CA2682191C - Rapid deep-section cure silicone compositions - Google Patents
Rapid deep-section cure silicone compositions Download PDFInfo
- Publication number
- CA2682191C CA2682191C CA2682191A CA2682191A CA2682191C CA 2682191 C CA2682191 C CA 2682191C CA 2682191 A CA2682191 A CA 2682191A CA 2682191 A CA2682191 A CA 2682191A CA 2682191 C CA2682191 C CA 2682191C
- Authority
- CA
- Canada
- Prior art keywords
- weight percent
- amount
- curable sealant
- sealant composition
- composition
- 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.)
- Expired - Fee Related
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- 239000000203 mixture Substances 0.000 title claims abstract description 140
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 17
- 239000004590 silicone sealant Substances 0.000 claims abstract description 13
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 58
- 239000000565 sealant Substances 0.000 claims description 48
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 38
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 35
- 239000003054 catalyst Substances 0.000 claims description 32
- 239000011787 zinc oxide Substances 0.000 claims description 27
- 239000004971 Cross linker Substances 0.000 claims description 25
- 239000002318 adhesion promoter Substances 0.000 claims description 23
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 19
- 229920005645 diorganopolysiloxane polymer Polymers 0.000 claims description 18
- 239000000945 filler Substances 0.000 claims description 17
- 229910021485 fumed silica Inorganic materials 0.000 claims description 16
- 239000004014 plasticizer Substances 0.000 claims description 16
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 claims description 11
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 8
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000000377 silicon dioxide Substances 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 6
- 238000004132 cross linking Methods 0.000 claims description 6
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 239000010936 titanium Substances 0.000 claims description 6
- 229910052719 titanium Inorganic materials 0.000 claims description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 4
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 claims description 4
- 239000000499 gel Substances 0.000 claims description 4
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 claims description 3
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- -1 compounds stearate Chemical class 0.000 claims description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 claims description 3
- 239000010453 quartz Substances 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
- 150000003609 titanium compounds Chemical class 0.000 claims description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 2
- QMTFKWDCWOTPGJ-KVVVOXFISA-N (z)-octadec-9-enoic acid;tin Chemical compound [Sn].CCCCCCCC\C=C/CCCCCCCC(O)=O QMTFKWDCWOTPGJ-KVVVOXFISA-N 0.000 claims description 2
- QWOVEJBDMKHZQK-UHFFFAOYSA-N 1,3,5-tris(3-trimethoxysilylpropyl)-1,3,5-triazinane-2,4,6-trione Chemical compound CO[Si](OC)(OC)CCCN1C(=O)N(CCC[Si](OC)(OC)OC)C(=O)N(CCC[Si](OC)(OC)OC)C1=O QWOVEJBDMKHZQK-UHFFFAOYSA-N 0.000 claims description 2
- LPELHPXGKLFQNG-UHFFFAOYSA-J 2-(carboxylatomethoxy)propanoate titanium(4+) Chemical compound CC(C(=O)[O-])OCC(=O)[O-].CC(C(=O)[O-])OCC(=O)[O-].[Ti+4] LPELHPXGKLFQNG-UHFFFAOYSA-J 0.000 claims description 2
- KUQVFOOAIOMQOT-UHFFFAOYSA-N 2-methylpropyltin Chemical compound CC(C)C[Sn] KUQVFOOAIOMQOT-UHFFFAOYSA-N 0.000 claims description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 2
- BRUFYILNWNCKJT-UHFFFAOYSA-N 3-acetylpentane-2,4-dione;dibutyltin Chemical compound CCCC[Sn]CCCC.CC(=O)C(C(C)=O)C(C)=O BRUFYILNWNCKJT-UHFFFAOYSA-N 0.000 claims description 2
- NNTRMVRTACZZIO-UHFFFAOYSA-N 3-isocyanatopropyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)CCCN=C=O NNTRMVRTACZZIO-UHFFFAOYSA-N 0.000 claims description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 claims description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 2
- 239000005995 Aluminium silicate Substances 0.000 claims description 2
- APLAZHQZHGNZFQ-UHFFFAOYSA-L CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O.CC(C)O[Ti+2]OC(C)C Chemical compound CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O.CC(C)O[Ti+2]OC(C)C APLAZHQZHGNZFQ-UHFFFAOYSA-L 0.000 claims description 2
- WVAFBJDECCWPPT-UHFFFAOYSA-N CCO[Ti]OC(C)C Chemical compound CCO[Ti]OC(C)C WVAFBJDECCWPPT-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- 239000005909 Kieselgur Substances 0.000 claims description 2
- 239000005642 Oleic acid Substances 0.000 claims description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 235000021355 Stearic acid Nutrition 0.000 claims description 2
- 239000012963 UV stabilizer Substances 0.000 claims description 2
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- LHFURYICKMKJHJ-UHFFFAOYSA-L [benzoyloxy(dibutyl)stannyl] benzoate Chemical compound CCCC[Sn+2]CCCC.[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 LHFURYICKMKJHJ-UHFFFAOYSA-L 0.000 claims description 2
- HAAANJSJNWKVMX-UHFFFAOYSA-L [butanoyloxy(dimethyl)stannyl] butanoate Chemical compound CCCC(=O)O[Sn](C)(C)OC(=O)CCC HAAANJSJNWKVMX-UHFFFAOYSA-L 0.000 claims description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 235000012211 aluminium silicate Nutrition 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- 239000000440 bentonite Substances 0.000 claims description 2
- 229910000278 bentonite Inorganic materials 0.000 claims description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims description 2
- 230000003115 biocidal effect Effects 0.000 claims description 2
- 239000003139 biocide Substances 0.000 claims description 2
- MTKOCRSQUPLVTD-UHFFFAOYSA-N butan-1-olate;titanium(2+) Chemical compound CCCCO[Ti]OCCCC MTKOCRSQUPLVTD-UHFFFAOYSA-N 0.000 claims description 2
- 239000006229 carbon black Substances 0.000 claims description 2
- 239000004359 castor oil Substances 0.000 claims description 2
- 235000019438 castor oil Nutrition 0.000 claims description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 2
- ZXDVQYBUEVYUCG-UHFFFAOYSA-N dibutyltin(2+);methanolate Chemical compound CCCC[Sn](OC)(OC)CCCC ZXDVQYBUEVYUCG-UHFFFAOYSA-N 0.000 claims description 2
- HZFCYILHRCIPJG-UHFFFAOYSA-N dioctyltin;tripropoxysilicon Chemical compound CCCO[Si](OCCC)OCCC.CCCO[Si](OCCC)OCCC.CCCCCCCC[Sn]CCCCCCCC HZFCYILHRCIPJG-UHFFFAOYSA-N 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 229940093858 ethyl acetoacetate Drugs 0.000 claims description 2
- HTSRFYSEWIPFNI-UHFFFAOYSA-N ethyl-dimethoxy-methylsilane Chemical compound CC[Si](C)(OC)OC HTSRFYSEWIPFNI-UHFFFAOYSA-N 0.000 claims description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 2
- 239000010439 graphite Substances 0.000 claims description 2
- 229910002804 graphite Inorganic materials 0.000 claims description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 2
- GCHSKZYGFZYKBO-UHFFFAOYSA-N methoxycarbonyl(phenyl)tin Chemical compound COC(=O)[Sn]C1=CC=CC=C1 GCHSKZYGFZYKBO-UHFFFAOYSA-N 0.000 claims description 2
- 239000010445 mica Substances 0.000 claims description 2
- 229910052618 mica group Inorganic materials 0.000 claims description 2
- 229910052901 montmorillonite Inorganic materials 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
- KVIKMJYUMZPZFU-UHFFFAOYSA-N propan-2-ol;titanium Chemical compound [Ti].CC(C)O.CC(C)O KVIKMJYUMZPZFU-UHFFFAOYSA-N 0.000 claims description 2
- 239000002516 radical scavenger Substances 0.000 claims description 2
- 239000008117 stearic acid Substances 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 claims description 2
- 239000013008 thixotropic agent Substances 0.000 claims description 2
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 claims description 2
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 claims description 2
- 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 claims description 2
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 claims description 2
- CPRPKIMXLHBUGA-UHFFFAOYSA-N triethyltin Chemical compound CC[Sn](CC)CC CPRPKIMXLHBUGA-UHFFFAOYSA-N 0.000 claims description 2
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 claims description 2
- HXLAEGYMDGUSBD-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN HXLAEGYMDGUSBD-UHFFFAOYSA-N 0.000 claims 2
- 239000012974 tin catalyst Substances 0.000 claims 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims 1
- 229910020388 SiO1/2 Inorganic materials 0.000 claims 1
- CMDJFOLCTRJTAN-UHFFFAOYSA-N [Ti+2].CC(C)C[O-].CC(C)C[O-] Chemical compound [Ti+2].CC(C)C[O-].CC(C)C[O-] CMDJFOLCTRJTAN-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 239000004927 clay Substances 0.000 claims 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical group CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 claims 1
- FRDNYWXDODPUJV-UHFFFAOYSA-N n-ethyl-2-methyl-3-trimethoxysilylpropan-1-amine Chemical compound CCNCC(C)C[Si](OC)(OC)OC FRDNYWXDODPUJV-UHFFFAOYSA-N 0.000 claims 1
- 229940088417 precipitated calcium carbonate Drugs 0.000 claims 1
- JTQPTNQXCUMDRK-UHFFFAOYSA-N propan-2-olate;titanium(2+) Chemical compound CC(C)O[Ti]OC(C)C JTQPTNQXCUMDRK-UHFFFAOYSA-N 0.000 claims 1
- 230000001256 tonic effect Effects 0.000 claims 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims 1
- 239000011521 glass Substances 0.000 abstract description 4
- 235000010216 calcium carbonate Nutrition 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 18
- 238000001723 curing Methods 0.000 description 15
- 239000004615 ingredient Substances 0.000 description 13
- 238000002156 mixing Methods 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000010348 incorporation Methods 0.000 description 9
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 9
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 8
- 238000009472 formulation Methods 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000004809 Teflon Substances 0.000 description 6
- 229920006362 Teflon® Polymers 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 238000013329 compounding Methods 0.000 description 4
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 4
- 229920005573 silicon-containing polymer Polymers 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 230000002431 foraging effect Effects 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
- 150000003606 tin compounds Chemical class 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229920002631 room-temperature vulcanizate silicone Polymers 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- LFMQNMXVVXHZCC-UHFFFAOYSA-N 1,3-benzothiazol-2-yl n,n-diethylcarbamodithioate Chemical compound C1=CC=C2SC(SC(=S)N(CC)CC)=NC2=C1 LFMQNMXVVXHZCC-UHFFFAOYSA-N 0.000 description 1
- URXZKGGRKRRVDC-UHFFFAOYSA-N 1-[dimethoxy(propyl)silyl]oxyethanamine Chemical compound CCC[Si](OC)(OC)OC(C)N URXZKGGRKRRVDC-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004614 Process Aid Substances 0.000 description 1
- 101150057833 THEG gene Proteins 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- QVYYOKWPCQYKEY-UHFFFAOYSA-N [Fe].[Co] Chemical compound [Fe].[Co] QVYYOKWPCQYKEY-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000005253 cladding Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000013008 moisture curing Methods 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- 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
-
- 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
- C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl 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
- C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side 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
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Sealing Material Composition (AREA)
- Joining Of Glass To Other Materials (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/728,904 US8217107B2 (en) | 2007-03-27 | 2007-03-27 | Rapid deep-section cure silicone compositions |
| US11/728,904 | 2007-03-27 | ||
| PCT/US2008/003950 WO2008118461A2 (en) | 2007-03-27 | 2008-03-26 | Rapid deep-section cure silicone compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2682191A1 CA2682191A1 (en) | 2008-10-02 |
| CA2682191C true CA2682191C (en) | 2016-09-06 |
Family
ID=39789199
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2682191A Expired - Fee Related CA2682191C (en) | 2007-03-27 | 2008-03-26 | Rapid deep-section cure silicone compositions |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8217107B2 (enExample) |
| EP (1) | EP2134790B1 (enExample) |
| JP (1) | JP5324560B2 (enExample) |
| KR (1) | KR101607631B1 (enExample) |
| CN (1) | CN101679749B (enExample) |
| AU (1) | AU2008231295B2 (enExample) |
| BR (1) | BRPI0809464A2 (enExample) |
| CA (1) | CA2682191C (enExample) |
| RU (1) | RU2481363C2 (enExample) |
| TW (1) | TW200902631A (enExample) |
| WO (1) | WO2008118461A2 (enExample) |
| ZA (1) | ZA200906693B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8501856B2 (en) * | 2007-07-13 | 2013-08-06 | Momentive Performance Materials Inc. | Curable silicon-containing compositions possessing high translucency |
| DE102008055146A1 (de) * | 2008-12-23 | 2010-07-01 | Wacker Chemie Ag | Vernetzbare Massen auf der Basis von Organosiliciumverbindungen |
| CN101792653B (zh) * | 2010-03-19 | 2012-10-10 | 江苏明昊新材料科技有限公司 | 丙烯酸酯改性太阳能光伏组件用密封胶及其制备方法 |
| CN101787260B (zh) * | 2010-03-19 | 2012-10-10 | 江苏明昊新材料科技有限公司 | 防水蒸汽透过的硅酮密封胶及其制备方法 |
| CN103013430A (zh) * | 2012-12-24 | 2013-04-03 | 成都硅宝科技股份有限公司 | 一种环保型有机硅密封胶及其制造方法 |
| WO2015139135A1 (en) * | 2014-03-19 | 2015-09-24 | Csl Silicones Inc. | Air-water barrier silicone coatings |
| CN104087056B (zh) * | 2014-06-26 | 2017-01-25 | 杭州博创纳米材料有限公司 | 一种有机硅改性亲水性活性剂及其应用 |
| DE102014212291A1 (de) * | 2014-06-26 | 2015-12-31 | Henkel Ag & Co. Kgaa | Titankomplexe als Vulkanisationskatalysatoren |
| CN104497313A (zh) * | 2014-12-05 | 2015-04-08 | 东莞兆舜有机硅新材料科技有限公司 | 一种无腐蚀有机锡催化剂及其制备方法和用途 |
| CN107530471B (zh) * | 2015-04-30 | 2020-10-16 | 科洛普拉斯特公司 | 粘合剂组合物 |
| CN105018018A (zh) * | 2015-07-01 | 2015-11-04 | 常熟市长江胶带有限公司 | 一种胶带用强力胶水 |
| KR102803453B1 (ko) | 2016-01-27 | 2025-05-07 | 모멘티브 퍼포먼스 머티리얼즈 인크. | 오염물 부착 방지성 실리콘 코팅 조성물 |
| JP6625453B2 (ja) * | 2016-03-14 | 2019-12-25 | Ｊｘｔｇエネルギー株式会社 | シラン化合物、ゴム組成物およびタイヤ |
| KR102327613B1 (ko) | 2018-10-02 | 2021-11-17 | 보레알리스 아게 | 실란-그래프팅된 플라스토머를 위한 저속 가교 촉매 |
| CN111500191A (zh) * | 2019-01-30 | 2020-08-07 | 佐敦有限公司 | 水性底漆 |
| US12378363B2 (en) | 2019-06-21 | 2025-08-05 | Dow Silicones Corporation | Thermal conductive silicone composition |
| JP7675026B2 (ja) | 2019-06-21 | 2025-05-12 | ダウ シリコーンズ コーポレーション | チキソトロピック性の硬化性シリコーン組成物の製造方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU910697A1 (ru) * | 1980-07-23 | 1982-03-07 | Московский Филиал Всесоюзного Научно-Исследовательского И Проектного Института Химической Промышленности | Композици на основе полистиролсилоксанового каучука |
| JPS57172949A (en) | 1981-04-17 | 1982-10-25 | Kanegafuchi Chem Ind Co Ltd | One-pack composition |
| JPS60202153A (ja) * | 1984-03-26 | 1985-10-12 | Toshiba Silicone Co Ltd | シリコ−ンゴム用触媒組成物 |
| JP3318338B2 (ja) | 1992-02-28 | 2002-08-26 | 東レ・ダウコーニング・シリコーン株式会社 | 導電性ポリオルガノシロキサン組成物の製造方法 |
| US5292606A (en) | 1992-11-30 | 1994-03-08 | Eastman Kodak Company | Fuser roll for fixing toner to a substrate |
| US5786414A (en) * | 1995-12-22 | 1998-07-28 | Toto Ltd. | Building rubber members and method for imparting hydrophilic surface thereto |
| US5733960A (en) | 1996-04-04 | 1998-03-31 | Dow Corning Corporation | Enhanced longevity of surface drying oil on a sealant modified by incorporation of zinc oxide |
| US5973023A (en) * | 1996-04-04 | 1999-10-26 | Dow Corning Corporation | Sealants containing fungicides exhibiting less chromophoric development upon exposure to UV by the incorporation of zinc oxide |
| US6258878B1 (en) | 1999-03-29 | 2001-07-10 | Dow Corning Corporation | One-part moisture-curable hydrocarbon polymer composition |
| GB0028254D0 (en) * | 2000-11-21 | 2001-01-03 | Dow Corning Sa | Organopolysiloxane compositions and their preparation |
| JP3916403B2 (ja) * | 2001-01-30 | 2007-05-16 | 株式会社スリーボンド | 自動車用室温硬化性シール材組成物 |
| JP4395270B2 (ja) * | 2001-05-11 | 2010-01-06 | 信越化学工業株式会社 | 室温速硬化性オルガポリシロキサン組成物 |
| JP2004292724A (ja) * | 2003-03-28 | 2004-10-21 | Shin Etsu Chem Co Ltd | 室温硬化性オルガノポリシロキサン組成物 |
| RU2249027C1 (ru) * | 2003-08-21 | 2005-03-27 | Подшивалин Александр Викторович | Герметик на основе низкомолекулярного силоксанового каучука |
-
2007
- 2007-03-27 US US11/728,904 patent/US8217107B2/en not_active Expired - Fee Related
-
2008
- 2008-03-24 TW TW097110359A patent/TW200902631A/zh unknown
- 2008-03-26 EP EP08742280.4A patent/EP2134790B1/en not_active Not-in-force
- 2008-03-26 CA CA2682191A patent/CA2682191C/en not_active Expired - Fee Related
- 2008-03-26 JP JP2010500972A patent/JP5324560B2/ja not_active Expired - Fee Related
- 2008-03-26 KR KR1020097020287A patent/KR101607631B1/ko not_active Expired - Fee Related
- 2008-03-26 RU RU2009139644/05A patent/RU2481363C2/ru not_active IP Right Cessation
- 2008-03-26 BR BRPI0809464-0A patent/BRPI0809464A2/pt not_active IP Right Cessation
- 2008-03-26 WO PCT/US2008/003950 patent/WO2008118461A2/en not_active Ceased
- 2008-03-26 CN CN200880017726.9A patent/CN101679749B/zh not_active Expired - Fee Related
- 2008-03-26 AU AU2008231295A patent/AU2008231295B2/en not_active Ceased
-
2009
- 2009-09-25 ZA ZA200906693A patent/ZA200906693B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2010522803A (ja) | 2010-07-08 |
| KR101607631B1 (ko) | 2016-03-30 |
| WO2008118461A3 (en) | 2009-04-09 |
| JP5324560B2 (ja) | 2013-10-23 |
| ZA200906693B (en) | 2010-06-30 |
| KR20090130009A (ko) | 2009-12-17 |
| CN101679749B (zh) | 2016-05-25 |
| TW200902631A (en) | 2009-01-16 |
| WO2008118461A2 (en) | 2008-10-02 |
| EP2134790A2 (en) | 2009-12-23 |
| CA2682191A1 (en) | 2008-10-02 |
| EP2134790B1 (en) | 2018-11-14 |
| AU2008231295B2 (en) | 2013-09-12 |
| BRPI0809464A2 (pt) | 2014-09-16 |
| US20080242763A1 (en) | 2008-10-02 |
| RU2481363C2 (ru) | 2013-05-10 |
| CN101679749A (zh) | 2010-03-24 |
| US8217107B2 (en) | 2012-07-10 |
| AU2008231295A1 (en) | 2008-10-02 |
| RU2009139644A (ru) | 2011-05-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20130306 |
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| MKLA | Lapsed |
Effective date: 20210326 |