD2 dT1 eT2 fQg
ここで
M1=R23R24R25SiO1/2
M2=R26R27R28SiO1/2
D1=R29R30SiO2/2
D2=R31R32SiO2/2
T1=R33SiO3/2
T2=R34SiO3/2
Q=SiO4/2
ここでR23、R24、R25、R27、R28、R29、R30、R32、およびR33は、C1-C30炭化水素、C6-C30芳香族基、またはC1-C30アルコキシ基から独立して選択され、
R26、R31、およびR34は、C1-C30炭化水素、C6-C30芳香族基、C1-C30アルコキシ基、またはC2-C30アルケニル基から独立して選択され、但しR26、R31、および/またはR34のうちの1つまたは複数は、C2-C30アルケニル基から選択されるという条件であり、
下付き文字a、b、c、d、e、f、gは、ゼロまたは正であって、以下の制限:2<a+b+c+d+e+f+g<2000、b+d+f>0を受ける。
M3 hM4 iD3 jD4 kT3 mT4 nQo
ここで
M3=R35R36R37SiO1/2
M4=R38R39R40SiO1/2
D3=R41R42SiO2/2
D4=R43R44SiO2/2
T3=R45SiO3/2
T4=R46SiO3/2
Q=SiO4/2
ここでR35、R36、R37、R41、R42、R45は、C1-C30炭化水素、C6-C30芳香族基、またはC1-C30アルコキシ基から独立して選択され、
R38、R39、R40、R43、R44、およびR46は、水素、C1-C30炭化水素、C6-C30芳香族基、C1-C30アルコキシ基、またはC2-C30アルケニル基から独立して選択され、但しR38、R39、R40、R43、R44、および/またはR46は水素であるという条件であり、
下付き文字a、b、c、d、e、f、gは、ゼロまたは正であって、以下の制限:1<h+i+j+k+m+n+o<100、i+k+n>0を受ける。
R47-SiR48 r(OR49)3-r
ここでR47は水素またはヒドリド官能基であり;
R48はC1-C10炭化水素基から独立して選択され;各R49は、C1-C10炭化水素から独立して選択され、そしてr=0、1、または2である。
ここでR51、R52、およびR53は、H、C1-C10アルキル、または-OR54から独立して選択され、ここでR54はC1-C10アルキルであり、そしてR51、R52、およびR53のうちの少なくとも1つはHであり;そしてR50はC1-C30炭化水素;C6-C30アリール基;アルキルアクリレート基;アルキルカルボキシレート基;またはエステル基である。一実施形態では、式R47-SiR48 r(OR49)3-rのヒドリド官能性アルコキシシラン、R47は環状ヒドリドシロキサンであり、R50は、C1-C30炭化水素;C6-C30アリール基;アルキルアクリレート基;アルキルカルボキシレート基;またはエステル基であり、そして化合物がトリアルコキシシリル基を含むように、rは0である。一実施形態では、R50は、ケイ素原子に結合した側鎖を有し、以下の式で表される有機シリコン基であり、
Q1-C(O)-O-Q2
ここで
Q1は、ケイ素原子とエステル結合との間に2つ以上の炭素原子、実施形態では、2-20個の炭素原子、4-15個の炭素原子、または6-10個の炭素原子を有する炭素鎖を形成する直鎖状または分枝状のアルキレン基を表し、そして
Q2は、酸素原子と側鎖:SiR48 r(OR49)3-rにおけるケイ素原子との間に3つ以上の炭素原子、実施形態で、2-20個の炭素原子、4-15個の炭素原子、または6-10個の炭素原子を有する炭素鎖を形成する直鎖状または分岐のアルキレン基を表す。
R55-SiR56 n(OR57)3-n
ここでR55、R56、およびR57は、C1-C30炭化水素、および/またはC6-C30芳香族基から独立して選択され、そしてR55は、C1-C30炭化水素、C6-30芳香族基、C1-C30アルコキシ基、またはC2-C20不飽和炭化水素から選択される。
Claims (24)
- 硬化性シリコーン組成物であって、(a)アルケニル官能性シリコーン;(b)シリコーンベースの架橋剤;(c)充填剤;(d)第1の接着促進剤;(e)第2の接着促進剤;(f)任意選択でシラン;(g)抑制剤および(h)触媒を含み、ここで第1の接着促進剤は、式Z1-R1-O-Ar-O-R2-Z2の化合物から選択され、ここでR1およびR2は、C1-C30二価炭化水素;C2-C20二価炭化水素;C4-C10二価炭化水素;またはC1-C4二価炭化水素であり;
Z1およびZ2は、独立して
または
であり、
ここでR3、R4、R5、R6、R7、R8、R9、およびR10は、H、C1-C10アルキル、または-OR11から独立して選択され、ここでR11はC1-C10アルキルであり、そしてR3、R4、R5、R6、R7、R8、R9、および/またはR10の少なくとも1つはHであり、
xは1から10であり、
yは2から10であり、そして
Arは芳香族基である、
硬化性シリコーン組成物。 - 芳香族基Arは、C6-C30アリーレン基、または式-Ar1-X-Ar2-の基から選択することができ、ここでAr1およびAr2は、単環式の二価のアリール基から独立して選択され、そしてXは架橋基である、請求項1に記載の硬化性シリコーン組成物。
- Ar1およびAr2は、C6-C30アリーレン基から独立して選択され、Xは、Ar1とAr2をつなぐ結合、C1-C30二価炭化水素基、C5-C30二価環状炭化水素基、-O-、-S-、-S(O)-、-S(O)2-、または-C(O)-から選択される、請求項2に記載の硬化性シリコーン組成物。
- Ar1-X-Ar2は下記式の基であり、
ここでXは、Ar1とAr2をつなぐ結合、C1-C30二価炭化水素基、C5-C30二価環状炭化水素基、-O-、-S-、-S(O)-、-S(O)2-、または-C(O)-から選択され、R12およびR13は、互いに同じか異なるか、またはそれらが結合されている環内にあり、そして水素、C1-C10アルキル、C1-C10アルコキシ、C2-C8アルケニル、C2-C8アルケニルオキシ、C3-C8シクロアルキル、C3-C8シクロアルコキシ、C6-C10アリール、C6-C10アリールオキシ、C7-C10アラルコキシ、C7-C12アルキルアリール、またはC7-C12アルキルアリールオキシから選択され、そしてtおよびwは0-4であり、ここでtまたはwが4未満のとき、特定されていない単数または複数の原子価は水素によって占められている、請求項2に記載の硬化性シリコーン組成物。 - Xは-C(R22)2-であり、ここでR22は、水素、C1-C10アルキル、C3-C8シクロアルキル、またはC6-C10アリールから独立して選択される、請求項5に記載の硬化性シリコーン組成物。
- 第1の接着促進剤が、組成物の総重量に基づいて、約0.1重量%から約5重量%の量で存在する、請求項1から8のいずれか一項に記載の硬化性シリコーン組成物。
- 第2の接着促進剤は、式R47-SiR48 r(OR49)3-rの1つまたは複数の化合物から選択され、ここでR47は水素またはヒドリド官能基であり、R48はC1-C10炭化水素基から独立して選択され、各R49は、C1-C10炭化水素から独立して選択され、そしてrは0、1、または2である、請求項1から9のいずれか一項に記載の硬化性組成物。
- R47は、下記式の基を含む環状ヒドリドシロキサンであり、
ここでR51、R52、およびR53は、H、C1-C10アルキル、または-OR54から独立して選択され、ここでR54はC1-C10アルキルであり、そしてR51、R52、およびR53の少なくとも1つはHであり、そして
R50は、ケイ素原子に結合した側鎖を有する有機ケイ素基であり、そして次の式で表され、
Q1-C(O)-O-Q2
ここで
Q1は、ケイ素原子とエステル結合の間に2つ以上の炭素原子を有する炭素鎖を形成する直鎖または分岐のアルキレン基を表し、そして
Q2は、酸素原子と側鎖:SiR48 r(OR49)3-rのケイ素原子の間に3つ以上の炭素原子を有する炭素鎖を形成する直鎖状または分岐状のアルキレン基を表す、
請求項10に記載の硬化性組成物。 - rが0であり、そしてR49がC1-C10アルキル基である、請求項11に記載の硬化性組成物。
- 第2の接着促進剤が、組成物の総重量に基づいて、約0.1重量%から約10重量%の量で存在する、請求項1から12のいずれか一項に記載の硬化性組成物。
- 硬化性組成物であって、第2の接着促進剤(i)および(ii)を含み、ここで
第2の接着促進剤(i)は、式R47-SiR48 r(OR49)3-rの1つまたは複数の化合物から選択され、ここでR47は水素またはヒドリド官能基であり、R48はC1-C10炭化水素基から独立して選択され、各R49は、C1-C10炭化水素から独立して選択され、そしてrは0であり、そして
第2の接着促進剤(ii)は、式R47-SiR48 r(OR49)3-rの化合物から選択され、ここでR48はC1-C10炭化水素基から独立して選択され、各R49は、C1-C10炭化水素から独立して選択され、そしてrは0、1、または2であり、そしてR47は、下記式の基を含む環状ヒドリドシロキサンであり、
ここでR51、R52、およびR53は、H、C1-C10アルキル、または-OR54から独立して選択され、ここでR54はC1-C10アルキルであり、そしてR51、R52、およびR53の少なくとも1つおよび少なくとも1つはHであり、そしてR50はC1-C30炭化水素;C6-C30アリール基;アルキルアクリレート基;アルキルカルボキシレート基;またはエステル基である、請求項1から14のいずれか一項に記載の硬化性組成物。 - 第2の接着促進剤(i)は、約0.5重量%から約3重量%の量で存在し、そして接着促進剤(ii)は、約0.1重量%から約8重量%の量で存在する、請求項14に記載の硬化性シリコーン組成物。
- アルケニルシリコーンは、式M1 aM2 bD1 cD2 dT1 eT2 fQgの化合物から選択され、
ここで
M1=R23R24R25SiO1/2
M2=R26R27R28SiO1/2
D1=R29R30SiO2/2
D2=R31R32SiO2/2
T1=R33SiO3/2
T2=R34SiO3/2
Q=SiO4/2
ここでR23、R24、R25、R27、R28、R29、R30、R32、およびR33は、C1-C30炭化水素、C6-C30芳香族基、またはC1-C30アルコキシ基から独立して選択され、
R26、R31、およびR34は、C1-C30炭化水素、C6-C30芳香族基、C1-C30アルコキシ基、またはC2-C30アルケニル基から独立して選択され、但しR26、R31、および/またはR34のうちの1つまたは複数は、C2-C30アルケニル基から選択されるという条件であり、
下付き文字a、b、c、d、e、f、gは、ゼロまたは正であって、以下の制限:2<a+b+c+d+e+f+g<2000、b+d+f>0を受ける、
請求項1から15のいずれか一項に記載の硬化性シリコーン組成物。 - アルケニルシリコーンは、(i)cが約5から約1000である式M2D1 cM2を有する第1のアルケニル官能性シリコーン、および(ii)c’が約1000から約1500である式M2D1 c’M2を有する第2のアルケニル官能性シリコーンから選択されるアルケニルシリコーンの混合物を含む、請求項16に記載の硬化性シリコーン組成物。
- アルケニルシリコーンは、複数のQg単位および1つまたは複数のM2単位を含む分岐ポリオルガノシロキサンである、請求項1から17のいずれか一項に記載の硬化性組成物。
- シリコーンヒドリド架橋剤は、下記式の化合物から選択され、
M3 hM4 iD3 jD4 kT3 mT4 nQo
ここで
M3=R35R36R37SiO1/2
M4=R38R39R40SiO1/2
D3=R41R42SiO2/2
D4=R43R44SiO2/2
T3=R45SiO3/2
T4=R46SiO3/2
Q=SiO4/2
ここでR35、R36、R37、R41、R42、R45は、C1-C30炭化水素、C6-C30芳香族基、またはC1-C30アルコキシ基から独立して選択され、
R38、R39、R40、R43、R44、およびR46は、水素、C1-C30炭化水素、C6-C30芳香族基、C1-C30アルコキシ基、またはC2-C30アルケニル基から独立して選択され、但しR38、R39、R40、R43、R44、および/またはR46の1つまたは複数は水素であるという条件であり、
下付き文字a、b、c、d、e、f、gは、ゼロまたは正であって、以下の制限:1<h+i+j+k+m+n+o<100、i+k+n>0を受ける、請求項1から18のいずれか一項に記載の硬化性シリコーン組成物。 - 請求項1から19のいずれか一項に記載の組成物から形成された硬化シリコーン材料。
- 基材上に接着剤コーティングを形成する方法であって、請求項1から19のいずれか一項に記載の硬化性組成物を基材の表面に適用すること、および組成物を約50℃から約110℃の温度で加熱することを含む、方法。
- 組成物を約60℃から約100℃の温度で加熱することを含む、請求項21に記載の方法。
- 組成物が10分から約3時間の期間にわたって硬化される、請求項21または22に記載の方法。
- 基材が、プラスチック材料、金属、金属合金、金属化プラスチック、および/またはコーティングまたは塗装された金属から選択される、請求項21から24のいずれか一項に記載の方法。
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