TW200916453A - 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
- TW200916453A TW200916453A TW097107512A TW97107512A TW200916453A TW 200916453 A TW200916453 A TW 200916453A TW 097107512 A TW097107512 A TW 097107512A TW 97107512 A TW97107512 A TW 97107512A TW 200916453 A TW200916453 A TW 200916453A
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- Prior art keywords
- group
- epoxy
- decane
- oxygen
- rti
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 74
- 238000000034 method Methods 0.000 title claims description 23
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 230000008569 process Effects 0.000 title description 3
- 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 62
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 55
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 48
- 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 41
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 26
- 229910052757 nitrogen Chemical group 0.000 claims abstract description 23
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 8
- -1 dilute Chemical group 0.000 claims description 107
- AAMHBRRZYSORSH-UHFFFAOYSA-N 2-octyloxirane Chemical compound CCCCCCCCC1CO1 AAMHBRRZYSORSH-UHFFFAOYSA-N 0.000 claims description 99
- 239000004593 Epoxy Substances 0.000 claims description 73
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 71
- 125000003118 aryl group Chemical group 0.000 claims description 58
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 239000001257 hydrogen Substances 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- 229910052799 carbon Inorganic materials 0.000 claims description 40
- 150000001721 carbon Chemical group 0.000 claims description 37
- 238000006243 chemical reaction Methods 0.000 claims description 36
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 claims description 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 32
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 30
- 125000003342 alkenyl group Chemical group 0.000 claims description 28
- 239000003054 catalyst Substances 0.000 claims description 28
- 239000005056 polyisocyanate Substances 0.000 claims description 28
- 229920001228 polyisocyanate Polymers 0.000 claims description 28
- 238000000576 coating method Methods 0.000 claims description 25
- DLMVDBDHOIWEJZ-UHFFFAOYSA-N isocyanatooxyimino(oxo)methane Chemical compound O=C=NON=C=O DLMVDBDHOIWEJZ-UHFFFAOYSA-N 0.000 claims description 23
- 239000011248 coating agent Substances 0.000 claims description 22
- 150000002148 esters Chemical class 0.000 claims description 21
- 239000012948 isocyanate Substances 0.000 claims description 21
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 20
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- 150000002513 isocyanates Chemical class 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 229910052751 metal Inorganic materials 0.000 claims description 18
- 239000002184 metal Substances 0.000 claims description 18
- 230000009257 reactivity Effects 0.000 claims description 16
- 125000004434 sulfur atom Chemical group 0.000 claims description 16
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 14
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 13
- 239000004094 surface-active agent Substances 0.000 claims description 12
- XFEWMFDVBLLXFE-UHFFFAOYSA-N 1-isocyanatodecane Chemical compound CCCCCCCCCCN=C=O XFEWMFDVBLLXFE-UHFFFAOYSA-N 0.000 claims description 11
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 11
- 229930195733 hydrocarbon Natural products 0.000 claims description 11
- 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 11
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000004576 sand Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 9
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 9
- 229920000620 organic polymer Polymers 0.000 claims description 9
- 239000011347 resin Substances 0.000 claims description 9
- 229920005989 resin Polymers 0.000 claims description 9
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 8
- 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 7
- QRTXDOJSCJMUNR-UHFFFAOYSA-N CCCCCCCCCCCCCCCCCCCC[N+]#[C-] Chemical compound CCCCCCCCCCCCCCCCCCCC[N+]#[C-] QRTXDOJSCJMUNR-UHFFFAOYSA-N 0.000 claims description 7
- 125000002619 bicyclic group Chemical group 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000005442 diisocyanate group Chemical group 0.000 claims description 6
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- 239000002002 slurry Substances 0.000 claims description 6
- 238000012546 transfer Methods 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 5
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- 229910044991 metal oxide Inorganic materials 0.000 claims description 5
- 150000004706 metal oxides Chemical class 0.000 claims description 5
- 239000000080 wetting agent Substances 0.000 claims description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 150000002924 oxiranes Chemical class 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 239000005060 rubber Substances 0.000 claims description 4
- 239000002594 sorbent Substances 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
- 239000002216 antistatic agent Substances 0.000 claims description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000004382 potting Methods 0.000 claims description 3
- 239000013036 UV Light Stabilizer Substances 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 239000003365 glass fiber Substances 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 150000002602 lanthanoids Chemical class 0.000 claims description 2
- 239000003607 modifier Substances 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- 102200140291 rs863224148 Human genes 0.000 claims description 2
- 239000013008 thixotropic agent Substances 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 11
- 150000002829 nitrogen Chemical class 0.000 claims 4
- 229910052715 tantalum Inorganic materials 0.000 claims 4
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 239000004643 cyanate ester Substances 0.000 claims 1
- YZLDHQLGRXYVPY-UHFFFAOYSA-N decyl cyanate Chemical compound CCCCCCCCCCOC#N YZLDHQLGRXYVPY-UHFFFAOYSA-N 0.000 claims 1
- 239000002274 desiccant Substances 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 229910052746 lanthanum Inorganic materials 0.000 claims 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims 1
- PJSOCBVWZJGTHW-UHFFFAOYSA-N n-(1h-indazol-5-yl)-5-[3-methoxy-4-[2-(2-methoxyethoxy)ethoxy]phenyl]-1,3-oxazol-2-amine Chemical compound C1=C(OC)C(OCCOCCOC)=CC=C1C(O1)=CN=C1NC1=CC=C(NN=C2)C2=C1 PJSOCBVWZJGTHW-UHFFFAOYSA-N 0.000 claims 1
- 239000011236 particulate material Substances 0.000 claims 1
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- 239000011495 polyisocyanurate Substances 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 229910000077 silane Inorganic materials 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 239000012756 surface treatment agent Substances 0.000 claims 1
- XKXIQBVKMABYQJ-UHFFFAOYSA-N tert-butyl hydrogen carbonate Chemical compound CC(C)(C)OC(O)=O XKXIQBVKMABYQJ-UHFFFAOYSA-N 0.000 claims 1
- 239000000052 vinegar Substances 0.000 claims 1
- 235000021419 vinegar Nutrition 0.000 claims 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 description 45
- 239000002904 solvent Substances 0.000 description 33
- 238000001308 synthesis method Methods 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 229910052500 inorganic mineral Inorganic materials 0.000 description 12
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- 230000007062 hydrolysis Effects 0.000 description 11
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000000758 substrate Substances 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
- 150000002009 diols Chemical class 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
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- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical compound [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 6
- 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 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 5
- 239000000010 aprotic solvent Substances 0.000 description 5
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- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 5
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- 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
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- DGZPBRFJRXDRDD-UHFFFAOYSA-N 1-chloro-4-(triethoxymethyl)dodecane Chemical compound ClCCCC(C(OCC)(OCC)OCC)CCCCCCCC DGZPBRFJRXDRDD-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
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- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
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- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
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- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
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- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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)
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| US11/716,334 US7989651B2 (en) | 2007-03-09 | 2007-03-09 | Epoxysilanes, processes for their manufacture and curable compositions containing same |
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| TW200916453A true TW200916453A (en) | 2009-04-16 |
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| TW097107512A TW200916453A (en) | 2007-03-09 | 2008-03-04 | Epoxysilanes, processes for their manufacture and curable compositions containing same |
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| JP (1) | JP5588178B2 (https=) |
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| 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 |
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| 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 |
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-
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 |
| CA2679881A1 (en) | 2008-09-18 |
| 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 |
| JP5588178B2 (ja) | 2014-09-10 |
| CN103554168B (zh) | 2017-07-18 |
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