JP2003531942A - 硬化性シリコーン樹脂組成物及び反応性珪素化合物 - Google Patents
硬化性シリコーン樹脂組成物及び反応性珪素化合物Info
- Publication number
- JP2003531942A JP2003531942A JP2001580225A JP2001580225A JP2003531942A JP 2003531942 A JP2003531942 A JP 2003531942A JP 2001580225 A JP2001580225 A JP 2001580225A JP 2001580225 A JP2001580225 A JP 2001580225A JP 2003531942 A JP2003531942 A JP 2003531942A
- Authority
- JP
- Japan
- Prior art keywords
- group
- silicone resin
- bond
- mmol
- bis
- 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.)
- Pending
Links
- 229920002050 silicone resin Polymers 0.000 title claims abstract description 35
- 239000011342 resin composition Substances 0.000 title claims abstract description 11
- 150000003377 silicon compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 229910008051 Si-OH Inorganic materials 0.000 claims abstract description 7
- 229910006358 Si—OH Inorganic materials 0.000 claims abstract description 7
- 125000000524 functional group Chemical group 0.000 claims abstract description 7
- 150000002430 hydrocarbons Chemical group 0.000 claims abstract description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 6
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 6
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 15
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 14
- ZJBHFQKJEBGFNL-UHFFFAOYSA-N methylsilanetriol Chemical group C[Si](O)(O)O ZJBHFQKJEBGFNL-UHFFFAOYSA-N 0.000 claims description 12
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 11
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 11
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 10
- 229940089952 silanetriol Drugs 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 7
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- LLCSWKVOHICRDD-UHFFFAOYSA-N buta-1,3-diyne Chemical compound C#CC#C LLCSWKVOHICRDD-UHFFFAOYSA-N 0.000 claims 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims 1
- 230000000717 retained effect Effects 0.000 claims 1
- 125000005372 silanol group Chemical group 0.000 claims 1
- 239000012745 toughening agent Substances 0.000 claims 1
- 125000000732 arylene group Chemical group 0.000 abstract 1
- 239000000725 suspension Substances 0.000 description 41
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 27
- -1 phenylene, diphenylene Chemical group 0.000 description 27
- 229920005989 resin Polymers 0.000 description 27
- 239000011347 resin Substances 0.000 description 27
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 26
- 239000007787 solid Substances 0.000 description 23
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000377 silicon dioxide Substances 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000012230 colorless oil Substances 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 239000002243 precursor Substances 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 6
- SITVYBQUZUHZGY-UHFFFAOYSA-N trimethoxy-[4-(4-trimethoxysilylphenyl)phenyl]silane Chemical group C1=CC([Si](OC)(OC)OC)=CC=C1C1=CC=C([Si](OC)(OC)OC)C=C1 SITVYBQUZUHZGY-UHFFFAOYSA-N 0.000 description 6
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- RNTYMNVZOUMTRD-UHFFFAOYSA-N (4-iodophenyl)-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C1=CC=C(I)C=C1 RNTYMNVZOUMTRD-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 4
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 4
- 235000021286 stilbenes Nutrition 0.000 description 4
- NJPIZNXUDAFINV-UHFFFAOYSA-N trimethoxy-[4-[2-(4-trimethoxysilylphenyl)ethenyl]phenyl]silane Chemical compound C1=CC([Si](OC)(OC)OC)=CC=C1C=CC1=CC=C([Si](OC)(OC)OC)C=C1 NJPIZNXUDAFINV-UHFFFAOYSA-N 0.000 description 4
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 4
- ZQGCIQRBNOTUKL-UHFFFAOYSA-N (4-bromophenyl)-methyl-di(propan-2-yloxy)silane Chemical compound CC(C)O[Si](C)(OC(C)C)C1=CC=C(Br)C=C1 ZQGCIQRBNOTUKL-UHFFFAOYSA-N 0.000 description 3
- ZLRLHTVXSARHDM-UHFFFAOYSA-N (4-ethenylphenyl)-methyl-di(propan-2-yloxy)silane Chemical compound CC(C)O[Si](C)(OC(C)C)C1=CC=C(C=C)C=C1 ZLRLHTVXSARHDM-UHFFFAOYSA-N 0.000 description 3
- LPWKTPIGZASSSU-UHFFFAOYSA-N (4-ethynylphenyl)-dimethoxy-methylsilane Chemical group CO[Si](C)(OC)C1=CC=C(C#C)C=C1 LPWKTPIGZASSSU-UHFFFAOYSA-N 0.000 description 3
- HKGDCHDPFDDPPL-UHFFFAOYSA-N (4-iodophenyl)-methyl-di(propan-2-yloxy)silane Chemical compound CC(C)O[Si](C)(OC(C)C)C1=CC=C(I)C=C1 HKGDCHDPFDDPPL-UHFFFAOYSA-N 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- CZLCLQYJMGPQII-UHFFFAOYSA-N [4-[2-[4-[dimethoxy(methyl)silyl]phenyl]ethenyl]phenyl]-dimethoxy-methylsilane Chemical compound C1=CC([Si](C)(OC)OC)=CC=C1C=CC1=CC=C([Si](C)(OC)OC)C=C1 CZLCLQYJMGPQII-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- PPDADIYYMSXQJK-UHFFFAOYSA-N trichlorosilicon Chemical group Cl[Si](Cl)Cl PPDADIYYMSXQJK-UHFFFAOYSA-N 0.000 description 3
- PXDIIXCXCVILQI-UHFFFAOYSA-N (4-ethenylphenyl)-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C1=CC=C(C=C)C=C1 PXDIIXCXCVILQI-UHFFFAOYSA-N 0.000 description 2
- UNMBSPSLHROROY-UHFFFAOYSA-N (4-ethynylphenyl)-trimethoxysilane Chemical group CO[Si](OC)(OC)C1=CC=C(C#C)C=C1 UNMBSPSLHROROY-UHFFFAOYSA-N 0.000 description 2
- QUPKMEWBEFLUBR-UHFFFAOYSA-N CC(C)O[SiH](CCl)OC(C)C Chemical group CC(C)O[SiH](CCl)OC(C)C QUPKMEWBEFLUBR-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
- 235000019502 Orange oil Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- LWGWTZDIATWCKU-UHFFFAOYSA-N [4-[4-[dihydroxy(methyl)silyl]phenyl]phenyl]-dihydroxy-methylsilane Chemical group C1=CC([Si](O)(O)C)=CC=C1C1=CC=C([Si](C)(O)O)C=C1 LWGWTZDIATWCKU-UHFFFAOYSA-N 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical compound [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 2
- 229960001231 choline Drugs 0.000 description 2
- 238000013005 condensation curing Methods 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 229920002379 silicone rubber Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- LKEAKQGXUNALMI-UHFFFAOYSA-N trihydroxy-[2-(4-phenylbuta-1,3-diynyl)phenyl]silane Chemical compound O[Si](O)(O)C1=C(C=CC=C1)C#CC#CC1=CC=CC=C1 LKEAKQGXUNALMI-UHFFFAOYSA-N 0.000 description 2
- BKGXDDRMHPXVDW-UHFFFAOYSA-N trihydroxy-[4-(4-trihydroxysilylphenyl)phenyl]silane Chemical group C1=CC([Si](O)(O)O)=CC=C1C1=CC=C([Si](O)(O)O)C=C1 BKGXDDRMHPXVDW-UHFFFAOYSA-N 0.000 description 2
- FDKMYWXNDIQJJT-UHFFFAOYSA-N trimethoxy-[4-[2-(4-trimethoxysilylphenyl)ethynyl]phenyl]silane Chemical group C1=CC([Si](OC)(OC)OC)=CC=C1C#CC1=CC=C([Si](OC)(OC)OC)C=C1 FDKMYWXNDIQJJT-UHFFFAOYSA-N 0.000 description 2
- SOHMJTZHJJJSNB-UHFFFAOYSA-N trimethoxy-[4-[4-(4-trimethoxysilylphenyl)buta-1,3-diynyl]phenyl]silane Chemical group C1=CC([Si](OC)(OC)OC)=CC=C1C#CC#CC1=CC=C([Si](OC)(OC)OC)C=C1 SOHMJTZHJJJSNB-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
- LFMWZTSOMGDDJU-UHFFFAOYSA-N 1,4-diiodobenzene Chemical compound IC1=CC=C(I)C=C1 LFMWZTSOMGDDJU-UHFFFAOYSA-N 0.000 description 1
- 125000004958 1,4-naphthylene group Chemical group 0.000 description 1
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- WGKZYJXRTIPTCV-UHFFFAOYSA-N 2-butoxypropan-1-ol Chemical compound CCCCOC(C)CO WGKZYJXRTIPTCV-UHFFFAOYSA-N 0.000 description 1
- YTTFFPATQICAQN-UHFFFAOYSA-N 2-methoxypropan-1-ol Chemical compound COC(C)CO YTTFFPATQICAQN-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 101100484954 Arabidopsis thaliana VQ20 gene Proteins 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 238000007341 Heck reaction Methods 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910018540 Si C Inorganic materials 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- FLFPQKQWRPBPMW-UHFFFAOYSA-N [4-[2-[4-[dihydroxy(methyl)silyl]phenyl]ethynyl]phenyl]-dihydroxy-methylsilane Chemical group C1=CC([Si](O)(O)C)=CC=C1C#CC1=CC=C([Si](C)(O)O)C=C1 FLFPQKQWRPBPMW-UHFFFAOYSA-N 0.000 description 1
- NCAWGXKNYCIFNO-UHFFFAOYSA-N [4-[2-[4-[dimethoxy(methyl)silyl]phenyl]ethynyl]phenyl]-dimethoxy-methylsilane Chemical group C1=CC([Si](C)(OC)OC)=CC=C1C#CC1=CC=C([Si](C)(OC)OC)C=C1 NCAWGXKNYCIFNO-UHFFFAOYSA-N 0.000 description 1
- OSSQPVMQSUBBQM-UHFFFAOYSA-N [4-[4-[dimethoxy(methyl)silyl]phenyl]phenyl]-dimethoxy-methylsilane Chemical group C1=CC([Si](C)(OC)OC)=CC=C1C1=CC=C([Si](C)(OC)OC)C=C1 OSSQPVMQSUBBQM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000005370 alkoxysilyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000003190 augmentative effect Effects 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical group C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 description 1
- 229940045348 brown mixture Drugs 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 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
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- CBVJWBYNOWIOFJ-UHFFFAOYSA-N chloro(trimethoxy)silane Chemical compound CO[Si](Cl)(OC)OC CBVJWBYNOWIOFJ-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- RLJHDCMUFNVFPQ-UHFFFAOYSA-N cyclopenta-1,4-dien-1-yl(trihydroxy)silane iron(2+) Chemical compound [Fe++].O[Si](O)(O)[c-]1cccc1.O[Si](O)(O)[c-]1cccc1 RLJHDCMUFNVFPQ-UHFFFAOYSA-N 0.000 description 1
- NXXUIADBFLWSCR-UHFFFAOYSA-N cyclopenta-1,4-dien-1-yl(trimethoxy)silane iron(2+) Chemical compound [Fe++].CO[Si](OC)(OC)[c-]1cccc1.CO[Si](OC)(OC)[c-]1cccc1 NXXUIADBFLWSCR-UHFFFAOYSA-N 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical group C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- YEMJITXWLIHJHJ-UHFFFAOYSA-N di(propan-2-yloxy)silane Chemical compound CC(C)O[SiH2]OC(C)C YEMJITXWLIHJHJ-UHFFFAOYSA-N 0.000 description 1
- FNLUYENEAPLWBT-UHFFFAOYSA-N dimethoxymethyl(phenyl)silane Chemical compound COC(OC)[SiH2]C1=CC=CC=C1 FNLUYENEAPLWBT-UHFFFAOYSA-N 0.000 description 1
- XLFFRQQBXIZDDB-UHFFFAOYSA-N dimethoxymethyl-[4-(dimethoxymethylsilyl)-1-phenylcyclohexa-2,4-dien-1-yl]silane Chemical group COC(OC)[SiH2]C1(CC=C(C=C1)[SiH2]C(OC)OC)C1=CC=CC=C1 XLFFRQQBXIZDDB-UHFFFAOYSA-N 0.000 description 1
- WYCNMJQFHMADDJ-UHFFFAOYSA-N dimethoxymethyl-[4-(dimethoxymethylsilyl)phenyl]silane Chemical compound COC(OC)[SiH2]C1=CC=C(C=C1)[SiH2]C(OC)OC WYCNMJQFHMADDJ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000009815 homocoupling reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 238000013017 mechanical damping Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- HLXDKGBELJJMHR-UHFFFAOYSA-N methyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](C)(OC(C)C)OC(C)C HLXDKGBELJJMHR-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005474 octanoate group Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-O phenylazanium Chemical class [NH3+]C1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-O 0.000 description 1
- 238000013001 point bending Methods 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010125 resin casting Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- FWSPXZXVNVQHIF-UHFFFAOYSA-N triethyl(ethynyl)silane Chemical group CC[Si](CC)(CC)C#C FWSPXZXVNVQHIF-UHFFFAOYSA-N 0.000 description 1
- QQUBYBOFPPCWDM-UHFFFAOYSA-N trihydroxy-(4-trihydroxysilylphenyl)silane Chemical compound O[Si](O)(O)C1=CC=C([Si](O)(O)O)C=C1 QQUBYBOFPPCWDM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
- C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
-
- 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
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0836—Compounds with one or more Si-OH or Si-O-metal linkage
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/44—Block-or graft-polymers containing polysiloxane sequences containing only polysiloxane sequences
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Silicon Polymers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00401160 | 2000-04-27 | ||
| EP00401160.7 | 2000-04-27 | ||
| PCT/EP2001/004606 WO2001083608A1 (en) | 2000-04-27 | 2001-04-24 | Curable silicone resin composition and reactive silicon compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003531942A true JP2003531942A (ja) | 2003-10-28 |
| JP2003531942A5 JP2003531942A5 (enExample) | 2011-06-16 |
Family
ID=8173660
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001580225A Pending JP2003531942A (ja) | 2000-04-27 | 2001-04-24 | 硬化性シリコーン樹脂組成物及び反応性珪素化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6780471B2 (enExample) |
| EP (1) | EP1276807B1 (enExample) |
| JP (1) | JP2003531942A (enExample) |
| AT (1) | ATE306518T1 (enExample) |
| AU (1) | AU2001273963A1 (enExample) |
| DE (1) | DE60120147T2 (enExample) |
| WO (1) | WO2001083608A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009136647A1 (ja) * | 2008-05-07 | 2009-11-12 | 住友ベークライト株式会社 | ポジ型感光性樹脂組成物、硬化膜、保護膜及び絶縁膜、並びにそれを用いた半導体装置及び表示体装置 |
| KR20200054896A (ko) * | 2018-11-12 | 2020-05-20 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 요오드 함유 규소 화합물의 제조 방법 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101266290B1 (ko) * | 2008-12-30 | 2013-05-22 | 제일모직주식회사 | 레지스트 하층막용 하드마스크 조성물 및 이를 이용한 반도체 집적회로 디바이스의 제조방법 |
| KR101266291B1 (ko) * | 2008-12-30 | 2013-05-22 | 제일모직주식회사 | 레지스트 하층막용 조성물 및 이를 이용한 반도체 집적회로디바이스의 제조방법 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6131461A (ja) * | 1984-07-24 | 1986-02-13 | Shin Etsu Chem Co Ltd | 室温硬化性オルガノシロキサン組成物 |
| JPS6164753A (ja) * | 1984-09-06 | 1986-04-03 | Shin Etsu Chem Co Ltd | 室温硬化性オルガノシロキサン組成物 |
| JPH08269331A (ja) * | 1995-04-03 | 1996-10-15 | Shin Etsu Chem Co Ltd | シリコーンゲル組成物及びポッティング材 |
| JP2000265062A (ja) * | 1999-03-12 | 2000-09-26 | Shin Etsu Chem Co Ltd | 室温硬化性オルガノポリシロキサン組成物 |
| JP2001506283A (ja) * | 1993-12-17 | 2001-05-15 | ハイトコ カーボン コンポジッツ インコーポレイテッド | 高温抵抗性を有するシリコーン複合体 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA691206A (en) | 1964-07-21 | Dow Corning Corporation | Method of damping vibration | |
| GB1119666A (en) | 1965-08-06 | 1968-07-10 | Ici Ltd | Organosilicon polymers |
| GB1101589A (en) | 1965-09-09 | 1968-01-31 | Ici Ltd | Organosilicon resins |
| US5034061A (en) | 1990-03-15 | 1991-07-23 | General Electric Company | Transparent shatter-resistant silicone coating |
| US5747608A (en) | 1996-12-31 | 1998-05-05 | Dow Corning Corporation | Rubber-modified rigid silicone resins and composites produced therefrom |
| US5830950A (en) | 1996-12-31 | 1998-11-03 | Dow Corning Corporation | Method of making rubber-modified rigid silicone resins and composites produced therefrom |
-
2001
- 2001-04-24 AU AU2001273963A patent/AU2001273963A1/en not_active Abandoned
- 2001-04-24 US US10/258,722 patent/US6780471B2/en not_active Expired - Fee Related
- 2001-04-24 JP JP2001580225A patent/JP2003531942A/ja active Pending
- 2001-04-24 AT AT01940358T patent/ATE306518T1/de not_active IP Right Cessation
- 2001-04-24 EP EP01940358A patent/EP1276807B1/en not_active Expired - Lifetime
- 2001-04-24 DE DE60120147T patent/DE60120147T2/de not_active Expired - Fee Related
- 2001-04-24 WO PCT/EP2001/004606 patent/WO2001083608A1/en not_active Ceased
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6131461A (ja) * | 1984-07-24 | 1986-02-13 | Shin Etsu Chem Co Ltd | 室温硬化性オルガノシロキサン組成物 |
| JPS6164753A (ja) * | 1984-09-06 | 1986-04-03 | Shin Etsu Chem Co Ltd | 室温硬化性オルガノシロキサン組成物 |
| JP2001506283A (ja) * | 1993-12-17 | 2001-05-15 | ハイトコ カーボン コンポジッツ インコーポレイテッド | 高温抵抗性を有するシリコーン複合体 |
| JPH08269331A (ja) * | 1995-04-03 | 1996-10-15 | Shin Etsu Chem Co Ltd | シリコーンゲル組成物及びポッティング材 |
| JP2000265062A (ja) * | 1999-03-12 | 2000-09-26 | Shin Etsu Chem Co Ltd | 室温硬化性オルガノポリシロキサン組成物 |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009136647A1 (ja) * | 2008-05-07 | 2009-11-12 | 住友ベークライト株式会社 | ポジ型感光性樹脂組成物、硬化膜、保護膜及び絶縁膜、並びにそれを用いた半導体装置及び表示体装置 |
| JPWO2009136647A1 (ja) * | 2008-05-07 | 2011-09-08 | 住友ベークライト株式会社 | ポジ型感光性樹脂組成物、硬化膜、保護膜及び絶縁膜、並びにそれを用いた半導体装置及び表示体装置 |
| US8492469B2 (en) | 2008-05-07 | 2013-07-23 | Sumitomo Bakelite Co., Ltd. | Positive-type photosensitive resin composition, cured film, protective film, insulating film, and semiconductor device and display device including the cured film |
| KR20200054896A (ko) * | 2018-11-12 | 2020-05-20 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 요오드 함유 규소 화합물의 제조 방법 |
| JP2020079208A (ja) * | 2018-11-12 | 2020-05-28 | 信越化学工業株式会社 | ヨウ素含有ケイ素化合物の製造方法 |
| KR102376869B1 (ko) * | 2018-11-12 | 2022-03-18 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 요오드 함유 규소 화합물의 제조 방법 |
| US11518774B2 (en) | 2018-11-12 | 2022-12-06 | Shin-Etsu Chemical Co., Ltd. | Method for producing iodine-containing silicon compound |
| JP7406300B2 (ja) | 2018-11-12 | 2023-12-27 | 信越化学工業株式会社 | ヨウ素含有ケイ素化合物の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20030130389A1 (en) | 2003-07-10 |
| EP1276807A1 (en) | 2003-01-22 |
| AU2001273963A1 (en) | 2001-11-12 |
| DE60120147T2 (de) | 2006-09-28 |
| EP1276807B1 (en) | 2005-10-12 |
| WO2001083608A1 (en) | 2001-11-08 |
| DE60120147D1 (de) | 2006-07-06 |
| ATE306518T1 (de) | 2005-10-15 |
| US6780471B2 (en) | 2004-08-24 |
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