WO2005054371A2 - Addition-curable organopolysiloxane resin composition and an optical material - Google Patents
Addition-curable organopolysiloxane resin composition and an optical material Download PDFInfo
- Publication number
- WO2005054371A2 WO2005054371A2 PCT/JP2004/018093 JP2004018093W WO2005054371A2 WO 2005054371 A2 WO2005054371 A2 WO 2005054371A2 JP 2004018093 W JP2004018093 W JP 2004018093W WO 2005054371 A2 WO2005054371 A2 WO 2005054371A2
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- WO
- WIPO (PCT)
- Prior art keywords
- groups
- range
- comprised
- weight
- alkenyl groups
- Prior art date
Links
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 54
- 239000011342 resin composition Substances 0.000 title claims abstract description 43
- 230000003287 optical effect Effects 0.000 title claims abstract description 30
- 239000000463 material Substances 0.000 title claims abstract description 28
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 66
- 239000000203 mixture Substances 0.000 claims abstract description 55
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 53
- 229920005989 resin Polymers 0.000 claims abstract description 39
- 239000011347 resin Substances 0.000 claims abstract description 39
- 238000007259 addition reaction Methods 0.000 claims abstract description 14
- 229920006136 organohydrogenpolysiloxane Polymers 0.000 claims abstract description 8
- 230000003197 catalytic effect Effects 0.000 claims abstract description 5
- 239000007809 chemical reaction catalyst Substances 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 239000004793 Polystyrene Substances 0.000 claims description 13
- 238000005227 gel permeation chromatography Methods 0.000 claims description 13
- 229920002223 polystyrene Polymers 0.000 claims description 13
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 8
- 229910014307 bSiO Inorganic materials 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- -1 methylphenylvinylsiloxane Chemical class 0.000 description 28
- 230000015572 biosynthetic process Effects 0.000 description 27
- 238000003786 synthesis reaction Methods 0.000 description 26
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 23
- 238000010992 reflux Methods 0.000 description 23
- 239000000047 product Substances 0.000 description 22
- 239000007787 solid Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 150000002430 hydrocarbons Chemical group 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 11
- 238000002834 transmittance Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical compound C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 238000011068 loading method Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- 229910020447 SiO2/2 Inorganic materials 0.000 description 7
- SORVFRRXWOKHGG-UHFFFAOYSA-N bis(2-methylprop-1-enylsilyloxy)-diphenylsilane Chemical class 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 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 229920002050 silicone resin Polymers 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 6
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- 238000000926 separation method Methods 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
- 239000002253 acid Substances 0.000 description 4
- 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 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- YLJJAVFOBDSYAN-UHFFFAOYSA-N dichloro-ethenyl-methylsilane Chemical compound C[Si](Cl)(Cl)C=C YLJJAVFOBDSYAN-UHFFFAOYSA-N 0.000 description 3
- 239000005054 phenyltrichlorosilane Substances 0.000 description 3
- 239000000377 silicon dioxide 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
- 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
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000006459 hydrosilylation reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000011417 postcuring Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- 238000012360 testing method Methods 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
- WZJUBBHODHNQPW-UHFFFAOYSA-N 2,4,6,8-tetramethyl-1,3,5,7,2$l^{3},4$l^{3},6$l^{3},8$l^{3}-tetraoxatetrasilocane Chemical compound C[Si]1O[Si](C)O[Si](C)O[Si](C)O1 WZJUBBHODHNQPW-UHFFFAOYSA-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
- 229910004668 SiO0.6 Inorganic materials 0.000 description 1
- 229910004747 SiO0.85 Inorganic materials 0.000 description 1
- 229910004731 SiO0.9 Inorganic materials 0.000 description 1
- 229910004738 SiO1 Inorganic materials 0.000 description 1
- 229910020487 SiO3/2 Inorganic materials 0.000 description 1
- 229910020485 SiO4/2 Inorganic materials 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000004132 cross linking 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
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000001993 dienes Chemical class 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
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 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 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
- 238000001125 extrusion Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000706 filtrate 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
- 238000007542 hardness measurement Methods 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920001843 polymethylhydrosiloxane Chemical group 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
- 230000009257 reactivity Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- 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
- 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
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
-
- 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
- C08G77/20—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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE602004025379T DE602004025379D1 (en) | 2003-12-02 | 2004-11-29 | ADDITION-CURABLE ORGANOPOLYSILOXANE-RESIN COMPOSITION AND OPTICAL MATERIAL |
AT04799945T ATE456624T1 (en) | 2003-12-02 | 2004-11-29 | ADDITION CURED ORGANOPOLYSILOXANE RESIN COMPOSITION AND OPTICAL MATERIAL |
EP04799945A EP1699875B1 (en) | 2003-12-02 | 2004-11-29 | Addition-curable organopolysiloxane resin composition and an optical material |
US10/581,422 US7625986B2 (en) | 2003-12-02 | 2004-11-29 | Additional-curable organopolysiloxane resin composition and an optical material |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2003402810A JP2005162859A (en) | 2003-12-02 | 2003-12-02 | Addition reaction curing type organopolysiloxane resin composition and optical member |
JP2003-402810 | 2003-12-02 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2005054371A2 true WO2005054371A2 (en) | 2005-06-16 |
WO2005054371A3 WO2005054371A3 (en) | 2005-08-11 |
Family
ID=34650044
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2004/018093 WO2005054371A2 (en) | 2003-12-02 | 2004-11-29 | Addition-curable organopolysiloxane resin composition and an optical material |
Country Status (10)
Country | Link |
---|---|
US (1) | US7625986B2 (en) |
EP (1) | EP1699875B1 (en) |
JP (1) | JP2005162859A (en) |
KR (1) | KR101150744B1 (en) |
CN (1) | CN100465233C (en) |
AT (1) | ATE456624T1 (en) |
DE (1) | DE602004025379D1 (en) |
MY (1) | MY140964A (en) |
TW (1) | TWI366589B (en) |
WO (1) | WO2005054371A2 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1878768A1 (en) | 2006-07-14 | 2008-01-16 | Shin-Etsu Chemical Co., Ltd. | Curable silicone rubber compositions and cured product thereof |
WO2009065644A1 (en) * | 2007-11-21 | 2009-05-28 | Evonik Goldschmidt Gmbh | Method for producing branched sih functional polysiloxanes and the use thereof for producting sic- and sioc-linked, branched organomodified polysiloxanes |
US7863392B2 (en) * | 2005-06-28 | 2011-01-04 | Dow Corning Toray Company, Ltd. | Curable organopolysiloxane resin composition and optical part molded therefrom |
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CN101163748B (en) * | 2005-05-26 | 2011-04-13 | 陶氏康宁公司 | Process and silicone encapsulant composition for molding small shapes |
EP1987084B1 (en) * | 2006-02-24 | 2014-11-05 | Dow Corning Corporation | Light emitting device encapsulated with silicones and curable silicone compositions for preparing the silicones |
JP5148088B2 (en) * | 2006-08-25 | 2013-02-20 | 東レ・ダウコーニング株式会社 | Curable organopolysiloxane composition and semiconductor device |
JP5085089B2 (en) * | 2006-10-17 | 2012-11-28 | モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社 | Silicone rubber composition |
WO2011125753A1 (en) * | 2010-04-02 | 2011-10-13 | 株式会社カネカ | Curable resin composition, curable resin composition tablet, molded body, semiconductor package, semiconductor component and light emitting diode |
KR101274418B1 (en) * | 2010-06-24 | 2013-06-17 | 세키스이가가쿠 고교가부시키가이샤 | Sealant for optical semiconductor devices and optical semiconductor device using same |
JP2012097225A (en) * | 2010-11-04 | 2012-05-24 | Daicel Corp | Curable resin composition and cured article |
KR20130140815A (en) * | 2010-12-08 | 2013-12-24 | 다우 코닝 코포레이션 | Siloxane compositions suitable for forming encapsulants |
EP2649131A1 (en) * | 2010-12-08 | 2013-10-16 | Dow Corning Corporation | Siloxane compositions including titanium dioxide nanoparticles suitable for forming encapsulants |
JP5992666B2 (en) * | 2011-06-16 | 2016-09-14 | 東レ・ダウコーニング株式会社 | Crosslinkable silicone composition and crosslinked product thereof |
KR101562091B1 (en) | 2011-11-25 | 2015-10-21 | 주식회사 엘지화학 | Curable composition |
EP2850122B1 (en) | 2012-05-14 | 2018-08-01 | Momentive Performance Materials Inc. | High refractive index material |
JP6046395B2 (en) * | 2012-06-29 | 2016-12-14 | 東レ・ダウコーニング株式会社 | Reactive silicone composition, reactive thermoplastic, cured product, and optical semiconductor device |
JP6400904B2 (en) * | 2012-08-03 | 2018-10-03 | 横浜ゴム株式会社 | Curable resin composition |
JP6157085B2 (en) | 2012-10-24 | 2017-07-05 | 東レ・ダウコーニング株式会社 | Curable silicone composition, cured product thereof, and optical semiconductor device |
JP6084808B2 (en) | 2012-10-24 | 2017-02-22 | 東レ・ダウコーニング株式会社 | Organopolysiloxane, curable silicone composition, cured product thereof, and optical semiconductor device |
JP6081774B2 (en) * | 2012-10-30 | 2017-02-15 | 東レ・ダウコーニング株式会社 | Curable silicone composition, cured product thereof, and optical semiconductor device |
CN103012456B (en) * | 2012-12-18 | 2015-11-18 | 烟台德邦先进硅材料有限公司 | A kind of preparation method of high-power LED encapsulation organosilicon oligomer |
US9470395B2 (en) | 2013-03-15 | 2016-10-18 | Abl Ip Holding Llc | Optic for a light source |
CN103232707B (en) * | 2013-04-19 | 2015-12-09 | 深圳新宙邦科技股份有限公司 | Curable silicone rubber composition and solidifying product thereof and coating and curing method |
US10807329B2 (en) | 2013-05-10 | 2020-10-20 | Abl Ip Holding Llc | Silicone optics |
KR20150097947A (en) * | 2014-02-19 | 2015-08-27 | 다우 코닝 코포레이션 | Reactive silicone composition, hotmelt material made therefrom, and curable hotmelt composition |
CN104892940B (en) * | 2014-03-05 | 2018-08-24 | 马凤国 | A kind of preparation method of siloxanes |
TW201602174A (en) * | 2014-05-23 | 2016-01-16 | Daicel Corp | Branched-chain polyorganosiloxycyl alkylene, method for producing same, curable resin composition, and semiconductor device |
CN105199397B (en) * | 2014-06-17 | 2018-05-08 | 广州慧谷化学有限公司 | A kind of curable organopolysiloxane composition and semiconductor devices |
DE102015225906A1 (en) * | 2015-12-18 | 2017-06-22 | Wacker Chemie Ag | Siloxanharzzusammensetzungen |
WO2017143508A1 (en) * | 2016-02-23 | 2017-08-31 | Dow Corning Corporation | Curable high hardness silicone composition and composite articles made thereof |
EP3808799A4 (en) * | 2018-06-12 | 2022-03-09 | Momentive Performance Materials Japan LLC | Manufacturing method for cured silicone product, cured silicone product, and optical member |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4198131A (en) * | 1978-03-23 | 1980-04-15 | Dow Corning Corporation | Silicone resin optical devices |
US6313190B1 (en) * | 1996-04-18 | 2001-11-06 | Kettenbach Gmbh & Co. Kg | Addition cross-linking, two-component silicone material with high shore hardness and high modulus of elasticity |
US20010039323A1 (en) * | 2000-04-06 | 2001-11-08 | Wacker-Chemie Gmbh | Addition-crosslinkable silicone compositions comprising low-molecular weight alkenyl-terminated polydiorganosiloxanes |
US20020161140A1 (en) * | 2001-03-06 | 2002-10-31 | Shin-Etsu Chemical Co., Ltd. | Addition curing type silicone resin composition |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3732330A (en) | 1972-03-08 | 1973-05-08 | Dow Corning | Curable compositions containing hydrogen-functional organopolysiloxanes |
US3944519A (en) | 1975-03-13 | 1976-03-16 | Dow Corning Corporation | Curable organopolysiloxane compositions |
US3948848A (en) | 1975-08-04 | 1976-04-06 | Dow Corning Corporation | Low temperature solventless silicone resins |
CA1133169A (en) | 1978-06-05 | 1982-10-05 | Dow Corning Corporation | Curable solventless organopolysiloxane compositions |
US4234713A (en) | 1979-05-29 | 1980-11-18 | Dow Corning Corporation | Curable solventless organopolysiloxane compositions |
JPH07292320A (en) * | 1994-04-22 | 1995-11-07 | Shin Etsu Chem Co Ltd | Primer composition and silicone laminate |
JPH0853622A (en) * | 1994-06-07 | 1996-02-27 | Shin Etsu Chem Co Ltd | Silicone gel composition |
JP3489639B2 (en) * | 1994-06-17 | 2004-01-26 | 信越化学工業株式会社 | Solvent-free releasable organopolysiloxane composition |
JPH10158400A (en) * | 1996-11-27 | 1998-06-16 | Shin Etsu Polymer Co Ltd | Optical lens |
JP3344286B2 (en) * | 1997-06-12 | 2002-11-11 | 信越化学工業株式会社 | Addition-curable silicone resin composition |
-
2003
- 2003-12-02 JP JP2003402810A patent/JP2005162859A/en active Pending
-
2004
- 2004-11-29 WO PCT/JP2004/018093 patent/WO2005054371A2/en active Application Filing
- 2004-11-29 US US10/581,422 patent/US7625986B2/en not_active Expired - Fee Related
- 2004-11-29 EP EP04799945A patent/EP1699875B1/en not_active Not-in-force
- 2004-11-29 DE DE602004025379T patent/DE602004025379D1/en active Active
- 2004-11-29 CN CNB2004800358196A patent/CN100465233C/en not_active Expired - Fee Related
- 2004-11-29 AT AT04799945T patent/ATE456624T1/en not_active IP Right Cessation
- 2004-11-30 MY MYPI20044941A patent/MY140964A/en unknown
- 2004-12-02 TW TW93137211A patent/TWI366589B/en not_active IP Right Cessation
-
2006
- 2006-06-30 KR KR20067013243A patent/KR101150744B1/en active IP Right Grant
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4198131A (en) * | 1978-03-23 | 1980-04-15 | Dow Corning Corporation | Silicone resin optical devices |
US6313190B1 (en) * | 1996-04-18 | 2001-11-06 | Kettenbach Gmbh & Co. Kg | Addition cross-linking, two-component silicone material with high shore hardness and high modulus of elasticity |
US20010039323A1 (en) * | 2000-04-06 | 2001-11-08 | Wacker-Chemie Gmbh | Addition-crosslinkable silicone compositions comprising low-molecular weight alkenyl-terminated polydiorganosiloxanes |
US20020161140A1 (en) * | 2001-03-06 | 2002-10-31 | Shin-Etsu Chemical Co., Ltd. | Addition curing type silicone resin composition |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7863392B2 (en) * | 2005-06-28 | 2011-01-04 | Dow Corning Toray Company, Ltd. | Curable organopolysiloxane resin composition and optical part molded therefrom |
KR101267306B1 (en) | 2005-06-28 | 2013-05-29 | 다우 코닝 도레이 캄파니 리미티드 | Curable organopolysiloxane resin composition and optical part molded therefrom |
EP1878768A1 (en) | 2006-07-14 | 2008-01-16 | Shin-Etsu Chemical Co., Ltd. | Curable silicone rubber compositions and cured product thereof |
US7989574B2 (en) | 2006-07-14 | 2011-08-02 | Shin-Etsu Chemical Co., Ltd. | Curable silicone rubber composition and cured product thereof |
KR101369115B1 (en) | 2006-07-14 | 2014-03-04 | 신에쓰 가가꾸 고교 가부시끼가이샤 | Curable silicone rubber composition and cured products thereof |
WO2009065644A1 (en) * | 2007-11-21 | 2009-05-28 | Evonik Goldschmidt Gmbh | Method for producing branched sih functional polysiloxanes and the use thereof for producting sic- and sioc-linked, branched organomodified polysiloxanes |
CN101842415B (en) * | 2007-11-21 | 2012-11-28 | 赢创高施米特有限公司 | Method for producing branched SiH functional polysiloxanes and the use thereof for producting SiC- and SiOC-linked, branched organomodified polysiloxanes |
US8598295B2 (en) | 2007-11-21 | 2013-12-03 | Evonik Goldschmidt Gmbh | Method for producing branched SiH functional polysiloxanes and the use thereof for producing SiC- and SiOC-linked, branched organomodified polysiloxanes |
Also Published As
Publication number | Publication date |
---|---|
WO2005054371A3 (en) | 2005-08-11 |
JP2005162859A (en) | 2005-06-23 |
KR20060135684A (en) | 2006-12-29 |
DE602004025379D1 (en) | 2010-03-18 |
TW200528518A (en) | 2005-09-01 |
EP1699875A2 (en) | 2006-09-13 |
MY140964A (en) | 2010-02-12 |
TWI366589B (en) | 2012-06-21 |
US20080033120A1 (en) | 2008-02-07 |
KR101150744B1 (en) | 2012-06-08 |
US7625986B2 (en) | 2009-12-01 |
CN100465233C (en) | 2009-03-04 |
CN1890324A (en) | 2007-01-03 |
ATE456624T1 (en) | 2010-02-15 |
EP1699875B1 (en) | 2010-01-27 |
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