JP5567474B2 - 揮発性有機化合物（ｖｏｃ）を発生する可能性の低い加水分解性シランおよびそれを含有する樹脂組成物 - Google Patents
揮発性有機化合物（ｖｏｃ）を発生する可能性の低い加水分解性シランおよびそれを含有する樹脂組成物 Download PDFInfo
- Publication number
- JP5567474B2 JP5567474B2 JP2010502109A JP2010502109A JP5567474B2 JP 5567474 B2 JP5567474 B2 JP 5567474B2 JP 2010502109 A JP2010502109 A JP 2010502109A JP 2010502109 A JP2010502109 A JP 2010502109A JP 5567474 B2 JP5567474 B2 JP 5567474B2
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- Prior art keywords
- methyl
- dioxacillinan
- group
- yloxy
- silane
- 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.)
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- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 title claims description 84
- 229910000077 silane Inorganic materials 0.000 title claims description 84
- 239000011342 resin composition Substances 0.000 title claims description 23
- 239000012855 volatile organic compound Substances 0.000 title description 21
- 229920005989 resin Polymers 0.000 claims description 52
- 239000011347 resin Substances 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 48
- -1 2-amino- Ethylamino Chemical group 0.000 claims description 34
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 125000005842 heteroatom Chemical group 0.000 claims description 26
- 150000004756 silanes Chemical class 0.000 claims description 25
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 24
- 229910052710 silicon Inorganic materials 0.000 claims description 23
- 125000000524 functional group Chemical group 0.000 claims description 18
- 239000004593 Epoxy Substances 0.000 claims description 16
- 239000000853 adhesive Substances 0.000 claims description 14
- 239000004202 carbamide Substances 0.000 claims description 14
- 230000007062 hydrolysis Effects 0.000 claims description 14
- 238000006460 hydrolysis reaction Methods 0.000 claims description 14
- 229920005862 polyol Polymers 0.000 claims description 14
- 230000001070 adhesive effect Effects 0.000 claims description 13
- 150000003077 polyols Chemical class 0.000 claims description 12
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Substances CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 10
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 8
- 239000000945 filler Substances 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 8
- 238000003860 storage Methods 0.000 claims description 8
- 229920002635 polyurethane Polymers 0.000 claims description 7
- 239000004814 polyurethane Substances 0.000 claims description 7
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 6
- 239000010703 silicon Substances 0.000 claims description 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 6
- 238000004132 cross linking Methods 0.000 claims description 5
- 230000002452 interceptive effect Effects 0.000 claims description 5
- 239000004014 plasticizer Substances 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 238000007334 copolymerization reaction Methods 0.000 claims description 4
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 3
- 239000003139 biocide Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 230000003993 interaction Effects 0.000 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 239000004800 polyvinyl chloride Substances 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000004734 Polyphenylene sulfide Substances 0.000 claims description 2
- 239000004793 Polystyrene Substances 0.000 claims description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 2
- 229920001328 Polyvinylidene chloride Polymers 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- 230000000704 physical effect Effects 0.000 claims description 2
- 229920002401 polyacrylamide Polymers 0.000 claims description 2
- 229920000058 polyacrylate Polymers 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920000193 polymethacrylate Polymers 0.000 claims description 2
- 229920000069 polyphenylene sulfide Polymers 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 2
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 2
- 239000005033 polyvinylidene chloride Substances 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 230000009974 thixotropic effect Effects 0.000 claims description 2
- 238000005411 Van der Waals force Methods 0.000 claims 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N Butanol Natural products CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 229920000098 polyolefin Polymers 0.000 claims 1
- 229920005672 polyolefin resin Polymers 0.000 claims 1
- 238000007789 sealing Methods 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 description 60
- 229910052760 oxygen Inorganic materials 0.000 description 31
- 239000001301 oxygen Substances 0.000 description 31
- 229910052799 carbon Inorganic materials 0.000 description 28
- 125000000217 alkyl group Chemical group 0.000 description 27
- 239000000565 sealant Substances 0.000 description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 150000001721 carbon Chemical group 0.000 description 23
- 125000001183 hydrocarbyl group Chemical group 0.000 description 21
- 125000003118 aryl group Chemical group 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 125000003342 alkenyl group Chemical group 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000002318 adhesion promoter Substances 0.000 description 8
- 125000003710 aryl alkyl group Chemical group 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 7
- 125000005282 allenyl group Chemical group 0.000 description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 7
- 229920000570 polyether Polymers 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
- 239000008199 coating composition Substances 0.000 description 5
- 238000001723 curing Methods 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000000732 arylene group Chemical group 0.000 description 4
- 125000002619 bicyclic group Chemical group 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 4
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229920005749 polyurethane resin Polymers 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 125000004450 alkenylene group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- BUZRAOJSFRKWPD-UHFFFAOYSA-N isocyanatosilane Chemical class [SiH3]N=C=O BUZRAOJSFRKWPD-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- DVYVMJLSUSGYMH-UHFFFAOYSA-N n-methyl-3-trimethoxysilylpropan-1-amine Chemical compound CNCCC[Si](OC)(OC)OC DVYVMJLSUSGYMH-UHFFFAOYSA-N 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- MGHCZWMNRPSMRI-UHFFFAOYSA-N 1-[dimethoxy(2-methylpropyl)silyl]oxy-n-methylmethanamine Chemical compound CNCO[Si](OC)(OC)CC(C)C MGHCZWMNRPSMRI-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 229910021485 fumed silica Inorganic materials 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 238000013008 moisture curing Methods 0.000 description 2
- FYZBRYMWONGDHC-UHFFFAOYSA-N n-ethyl-3-trimethoxysilylpropan-1-amine Chemical compound CCNCCC[Si](OC)(OC)OC FYZBRYMWONGDHC-UHFFFAOYSA-N 0.000 description 2
- PIQILASEWZVACI-UHFFFAOYSA-N n-methyl-4-triethoxysilylbutan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCCNC PIQILASEWZVACI-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 230000036314 physical performance Effects 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 239000002952 polymeric resin Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- 125000003396 thiol group Chemical class [H]S* 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- LAMKPXRKDFNPPG-UHFFFAOYSA-N 1-[methoxy(dimethyl)silyl]propane-2-thiol Chemical compound CO[Si](C)(C)CC(C)S LAMKPXRKDFNPPG-UHFFFAOYSA-N 0.000 description 1
- BSMRGOIIVKNSIY-UHFFFAOYSA-N 2,2,4,4,6-pentamethyl-1,3,2-dioxasilinane Chemical compound CC1CC(C)(C)O[Si](C)(C)O1 BSMRGOIIVKNSIY-UHFFFAOYSA-N 0.000 description 1
- NXQMCAOPTPLPRL-UHFFFAOYSA-N 2-(2-benzoyloxyethoxy)ethyl benzoate Chemical class C=1C=CC=CC=1C(=O)OCCOCCOC(=O)C1=CC=CC=C1 NXQMCAOPTPLPRL-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- DVNPFNZTPMWRAX-UHFFFAOYSA-N 2-triethoxysilylethanethiol Chemical compound CCO[Si](CCS)(OCC)OCC DVNPFNZTPMWRAX-UHFFFAOYSA-N 0.000 description 1
- COKJRLGVRSCWTK-UHFFFAOYSA-N 3-[diethoxy(methoxy)silyl]-n-methylpropan-1-amine Chemical compound CCO[Si](OCC)(OC)CCCNC COKJRLGVRSCWTK-UHFFFAOYSA-N 0.000 description 1
- IKYAJDOSWUATPI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propane-1-thiol Chemical compound CO[Si](C)(OC)CCCS IKYAJDOSWUATPI-UHFFFAOYSA-N 0.000 description 1
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 description 1
- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- MXUKOTHXQPEXQB-UHFFFAOYSA-N 4-[diethoxy(ethyl)silyl]-n-methylbutan-1-amine Chemical compound CCO[Si](CC)(OCC)CCCCNC MXUKOTHXQPEXQB-UHFFFAOYSA-N 0.000 description 1
- QJKFZTYBTUFBMQ-UHFFFAOYSA-N 4-[ethoxy(diethyl)silyl]-n-methylbutan-1-amine Chemical compound CCO[Si](CC)(CC)CCCCNC QJKFZTYBTUFBMQ-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- LZTPDAOCHZQFMA-UHFFFAOYSA-N CNCO[Si](C)(C)CCC Chemical compound CNCO[Si](C)(C)CCC LZTPDAOCHZQFMA-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229920002121 Hydroxyl-terminated polybutadiene Polymers 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical group [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 description 1
- OGFYGJDCQZJOFN-UHFFFAOYSA-N [O].[Si].[Si] Chemical compound [O].[Si].[Si] OGFYGJDCQZJOFN-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000013466 adhesive and sealant Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminum chloride Substances Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- YXFMVUFVHIWUHX-UHFFFAOYSA-N butyl-(isocyanatomethoxy)-dimethoxysilane Chemical compound CCCC[Si](OC)(OC)OCN=C=O YXFMVUFVHIWUHX-UHFFFAOYSA-N 0.000 description 1
- VXJDLQFZZQAZRL-UHFFFAOYSA-N butyl-diethoxy-(1-isocyanatoethoxy)silane Chemical compound CCCC[Si](OCC)(OCC)OC(C)N=C=O VXJDLQFZZQAZRL-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- IWIIWGQTAGYXDO-UHFFFAOYSA-N diethoxy-(1-isocyanatoethoxy)-propan-2-ylsilane Chemical compound CCO[Si](OCC)(C(C)C)OC(C)N=C=O IWIIWGQTAGYXDO-UHFFFAOYSA-N 0.000 description 1
- OCNXBDSYTXVOIV-UHFFFAOYSA-N diethoxy-(isocyanatomethyl)-methylsilane Chemical compound CCO[Si](C)(OCC)CN=C=O OCNXBDSYTXVOIV-UHFFFAOYSA-N 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical group OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- HTSRFYSEWIPFNI-UHFFFAOYSA-N ethyl-dimethoxy-methylsilane Chemical compound CC[Si](C)(OC)OC HTSRFYSEWIPFNI-UHFFFAOYSA-N 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
- LNPBPTWRUYPAFK-UHFFFAOYSA-N isocyanatomethoxy-dimethoxy-propan-2-ylsilane Chemical compound CO[Si](OC)(C(C)C)OCN=C=O LNPBPTWRUYPAFK-UHFFFAOYSA-N 0.000 description 1
- QRFPECUQGPJPMV-UHFFFAOYSA-N isocyanatomethyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CN=C=O QRFPECUQGPJPMV-UHFFFAOYSA-N 0.000 description 1
- HENJUOQEQGBPSV-UHFFFAOYSA-N isocyanatomethyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)CN=C=O HENJUOQEQGBPSV-UHFFFAOYSA-N 0.000 description 1
- NONOKGVFTBWRLD-UHFFFAOYSA-N isocyanatosulfanylimino(oxo)methane Chemical compound O=C=NSN=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- IYMSIPPWHNIMGE-UHFFFAOYSA-N silylurea Chemical class NC(=O)N[SiH3] IYMSIPPWHNIMGE-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CFWKOXVDRYZCQI-UHFFFAOYSA-N tert-butyl-(isocyanatomethoxy)-dimethoxysilane Chemical compound CO[Si](OC)(C(C)(C)C)OCN=C=O CFWKOXVDRYZCQI-UHFFFAOYSA-N 0.000 description 1
- KGXPCPDJIFECBX-UHFFFAOYSA-N tert-butyl-diethoxy-(1-isocyanatoethoxy)silane Chemical compound CCO[Si](OCC)(C(C)(C)C)OC(C)N=C=O KGXPCPDJIFECBX-UHFFFAOYSA-N 0.000 description 1
- 150000003553 thiiranes Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- BOTMPGMIDPRZGP-UHFFFAOYSA-N triethoxy(isocyanatomethyl)silane Chemical compound CCO[Si](OCC)(OCC)CN=C=O BOTMPGMIDPRZGP-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions 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; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Combustion & Propulsion (AREA)
- Thermal Sciences (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
- Epoxy Resins (AREA)
- Silicon Polymers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/731,577 | 2007-03-30 | ||
| US11/731,577 US8088940B2 (en) | 2007-03-30 | 2007-03-30 | Hydrolyzable silanes of low VOC-generating potential and resinous compositions containing same |
| PCT/US2008/004128 WO2008121360A1 (en) | 2007-03-30 | 2008-03-28 | Hydrolyzable silanes of low voc-generating potential and resinous compositions containing same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010523561A JP2010523561A (ja) | 2010-07-15 |
| JP2010523561A5 JP2010523561A5 (enExample) | 2011-05-06 |
| JP5567474B2 true JP5567474B2 (ja) | 2014-08-06 |
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| JP2010502109A Active JP5567474B2 (ja) | 2007-03-30 | 2008-03-28 | 揮発性有機化合物（ｖｏｃ）を発生する可能性の低い加水分解性シランおよびそれを含有する樹脂組成物 |
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| US (1) | US8088940B2 (enExample) |
| EP (1) | EP2142558B1 (enExample) |
| JP (1) | JP5567474B2 (enExample) |
| CN (1) | CN101679462B (enExample) |
| BR (1) | BRPI0809486B1 (enExample) |
| TW (1) | TW200904822A (enExample) |
| WO (1) | WO2008121360A1 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2010053092A1 (ja) * | 2008-11-07 | 2010-05-14 | 日東電工株式会社 | 透明基板およびその製造方法 |
| JP5416546B2 (ja) | 2009-10-23 | 2014-02-12 | 日東電工株式会社 | 透明基板 |
| JP2014108923A (ja) * | 2012-11-30 | 2014-06-12 | Daiso Co Ltd | 有機珪素化合物 |
| US11686094B2 (en) * | 2013-03-15 | 2023-06-27 | Holcim Technology Ltd | Bonding adhesive and adhered roofing systems prepared using the same |
| US20230304291A1 (en) * | 2013-03-15 | 2023-09-28 | Holcim Technology Ltd | Bonding adhesive and adhered roofing systems prepared using the same |
| WO2015074031A1 (en) | 2013-11-18 | 2015-05-21 | Firestone Building Products Co., LLC | Bonding adhesive and adhered roofing systems prepared using the same |
| BR112016013613B1 (pt) | 2013-12-13 | 2021-08-24 | Momentive Performance Materials Inc | Processo para produzir uma poliolefina reticulada com silano, composição de silano enxertável e poliolefina reticulada com silano |
| US10308838B2 (en) * | 2013-12-23 | 2019-06-04 | Dow Silicones Corporation | Moisture curable compositions |
| US20150203624A1 (en) * | 2014-01-21 | 2015-07-23 | Vladimyr Wolan | Second generation hybrid silane modified polymers of low viscosity for low toxicity rtv sealants and adhesives |
| KR101724795B1 (ko) * | 2014-07-30 | 2017-04-07 | 주식회사 엘지화학 | 변성 공액 디엔계 중합체, 이를 포함하는 변성 고무 조성물 및 변성 공액 디엔계 중합체의 제조방법 |
| KR102430183B1 (ko) | 2014-09-26 | 2022-08-08 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | 아이소시아네이트 유도된 유기실란 |
| KR101788082B1 (ko) * | 2015-02-27 | 2017-11-15 | 서강대학교산학협력단 | 재가 남지 않는 환형 유기 폴리올 및 이를 이용한 반응형 기공형성제, 이를 이용하여 제조된 초저유전박막 |
| CN108026280B (zh) * | 2015-07-29 | 2020-11-20 | 株式会社普利司通 | 用于制备官能化聚合物的方法、相关的官能化化合物及其制备 |
| WO2017223173A1 (en) | 2016-06-21 | 2017-12-28 | Bridgestone Americas Tire Operations, Llc | Methods for treating inner liner surface, inner liners resulting therefrom and tires containing such inner liners |
| JP6700440B2 (ja) | 2016-06-30 | 2020-05-27 | ブリヂストン アメリカズ タイヤ オペレーションズ、 エルエルシー | インナーライナーを処理するための方法、処理の結果として生じるインナーライナー、及びそのようなインナーライナーを含むタイヤ |
| US12103338B2 (en) | 2016-12-15 | 2024-10-01 | Bridgestone Americas Tire Operations, Llc | Sealant layer with barrier, tire containing same, and related processes |
| WO2018112117A2 (en) | 2016-12-15 | 2018-06-21 | Bridgestone Americas Tire Operations, Llc | Methods for producing polymer-containing coatings upon cured inner liners, methods for producing tires containing such inner liners, and tires containing such inner liners |
| WO2018112125A1 (en) | 2016-12-15 | 2018-06-21 | Bridgestone Americas Tire Operations, Llc | Sealant-containing tire and related processes |
| US11891546B2 (en) * | 2018-06-25 | 2024-02-06 | Sika Technology Ag | Catalyst-free curable compositions based on silane-functional polymers |
| JP7621950B2 (ja) | 2019-02-13 | 2025-01-27 | シーカ テクノロジー アクチェンゲゼルシャフト | 熱伝導性硬化性組成物 |
| TWI883391B (zh) | 2020-02-18 | 2025-05-11 | 美商基利科學股份有限公司 | 抗病毒化合物 |
| EP4644394A2 (en) | 2020-02-18 | 2025-11-05 | Gilead Sciences, Inc. | Antiviral compounds |
| TWI775313B (zh) | 2020-02-18 | 2022-08-21 | 美商基利科學股份有限公司 | 抗病毒化合物 |
| US11821210B1 (en) | 2020-09-15 | 2023-11-21 | Holcim Technology Ltd | Peel-and-stick roofing membranes and methods for forming fully-adhered roofing systems |
| US20240093497A1 (en) | 2021-01-15 | 2024-03-21 | Holcim Technology Ltd | Roofing systems utilizing a primer including a silicon-terminated polymer |
| AU2022256476B2 (en) | 2021-04-16 | 2025-06-05 | Gilead Sciences, Inc. | Methods of preparing carbanucleosides using amides |
| US20240166850A1 (en) | 2021-04-21 | 2024-05-23 | Sika Technology Ag | Rapid-curing two-component composition of silylated polymers having a long open time |
| JP7719954B2 (ja) | 2021-08-18 | 2025-08-06 | ギリアード サイエンシーズ， インコーポレイテッド | リン脂質化合物並びにその製造方法及び使用方法 |
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| DE19715426A1 (de) * | 1997-04-14 | 1998-10-15 | Bayer Ag | Blockierte Isocyanatgruppen aufweisende kolloidale Metalloxide |
| US6319311B1 (en) * | 1998-04-24 | 2001-11-20 | Osi Specialties, Inc. | Powder coatings employing silyl carbamates |
| US6440876B1 (en) * | 2000-10-10 | 2002-08-27 | The Boc Group, Inc. | Low-K dielectric constant CVD precursors formed of cyclic siloxanes having in-ring SI—O—C, and uses thereof |
| WO2002070528A1 (en) | 2001-03-02 | 2002-09-12 | Crompton Corporation | Continuous transesterification process for alkoxyorganosilicon compounds |
| US20050245753A1 (en) * | 2004-05-03 | 2005-11-03 | Cruse Richard W | Cyclic diol-derived blocked mercaptofunctional silane compositions |
| WO2005123751A1 (en) * | 2004-06-15 | 2005-12-29 | Lg Chem, Ltd. | Novel silane coupling agent and method for manufacturing the same |
| US7960576B2 (en) * | 2004-08-13 | 2011-06-14 | Momentive Performance Materials Inc. | Diol-derived organofunctional silane and compositions containing same |
| US20060177657A1 (en) * | 2005-02-08 | 2006-08-10 | Keith Weller | Sizing compositions for fibers utilizing low VOC silanes |
| US8987351B2 (en) * | 2005-02-08 | 2015-03-24 | Momentive Performance Materials Inc. | Filler treatments utilizing low VOC silanes |
| US7326753B2 (en) * | 2005-02-08 | 2008-02-05 | Momentive Performance Materials Inc. | Process for the production of crosslinked polymer employing low VOC-producing silane crosslinker and resulting crosslinked polymer |
| US7417105B2 (en) * | 2005-02-15 | 2008-08-26 | Momentive Performance Materials Inc. | Crosslinkable silane-terminated polymer and sealant composition made with same |
| US7686878B2 (en) * | 2005-03-10 | 2010-03-30 | Momentive Performance Materials, Inc. | Coating composition containing a low VOC-producing silane |
| US7510670B2 (en) * | 2006-02-21 | 2009-03-31 | Momentive Performance Materials Inc. | Free flowing filler composition based on organofunctional silane |
| US7368584B2 (en) * | 2006-08-14 | 2008-05-06 | Momentive Performance Materials Inc. | Mercapto-functional silane |
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2007
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2008
- 2008-03-26 TW TW097110771A patent/TW200904822A/zh unknown
- 2008-03-28 BR BRPI0809486-1A patent/BRPI0809486B1/pt active IP Right Grant
- 2008-03-28 WO PCT/US2008/004128 patent/WO2008121360A1/en not_active Ceased
- 2008-03-28 CN CN2008800183359A patent/CN101679462B/zh active Active
- 2008-03-28 JP JP2010502109A patent/JP5567474B2/ja active Active
- 2008-03-28 EP EP08742377.8A patent/EP2142558B1/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN101679462A (zh) | 2010-03-24 |
| CN101679462B (zh) | 2013-11-06 |
| EP2142558A1 (en) | 2010-01-13 |
| BRPI0809486B1 (pt) | 2019-10-08 |
| US20080237537A1 (en) | 2008-10-02 |
| TW200904822A (en) | 2009-02-01 |
| US8088940B2 (en) | 2012-01-03 |
| BRPI0809486A2 (pt) | 2014-09-09 |
| EP2142558B1 (en) | 2016-10-05 |
| JP2010523561A (ja) | 2010-07-15 |
| WO2008121360A1 (en) | 2008-10-09 |
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