JP7420705B2 - 湿気硬化性組成物 - Google Patents
湿気硬化性組成物 Download PDFInfo
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- JP7420705B2 JP7420705B2 JP2020504141A JP2020504141A JP7420705B2 JP 7420705 B2 JP7420705 B2 JP 7420705B2 JP 2020504141 A JP2020504141 A JP 2020504141A JP 2020504141 A JP2020504141 A JP 2020504141A JP 7420705 B2 JP7420705 B2 JP 7420705B2
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- Prior art keywords
- bis
- amine
- weight
- urea
- methylamine
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 82
- 239000003054 catalyst Substances 0.000 claims description 95
- -1 ethoxysilylbutyl Chemical group 0.000 claims description 43
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 36
- 229920000642 polymer Polymers 0.000 claims description 35
- 229910000077 silane Inorganic materials 0.000 claims description 25
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 24
- 229920001296 polysiloxane Polymers 0.000 claims description 20
- 239000012763 reinforcing filler Substances 0.000 claims description 19
- 239000002318 adhesion promoter Substances 0.000 claims description 16
- 239000003431 cross linking reagent Substances 0.000 claims description 16
- 229920000570 polyether Polymers 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 229920000620 organic polymer Polymers 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 14
- 238000013008 moisture curing Methods 0.000 claims description 13
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 12
- 229920000058 polyacrylate Polymers 0.000 claims description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 11
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 10
- 235000013877 carbamide Nutrition 0.000 claims description 10
- 239000011521 glass Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 238000000576 coating method Methods 0.000 claims description 9
- 239000011248 coating agent Substances 0.000 claims description 8
- 150000004756 silanes Chemical class 0.000 claims description 8
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 239000004202 carbamide Substances 0.000 claims description 6
- TZZGHGKTHXIOMN-UHFFFAOYSA-N 3-trimethoxysilyl-n-(3-trimethoxysilylpropyl)propan-1-amine Chemical compound CO[Si](OC)(OC)CCCNCCC[Si](OC)(OC)OC TZZGHGKTHXIOMN-UHFFFAOYSA-N 0.000 claims description 5
- 238000009434 installation Methods 0.000 claims description 5
- 150000003672 ureas Chemical class 0.000 claims description 4
- NLUBWVOYYFNGKI-UHFFFAOYSA-N 3-dimethoxysilyl-N-(3-dimethoxysilylbutyl)butan-1-amine Chemical compound CO[SiH](OC)C(C)CCNCCC(C)[SiH](OC)OC NLUBWVOYYFNGKI-UHFFFAOYSA-N 0.000 claims description 3
- RWLDCNACDPTRMY-UHFFFAOYSA-N 3-triethoxysilyl-n-(3-triethoxysilylpropyl)propan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCNCCC[Si](OCC)(OCC)OCC RWLDCNACDPTRMY-UHFFFAOYSA-N 0.000 claims description 3
- 229910021485 fumed silica Inorganic materials 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- HOBIHBQJHORMMP-UHFFFAOYSA-N 1,3-bis(3-triethoxysilylpropyl)urea Chemical compound CCO[Si](OCC)(OCC)CCCNC(=O)NCCC[Si](OCC)(OCC)OCC HOBIHBQJHORMMP-UHFFFAOYSA-N 0.000 claims description 2
- HSDGFGSXXVWDET-UHFFFAOYSA-N 1,3-bis(3-trimethoxysilylpropyl)urea Chemical compound CO[Si](OC)(OC)CCCNC(=O)NCCC[Si](OC)(OC)OC HSDGFGSXXVWDET-UHFFFAOYSA-N 0.000 claims description 2
- RJWFPXFLXSPWFW-UHFFFAOYSA-N 1,3-bis(4-trimethoxysilylbutyl)urea Chemical compound CO[Si](CCCCNC(NCCCC[Si](OC)(OC)OC)=O)(OC)OC RJWFPXFLXSPWFW-UHFFFAOYSA-N 0.000 claims description 2
- GJXJKDHPFKCGFF-UHFFFAOYSA-N 1,3-bis[3-(2,2-dimethoxyethylsilyl)propyl]urea Chemical compound COC(C[SiH2]CCCNC(=O)NCCC[SiH2]CC(OC)OC)OC GJXJKDHPFKCGFF-UHFFFAOYSA-N 0.000 claims description 2
- ADQVDENPLNWINA-UHFFFAOYSA-N 1,3-bis[3-(diethoxymethylsilyl)propyl]urea Chemical compound C(C)OC(OCC)[SiH2]CCCNC(=O)NCCC[SiH2]C(OCC)OCC ADQVDENPLNWINA-UHFFFAOYSA-N 0.000 claims description 2
- VXWNUHGXDYPQNX-UHFFFAOYSA-N 1,3-bis[3-(dimethoxymethylsilyl)propyl]urea Chemical compound COC(OC)[SiH2]CCCNC(=O)NCCC[SiH2]C(OC)OC VXWNUHGXDYPQNX-UHFFFAOYSA-N 0.000 claims description 2
- PBGIZDSJTUQFQR-UHFFFAOYSA-N 1,3-bis[4-(2,2-dimethoxyethylsilyl)butyl]urea Chemical compound COC(C[SiH2]CCCCNC(=O)NCCCC[SiH2]CC(OC)OC)OC PBGIZDSJTUQFQR-UHFFFAOYSA-N 0.000 claims description 2
- OWIYDYLAESMOKX-UHFFFAOYSA-N 3-(2,2-diethoxyethylsilyl)-N-[3-(2,2-diethoxyethylsilyl)propyl]-N-methylpropan-1-amine Chemical compound C(C)OC(C[SiH2]CCCN(C)CCC[SiH2]CC(OCC)OCC)OCC OWIYDYLAESMOKX-UHFFFAOYSA-N 0.000 claims description 2
- UOEFJHDQTLEFJW-UHFFFAOYSA-N 3-(2,2-diethoxyethylsilyl)-N-[3-(2,2-diethoxyethylsilyl)propyl]propan-1-amine Chemical compound C(C)OC(C[SiH2]CCCNCCC[SiH2]CC(OCC)OCC)OCC UOEFJHDQTLEFJW-UHFFFAOYSA-N 0.000 claims description 2
- ULYSOPIJMPLQOR-UHFFFAOYSA-N 3-(2,2-dimethoxyethylsilyl)-N-[3-(2,2-dimethoxyethylsilyl)propyl]propan-1-amine Chemical compound COC(C[SiH2]CCCNCCC[SiH2]CC(OC)OC)OC ULYSOPIJMPLQOR-UHFFFAOYSA-N 0.000 claims description 2
- YMXRPHMIOQYZOO-UHFFFAOYSA-N 3-(diethoxymethylsilyl)-N-[3-(diethoxymethylsilyl)propyl]-N-methylpropan-1-amine Chemical compound C(C)OC(OCC)[SiH2]CCCN(C)CCC[SiH2]C(OCC)OCC YMXRPHMIOQYZOO-UHFFFAOYSA-N 0.000 claims description 2
- YKQFFWZLUJYSEF-UHFFFAOYSA-N 3-(diethoxymethylsilyl)-N-[3-(diethoxymethylsilyl)propyl]propan-1-amine Chemical compound CCOC(OCC)[SiH2]CCCNCCC[SiH2]C(OCC)OCC YKQFFWZLUJYSEF-UHFFFAOYSA-N 0.000 claims description 2
- GUAWJTGMZCKVOU-UHFFFAOYSA-N 3-(dimethoxymethylsilyl)-N-[3-(dimethoxymethylsilyl)propyl]-N-methylpropan-1-amine Chemical compound COC(OC)[SiH2]CCCN(C)CCC[SiH2]C(OC)OC GUAWJTGMZCKVOU-UHFFFAOYSA-N 0.000 claims description 2
- WLKJPTNYLNKNMG-UHFFFAOYSA-N 3-diethoxysilyl-n-(3-diethoxysilylbutyl)butan-1-amine Chemical compound CCO[SiH](OCC)C(C)CCNCCC(C)[SiH](OCC)OCC WLKJPTNYLNKNMG-UHFFFAOYSA-N 0.000 claims description 2
- AUBMIVAHTUTDRC-UHFFFAOYSA-N 4-(2,2-dimethoxyethylsilyl)-N-[4-(2,2-dimethoxyethylsilyl)butyl]butan-1-amine Chemical compound COC(C[SiH2]CCCCNCCCC[SiH2]CC(OC)OC)OC AUBMIVAHTUTDRC-UHFFFAOYSA-N 0.000 claims description 2
- HENLCPWKLYRGTE-UHFFFAOYSA-N 4-(diethoxymethylsilyl)-N-[4-(diethoxymethylsilyl)butyl]butan-1-amine Chemical compound C(C)OC(OCC)[SiH2]CCCCNCCCC[SiH2]C(OCC)OCC HENLCPWKLYRGTE-UHFFFAOYSA-N 0.000 claims description 2
- UARIWHQEQIQGOG-UHFFFAOYSA-N 4-(dimethoxymethylsilyl)-N-[4-(dimethoxymethylsilyl)butyl]butan-1-amine Chemical compound COC(OC)[SiH2]CCCCNCCCC[SiH2]C(OC)OC UARIWHQEQIQGOG-UHFFFAOYSA-N 0.000 claims description 2
- POMJOPKMZVOANV-UHFFFAOYSA-N 4-trimethoxysilyl-n-(4-trimethoxysilylbutyl)butan-1-amine Chemical compound CO[Si](OC)(OC)CCCCNCCCC[Si](OC)(OC)OC POMJOPKMZVOANV-UHFFFAOYSA-N 0.000 claims description 2
- YEUIUVUELRLLMK-UHFFFAOYSA-N C(C)OC(C[SiH2]CCCCNCCCC[SiH2]CC(OCC)OCC)OCC Chemical compound C(C)OC(C[SiH2]CCCCNCCCC[SiH2]CC(OCC)OCC)OCC YEUIUVUELRLLMK-UHFFFAOYSA-N 0.000 claims description 2
- IWJMABSWQVWQPQ-UHFFFAOYSA-N C(C)OC(C[SiH2]CCCNC(NCCC[SiH2]CC(OCC)OCC)=O)OCC Chemical compound C(C)OC(C[SiH2]CCCNC(NCCC[SiH2]CC(OCC)OCC)=O)OCC IWJMABSWQVWQPQ-UHFFFAOYSA-N 0.000 claims description 2
- XJCAYMRKVOAEOH-UHFFFAOYSA-N COC(C[SiH2]CCCCN(C)CCCC[SiH2]CC(OC)OC)OC Chemical compound COC(C[SiH2]CCCCN(C)CCCC[SiH2]CC(OC)OC)OC XJCAYMRKVOAEOH-UHFFFAOYSA-N 0.000 claims description 2
- XRTJQRJGSNPFCS-UHFFFAOYSA-N COC(C[SiH2]CCCN(C)CCC[SiH2]CC(OC)OC)OC Chemical compound COC(C[SiH2]CCCN(C)CCC[SiH2]CC(OC)OC)OC XRTJQRJGSNPFCS-UHFFFAOYSA-N 0.000 claims description 2
- HBAJCDMHVJWTPP-UHFFFAOYSA-N COC(OC)[SiH2]CCCCN(C)CCCC[SiH2]C(OC)OC Chemical compound COC(OC)[SiH2]CCCCN(C)CCCC[SiH2]C(OC)OC HBAJCDMHVJWTPP-UHFFFAOYSA-N 0.000 claims description 2
- PYDFMRHCUXNFJU-UHFFFAOYSA-N COC(OC)[SiH2]CCCCNC(=O)NCCCC[SiH2]C(OC)OC Chemical compound COC(OC)[SiH2]CCCCNC(=O)NCCCC[SiH2]C(OC)OC PYDFMRHCUXNFJU-UHFFFAOYSA-N 0.000 claims description 2
- QMULOJQODCVJAF-UHFFFAOYSA-N COC(OC)[SiH2]CCCNCCC[SiH2]C(OC)OC Chemical compound COC(OC)[SiH2]CCCNCCC[SiH2]C(OC)OC QMULOJQODCVJAF-UHFFFAOYSA-N 0.000 claims description 2
- FZCTZEDRYNNOAM-UHFFFAOYSA-N N-methyl-4-trimethoxysilyl-N-(4-trimethoxysilylbutyl)butan-1-amine Chemical compound CO[Si](CCCCN(C)CCCC[Si](OC)(OC)OC)(OC)OC FZCTZEDRYNNOAM-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 230000000712 assembly Effects 0.000 claims description 2
- 238000000429 assembly Methods 0.000 claims description 2
- 230000004888 barrier function Effects 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- HZGIOLNCNORPKR-UHFFFAOYSA-N n,n'-bis(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCNCCC[Si](OC)(OC)OC HZGIOLNCNORPKR-UHFFFAOYSA-N 0.000 claims description 2
- AUWJDAPPVUMSJY-UHFFFAOYSA-N n-methyl-3-triethoxysilyl-n-(3-triethoxysilylpropyl)propan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCN(C)CCC[Si](OCC)(OCC)OCC AUWJDAPPVUMSJY-UHFFFAOYSA-N 0.000 claims description 2
- WTXITWGJFPAEIU-UHFFFAOYSA-N n-methyl-3-trimethoxysilyl-n-(3-trimethoxysilylpropyl)propan-1-amine Chemical compound CO[Si](OC)(OC)CCCN(C)CCC[Si](OC)(OC)OC WTXITWGJFPAEIU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- NSRRQJNPCVHGJN-UHFFFAOYSA-N 4-triethoxysilyl-n-(4-triethoxysilylbutyl)butan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCCNCCCC[Si](OCC)(OCC)OCC NSRRQJNPCVHGJN-UHFFFAOYSA-N 0.000 claims 1
- 150000003973 alkyl amines Chemical group 0.000 claims 1
- 238000012423 maintenance Methods 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 229940088417 precipitated calcium carbonate Drugs 0.000 claims 1
- 239000000945 filler Substances 0.000 description 17
- 239000000565 sealant Substances 0.000 description 17
- 239000000758 substrate Substances 0.000 description 15
- 230000001070 adhesive effect Effects 0.000 description 14
- 239000000853 adhesive Substances 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 238000001723 curing Methods 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 239000004721 Polyphenylene oxide Substances 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 238000005259 measurement Methods 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 8
- 239000003139 biocide Substances 0.000 description 7
- 239000004971 Cross linker Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000012974 tin catalyst Substances 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000005370 alkoxysilyl group Chemical group 0.000 description 5
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 229920001707 polybutylene terephthalate Polymers 0.000 description 5
- 229910052604 silicate mineral Inorganic materials 0.000 description 5
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- 229920002367 Polyisobutene Polymers 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000013005 condensation curing Methods 0.000 description 4
- 229920005645 diorganopolysiloxane polymer Polymers 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 238000006459 hydrosilylation reaction Methods 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 238000005191 phase separation Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 3
- 229920002396 Polyurea Polymers 0.000 description 3
- FGPCETMNRYMFJR-UHFFFAOYSA-L [7,7-dimethyloctanoyloxy(dimethyl)stannyl] 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC(=O)O[Sn](C)(C)OC(=O)CCCCCC(C)(C)C FGPCETMNRYMFJR-UHFFFAOYSA-L 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 3
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- 239000000047 product Substances 0.000 description 3
- LUYIHWDYPAZCNN-UHFFFAOYSA-N 2-butyl-1,2-benzothiazol-3-one Chemical compound C1=CC=C2C(=O)N(CCCC)SC2=C1 LUYIHWDYPAZCNN-UHFFFAOYSA-N 0.000 description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
- PORQOHRXAJJKGK-UHFFFAOYSA-N 4,5-dichloro-2-n-octyl-3(2H)-isothiazolone Chemical compound CCCCCCCCN1SC(Cl)=C(Cl)C1=O PORQOHRXAJJKGK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000012963 UV stabilizer Substances 0.000 description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 description 2
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- 125000004103 aminoalkyl group Chemical group 0.000 description 2
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 2
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl 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])[H] 0.000 description 2
- 229910052609 olivine Inorganic materials 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 125000005702 oxyalkylene group Chemical group 0.000 description 2
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- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
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- 150000004760 silicates Chemical class 0.000 description 2
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- 238000004381 surface treatment Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
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- 239000013464 silicone adhesive Substances 0.000 description 1
- 239000013467 silicone adhesive and sealant Substances 0.000 description 1
- GRJISGHXMUQUMC-UHFFFAOYSA-N silyl prop-2-enoate Chemical compound [SiH3]OC(=O)C=C GRJISGHXMUQUMC-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 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
- 229910000018 strontium carbonate Inorganic materials 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- HIAIVILTZQDDNY-UHFFFAOYSA-J tin(4+);trifluoromethanesulfonate Chemical compound [Sn+4].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F HIAIVILTZQDDNY-UHFFFAOYSA-J 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- LSZKGNJKKQYFLR-UHFFFAOYSA-J tri(butanoyloxy)stannyl butanoate Chemical compound [Sn+4].CCCC([O-])=O.CCCC([O-])=O.CCCC([O-])=O.CCCC([O-])=O LSZKGNJKKQYFLR-UHFFFAOYSA-J 0.000 description 1
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- IZRJPHXTEXTLHY-UHFFFAOYSA-N triethoxy(2-triethoxysilylethyl)silane Chemical compound CCO[Si](OCC)(OCC)CC[Si](OCC)(OCC)OCC IZRJPHXTEXTLHY-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
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- CPRPKIMXLHBUGA-UHFFFAOYSA-N triethyltin Chemical compound CC[Sn](CC)CC CPRPKIMXLHBUGA-UHFFFAOYSA-N 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- JBYXACURRYATNJ-UHFFFAOYSA-N trimethoxy(1-trimethoxysilylhexyl)silane Chemical compound CCCCCC([Si](OC)(OC)OC)[Si](OC)(OC)OC JBYXACURRYATNJ-UHFFFAOYSA-N 0.000 description 1
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
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Description
(i)(R4O)m(Y1)3-m-Si末端有機ポリマー[式中、R4はC1~10アルキル基であり、Y1は、1~8個の炭素を含有するアルキル基であり、mは1、2又は3であり、有機ポリマーは、ポリエーテル、炭化水素ポリマー、アクリレートポリマー、ポリウレタン及びポリ尿素から選択される]と、
(ii)式
(R4O)m(Y1)3-m-Si(CH2)x-((NHCH2CH2)t-Q(CH2)x)n-Si(OR4)m(Y1)3-m
[式中、R4は、C1~10アルキル基であり、Y1は、1~8個の炭素を含有するアルキル基であり、
Qは、孤立電子対を有するヘテロ原子を含有する化学基であり、各xは、1~6の整数であり、tは0又は1であり、各mは、独立して1、2又は3であり、nは0又は1である]に従う1つ以上の二脚状シランと、
(iii)非二脚状接着促進剤と、
(iv)スズ系触媒と、任意選択的に
(v)架橋剤と、を含む。
任意の好適な基剤成分を利用してもよい。例えば、基剤成分は、
(a)25℃で粘度が1000~200,000mPa.sである、少なくとも2つの末端ヒドロキシル基又は加水分解性基を有するシロキサンポリマーと、
(b)1つ以上の補強性充填剤と、任意選択的に
(c)1つ以上の非補強性充填剤と、
を含み得る。
この基材成分は、
(a)25℃で粘度が1000~200,000mPa.s、あるいは2000~150000mPa.sである、少なくとも2つの末端ヒドロキシル基又は加水分解性基を有するシロキサンポリマーと、
(b)1つ以上の補強性充填剤と、任意選択的に
(c)1つ以上の非補強性充填剤と、
を含み、
及び
触媒パッケージは、
(i)(R4O)m(Y1)3-m-Si末端有機ポリマー[式中、R4はC1~10アルキル基であり、Y1は、1~8個の炭素を含有するアルキル基であり、mは1、2又は3であり、有機ポリマーは、ポリエーテル、炭化水素ポリマー、アクリレートポリマー、ポリウレタン及びポリ尿素から選択される]と、
(ii)式
(R4O)m(Y1)3-m-Si(CH2)x-(NHCH2CH2)t-Q(CH2)x-Si(OR4)m(Y1)3-m
[式中、R4は、C1~10アルキル基であり、Y1は、1~8個の炭素を含有するアルキル基であり、
Qは、孤立電子対を有するヘテロ原子を含有する化学基であり、各xは1~6の整数であり、tは0又は1であり、各mは独立して、1、2又は3である]に従う1つ以上の二脚状シランと、
(iii)非二脚状接着促進剤と、
(iv)スズ系触媒と、任意選択的に
(v)架橋剤と、を含む。
X3-aRaSi-Zb-O-(R1 ySiO(4-y)/2)z-Zb-Si-RaX3-a(1)
[式中、
aは、0、1又は3であり、
bは0又は1であり、
zは、300~5000の整数であり、
yは、0、1又は2、好ましくは2である。
R1 ySiO(4-y)/2の少なくとも97%(すなわち、97%~100%)は、y=2で特徴付けられる。
xは、ヒドロキシル基又は任意の縮合性基若しくは任意の加水分解性基である]。
追加の一級アミン系接着促進剤、及び又はスズ触媒を導入することによって硬化速度を上げると、触媒パッケージ中の非反応性シロキサン担体が実に不安定になり、劣化して触媒パッケージの粘度が低下し、貯蔵不安定性が生じることが判明した。しかし、本明細書に記載の触媒パッケージが開発され、分解せずに必要とされる硬化速度の改善がもたらされた。
-[Re-O-(-Rf-O-)h-Pn-CRg 2-Pn-O-(-Rf-O-)q1-Re]-
[式中、Pnは、1,4-フェニレン基、Reは、各々、同一又は異なり、2~8個の炭素原子を有する、二価の炭化水素基であり、Rfは、各々、同一又は異なり、エチレン基又はプロピレン基であり、Rgは、各々、同一又は異なり、水素原子又はメチル基であり、下付文字h及びq1の各々は、3~30の範囲の正の整数である。]の単位を含んでもよい。
(R4O)m(Y1)3-m-Si(CH2)x-(NHCH2CH2)t-Q(CH2)x-Si(OR4)m(Y1)3-m
[式中、R4はC1~10アルキル基であり、Y1は炭素数1~8のアルキル基であり、Qは孤立電子対を有するヘテロ原子を含有する化学基、あるいはアミン又は尿素であり、各xは、1~6の整数であり、tは0又は1であり、各mは、独立して、1、2又は3、あるいは2又は3であり、更なる代替例では、m=3である]。
(R4O)3-Si(CH2)x-(NHCH2CH2)t-NH(CH2)x-Si(OR4)3
本明細書に記載の2成分型湿気硬化シリコーン組成物のために触媒パッケージに任意選択的に組み込まれ得る非二脚状接着促進剤(v)の例としては、(エチレンジアミンプロピル)トリメトキシシラン、アミノアルキルアルコキシシラン(例えば、γ-アミノプロピルトリエトキシシラン又はγ-アミノプロピルトリメトキシシラン)などのアルコシキシラン、エポキシアルキルアルコキシシラン(例えば、3-グリシドキシプロピルトリメトキシシラン及びグリシドキシプロピルトリエトキシシラン)、メルカプト-アルキルアルコキシシラン、及びエチレンジアミンとシリルアクリレートとの反応生成物が挙げられる。ケイ素基を含むイソシアヌレート(1,3,5-トリス(トリアルコキシシリアルキル)イソシヌレートなど)を、更に用いてもよい。更に好適な接着促進剤(v)には、エポキシアルキルアルコキシシラン(3-グリシドキシプロピルトリメトキシシランなど)の、アミノ置換アルコキシシラン(3-アミノプロピルトリメトキシシランなど)との、及び任意選択的にアルキルアルコキシシラン(メチルトリメトキシシランなど)との反応生成物がある。典型的には、これらは、二脚状シラン(ii)と組み合わせて接着性を向上させるために、非二脚状接着促進剤(iii)の1~25重量%の、あるいは触媒パッケージの2~20重量%の範囲で存在する。
触媒パッケージ中の第4の必須成分は、基剤成分と触媒パッケージ成分とを一緒に混合した後の硬化反応の触媒として使用するのに好適なスズ系縮合触媒(iv)である。例としては、スズトリフレート、有機スズ金属触媒、例えば、トリエチルスズタートレート、スズオクトエート、スズオレエート、スズナフテート、ブチルスズトリ-2-エチルヘキソエート、スズブチレート、カルボメトキシフェニルスズトリスベレート、イソブチルスズトリセロエート、及びジオルガノスズ塩、特に、ジオルガノスズジカルボキシレート化合物、例えば、ジブチルスズジラウレート、ジメチルスズジブチレート、ジブチルスズジメトキシド、ジブチルスズジアセテート、ジメチルスズビスネオデカノエート、ジブチルスズジベンゾエート、第一スズオクトエート、ジメチルスズジネオデカノエート(DMTDN)及びジブチルスズジオクトエートが挙げられる。スズ触媒は、触媒パッケージの0.01~3重量%、あるいは、0.1~0.5重量%の量で存在してもよい。
必要に応じて、任意の好適な架橋剤を架橋剤(v)として使用してもよい。前述の硬化性組成物中に架橋剤(v)が存在する場合、ケイ素結合加水分解性基、例えばアシルオキシ基(例えば、アセトキシ基、オクタノイルオキシ基、及びベンゾイルオキシ基);ケトキシミノ基(例えば、ジメチルケトキシモ(ketoximo)基及びイソブチルケトキシミノ(isobutylketoximino)基);アルコキシ基(例えばメトキシ基、エトキシ基、イソブトキシ基及びプロポキシ基)、並びにアルケニルオキシ基(例えば、イソプロペニルオキシ基及び1-エチル-2-メチルビニルオキシ基)を含む、1つ以上のシラン又はシロキサンであり得る。
顔料を、必要に応じて組成物を着色するため用いる。組成物と相溶性である限り、任意の好適な顔料を用いてもよい。2部型組成物では、顔料及び/又は着色された(非白色)充填剤、例えばカーボンブラックを触媒パッケージに利用して、最終のシーラント製品を着色してもよい。存在する場合、カーボンブラックは、充填剤及び着色剤の両方として機能する。
基剤成分に使用される充填剤のうちの1つは、適切であると判断された時/場合、触媒パッケージに使用されてもよい。シリカ、例えば、ヒュームドシリカ及び/又は炭酸カルシウムが好ましい。充填剤(vii)は、組成物の2つの部の混合比に応じて、0~50重量%の量で触媒パッケージ中に存在してもよい。
必要な場合、殺生物剤を組成物中で更に用いてもよい。用語「殺生物剤」は、殺菌剤、殺真菌剤、及び殺藻剤などを包含するものである。本明細書に記載の組成物中で用いてもよい有用な殺生物剤の好適な例としては、例えば、
10~90重量%のシロキサンポリマー(a)と、
10~80重量%の補強性充填剤(b)と、
0~20重量%の非補強性充填剤(c)と、
を含み、
触媒パッケージにおいて、触媒パッケージの総重量%を100重量%として、
30~80重量%のアルコキシシリル末端有機ポリマー(i)が、担体として触媒パッケージ中に存在し、触媒パッケージの総重量の30~80重量%あるいは40~65重量%の量で触媒パッケージ中に存在し、5~50重量%の二脚状シラン(ii)、あるいは10~30重量%の二脚状シラン(ii)と、
5~25重量%、あるいは2~20重量%の非二脚状接着促進剤(iii)と、
3重量%までのスズ系触媒と、あるいは、0.1~0.5重量%のスズ系触媒(iv)と、
0~25重量%、あるいは2~20重量%の架橋剤(v)と、
を含む。
本明細書の意図は、基材間の接着強度を改善するために、ヒドロシリル化硬化材料の代替として、LEDランプ基材用の縮合硬化接着剤/シーラントを提供することであった。2部型縮合硬化接着剤/シーラントは、速い深部硬化(24時間で90%超の強度)を提供し、20~120分間の典型的なスナップ時間を有する)、ほとんどの基材に対して良好な接着性を有する。これらは、このような組成物を硬化させるために使用されるスズ触媒が、例えば硫黄及びリンを含む他の化学物質によって不活性化されないという付加的な利点を有する。LED照明用途に好適であるために、スナップ時間を3~6分間に著しく低減する必要があり、接着性及び強度の増加は、30分以内に十分迅速である必要があった。
表1dで規定された各期間後、分析した触媒パッケージを、上記の表1bの基剤(1)と混合し、スナップ時間を測定した。以下の表1eに値を示す。
この試験例では、2つの触媒パッケージ例1及び例2の前述と同様の試験による安定性を、本発明に対応する先行技術の非反応性シリコーン担体材料の安定性と比較する。使用した触媒パッケージの組成を表2aに示す。ポリエーテル(1)は、25℃で32000~45000mPa.sの粘度を有するトリメトキシシリル末端ポリエーテルであり、ポリエーテル(2)は、25℃で約120,000mPa.sの粘度を有するトリメトキシシリル末端ポリエーテルであった。
この研究では、二脚状シラン(ii)の非存在下での高濃度の触媒の効果を測定することを意図しており、及びまた二脚状シラン(ii)の存在は、スナップ時間に影響を及ぼした。評価に使用した組成を表3aに示し、得られた結果を表3bに示す。
接着破壊(AF)は、試料が基材表面からきれいに分離している(剥がれている)状態を指す。凝集破壊(CF)は、コーティング自体が基材表面から分離せずに破断するときに観察される。ほとんどの場合、凝集破壊は、それの以前に引き離された積層体上で観察された。いくつかの場合では、混合された破壊型が観察された。すなわち、一部の領域は、はがれている(すなわちAF)が、一部はコーティングで覆われたまま(すなわちCF)である。このような場合、CF(CF%)を示す割合を記録する(CF%+AF%=100%を念頭に置く)。この試験例では、触媒パッケージを基剤1と混合した。
この試験例では、スズ系触媒(iii)なしで組成物が硬化するかどうかを判定することが求められた。使用した組成物を表4aに示す。
触媒パッケージを、以下の表5aに示されている触媒パッケージの組成を有する代替のアルコキシシリル末端有機ポリマー(i)の選択を用いて調製した。ここで、アルコキシシリル末端有機ポリマー(i)は以下のとおりであった。
Claims (12)
- 基剤成分及び触媒パッケージ成分を有する、2成分型湿気硬化シリコーン組成物であって、前記触媒パッケージ成分が、
(i)(R4O)m(Y1)3-m-Si末端有機ポリマー[式中、R4はC1~10アルキル基であり、Y1は1~8個の炭素を含有するアルキル基であり、mは1,2又は3であり、前記有機ポリマーは、ポリエーテル及びアクリレートポリマーから選択される]と、
(ii)式:
(R4O)m(Y1)3-m-Si(CH2)x-(NHCH2CH2)t-Q(CH2)x-Si(OR4)m(Y1)3-m
[式中、R4はC1~10アルキル基であり、Y1は1~8個の炭素を含有するアルキル基であり、Qは孤立電子対を有する窒素原子を含有するアミン基又は尿素基であり、各xは1~6の整数であり、tは0又は1であり、各mは独立して、1、2又は3である]
に従う1つ以上の二脚状シランと、
(iii)非二脚状接着促進剤と、
(iv)スズ系触媒と、任意選択的に
(v)架橋剤と、
を含む、2成分型湿気硬化シリコーン組成物。 - 前記基剤成分が、
(a)25℃で粘度が1000~200,000mPa.sである、少なくとも2つの末端ヒドロキシル基又は加水分解性基を有するシロキサンポリマーと、
(b)ヒュームドシリカ、沈降シリカ、及び沈降炭酸カルシウムから選択される1つ以上の補強性充填剤と、任意選択的に
(c)1つ以上の非補強性充填剤と、
を含む、請求項1に記載の2成分型湿気硬化シリコーン組成物。 - 二脚状シラン(ii)が、ビス(トリアルコキシシリルアルキル)アミン、ビス(ジアルコキシアルキルシリルアルキル)アミン、ビス(トリアルコキシシリルアルキル)N-アルキルアミン、ビス(ジアルコキシアルキルシリルアルキル)N-アルキルアミン及びビス(トリアルコキシシリルアルキル)尿素及びビス(ジアルコキシアルキルシリルアルキル)尿素から選択されることを特徴とする、請求項1又は2に記載の2成分型湿気硬化シリコーン組成物。
- 二脚状シラン(ii)が、ビス(3-トリメトキシシリルプロピル)アミン、ビス(3-トリエトキシシリルプロピル)アミン、ビス(4-トリメトキシシリルブチル)アミン、ビス(4-トリエトキシシリルブチル)アミン、ビス(3-トリメトキシシリルプロピル)N-メチルアミン、ビス(3-トリエトキシシリルプロピル)N-メチルアミン、ビス(4-トリメトキシシリルブチル)N-メチルアミン、ビス(4-トリエトキシシリルブチル)N-メチルアミン、ビス(3-トリメトキシシリルプロピル)尿素、ビス(3-トリエトキシシリルプロピル)尿素、ビス(4-トリメトキシシリルブチル)尿素、ビス(4-トリエトキシシリルブチル)尿素、ビス(3-ジメトキシメチルシリルプロピル)アミン、ビス(3-ジエトキシメチルシリルプロピル)アミン、ビス(4-ジメトキシメチルシリルブチル)アミン、ビス(4-ジエトキシメチルシリルブチル)アミン、ビス(3-ジメトキシメチルシリルプロピル)N-メチルアミン、ビス(3-ジエトキシメチルシリルプロピル)N-メチルアミン、ビス(4-ジメトキシメチルシリルブチル)N-メチルアミン、ビス(4-ジエトキシメチルシリルブチル)N-メチルアミン、ビス(3-ジメトキシメチルシリルプロピル)尿素、ビス(3-ジエトキシメチルシリルプロピル)尿素、ビス(4-ジメトキシメチルシリルブチル)尿素、ビス(4-ジエトキシメチルシリルブチル)尿素、ビス(3-ジメトキシエチルシリルプロピル)アミン、ビス(3-ジエトキシエチルシリルプロピル)アミン、ビス(4-ジメトキシエチルシリルブチル)アミン、ビス(4-ジエトキシエチルシリルブチル)アミン、ビス(3-ジメトキシエチルシリルプロピル)N-メチルアミン、ビス(3-ジエトキシエチルシリルプロピル)N-メチルアミン、ビス(4-ジメトキシエチルシリルブチル)N-メチルアミン、ビス(4-ジエトキシエチルシリルブチル)N-メチルアミン、ビス(3-ジメトキシエチルシリルプロピル)尿素、ビス(3-ジエトキシエチルシリルプロピル)尿素、ビス(4-ジメトキシエチルシリルブチル)尿素及びビス(4-ジエトキシエチルシリルブチル)尿素から選択されることを特徴とする、請求項1~3のいずれか一項に記載の2成分型湿気硬化シリコーン組成物。
- 二脚状シラン(ii)が、一般構造
(R4O)3-Si(CH2)x-(NHCH2CH2)t-NH(CH2)x-Si(OR4)3
を有することを特徴とする、請求項1又は2に記載の2成分型湿気硬化シリコーン組成物。 - 二脚状シラン(ii)が、ビス(3-トリプロピルオキシシリルプロピル)アミン、ビス(3-メチルジエトキシシリルプロピル)アミン、ビス(3-メチルジメトキシシリルプロピル)アミン、ビス(3-トリエトキシシリルプロピル)アミン、ビス(3-トリメトキシシリルプロピル)アミン、及びN,N’-ビス[(3-トリメトキシシリル)プロピル]エチレンジアミンから選択されることを特徴とする、請求項1又は2に記載の2成分型湿気硬化シリコーン組成物。
- シロキサンポリマー(a)が、前記基剤成分の総重量に基づいて、10~90重量%の量で、前記組成物中に存在することを特徴とする、請求項2に記載の2成分型湿気硬化シリコーン組成物。
- 混合する場合、前記基剤成分:前記触媒パッケージ成分の重量比が、15:1~1:1であることを特徴とする、請求項1~7のいずれか一項に記載の2成分型湿気硬化シリコーン組成物。
- 前記基剤成分が、前記基剤成分の総重量%を100重量%として、
10~90重量%のシロキサンポリマー(a)と、
10~80重量%の補強性充填剤(b)と、
0~20重量%の非補強性充填剤(c)と、
を含むことを特徴とする、請求項2に記載の2成分型湿気硬化シリコーン組成物。 - 前記触媒パッケージ成分が、前記触媒パッケージ成分の総重量%を100重量%として、
30~80重量%のアルコキシシリル末端有機ポリマー(i)と、
5~50重量%の二脚状シラン(ii)と、
5~25重量%の非二脚状接着促進剤(iii)と、
0.01~3重量%のスズ系触媒(iv)と、
0~25重量%の架橋剤(v)と、
を含むことを特徴とする、請求項1~9のいずれか一項に記載の2成分型湿気硬化シリコーン組成物。 - コーティング、コーキング、金型作製材料、又は封入材料である、請求項1~10のいずれか一項に記載の2成分型湿気硬化シリコーン組成物の使用。
- 構造物、構造ガラス取付け及び/又は絶縁ガラス取付け用途、建物の外装要素、ガス充填遮断構造物パネル、太陽電池用途、自動車用途、電子機器用途、LED照明及び他の電子機器用途並びに工業用アセンブリ及びメンテナンス用途のいずれかにおける、請求項11に記載の使用。
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EP3661996A4 (en) | 2021-05-05 |
US20210095078A1 (en) | 2021-04-01 |
EP3661997B1 (en) | 2022-11-09 |
JP2020528955A (ja) | 2020-10-01 |
EP3661997A4 (en) | 2021-06-16 |
CN111051387A (zh) | 2020-04-21 |
EP3661996A1 (en) | 2020-06-10 |
US11168213B2 (en) | 2021-11-09 |
WO2019024429A1 (en) | 2019-02-07 |
KR20200037266A (ko) | 2020-04-08 |
WO2019024430A1 (en) | 2019-02-07 |
CN110997756B (zh) | 2022-06-07 |
EP3661996B1 (en) | 2022-07-20 |
CN111051387B (zh) | 2022-02-18 |
JP2020530505A (ja) | 2020-10-22 |
US20210087398A1 (en) | 2021-03-25 |
EP3661997A1 (en) | 2020-06-10 |
WO2019023842A1 (en) | 2019-02-07 |
KR20200037275A (ko) | 2020-04-08 |
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