JP4801320B2 - 付加反応硬化型オルガノポリシロキサン樹脂組成物 - Google Patents
付加反応硬化型オルガノポリシロキサン樹脂組成物 Download PDFInfo
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- JP4801320B2 JP4801320B2 JP2003423726A JP2003423726A JP4801320B2 JP 4801320 B2 JP4801320 B2 JP 4801320B2 JP 2003423726 A JP2003423726 A JP 2003423726A JP 2003423726 A JP2003423726 A JP 2003423726A JP 4801320 B2 JP4801320 B2 JP 4801320B2
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- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 66
- 239000011342 resin composition Substances 0.000 title claims abstract description 52
- 238000007259 addition reaction Methods 0.000 title claims description 55
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 37
- 229920005989 resin Polymers 0.000 claims abstract description 33
- 239000011347 resin Substances 0.000 claims abstract description 33
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 27
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 21
- 239000003054 catalyst Substances 0.000 claims abstract description 16
- 229920006136 organohydrogenpolysiloxane Polymers 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 42
- 238000002834 transmittance Methods 0.000 claims description 37
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 239000012298 atmosphere Substances 0.000 claims description 13
- 238000005452 bending Methods 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 230000003197 catalytic effect Effects 0.000 claims description 5
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000010703 silicon Substances 0.000 abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 108
- -1 diphenylsiloxane units Chemical group 0.000 description 51
- 239000000047 product Substances 0.000 description 48
- 239000000243 solution Substances 0.000 description 43
- 239000010410 layer Substances 0.000 description 38
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- 230000015572 biosynthetic process Effects 0.000 description 29
- 238000003786 synthesis reaction Methods 0.000 description 27
- 238000003756 stirring Methods 0.000 description 20
- 238000001816 cooling Methods 0.000 description 17
- 229910052697 platinum Inorganic materials 0.000 description 16
- 238000001723 curing Methods 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 230000007423 decrease Effects 0.000 description 12
- 230000003287 optical effect Effects 0.000 description 12
- BITPLIXHRASDQB-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)C=C BITPLIXHRASDQB-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical compound C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 150000002430 hydrocarbons Chemical group 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229920002050 silicone resin Polymers 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000006459 hydrosilylation reaction Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 5
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 5
- KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 description 4
- 229910004298 SiO 2 Inorganic materials 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- OOGRAMOPTBMVKO-UHFFFAOYSA-N bis[[ethenyl(dimethyl)silyl]oxy]-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](O[Si](C)(C)C=C)(O[Si](C)(C)C=C)C1=CC=CC=C1 OOGRAMOPTBMVKO-UHFFFAOYSA-N 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 230000001771 impaired effect Effects 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 239000005054 phenyltrichlorosilane Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 3
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000007809 chemical reaction catalyst Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- YLJJAVFOBDSYAN-UHFFFAOYSA-N dichloro-ethenyl-methylsilane Chemical compound C[Si](Cl)(Cl)C=C YLJJAVFOBDSYAN-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 2
- RCNRJBWHLARWRP-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane;platinum Chemical compound [Pt].C=C[Si](C)(C)O[Si](C)(C)C=C RCNRJBWHLARWRP-UHFFFAOYSA-N 0.000 description 2
- 239000011229 interlayer Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000003204 osmotic effect Effects 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 230000007261 regionalization Effects 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- VEJOYRPGKZZTJW-FDGPNNRMSA-N (z)-4-hydroxypent-3-en-2-one;platinum Chemical compound [Pt].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O VEJOYRPGKZZTJW-FDGPNNRMSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241001620634 Roger Species 0.000 description 1
- 229910004283 SiO 4 Inorganic materials 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- WYUIWUCVZCRTRH-UHFFFAOYSA-N [[[ethenyl(dimethyl)silyl]amino]-dimethylsilyl]ethene Chemical compound C=C[Si](C)(C)N[Si](C)(C)C=C WYUIWUCVZCRTRH-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000003491 array Methods 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- SORVFRRXWOKHGG-UHFFFAOYSA-N bis(2-methylprop-1-enylsilyloxy)-diphenylsilane Chemical compound C1(=CC=CC=C1)[Si](O[SiH2]C=C(C)C)(O[SiH2]C=C(C)C)C1=CC=CC=C1 SORVFRRXWOKHGG-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=C([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])[H] 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000005388 dimethylhydrogensiloxy group Chemical group 0.000 description 1
- VDCSGNNYCFPWFK-UHFFFAOYSA-N diphenylsilane Chemical compound C=1C=CC=CC=1[SiH2]C1=CC=CC=C1 VDCSGNNYCFPWFK-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- GTFPSQNXDCNWLT-UHFFFAOYSA-N ethenyl-[[ethenyl(dimethyl)silyl]oxy-methylsilyl]oxy-dimethylsilane Chemical compound C=C[Si](C)(C)O[SiH](C)O[Si](C)(C)C=C GTFPSQNXDCNWLT-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 229940093858 ethyl acetoacetate Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- NYMPGSQKHIOWIO-UHFFFAOYSA-N hydroxy(diphenyl)silicon Chemical class C=1C=CC=CC=1[Si](O)C1=CC=CC=C1 NYMPGSQKHIOWIO-UHFFFAOYSA-N 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 238000011378 penetrating method Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000000411 transmission spectrum Methods 0.000 description 1
- VTYCDJPJGNRAHU-UHFFFAOYSA-N tris(2-methylprop-1-enylsilyloxy)-phenylsilane Chemical compound C1(=CC=CC=C1)[Si](O[SiH2]C=C(C)C)(O[SiH2]C=C(C)C)O[SiH2]C=C(C)C VTYCDJPJGNRAHU-UHFFFAOYSA-N 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/70—Siloxanes defined by use of the MDTQ nomenclature
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003423726A JP4801320B2 (ja) | 2003-12-19 | 2003-12-19 | 付加反応硬化型オルガノポリシロキサン樹脂組成物 |
| CNB2004800377939A CN100489563C (zh) | 2003-12-19 | 2004-12-17 | 可加成固化的有机聚硅氧烷树脂组合物 |
| US10/583,436 US7649059B2 (en) | 2003-12-19 | 2004-12-17 | Addition-curable organopolysiloxane resin composition |
| AT04807824T ATE442597T1 (de) | 2003-12-19 | 2004-12-17 | Additionsaushärtbare organopolysiloxan- harzzusammensetzung |
| EP04807824A EP1695124B1 (en) | 2003-12-19 | 2004-12-17 | Addition-curable organopolysiloxane resin composition |
| DE602004023118T DE602004023118D1 (de) | 2003-12-19 | 2004-12-17 | Additionsaushärtbare organopolysiloxan-harzzusammensetzung |
| KR1020067014390A KR101176931B1 (ko) | 2003-12-19 | 2004-12-17 | 부가반응 경화형 오가노폴리실록산 수지 조성물 |
| PCT/JP2004/019469 WO2005062080A2 (en) | 2003-12-19 | 2004-12-17 | Addition-curable organopolysiloxane resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003423726A JP4801320B2 (ja) | 2003-12-19 | 2003-12-19 | 付加反応硬化型オルガノポリシロキサン樹脂組成物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005179541A JP2005179541A (ja) | 2005-07-07 |
| JP2005179541A5 JP2005179541A5 (enExample) | 2008-06-05 |
| JP4801320B2 true JP4801320B2 (ja) | 2011-10-26 |
Family
ID=34708763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003423726A Expired - Fee Related JP4801320B2 (ja) | 2003-12-19 | 2003-12-19 | 付加反応硬化型オルガノポリシロキサン樹脂組成物 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7649059B2 (enExample) |
| EP (1) | EP1695124B1 (enExample) |
| JP (1) | JP4801320B2 (enExample) |
| KR (1) | KR101176931B1 (enExample) |
| CN (1) | CN100489563C (enExample) |
| AT (1) | ATE442597T1 (enExample) |
| DE (1) | DE602004023118D1 (enExample) |
| WO (1) | WO2005062080A2 (enExample) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006137895A (ja) * | 2004-11-15 | 2006-06-01 | Ge Toshiba Silicones Co Ltd | 光学材料用ポリオルガノシロキサン組成物 |
| JP5138158B2 (ja) * | 2005-05-23 | 2013-02-06 | 信越化学工業株式会社 | Led発光装置用シリコーンレンズ成形材料 |
| EP1905795A4 (en) | 2005-07-19 | 2010-08-11 | Dow Corning Toray Co Ltd | POLYSILOXAN AND MANUFACTURING METHOD THEREFOR |
| DE602007000068D1 (de) * | 2006-02-20 | 2008-09-25 | Shinetsu Chemical Co | Hitzeerhärtbare Silikonzusammensetzung |
| JP4822008B2 (ja) * | 2006-02-20 | 2011-11-24 | 信越化学工業株式会社 | 加熱硬化性シリコーン組成物 |
| JP5148088B2 (ja) * | 2006-08-25 | 2013-02-20 | 東レ・ダウコーニング株式会社 | 硬化性オルガノポリシロキサン組成物および半導体装置 |
| KR20090115803A (ko) | 2007-02-13 | 2009-11-06 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 렌즈를 갖는 led 소자 및 그 제조 방법 |
| US9944031B2 (en) * | 2007-02-13 | 2018-04-17 | 3M Innovative Properties Company | Molded optical articles and methods of making same |
| JP4927019B2 (ja) * | 2007-04-10 | 2012-05-09 | 信越化学工業株式会社 | 蛍光体含有接着性シリコーン組成物、該組成物からなる組成物シート、及び該シートを使用する発光装置の製造方法 |
| JP2009007515A (ja) * | 2007-06-29 | 2009-01-15 | Showa Denko Kk | 微細パターン転写材料用組成物および微細パターンの形成方法 |
| JP2009155442A (ja) * | 2007-12-26 | 2009-07-16 | Nippon Steel Chem Co Ltd | レンズ用樹脂組成物及びその硬化物 |
| US8101242B2 (en) * | 2008-03-07 | 2012-01-24 | Sri International | Method of imparting corrosion resistance to a substrate surface, and coated substrates prepared thereby |
| US8629222B2 (en) | 2008-03-28 | 2014-01-14 | Mitsubishi Chemical Corporation | Curable polysiloxane composition, and polysiloxane cured product, optical member, member for aerospace industry, semiconductor light-emitting device, illuminating device and image display device using the same |
| JP5287116B2 (ja) * | 2008-10-09 | 2013-09-11 | 三菱化学株式会社 | ポリオルガノシロキサン硬化物及び発光装置の製造方法 |
| JP5383250B2 (ja) * | 2009-02-26 | 2014-01-08 | 新日鉄住金化学株式会社 | 硬化性樹脂組成物及び硬化物 |
| FR2946657A1 (fr) * | 2009-06-12 | 2010-12-17 | Bluestar Silicones France | Procede d'etancheification et d'assemblage de composants d'un groupe moto-propulseur |
| FR2946656A1 (fr) * | 2009-06-12 | 2010-12-17 | Bluestar Silicones France | Procede d'etancheification et d'assemblage de composants d'un groupe moto-propulseur |
| FR2946981A1 (fr) * | 2009-06-19 | 2010-12-24 | Bluestar Silicones France | Composition silicone reticulable par deshydrogenocondensation en presence d'un catalyseur metallique |
| JP5554405B2 (ja) * | 2009-06-19 | 2014-07-23 | ブルースター・シリコーンズ・フランス・エスアエス | 非金属触媒の存在下において脱水素縮合によって架橋可能なシリコーン組成物 |
| KR101364798B1 (ko) * | 2009-06-19 | 2014-02-19 | 블루스타 실리콘즈 프랑스 에스에이에스 | 비-금속 촉매의 존재 하에 탈수소 축합에 의한 가교에 적합한 실리콘 조성물 |
| JP5170471B2 (ja) * | 2010-09-02 | 2013-03-27 | 信越化学工業株式会社 | 低ガス透過性シリコーン樹脂組成物及び光半導体装置 |
| JP5453326B2 (ja) * | 2011-01-11 | 2014-03-26 | 積水化学工業株式会社 | 光半導体装置用ダイボンド材及びそれを用いた光半導体装置 |
| JP5919903B2 (ja) * | 2011-03-31 | 2016-05-18 | 三菱化学株式会社 | 半導体発光装置用パッケージ及び該パッケージを有してなる半導体発光装置並びにそれらの製造方法 |
| FI127433B (fi) | 2011-06-14 | 2018-05-31 | Pibond Oy | Menetelmä siloksaanimonomeerien syntetisoimiseksi sekä näiden käyttö |
| JP5992666B2 (ja) * | 2011-06-16 | 2016-09-14 | 東レ・ダウコーニング株式会社 | 架橋性シリコーン組成物及びその架橋物 |
| JP6057503B2 (ja) * | 2011-09-21 | 2017-01-11 | 東レ・ダウコーニング株式会社 | 光半導体素子封止用硬化性シリコーン組成物、樹脂封止光半導体素子の製造方法、および樹脂封止光半導体素子 |
| WO2013096554A1 (en) * | 2011-12-20 | 2013-06-27 | 3M Innovative Properties Company | Dual condensation cure silicone |
| JP6046395B2 (ja) * | 2012-06-29 | 2016-12-14 | 東レ・ダウコーニング株式会社 | 反応性シリコーン組成物、反応性熱可塑体、硬化物、および光半導体装置 |
| JP6157085B2 (ja) | 2012-10-24 | 2017-07-05 | 東レ・ダウコーニング株式会社 | 硬化性シリコーン組成物、その硬化物、および光半導体装置 |
| JP6084808B2 (ja) | 2012-10-24 | 2017-02-22 | 東レ・ダウコーニング株式会社 | オルガノポリシロキサン、硬化性シリコーン組成物、その硬化物、および光半導体装置 |
| JP6081774B2 (ja) * | 2012-10-30 | 2017-02-15 | 東レ・ダウコーニング株式会社 | 硬化性シリコーン組成物、その硬化物、および光半導体装置 |
| WO2014105963A2 (en) * | 2012-12-28 | 2014-07-03 | Dow Corning Corporation | Curable organopolysiloxane composition for transducers and applications of such curable silicone composition for transducers |
| KR101775476B1 (ko) * | 2013-08-09 | 2017-09-06 | 요코하마 고무 가부시키가이샤 | 경화성 수지 조성물 |
| CN105199397B (zh) * | 2014-06-17 | 2018-05-08 | 广州慧谷化学有限公司 | 一种可固化的有机聚硅氧烷组合物及半导体器件 |
| KR102757326B1 (ko) | 2018-06-12 | 2025-01-20 | 모멘티브 파포만스 마테리아루즈 쟈판 고도가이샤 | 실리콘 경화물의 제조 방법, 실리콘 경화물 및 광학용 부재 |
| JP7170450B2 (ja) | 2018-07-31 | 2022-11-14 | 信越化学工業株式会社 | 付加硬化型シリコーン樹脂組成物及び半導体装置 |
| EP3853299B1 (en) | 2018-09-19 | 2025-08-20 | Dow Silicones Corporation | Aryl scission inhibition in aryl-functionalized polysiloxane |
| EP3954739A4 (en) * | 2019-03-29 | 2022-12-28 | Dow Toray Co., Ltd. | CURABLE SILICONE COMPOSITION, CURED PRODUCT THEREOF AND METHOD OF MAKING THEREOF |
| CN115353857B (zh) * | 2022-07-11 | 2023-06-27 | 武汉飞恩微电子有限公司 | 一种压力传感器芯片用封装介质及其制备方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3732330A (en) | 1972-03-08 | 1973-05-08 | Dow Corning | Curable compositions containing hydrogen-functional organopolysiloxanes |
| CA1133169A (en) | 1978-06-05 | 1982-10-05 | Dow Corning Corporation | Curable solventless organopolysiloxane compositions |
| US4472563A (en) * | 1984-02-06 | 1984-09-18 | Dow Corning Corporation | Heat curable silicones having improved room temperature stability |
| JPS62215658A (ja) * | 1986-03-17 | 1987-09-22 | Shin Etsu Chem Co Ltd | 光硬化性オルガノポリシロキサン組成物 |
| JP3024475B2 (ja) * | 1993-12-21 | 2000-03-21 | 信越化学工業株式会社 | オルガノポリシロキサン組成物及び光ファイバ |
| FR2727119B1 (fr) * | 1994-11-18 | 1997-01-03 | Rhone Poulenc Chimie | Polyorganosiloxanes fonctionnalises et l'un de leurs procedes de preparation |
| CN1155562A (zh) * | 1995-10-11 | 1997-07-30 | 陶氏康宁公司 | 改进粘合性的可固化有机聚硅氧烷组合物 |
| JPH10101935A (ja) * | 1996-09-27 | 1998-04-21 | Toray Dow Corning Silicone Co Ltd | 加熱硬化性オルガノポリシロキサン組成物 |
| CN1194280A (zh) * | 1996-12-24 | 1998-09-30 | 陶氏康宁公司 | 具有改进粘合性的可固化有机硅组合物 |
| JP3983333B2 (ja) * | 1997-02-20 | 2007-09-26 | 信越化学工業株式会社 | 付加反応硬化型オルガノポリシロキサン組成物 |
| JP3344286B2 (ja) | 1997-06-12 | 2002-11-11 | 信越化学工業株式会社 | 付加硬化型シリコーン樹脂組成物 |
| JP2000336272A (ja) * | 1999-05-28 | 2000-12-05 | Shin Etsu Chem Co Ltd | 定着ロール用液状付加硬化型シリコーンゴム組成物及び定着ロール |
| JP4009067B2 (ja) | 2001-03-06 | 2007-11-14 | 信越化学工業株式会社 | 付加硬化型シリコーン樹脂組成物 |
| JP2004186168A (ja) * | 2002-11-29 | 2004-07-02 | Shin Etsu Chem Co Ltd | 発光ダイオード素子用シリコーン樹脂組成物 |
| US7160972B2 (en) * | 2003-02-19 | 2007-01-09 | Nusil Technology Llc | Optically clear high temperature resistant silicone polymers of high refractive index |
| DE10359705A1 (de) * | 2003-12-18 | 2005-07-14 | Wacker-Chemie Gmbh | Additionsvernetzende Siliconharzzusammensetzungen |
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2003
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2004
- 2004-12-17 EP EP04807824A patent/EP1695124B1/en not_active Expired - Lifetime
- 2004-12-17 KR KR1020067014390A patent/KR101176931B1/ko not_active Expired - Fee Related
- 2004-12-17 AT AT04807824T patent/ATE442597T1/de not_active IP Right Cessation
- 2004-12-17 CN CNB2004800377939A patent/CN100489563C/zh not_active Expired - Fee Related
- 2004-12-17 DE DE602004023118T patent/DE602004023118D1/de not_active Expired - Lifetime
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Also Published As
| Publication number | Publication date |
|---|---|
| DE602004023118D1 (de) | 2009-10-22 |
| KR101176931B1 (ko) | 2012-08-30 |
| ATE442597T1 (de) | 2009-09-15 |
| EP1695124A2 (en) | 2006-08-30 |
| WO2005062080A2 (en) | 2005-07-07 |
| CN1894600A (zh) | 2007-01-10 |
| US20070244214A1 (en) | 2007-10-18 |
| KR20070004581A (ko) | 2007-01-09 |
| CN100489563C (zh) | 2009-05-20 |
| JP2005179541A (ja) | 2005-07-07 |
| WO2005062080A3 (en) | 2006-03-02 |
| US7649059B2 (en) | 2010-01-19 |
| EP1695124B1 (en) | 2009-09-09 |
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