CA2679881A1 - Epoxysilanes, processes for their manufacture and curable compositions containing same - Google Patents
Epoxysilanes, processes for their manufacture and curable compositions containing same Download PDFInfo
- Publication number
- CA2679881A1 CA2679881A1 CA002679881A CA2679881A CA2679881A1 CA 2679881 A1 CA2679881 A1 CA 2679881A1 CA 002679881 A CA002679881 A CA 002679881A CA 2679881 A CA2679881 A CA 2679881A CA 2679881 A1 CA2679881 A1 CA 2679881A1
- Authority
- CA
- Canada
- Prior art keywords
- epoxysilane
- group
- oxygen
- sulfur
- propyl
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims description 72
- 238000000034 method Methods 0.000 title claims description 58
- 230000008569 process Effects 0.000 title claims description 52
- 238000004519 manufacturing process Methods 0.000 title description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 68
- 239000001301 oxygen Substances 0.000 claims abstract description 68
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 63
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 52
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 49
- 239000011593 sulfur Chemical group 0.000 claims abstract description 47
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 46
- 229910052757 nitrogen Chemical group 0.000 claims abstract description 27
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims abstract description 26
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 16
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 13
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 6
- -1 arenyl Chemical group 0.000 claims description 93
- 125000004432 carbon atom Chemical group C* 0.000 claims description 48
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 40
- 229910052799 carbon Inorganic materials 0.000 claims description 38
- 150000001721 carbon Chemical group 0.000 claims description 34
- 239000005056 polyisocyanate Substances 0.000 claims description 33
- 229920001228 polyisocyanate Polymers 0.000 claims description 33
- 239000004593 Epoxy Substances 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 239000003054 catalyst Substances 0.000 claims description 28
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 27
- 125000003342 alkenyl group Chemical group 0.000 claims description 26
- DLMVDBDHOIWEJZ-UHFFFAOYSA-N isocyanatooxyimino(oxo)methane Chemical compound O=C=NON=C=O DLMVDBDHOIWEJZ-UHFFFAOYSA-N 0.000 claims description 26
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 21
- BUZRAOJSFRKWPD-UHFFFAOYSA-N isocyanatosilane Chemical compound [SiH3]N=C=O BUZRAOJSFRKWPD-UHFFFAOYSA-N 0.000 claims description 20
- 239000000945 filler Substances 0.000 claims description 18
- 229910052751 metal Inorganic materials 0.000 claims description 18
- 239000002184 metal Substances 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 230000009257 reactivity Effects 0.000 claims description 17
- 125000004434 sulfur atom Chemical group 0.000 claims description 17
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 15
- 150000002513 isocyanates Chemical class 0.000 claims description 15
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 14
- 238000000576 coating method Methods 0.000 claims description 14
- 239000012948 isocyanate Substances 0.000 claims description 14
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 239000004094 surface-active agent Substances 0.000 claims description 12
- 239000011248 coating agent Substances 0.000 claims description 11
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 11
- 150000002118 epoxides Chemical class 0.000 claims description 11
- 229920005989 resin Polymers 0.000 claims description 11
- 239000011347 resin Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 10
- 125000000732 arylene group Chemical group 0.000 claims description 9
- JCHANMMPPLAHIA-UHFFFAOYSA-N 3-triethoxysilylpropylcarbamic acid Chemical compound CCO[Si](OCC)(OCC)CCCNC(O)=O JCHANMMPPLAHIA-UHFFFAOYSA-N 0.000 claims description 8
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000005442 diisocyanate group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 150000002829 nitrogen Chemical class 0.000 claims description 8
- 229920000620 organic polymer Polymers 0.000 claims description 8
- 125000002619 bicyclic group Chemical group 0.000 claims description 7
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 7
- WJIOHMVWGVGWJW-UHFFFAOYSA-N 3-methyl-n-[4-[(3-methylpyrazole-1-carbonyl)amino]butyl]pyrazole-1-carboxamide Chemical compound N1=C(C)C=CN1C(=O)NCCCCNC(=O)N1N=C(C)C=C1 WJIOHMVWGVGWJW-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004450 alkenylene group Chemical group 0.000 claims description 6
- 239000000565 sealant Substances 0.000 claims description 6
- OKVHMJBNYSHURR-UHFFFAOYSA-N 3-trimethoxysilylpropylcarbamic acid Chemical compound CO[Si](OC)(OC)CCCNC(O)=O OKVHMJBNYSHURR-UHFFFAOYSA-N 0.000 claims description 5
- 239000000853 adhesive Substances 0.000 claims description 5
- 230000001070 adhesive effect Effects 0.000 claims description 5
- 238000007739 conversion coating Methods 0.000 claims description 5
- 229920001971 elastomer Polymers 0.000 claims description 5
- 229910044991 metal oxide Inorganic materials 0.000 claims description 5
- 150000004706 metal oxides Chemical class 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- 239000000080 wetting agent Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- 230000001737 promoting effect Effects 0.000 claims description 4
- 239000005060 rubber Substances 0.000 claims description 4
- 238000004513 sizing Methods 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000002216 antistatic agent Substances 0.000 claims description 3
- 238000004382 potting Methods 0.000 claims description 3
- TZOKHBJHUVWXQO-UHFFFAOYSA-N 1,3-bis(oxiran-2-ylmethoxy)propan-2-yl n-(3-triethoxysilylpropyl)carbamate Chemical compound C1OC1COCC(OC(=O)NCCC[Si](OCC)(OCC)OCC)COCC1CO1 TZOKHBJHUVWXQO-UHFFFAOYSA-N 0.000 claims description 2
- DXADIFLMKZKNLJ-UHFFFAOYSA-N 2-[dimethoxy(methyl)silyl]ethyl n-[3,4-bis(oxiran-2-ylmethoxycarbonylamino)phenyl]carbamate Chemical compound C1OC1COC(=O)NC1=CC(NC(=O)OCC[Si](C)(OC)OC)=CC=C1NC(=O)OCC1CO1 DXADIFLMKZKNLJ-UHFFFAOYSA-N 0.000 claims description 2
- JUNFNQSFCWDFJN-UHFFFAOYSA-N [1-(oxiran-2-yl)-3,3-diphenylbenzo[f]chromen-9-yl] n-(3-triethoxysilylpropyl)carbamate Chemical compound C1=2C3=CC(OC(=O)NCCC[Si](OCC)(OCC)OCC)=CC=C3C=CC=2OC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=C1C1CO1 JUNFNQSFCWDFJN-UHFFFAOYSA-N 0.000 claims description 2
- LDTYDHJZVGVAHY-UHFFFAOYSA-N [3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-(oxiran-2-yl)octyl] n-(3-triethoxysilylpropyl)carbamate Chemical compound CCO[Si](OCC)(OCC)CCCNC(=O)OC(CC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C1CO1 LDTYDHJZVGVAHY-UHFFFAOYSA-N 0.000 claims description 2
- QWHOIHWGSSRERG-UHFFFAOYSA-N [3-(oxiran-2-yl)-3-phenylprop-2-enyl] N-(3-triethoxysilylpropyl)carbamate Chemical compound C=1C=CC=CC=1C(=CCOC(=O)NCCC[Si](OCC)(OCC)OCC)C1CO1 QWHOIHWGSSRERG-UHFFFAOYSA-N 0.000 claims description 2
- RPBNYDASXIUBFR-UHFFFAOYSA-N [3-(oxiran-2-ylmethylcarbamoyloxy)-2-(oxiran-2-ylmethylcarbamoyloxymethyl)propyl] n-[3-[diethoxy(methyl)silyl]propyl]carbamate Chemical compound C1OC1CNC(=O)OCC(COC(=O)NCCC[Si](C)(OCC)OCC)COC(=O)NCC1CO1 RPBNYDASXIUBFR-UHFFFAOYSA-N 0.000 claims description 2
- CGQZHBYKIMFDLQ-UHFFFAOYSA-N [oxiran-2-yl(phenyl)methyl] n-(3-triethoxysilylpropyl)carbamate Chemical compound C=1C=CC=CC=1C(OC(=O)NCCC[Si](OCC)(OCC)OCC)C1CO1 CGQZHBYKIMFDLQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- 239000003365 glass fiber Substances 0.000 claims description 2
- ZKSPJWAAXFPGRZ-UHFFFAOYSA-N oxiran-2-ylmethyl n-[2-[2-[2-[2-(oxiran-2-ylmethoxycarbonylamino)ethoxy]ethoxy]-3-[2-oxo-2-(3-triethoxysilylpropylamino)ethoxy]propoxy]ethyl]carbamate Chemical compound C1OC1COC(=O)NCCOCCOC(COCC(=O)NCCC[Si](OCC)(OCC)OCC)COCCNC(=O)OCC1CO1 ZKSPJWAAXFPGRZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- 239000013008 thixotropic agent Substances 0.000 claims description 2
- 239000011256 inorganic filler Substances 0.000 claims 3
- 229910003475 inorganic filler Inorganic materials 0.000 claims 3
- 239000013036 UV Light Stabilizer Substances 0.000 claims 1
- XIAVRUMYZQTHGD-UHFFFAOYSA-N [2-methyl-1-(oxiran-2-yl)propan-2-yl] n-(3-triethoxysilylpropyl)carbamate Chemical compound CCO[Si](OCC)(OCC)CCCNC(=O)OC(C)(C)CC1CO1 XIAVRUMYZQTHGD-UHFFFAOYSA-N 0.000 claims 1
- PNJSKBHELVRGRG-UHFFFAOYSA-N [2-methyl-1-(oxiran-2-yl)propan-2-yl] n-(3-trimethoxysilylpropyl)carbamate Chemical compound CO[Si](OC)(OC)CCCNC(=O)OC(C)(C)CC1CO1 PNJSKBHELVRGRG-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 239000000499 gel Substances 0.000 claims 1
- 150000001282 organosilanes Chemical class 0.000 claims 1
- 239000003002 pH adjusting agent Substances 0.000 claims 1
- 239000011236 particulate material Substances 0.000 claims 1
- 239000002516 radical scavenger Substances 0.000 claims 1
- 102200152394 rs13031859 Human genes 0.000 claims 1
- 102200140291 rs863224148 Human genes 0.000 claims 1
- 239000000543 intermediate Substances 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 42
- 239000002904 solvent Substances 0.000 description 28
- 230000000670 limiting effect Effects 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- 230000007062 hydrolysis Effects 0.000 description 12
- 238000006460 hydrolysis reaction Methods 0.000 description 12
- 239000000376 reactant Substances 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 11
- 239000000758 substrate Substances 0.000 description 10
- 150000003553 thiiranes Chemical group 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 150000002009 diols Chemical class 0.000 description 9
- 229930195733 hydrocarbon Natural products 0.000 description 9
- 150000002430 hydrocarbons Chemical class 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 150000007524 organic acids Chemical class 0.000 description 8
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000003973 paint Substances 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 6
- 239000012975 dibutyltin dilaurate Substances 0.000 description 6
- 238000006735 epoxidation reaction Methods 0.000 description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 239000012764 mineral filler Substances 0.000 description 6
- 229920000647 polyepoxide Polymers 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 229910000077 silane Inorganic materials 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000000010 aprotic solvent Substances 0.000 description 5
- 150000007942 carboxylates Chemical class 0.000 description 5
- 239000007822 coupling agent Substances 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 229910052723 transition metal Inorganic materials 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000002318 adhesion promoter Substances 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 4
- 239000008199 coating composition Substances 0.000 description 4
- 239000006184 cosolvent Substances 0.000 description 4
- PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 238000006459 hydrosilylation reaction Methods 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004971 Cross linker Substances 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001621 bismuth Chemical class 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000010960 cold rolled steel Substances 0.000 description 3
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- 125000004122 cyclic group Chemical group 0.000 description 3
- 150000001934 cyclohexanes Chemical class 0.000 description 3
- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 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 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- 230000002028 premature Effects 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 3
- 229910000165 zinc phosphate Inorganic materials 0.000 description 3
- 125000006017 1-propenyl group Chemical group 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 2
- 229910000838 Al alloy Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
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- XZFFGKZBTQABBO-UHFFFAOYSA-N ethoxy(dimethyl)silane Chemical compound CCO[SiH](C)C XZFFGKZBTQABBO-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
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- 238000005984 hydrogenation reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
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- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- WARQUFORVQESFF-UHFFFAOYSA-N isocyanatoethene Chemical compound C=CN=C=O WARQUFORVQESFF-UHFFFAOYSA-N 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
- CPJRRXSHAYUTGL-UHFFFAOYSA-N isopentenyl alcohol Chemical compound CC(=C)CCO CPJRRXSHAYUTGL-UHFFFAOYSA-N 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Chemical group 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229910052752 metalloid Inorganic materials 0.000 description 1
- 150000002738 metalloids Chemical class 0.000 description 1
- VJOOEHFQQLYDJI-UHFFFAOYSA-N methoxy(dimethyl)silane Chemical compound CO[SiH](C)C VJOOEHFQQLYDJI-UHFFFAOYSA-N 0.000 description 1
- KWJGAZUCDCAJLU-UHFFFAOYSA-N methyl(tripropyl)silane Chemical compound CCC[Si](C)(CCC)CCC KWJGAZUCDCAJLU-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
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- 239000011733 molybdenum Substances 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
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- FYZBRYMWONGDHC-UHFFFAOYSA-N n-ethyl-3-trimethoxysilylpropan-1-amine Chemical compound CCNCCC[Si](OC)(OC)OC FYZBRYMWONGDHC-UHFFFAOYSA-N 0.000 description 1
- PIQILASEWZVACI-UHFFFAOYSA-N n-methyl-4-triethoxysilylbutan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCCNC PIQILASEWZVACI-UHFFFAOYSA-N 0.000 description 1
- JJZRJHQAQJQJDV-UHFFFAOYSA-N n-methyl-4-trimethoxysilylbutan-1-amine Chemical compound CNCCCC[Si](OC)(OC)OC JJZRJHQAQJQJDV-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- REJKHFKLPFJGAQ-UHFFFAOYSA-N oxiran-2-ylmethanethiol Chemical compound SCC1CO1 REJKHFKLPFJGAQ-UHFFFAOYSA-N 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- ICMWSAALRSINTC-UHFFFAOYSA-N penta-1,4-dien-3-ol Chemical compound C=CC(O)C=C ICMWSAALRSINTC-UHFFFAOYSA-N 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000007746 phosphate conversion coating Methods 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical group [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 125000005496 phosphonium group Chemical group 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002859 polyalkenylene Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007763 reverse roll coating Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000011734 sodium Chemical group 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 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
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 150000003554 thiirenes Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 150000003681 vanadium Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
- Epoxy Resins (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/716,334 | 2007-03-09 | ||
| US11/716,334 US7989651B2 (en) | 2007-03-09 | 2007-03-09 | Epoxysilanes, processes for their manufacture and curable compositions containing same |
| PCT/US2008/003049 WO2008112150A1 (en) | 2007-03-09 | 2008-03-06 | Epoxysilanes, processes for their manufacture and curable compositions containing same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2679881A1 true CA2679881A1 (en) | 2008-09-18 |
Family
ID=39365488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002679881A Abandoned CA2679881A1 (en) | 2007-03-09 | 2008-03-06 | Epoxysilanes, processes for their manufacture and curable compositions containing same |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7989651B2 (https=) |
| EP (1) | EP2137198B1 (https=) |
| JP (1) | JP5588178B2 (https=) |
| CN (2) | CN101675063B (https=) |
| BR (1) | BRPI0808652B1 (https=) |
| CA (1) | CA2679881A1 (https=) |
| TW (1) | TW200916453A (https=) |
| WO (1) | WO2008112150A1 (https=) |
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| US7863398B2 (en) * | 2007-03-27 | 2011-01-04 | Momentive Performance Materials Inc. | Process for making hydrolyzable silylated polymers |
| JP5170414B2 (ja) * | 2008-05-16 | 2013-03-27 | 信越化学工業株式会社 | 多官能エポキシ基含有有機ケイ素化合物、その製造方法、コーティング剤組成物、並びに該組成物が被覆処理されてなる物品 |
| CN102311478B (zh) * | 2010-07-09 | 2013-03-20 | 哈尔滨工业大学 | 含胆固醇基团的复合脂质及其用途 |
| US8729257B2 (en) | 2009-07-17 | 2014-05-20 | Harbin Institute Of Technology | Hybrid lipid compounds based on pentaerythritol, intermediates, preparation methods and use thereof |
| CN101613365B (zh) * | 2009-07-17 | 2012-02-08 | 哈尔滨工业大学 | 基于季戊四醇的复合脂质及其制备方法 |
| CN102311454B (zh) * | 2010-07-09 | 2014-06-04 | 哈尔滨工业大学 | 含卟啉环功能基团的复合脂质及其制备方法与用途 |
| CN102329335B (zh) * | 2010-07-13 | 2014-01-22 | 哈尔滨工业大学 | 基于季戊四醇的复合脂质，制备方法及用途 |
| BR112013010824A2 (pt) * | 2010-11-02 | 2018-05-02 | Systems And Materials Res Corporation | método e mecanismo para realizar e usar um fixador de vedação automática |
| KR101252063B1 (ko) | 2011-08-25 | 2013-04-12 | 한국생산기술연구원 | 알콕시실릴기를 갖는 에폭시 화합물, 이의 제조 방법, 이를 포함하는 조성물과 경화물 및 이의 용도 |
| KR101456025B1 (ko) | 2011-11-01 | 2014-11-03 | 한국생산기술연구원 | 알콕시실릴기를 갖는 이소시아누레이트 에폭시 화합물, 이의 제조 방법 및 이를 포함하는 조성물과 경화물 및 이의 용도 |
| KR101992845B1 (ko) * | 2012-03-14 | 2019-06-27 | 한국생산기술연구원 | 알콕시실릴기를 갖는 에폭시 화합물, 이를 포함하는 조성물, 경화물, 이의 용도 및 알콕시실릴기를 갖는 에폭시 화합물의 제조방법 |
| WO2013146130A1 (ja) * | 2012-03-30 | 2013-10-03 | 東レ株式会社 | シランカップリング剤、感光性樹脂組成物、硬化膜及びタッチパネル部材 |
| WO2013151308A1 (ko) | 2012-04-02 | 2013-10-10 | 한국생산기술연구원 | 알콕시실릴기를 갖는 에폭시 화합물, 이를 포함하는 조성물, 경화물, 이의 용도 및 알콕시실릴기를 갖는 에폭시 화합물의 제조방법 |
| KR101863111B1 (ko) | 2012-07-06 | 2018-06-01 | 한국생산기술연구원 | 노볼락계 에폭시 화합물, 이의 제조 방법, 이를 포함하는 조성물, 경화물 및 이의 용도 |
| CN104903332B (zh) * | 2012-09-17 | 2017-12-19 | 韩国生产技术研究院 | 含烷氧基甲硅烷基的环氧化合物、该化合物的制备方法、包含该化合物的组合物、由该组合物制备的固化产物和该组合物的应用 |
| JP5803870B2 (ja) * | 2012-10-03 | 2015-11-04 | 信越化学工業株式会社 | 多官能エポキシ基含有有機ケイ素化合物を含む粘着剤組成物、粘着偏光板及び液晶表示装置 |
| WO2014129877A1 (ko) * | 2013-02-25 | 2014-08-28 | 한국생산기술연구원 | 알콕시실릴기를 갖는 에폭시 화합물, 이의 제조 방법, 이를 포함하는 조성물과 경화물 및 이의 용도 |
| KR101749551B1 (ko) * | 2014-03-05 | 2017-06-23 | 한국생산기술연구원 | 알콕시실릴기를 갖는 에폭시 화합물, 이의 제조 방법, 이를 포함하는 조성물, 경화물 및 이의 용도 |
| CN107001397B (zh) | 2014-09-26 | 2020-10-13 | 科慕埃弗西有限公司 | 异氰酸酯衍生的有机硅烷 |
| EP3023428A1 (de) * | 2014-11-24 | 2016-05-25 | Sika Technology AG | Silangruppen-haltiges Polymer |
| US10767080B2 (en) * | 2016-05-27 | 2020-09-08 | The Sherwin-Williams Company | 1K waterborne dry-erase coating composition |
| CN110168033B (zh) * | 2017-01-20 | 2022-03-29 | 盛势达技研株式会社 | 光催化剂涂覆用套组 |
| KR101767139B1 (ko) * | 2017-03-10 | 2017-08-23 | 주식회사 세승 | 콘크리트 구조물의 보수 및 보강재 조성물 및 콘크리트 구조물의 보수 및 보강 공법 |
| WO2018225880A1 (ko) * | 2017-06-05 | 2018-12-13 | 한국생산기술연구원 | 알콕시실릴기 및 활성 에스테르기를 갖는 화합물, 이의 제조방법, 이를 포함하는 조성물 및 용도 |
| KR101876551B1 (ko) * | 2017-08-03 | 2018-07-09 | 주식회사 세승 | 콘크리트 보수 공법 |
| KR101809237B1 (ko) | 2017-09-15 | 2017-12-15 | 주식회사 세승 | 내장 속경형 폴리머시멘트 매트의 제조방법 및 매트의 조성물 |
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| JP7104489B2 (ja) * | 2018-03-30 | 2022-07-21 | 株式会社松風 | エポキシ環とウレタン基を有するシランカップリング化合物およびそれらを含有する医科歯科模型用硬化性組成物 |
| CN111808511B (zh) * | 2019-04-11 | 2022-04-01 | 娄从江 | 硅氧烷改性类密封胶用底涂树脂及其配制的底涂组合物 |
| KR102232340B1 (ko) | 2019-11-15 | 2021-03-26 | 한국생산기술연구원 | 알콕시실릴기를 갖는 에폭시 수지의 조성물 및 이의 복합체 |
| JP2021080365A (ja) * | 2019-11-19 | 2021-05-27 | メルク、パテント、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ ＧｍｂＨ | 密着促進組成物および積層体の製造方法、ならびに膜形成組成物および膜の製造方法 |
| CN116179117A (zh) * | 2022-12-30 | 2023-05-30 | 浙江志强涂料有限公司 | 一种新型环保高粘建筑胶水及其制备方法 |
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| US4625012A (en) * | 1985-08-26 | 1986-11-25 | Essex Specialty Products, Inc. | Moisture curable polyurethane polymers |
| US4705841A (en) * | 1986-03-21 | 1987-11-10 | Sternson Limited | TBEA linked epoxy-urethanes |
| GB2230783B (en) * | 1989-03-15 | 1992-11-25 | Kansai Paint Co Ltd | Curable composition comprising an epoxy/silanol resin system |
| JPH02252725A (ja) * | 1989-03-28 | 1990-10-11 | Kansai Paint Co Ltd | 樹脂組成物及び硬化性組成物 |
| JPH03254868A (ja) * | 1990-03-01 | 1991-11-13 | Kansai Paint Co Ltd | 塗膜形成法 |
| GB9409525D0 (en) * | 1994-05-12 | 1994-06-29 | Zeneca Ltd | Compositions |
| CA2161181A1 (en) * | 1994-10-25 | 1996-04-26 | Frank Kropfgans | Process for the preparation of 3-halo- and -pseudohaloalkylsilane esters |
| US5587502A (en) * | 1995-06-02 | 1996-12-24 | Minnesota Mining & Manufacturing Company | Hydroxy functional alkoxysilane and alkoxysilane functional polyurethane made therefrom |
| US5550272A (en) * | 1995-10-02 | 1996-08-27 | General Electric Company | Method for hydrosilating unsaturated monomers |
| US5905150A (en) * | 1997-08-27 | 1999-05-18 | General Electric Company | Process for preparing organosilanes |
| DE19737475A1 (de) * | 1997-08-28 | 1999-03-04 | Bayer Ag | Beschichtungszusammensetzungen auf der Basis von Epoxidgruppen enthaltenden Silanen |
| DK0924250T3 (da) * | 1997-12-15 | 2006-12-27 | Gen Electric | Latexforseglingsmidler indeholdende epoxysilaner |
| US6391999B1 (en) * | 1998-02-06 | 2002-05-21 | Rensselaer Polytechnic Institute | Epoxy alkoxy siloxane oligomers |
| US6197912B1 (en) * | 1999-08-20 | 2001-03-06 | Ck Witco Corporation | Silane endcapped moisture curable compositions |
| US6455158B1 (en) | 2000-06-16 | 2002-09-24 | Crompton Corporation | Treatment of minerals with alkylsilanes and alkylsilane copolymers |
| JP4316973B2 (ja) * | 2002-09-26 | 2009-08-19 | 富士フイルム株式会社 | 有機−無機ハイブリッド型プロトン伝導材料及び燃料電池 |
| US7423078B2 (en) * | 2002-09-26 | 2008-09-09 | Fujifilm Corporation | Organic-inorganic hybrid material, organic-inorganic hybrid proton-conductive material and fuel cell |
| US6849337B2 (en) * | 2002-10-04 | 2005-02-01 | Basf Corporation | Powder coatings containing oxirane groups beta to urethane or urea groups |
-
2007
- 2007-03-09 US US11/716,334 patent/US7989651B2/en active Active
-
2008
- 2008-03-04 TW TW097107512A patent/TW200916453A/zh unknown
- 2008-03-06 BR BRPI0808652A patent/BRPI0808652B1/pt not_active IP Right Cessation
- 2008-03-06 WO PCT/US2008/003049 patent/WO2008112150A1/en not_active Ceased
- 2008-03-06 EP EP08726560.9A patent/EP2137198B1/en active Active
- 2008-03-06 CN CN2008800147460A patent/CN101675063B/zh active Active
- 2008-03-06 CN CN201310485797.4A patent/CN103554168B/zh active Active
- 2008-03-06 JP JP2009553587A patent/JP5588178B2/ja not_active Expired - Fee Related
- 2008-03-06 CA CA002679881A patent/CA2679881A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0808652B1 (pt) | 2017-03-28 |
| US7989651B2 (en) | 2011-08-02 |
| JP2010520952A (ja) | 2010-06-17 |
| BRPI0808652A2 (pt) | 2014-08-19 |
| CN103554168A (zh) | 2014-02-05 |
| EP2137198A1 (en) | 2009-12-30 |
| US20080221238A1 (en) | 2008-09-11 |
| CN101675063A (zh) | 2010-03-17 |
| CN101675063B (zh) | 2013-11-13 |
| WO2008112150A1 (en) | 2008-09-18 |
| EP2137198B1 (en) | 2016-05-18 |
| TW200916453A (en) | 2009-04-16 |
| JP5588178B2 (ja) | 2014-09-10 |
| CN103554168B (zh) | 2017-07-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20130304 |
|
| FZDE | Discontinued |
Effective date: 20161130 |