JP4607600B2 - エポキシ官能性ハイブリッドコポリマー - Google Patents
エポキシ官能性ハイブリッドコポリマー Download PDFInfo
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- JP4607600B2 JP4607600B2 JP2004565245A JP2004565245A JP4607600B2 JP 4607600 B2 JP4607600 B2 JP 4607600B2 JP 2004565245 A JP2004565245 A JP 2004565245A JP 2004565245 A JP2004565245 A JP 2004565245A JP 4607600 B2 JP4607600 B2 JP 4607600B2
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- Prior art keywords
- epoxy
- copolymer
- bis
- reaction
- hybrid
- 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.)
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- 239000004593 Epoxy Substances 0.000 title claims description 124
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- 239000000203 mixture Substances 0.000 claims description 115
- -1 siloxane units Chemical group 0.000 claims description 26
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 20
- 229920001187 thermosetting polymer Polymers 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 14
- PRJNEUBECVAVAG-UHFFFAOYSA-N 1,3-bis(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1 PRJNEUBECVAVAG-UHFFFAOYSA-N 0.000 claims description 12
- WEERVPDNCOGWJF-UHFFFAOYSA-N 1,4-bis(ethenyl)benzene Chemical compound C=CC1=CC=C(C=C)C=C1 WEERVPDNCOGWJF-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 claims description 11
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
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- YTEISYFNYGDBRV-UHFFFAOYSA-N [(dimethyl-$l^{3}-silanyl)oxy-dimethylsilyl]oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)(C)O[Si](C)C YTEISYFNYGDBRV-UHFFFAOYSA-N 0.000 claims description 10
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- BCHXFGQPSOXSTC-UHFFFAOYSA-N 1-dimethylsilylethyl(dimethyl)silane Chemical compound C[SiH](C)C(C)[SiH](C)C BCHXFGQPSOXSTC-UHFFFAOYSA-N 0.000 claims description 8
- SCZZNWQQCGSWSZ-UHFFFAOYSA-N 1-prop-2-enoxy-4-[2-(4-prop-2-enoxyphenyl)propan-2-yl]benzene Chemical compound C=1C=C(OCC=C)C=CC=1C(C)(C)C1=CC=C(OCC=C)C=C1 SCZZNWQQCGSWSZ-UHFFFAOYSA-N 0.000 claims description 8
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- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 claims description 8
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- OQJPAHYVGNJBJK-UHFFFAOYSA-N (3-dimethylsilylphenyl)-dimethylsilane Chemical compound C[SiH](C)C1=CC=CC([SiH](C)C)=C1 OQJPAHYVGNJBJK-UHFFFAOYSA-N 0.000 claims description 7
- UHXCHUWSQRLZJS-UHFFFAOYSA-N (4-dimethylsilylidenecyclohexa-2,5-dien-1-ylidene)-dimethylsilane Chemical compound C[Si](C)C1=CC=C([Si](C)C)C=C1 UHXCHUWSQRLZJS-UHFFFAOYSA-N 0.000 claims description 7
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- MUUXBTFQEXVEEI-UHFFFAOYSA-N [2-(dimethyl-$l^{3}-silanyl)phenyl]-dimethylsilicon Chemical compound C[Si](C)C1=CC=CC=C1[Si](C)C MUUXBTFQEXVEEI-UHFFFAOYSA-N 0.000 claims description 7
- ILBWBNOBGCYGSU-UHFFFAOYSA-N [[(dimethyl-$l^{3}-silanyl)oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)(C)O[Si](C)(C)O[Si](C)C ILBWBNOBGCYGSU-UHFFFAOYSA-N 0.000 claims description 7
- WOCGGVRGNIEDSZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C=1C=C(O)C(CC=C)=CC=1C(C)(C)C1=CC=C(O)C(CC=C)=C1 WOCGGVRGNIEDSZ-UHFFFAOYSA-N 0.000 claims description 6
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 claims description 5
- TYMYJUHDFROXOO-UHFFFAOYSA-N 1,3-bis(prop-2-enoxy)-2,2-bis(prop-2-enoxymethyl)propane Chemical compound C=CCOCC(COCC=C)(COCC=C)COCC=C TYMYJUHDFROXOO-UHFFFAOYSA-N 0.000 claims description 5
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 claims description 5
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 claims description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 5
- 125000001033 ether group Chemical group 0.000 claims description 4
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims description 4
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 claims description 2
- GXBYFVGCMPJVJX-UHFFFAOYSA-N Epoxybutene Chemical compound C=CC1CO1 GXBYFVGCMPJVJX-UHFFFAOYSA-N 0.000 claims description 2
- 229940087305 limonene Drugs 0.000 claims description 2
- 235000001510 limonene Nutrition 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 96
- 238000007792 addition Methods 0.000 description 74
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 45
- 229920005989 resin Polymers 0.000 description 45
- 239000011347 resin Substances 0.000 description 45
- 238000009472 formulation Methods 0.000 description 37
- 229920000647 polyepoxide Polymers 0.000 description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
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- 239000000047 product Substances 0.000 description 23
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- 125000003700 epoxy group Chemical group 0.000 description 18
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- GJWAPAVRQYYSTK-UHFFFAOYSA-N [(dimethyl-$l^{3}-silanyl)amino]-dimethylsilicon Chemical compound C[Si](C)N[Si](C)C GJWAPAVRQYYSTK-UHFFFAOYSA-N 0.000 description 16
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- DQNSRQYYCSXZDF-UHFFFAOYSA-N 1,4-bis(ethenoxymethyl)cyclohexane Chemical compound C=COCC1CCC(COC=C)CC1 DQNSRQYYCSXZDF-UHFFFAOYSA-N 0.000 description 11
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Images
Classifications
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- 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
- C08G77/48—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/50—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon linkages
-
- 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
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
- C08G59/306—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen containing silicon
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/3254—Epoxy compounds containing three or more epoxy groups containing atoms other than carbon, hydrogen, oxygen or nitrogen
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
- Epoxy Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Sealing Material Composition (AREA)
- Paints Or Removers (AREA)
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| US7365135B2 (en) * | 2004-06-14 | 2008-04-29 | Chung-Shan Institute Of Science & Technology | Method for preparing a novolac phenolic resin/silica hybrid organic-inorganic nanocomposite |
| US20050282976A1 (en) * | 2004-06-22 | 2005-12-22 | Gelcore Llc. | Silicone epoxy formulations |
| DE102005009066A1 (de) * | 2005-02-28 | 2006-09-07 | Osram Opto Semiconductors Gmbh | Verfahren zur Herstellung eines optischen und eines strahlungsemittierenden Bauelementes und optisches sowie strahlungsemittierendes Bauelement |
| DE102005027404A1 (de) * | 2005-06-13 | 2006-12-14 | Schröders, Theo | Brandschutzglas und Verfahren zu dessen Herstellung |
| CN101460537B (zh) * | 2006-06-07 | 2012-07-04 | 昭和电工株式会社 | 新型环氧化合物及其制备方法 |
| KR100779560B1 (ko) | 2006-07-20 | 2007-11-29 | 연세대학교 산학협력단 | 유기 박막 트랜지스터용 자가 패턴성 유전체 박막, 그 제조 방법, 및 이를 구비한 유기 박막 트랜지스터 |
| US8084765B2 (en) * | 2007-05-07 | 2011-12-27 | Xerox Corporation | Electronic device having a dielectric layer |
| EP2192936B1 (en) * | 2007-08-20 | 2016-05-04 | Liebel-Flarsheim Company LLC | Fluid driven medical injectors |
| WO2009060862A1 (ja) * | 2007-11-07 | 2009-05-14 | Showa Denko K.K. | エポキシ基含有オルガノシロキサン化合物、転写材料用硬化性組成物および該組成物を用いた微細パターン形成方法 |
| WO2009119469A1 (ja) * | 2008-03-24 | 2009-10-01 | 昭和電工株式会社 | エポキシ化合物およびその製造方法 |
| US20100119796A1 (en) * | 2008-11-12 | 2010-05-13 | Brighten Engineering Co., Ltd. | Anticorrosive Nanocomposite Coating Material, and a Preparation Process Thereof |
| EP2445028A1 (en) * | 2010-10-25 | 2012-04-25 | Nederlandse Organisatie voor toegepast -natuurwetenschappelijk onderzoek TNO | Opto-electric device and method of manufacturing an opto-electric device |
| KR101252063B1 (ko) | 2011-08-25 | 2013-04-12 | 한국생산기술연구원 | 알콕시실릴기를 갖는 에폭시 화합물, 이의 제조 방법, 이를 포함하는 조성물과 경화물 및 이의 용도 |
| TWI629307B (zh) * | 2013-09-20 | 2018-07-11 | 日商信越化學工業股份有限公司 | Polyoxymethylene modified epoxy resin and its composition and hardened material |
| KR102315127B1 (ko) * | 2014-11-26 | 2021-10-20 | 에스케이이노베이션 주식회사 | 하드코팅층 형성용 조성물 |
| EP3321302B1 (en) | 2015-07-10 | 2021-06-30 | Sumitomo Seika Chemicals Co., Ltd. | Epoxy resin composition, process for producing same, and uses of said composition |
| EP3569653B1 (en) | 2017-01-10 | 2021-03-10 | Sumitomo Seika Chemicals Co. Ltd. | Epoxy resin composition |
| CN110177820B (zh) | 2017-01-10 | 2022-03-01 | 住友精化株式会社 | 环氧树脂组合物 |
| KR102459581B1 (ko) | 2017-01-10 | 2022-10-27 | 스미토모 세이카 가부시키가이샤 | 에폭시 수지 조성물 |
| CN110177819B (zh) | 2017-01-10 | 2022-11-08 | 住友精化株式会社 | 环氧树脂组合物 |
| KR102126045B1 (ko) * | 2017-07-21 | 2020-06-23 | 삼성에스디아이 주식회사 | 유기발광소자 봉지용 조성물 및 이로부터 제조된 유기발광소자 표시장치 |
| CN107814935B (zh) * | 2017-10-31 | 2020-11-24 | 江南大学 | 一种poss基有机-无机杂化八臂环氧树脂及其制备方法 |
| EP3578591A1 (en) | 2018-06-04 | 2019-12-11 | EMPA Eidgenössische Materialprüfungs- und Forschungsanstalt | Polymeric liquid molecular building block (mbb) material and method for producing the same |
| KR102232340B1 (ko) | 2019-11-15 | 2021-03-26 | 한국생산기술연구원 | 알콕시실릴기를 갖는 에폭시 수지의 조성물 및 이의 복합체 |
| CN111454689B (zh) * | 2019-12-31 | 2021-10-15 | 武汉长盈鑫科技有限公司 | 一种高玻璃化温度的导热胶及其制备方法 |
| CN117003991A (zh) * | 2022-04-29 | 2023-11-07 | 华为技术有限公司 | 环氧树脂及其制备方法和树脂组合物 |
| WO2025013726A1 (ja) * | 2023-07-07 | 2025-01-16 | 株式会社レゾナック | 接着剤組成物 |
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| US2946701A (en) | 1957-11-12 | 1960-07-26 | Dow Corning | Method of treating glass with epoxysilanes and their epoxy-amine adducts, and the articles made thereby |
| US2970150A (en) | 1957-12-17 | 1961-01-31 | Union Carbide Corp | Processes for the reaction of silanic hydrogen-bonded siloxanes with unsaturated organic compounds with a platinum catalyst |
| US2997458A (en) | 1958-10-03 | 1961-08-22 | Westinghouse Electric Corp | Epoxy-substituted organosilicone compounds |
| US4150048A (en) | 1978-03-28 | 1979-04-17 | Union Carbide Corporation | Nonhydrolyzable siloxane block copolymers of organosiloxanes and organic ethers |
| US4477326A (en) | 1983-06-20 | 1984-10-16 | Loctite Corporation | Polyphotoinitiators and compositions thereof |
| US5037861A (en) | 1989-08-09 | 1991-08-06 | General Electric Company | Novel highly reactive silicon-containing epoxides |
| US5260399A (en) | 1992-06-08 | 1993-11-09 | General Electric Company | Regiospecific catalyst for the synthesis of epoxysiloxane monomers and polymers |
| US5227410A (en) * | 1991-12-05 | 1993-07-13 | General Electric Company | Uv-curable epoxysilicone-polyether block copolymers |
| US5169962A (en) | 1990-09-17 | 1992-12-08 | General Electric Company | Preparation of epoxysilicon compounds using rhodium catalysts |
| US5387698A (en) | 1992-06-11 | 1995-02-07 | General Electric Company | Rhodium containing selective catalysts for the synthesis of epoxysiloxane/epoxysilicone monomers and polymers |
| JPH0774222B2 (ja) * | 1991-12-24 | 1995-08-09 | 信越化学工業株式会社 | シロキサン化合物 |
| US5378790A (en) | 1992-09-16 | 1995-01-03 | E. I. Du Pont De Nemours & Co. | Single component inorganic/organic network materials and precursors thereof |
| US5484950A (en) | 1992-12-21 | 1996-01-16 | Polyset Company, Inc. | Process for selective monoaddition to silanes containing two silicon-hydrogen bonds and products thereof |
| US5677410A (en) | 1995-05-16 | 1997-10-14 | Bayer Ag | Carbosilane-dendrimers, carbosilane-hybrid materials, methods for manufacturing them and a method for manufacturing coatings from the carbosilane-dendrimers |
| US5863970A (en) * | 1995-12-06 | 1999-01-26 | Polyset Company, Inc. | Epoxy resin composition with cycloaliphatic epoxy-functional siloxane |
| FI103051B (fi) * | 1997-08-22 | 1999-04-15 | Schering Oy | Uusia blokkikopolymeerejä ja niiden valmistus |
| US6184407B1 (en) | 1998-05-29 | 2001-02-06 | Dow Corning Toray Silicone Co., Ltd. | Carbosiloxane dendrimers |
| US6184313B1 (en) | 1999-07-08 | 2001-02-06 | National Research Council Of Canada | Hybrid silane dendrimer-star polymers |
| JP4236342B2 (ja) | 1999-07-30 | 2009-03-11 | 東レ・ダウコーニング株式会社 | カルボシロキサンデンドリマーおよびデンドリマー含有有機重合体 |
| US6476174B1 (en) | 2001-06-15 | 2002-11-05 | Industrial Technology Research Institute | Process for preparing a silica-based organic-inorganic hybrid resin and the organic-inorganic hybrid resin prepared therefrom |
-
2002
- 2002-12-20 US US10/327,353 patent/US7034089B2/en not_active Expired - Fee Related
-
2003
- 2003-12-08 AU AU2003296306A patent/AU2003296306A1/en not_active Abandoned
- 2003-12-08 CN CNB2003801097786A patent/CN100396716C/zh not_active Expired - Fee Related
- 2003-12-08 KR KR1020057011443A patent/KR20050085802A/ko not_active Abandoned
- 2003-12-08 EP EP03814660A patent/EP1572781A1/en not_active Withdrawn
- 2003-12-08 WO PCT/US2003/038875 patent/WO2004060976A1/en not_active Ceased
- 2003-12-08 JP JP2004565245A patent/JP4607600B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1747987A (zh) | 2006-03-15 |
| US7034089B2 (en) | 2006-04-25 |
| AU2003296306A1 (en) | 2004-07-29 |
| EP1572781A1 (en) | 2005-09-14 |
| CN100396716C (zh) | 2008-06-25 |
| WO2004060976A1 (en) | 2004-07-22 |
| US20040122186A1 (en) | 2004-06-24 |
| KR20050085802A (ko) | 2005-08-29 |
| JP2006511664A (ja) | 2006-04-06 |
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