JP4259867B2 - 液晶のレオロジー及び転移温度を調節するための新規な方法及びブレンド - Google Patents
液晶のレオロジー及び転移温度を調節するための新規な方法及びブレンド Download PDFInfo
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- JP4259867B2 JP4259867B2 JP2002559621A JP2002559621A JP4259867B2 JP 4259867 B2 JP4259867 B2 JP 4259867B2 JP 2002559621 A JP2002559621 A JP 2002559621A JP 2002559621 A JP2002559621 A JP 2002559621A JP 4259867 B2 JP4259867 B2 JP 4259867B2
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- 238000003828 vacuum filtration Methods 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
- C09K2019/2078—Ph-COO-Ph-COO-Ph
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S585/00—Chemistry of hydrocarbon compounds
- Y10S585/929—Special chemical considerations
- Y10S585/93—Process including synthesis of nonhydrocarbon intermediate
- Y10S585/935—Halogen-containing
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (4)
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| US26339201P | 2001-01-23 | 2001-01-23 | |
| US26338801P | 2001-01-23 | 2001-01-23 | |
| US26338701P | 2001-01-23 | 2001-01-23 | |
| PCT/US2002/001905 WO2002059553A2 (en) | 2001-01-23 | 2002-01-23 | Novel methods and blends for controlling rehology and transition temperature of liquid crystals |
Publications (3)
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| JP2004526816A JP2004526816A (ja) | 2004-09-02 |
| JP2004526816A5 JP2004526816A5 (enExample) | 2005-12-22 |
| JP4259867B2 true JP4259867B2 (ja) | 2009-04-30 |
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| EP (1) | EP1366133B1 (enExample) |
| JP (1) | JP4259867B2 (enExample) |
| AT (1) | ATE461986T1 (enExample) |
| AU (1) | AU2002243644A1 (enExample) |
| CA (1) | CA2435644C (enExample) |
| DE (1) | DE60235748D1 (enExample) |
| WO (1) | WO2002059553A2 (enExample) |
Families Citing this family (25)
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| US6194481B1 (en) * | 1999-05-19 | 2001-02-27 | Board Of Regents Of The University Of Texas System | Mechanically strong and transparent or translucent composites made using zirconium oxide nanoparticles |
| DE60235748D1 (de) * | 2001-01-23 | 2010-05-06 | Southwest Res Inst | Neue verfahren und mischungen zum einstellen des rheologischen verhaltens und der übergangstemperatur von flüssigkristallen |
| US20040199004A1 (en) * | 2001-01-23 | 2004-10-07 | Southwest Research Institute | Novel mesogens |
| US7147800B2 (en) * | 2001-01-23 | 2006-12-12 | Southwest Research Institute | Selective ether cleavage synthesis of liquid crystals |
| DE60207838T2 (de) * | 2001-03-07 | 2006-07-06 | The University Of Texas System, Austin | Verbundharze mit ultraniedriger schrumpfung auf grundlage von mischungen nematischer flüssigkristallmonomere |
| JP4223394B2 (ja) | 2001-07-09 | 2009-02-12 | サウスウェスト リサーチ インスティテュート | 新規メソゲン及びそれらの合成及び使用 |
| US7632540B2 (en) | 2003-07-01 | 2009-12-15 | Transitions Optical, Inc. | Alignment facilities for optical dyes |
| CA2584104C (en) * | 2004-10-19 | 2012-12-11 | Rolls-Royce Corporation | Method and apparatus associated with anisotropic shrink in sintered ceramic items |
| JP5227623B2 (ja) * | 2008-03-18 | 2013-07-03 | 富士フイルム株式会社 | 複屈折パターンを有する物品の製造方法 |
| US20100014010A1 (en) * | 2008-06-27 | 2010-01-21 | Transitions Optical, Inc. | Formulations comprising mesogen containing compounds |
| US20090326186A1 (en) * | 2008-06-27 | 2009-12-31 | Transitions Optical, Inc. | Mesogen containing compounds |
| US8349210B2 (en) | 2008-06-27 | 2013-01-08 | Transitions Optical, Inc. | Mesogenic stabilizers |
| US8628685B2 (en) * | 2008-06-27 | 2014-01-14 | Transitions Optical, Inc | Mesogen-containing compounds |
| US8623238B2 (en) | 2008-06-27 | 2014-01-07 | Transitions Optical, Inc. | Mesogenic stabilizers |
| US8613868B2 (en) | 2008-06-27 | 2013-12-24 | Transitions Optical, Inc | Mesogenic stabilizers |
| US7910020B2 (en) * | 2008-06-27 | 2011-03-22 | Transitions Optical, Inc. | Liquid crystal compositions comprising mesogen containing compounds |
| US7910019B2 (en) | 2008-06-27 | 2011-03-22 | Transitions Optical, Inc. | Mesogen containing compounds |
| US8431039B2 (en) | 2008-06-27 | 2013-04-30 | Transitions Optical, Inc. | Mesogenic stabilizers |
| US9475901B2 (en) | 2009-12-08 | 2016-10-25 | Transitions Optical, Inc. | Photoalignment materials having improved adhesion |
| US9103046B2 (en) | 2010-07-07 | 2015-08-11 | Southwest Research Institute | Electrophoretic formation of nanostructured composites |
| WO2015141784A1 (ja) * | 2014-03-19 | 2015-09-24 | 日本ゼオン株式会社 | 重合性化合物の製造方法 |
| CN109689366B (zh) | 2016-05-05 | 2022-12-02 | 西南研究院 | 用于细胞扩增和相关应用的三维生物反应器 |
| US11149244B2 (en) | 2018-04-04 | 2021-10-19 | Southwest Research Institute | Three-dimensional bioreactor for T-cell activation and expansion for immunotherapy |
| US11447731B2 (en) | 2018-09-24 | 2022-09-20 | Southwest Research Institute | Three-dimensional bioreactors |
| US11492580B2 (en) | 2020-05-12 | 2022-11-08 | Southwest Research Institute | Method using a three-dimensional bioprocessor |
Family Cites Families (103)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1393216A (en) * | 1972-10-05 | 1975-05-07 | Werk Fernsehelektronik Veb | Liquid crystalline nematic substance comprising diesters of 2-substituted hydroquinone and applications thereof |
| US4201856A (en) | 1978-05-08 | 1980-05-06 | Eastman Kodak Company | Liquid crystal copolyesters containing terephthalic acid, 2,6-naphthalenedicarboxylic acid, hydroquinone and resorcinol |
| US4215033A (en) * | 1978-09-08 | 1980-07-29 | American Dental Association Health Foundation | Composite dental material |
| USRE32073E (en) * | 1980-09-08 | 1986-01-28 | Minnesota Mining And Manufacturing Company | Dental filling composition utilizing zinc-containing inorganic filler |
| US4659751A (en) | 1983-01-10 | 1987-04-21 | American Dental Association Health Foundation | Simplified method for obtained strong adhesive bonding of composites to dentin, enamel and other substrates |
| US4588756A (en) * | 1983-01-10 | 1986-05-13 | American Dental Association Health Foundation | Multi-step method for obtaining strong adhesive bonding of composites to dentin, enamel and other substrates |
| US4539048A (en) | 1983-02-09 | 1985-09-03 | Jos. Cavedon Company Inc. | Aluminum zirconium metallo-organic complexes useful as coupling agents |
| US4503169A (en) | 1984-04-19 | 1985-03-05 | Minnesota Mining And Manufacturing Company | Radiopaque, low visual opacity dental composites containing non-vitreous microparticles |
| US4753652A (en) | 1984-05-04 | 1988-06-28 | Children's Medical Center Corporation | Biomaterial implants which resist calcification |
| US4623738A (en) | 1985-04-22 | 1986-11-18 | Kenrich Petrochemicals, Inc. | Neoalkoxy organo-titanates and organo-zirconates useful as coupling and polymer processing agents |
| US5276068A (en) * | 1985-03-29 | 1994-01-04 | Jeneric/Pentron, Inc. | Dental resin materials |
| US4663147A (en) * | 1985-09-03 | 1987-05-05 | International Minerals & Chemical Corp. | Disc-like sustained release formulation |
| EP0242278A3 (en) | 1986-04-11 | 1989-06-14 | The Board Of Trustees Of The University Of Illinois | Polymers having enhanced electrical and magnetic properties |
| US5057018A (en) | 1986-05-13 | 1991-10-15 | American Dental Association - Health Foundation | Microcrystalline inserts for megafilled composite dental restorations |
| DE3726999A1 (de) * | 1987-08-13 | 1989-02-23 | Consortium Elektrochem Ind | Dimethylsilyl-substituierte benzoylchloride und verfahren zu ihrer herstellung |
| US4964911A (en) * | 1987-10-13 | 1990-10-23 | Den-Mat Corporation | Adhesive bonding of acrylic resins, especially in dentistry |
| US4978640A (en) | 1988-02-24 | 1990-12-18 | Massachusetts Institute Of Technology | Dispersion strengthened composite |
| DE3824333A1 (de) | 1988-07-18 | 1990-01-25 | Fraunhofer Ges Forschung | Verfahren zur fixierung einer anorganischen spezies in einer organischen matrix |
| US5151453A (en) * | 1989-04-06 | 1992-09-29 | Den-Mat Corporation | Light-curable ionomer dental cement |
| NL8901167A (nl) * | 1989-05-10 | 1990-12-03 | Philips Nv | Methode voor de vervaardiging van een polarisatiefilter, een aldus verkregen polarisatiefilter en een display dat voorzien is van het polarisatiefilter. |
| JPH04305001A (ja) | 1989-08-23 | 1992-10-28 | Fraunhofer Ges | 酸化物マトリックス中に金属小粒子または金属酸化物小粒子を含む複合材料の製造方法 |
| DE69017347T2 (de) * | 1989-10-18 | 1995-09-21 | Philips Electronics Nv | Molekular orientierte Kunststoffzusammensetzung. |
| US5073294A (en) * | 1990-03-07 | 1991-12-17 | Hercules Incorporated | Process of preparing compositions having multiple oriented mesogens |
| JPH0649737B2 (ja) | 1990-04-20 | 1994-06-29 | 株式会社総合歯科医療研究所 | 強靭な厚肉注型品製造用の光硬化型樹脂用組成物 |
| US5202053A (en) | 1991-02-22 | 1993-04-13 | Hercules Incorporated | Polymerizable nematic monomer compositions |
| DE9103321U1 (de) | 1991-03-19 | 1992-08-27 | Thera Patent GmbH & Co KG Gesellschaft für industrielle Schutzrechte, 8031 Seefeld | Transparentversiegelter Dentalkunststoffkörper |
| JP3108783B2 (ja) | 1991-07-10 | 2000-11-13 | 石原薬品株式会社 | 新規アゾール化合物、及び該化合物を含有する錫、鉛または錫−鉛合金めっき浴 |
| JP3071280B2 (ja) | 1991-12-26 | 2000-07-31 | 株式会社トクヤマ | 2官能(メタ)アクリレート |
| JP2642554B2 (ja) | 1991-12-27 | 1997-08-20 | 電気化学工業株式会社 | 接着剤組成物 |
| EP0591508B2 (en) * | 1992-04-27 | 2003-01-15 | MERCK PATENT GmbH | Electrooptical liquid crystal system |
| JP2611093B2 (ja) | 1992-07-07 | 1997-05-21 | ホーヤ株式会社 | 硬化膜を有する光学部材 |
| JP2980457B2 (ja) * | 1992-08-04 | 1999-11-22 | 東陶機器株式会社 | 衛生陶器用素地及びその製造方法 |
| DE59309022D1 (de) * | 1992-11-25 | 1998-11-05 | Rauter Vita Zahnfabrik | Verfahren zur Herstellung von Zahnersatz auf Keramikbasis |
| WO1994016129A1 (en) | 1993-01-13 | 1994-07-21 | Ppg Industries, Inc. | Chemically treated inorganic oxide fibers with thermal stability suitable for high temperature polymers |
| JPH06265830A (ja) * | 1993-03-11 | 1994-09-22 | Nikon Corp | 着色されたプラスチックレンズ |
| US6258974B1 (en) * | 1993-04-13 | 2001-07-10 | Southwest Research Institute | Metal oxide compositions composites thereof and method |
| US5372796A (en) | 1993-04-13 | 1994-12-13 | Southwest Research Institute | Metal oxide-polymer composites |
| US5720805A (en) * | 1993-04-13 | 1998-02-24 | Southwest Research Institute | Titanium-tin-oxide nanoparticles, compositions utilizing the same, and the method of forming the same |
| US6696585B1 (en) * | 1993-04-13 | 2004-02-24 | Southwest Research Institute | Functionalized nanoparticles |
| US6417244B1 (en) * | 1993-04-13 | 2002-07-09 | Southwest Research Institute | Metal oxide compositions and methods |
| US6500879B1 (en) | 1993-04-19 | 2002-12-31 | Dentsply Research & Development Corp. | Dental composition and method |
| US5998499A (en) | 1994-03-25 | 1999-12-07 | Dentsply G.M.B.H. | Liquid crystalline (meth)acrylate compounds, composition and method |
| US5624976A (en) * | 1994-03-25 | 1997-04-29 | Dentsply Gmbh | Dental filling composition and method |
| US5502087A (en) * | 1993-06-23 | 1996-03-26 | Dentsply Research & Development Corp. | Dental composition, prosthesis, and method for making dental prosthesis |
| DE4324431A1 (de) * | 1993-07-21 | 1995-01-26 | Bayer Ag | Acrylate und Methacrylate aus Basis von Cyclohexyldiphenolen |
| US5530038A (en) * | 1993-08-02 | 1996-06-25 | Sun Medical Co., Ltd. | Primer composition and curable composition |
| DE4332733A1 (de) | 1993-09-25 | 1995-03-30 | Basf Ag | Flüssigkristalline Verbindungen |
| DE69422256D1 (de) | 1993-10-15 | 2000-01-27 | Merck Patent Gmbh | Reaktive Flüssigkristallverbindungen |
| DE4408171A1 (de) * | 1994-03-11 | 1995-09-14 | Basf Ag | Neue polymerisierbare flüssigkristalline Verbindungen |
| US5507981A (en) * | 1994-05-31 | 1996-04-16 | Tel Ventures, Inc. | Method for molding dental restorations |
| EP0689065B1 (de) * | 1994-06-24 | 2001-06-27 | Rolic AG | Optisches Bauelement |
| JP3085570B2 (ja) | 1994-07-08 | 2000-09-11 | 株式会社トクヤマ | 重合性組成物 |
| US5563230A (en) * | 1994-09-09 | 1996-10-08 | National Science Council | Chiral smectic liquid crystalline polymers |
| DE4442831A1 (de) | 1994-12-01 | 1996-06-05 | Consortium Elektrochem Ind | Verfahren zur Herstellung von Benzoesäure(4-hydroxyphenylester)-Derivaten |
| DE4443702A1 (de) * | 1994-12-08 | 1996-06-13 | Ivoclar Ag | Feinkörnige unter Druck oder Scherbeanspruchung fließfähige polymerisierbare Zusammensetzungen |
| JPH08157597A (ja) | 1994-12-09 | 1996-06-18 | Shin Etsu Chem Co Ltd | ポリイミド共重合体及びその製造方法 |
| DE19500674A1 (de) | 1995-01-12 | 1996-07-18 | Degussa | Oberflächenmodifizierte pyrogen hergestellte Mischoxide, Verfahren zu ihrer Herstellung und Verwendung |
| CN1173891A (zh) | 1995-02-06 | 1998-02-18 | 默克专利股份有限公司 | 双活性内消旋化合物及其中间产物 |
| GB2297549B (en) | 1995-02-06 | 1999-06-30 | Merck Patent Gmbh | Direactive mesogenic compound |
| DE19511448A1 (de) | 1995-03-30 | 1996-10-02 | Basf Ag | Flüssigkristalline Allene |
| JPH08291016A (ja) | 1995-04-17 | 1996-11-05 | G C:Kk | 光重合性義歯床用裏装材 |
| DE19525941C2 (de) | 1995-07-18 | 1999-11-25 | Ivoclar Ag Schaan | Polymerisierbares flüssigkristallines Monomer, Dentalmaterialien auf der Basis von flüssig-kristallinen Monomeren und Verwendung eines polymerisierbaren Monomers mit flüssigkristallinen Eigenschaften zur Herstellung eines Dentalmaterials |
| DE19529049C1 (de) * | 1995-07-31 | 1997-03-20 | Mannesmann Ag | Hochgeschwindigkeits-Dünnbrammenanlage |
| US5811504A (en) * | 1995-08-03 | 1998-09-22 | Cornell Research Foundation, Inc. | Liquid crystalline epoxy monomer and liquid crystalline epoxy resin containing mesogen twins |
| DE19532408A1 (de) * | 1995-09-01 | 1997-03-06 | Basf Ag | Polymerisierbare flüssigkristalline Verbindungen |
| GB9522176D0 (en) | 1995-10-30 | 1996-01-03 | Iaf Biochem Int | Morphinan derivatives having neuroprotective activity |
| WO1997030136A1 (en) * | 1996-02-15 | 1997-08-21 | Merck Patent Gmbh | Cholesteric flakes |
| US5730601A (en) | 1996-03-11 | 1998-03-24 | The Regents Of The University Of Colorado | Method and material for use with dental composites for improving conversion of monomers to polymers and reducing volume shrinkage |
| KR100422497B1 (ko) * | 1996-03-19 | 2004-05-17 | 메르크 파텐트 게젤샤프트 미트 베쉬랭크터 하프퉁 | 액정표시장치 |
| DE19613314A1 (de) | 1996-04-03 | 1997-10-09 | Basf Ag | Polymerisierte flüssigkristalline Zusammensetzungen |
| GB2329636B (en) * | 1996-07-01 | 2000-07-19 | Merck Patent Gmbh | Chiral dopants |
| GB2315072B (en) * | 1996-07-04 | 2000-09-13 | Merck Patent Gmbh | Circular UV polariser |
| GB2315760B (en) * | 1996-07-25 | 2001-01-10 | Merck Patent Gmbh | Thermochromic polymerizable mesogenic composition |
| JP2852737B2 (ja) * | 1996-07-31 | 1999-02-03 | 象印チエンブロック株式会社 | ベルト式巻上機 |
| TW472081B (en) * | 1996-09-17 | 2002-01-11 | Merck Patent Gmbh | Optical retardation film |
| WO1998013008A1 (en) * | 1996-09-27 | 1998-04-02 | Southwest Research Institute | Metal oxide compositions and methods |
| DE19649056A1 (de) | 1996-11-27 | 1998-05-28 | Basf Ag | Polymerisierbare Oligomesogene |
| US5808108A (en) * | 1997-01-15 | 1998-09-15 | Chappelow; Cecil C. | Polymeric compositions and composites prepared from spiroorthocarbonates and epoxy monomers |
| US5995514A (en) * | 1997-01-31 | 1999-11-30 | Advanced Micro Devices, Inc. | Reversible media independent interface |
| US5865623A (en) * | 1997-03-12 | 1999-02-02 | Bisco, Inc. | Flexible dental composite compositions and restorative methods using flexible dental compositions |
| DE19714119A1 (de) | 1997-04-05 | 1998-10-08 | Daimler Benz Ag | Verbindungen, Verfahren zu deren Herstellung sowie Verfahren zur Herstellung flüssigkristalliner Polymere unter Verwendung dieser Verbindungen |
| US5871865A (en) | 1997-05-15 | 1999-02-16 | Valence Technology, Inc. | Methods of fabricating electrochemical cells |
| US5859089A (en) * | 1997-07-01 | 1999-01-12 | The Kerr Corporation | Dental restorative compositions |
| JPH1195205A (ja) * | 1997-09-18 | 1999-04-09 | Dainippon Ink & Chem Inc | 光学異方体フィルムとその製造方法及び液晶表示装置 |
| JP4451501B2 (ja) | 1997-10-03 | 2010-04-14 | デンツプライ インターナショナル インコーポレーテッド | ナノスケールの充填剤を含む歯科材料 |
| DE19843724A1 (de) | 1997-10-08 | 1999-04-15 | Basf Ag | Polymerisierbare chirale Verbindungen und deren Verwendung |
| DE69932272T2 (de) * | 1998-03-05 | 2007-07-12 | Rockwell International Corp., Thousand Oaks | Optische Verzögerungsschicht |
| JP4246813B2 (ja) * | 1998-05-18 | 2009-04-02 | 日産自動車株式会社 | 自動車用非石綿ディスクブレーキパッド |
| US5852248A (en) | 1998-05-21 | 1998-12-22 | Den-Mat Corporation | Method for accurate replication of shaped articles using sinterable powders |
| DE19824972A1 (de) | 1998-06-04 | 1999-12-09 | Basf Ag | Verwendung von cholesterisch-flüssigkristallinen Zusammensetzungen als UV-Filter in kosmetischen und pharmazeutischen Zubereitungen |
| US6204302B1 (en) * | 1998-11-20 | 2001-03-20 | Bisco, Inc. | Photosensitizers for free radical polymerization initiation resins and method of making the same |
| GB9907801D0 (en) * | 1999-04-06 | 1999-06-02 | Rolic Ag | Photoactive polymers |
| US6194481B1 (en) * | 1999-05-19 | 2001-02-27 | Board Of Regents Of The University Of Texas System | Mechanically strong and transparent or translucent composites made using zirconium oxide nanoparticles |
| US6087816A (en) * | 1999-06-29 | 2000-07-11 | Maxim Integrated Products, Inc. | Step-up/step-down switching regulators and pulse width modulation control therefor |
| DE10016524A1 (de) | 2000-04-03 | 2001-10-04 | Basf Ag | Polymerisierbare Flüssigkristalle |
| US6371806B1 (en) * | 2000-11-08 | 2002-04-16 | Hon Hai Precision Ind. Co., Ltd. | Cable end connector having accurately positioned connection terminal therein |
| WO2002059227A2 (en) * | 2001-01-23 | 2002-08-01 | Southwest Research Institute | Novel mesogens |
| DE60235748D1 (de) | 2001-01-23 | 2010-05-06 | Southwest Res Inst | Neue verfahren und mischungen zum einstellen des rheologischen verhaltens und der übergangstemperatur von flüssigkristallen |
| US7147800B2 (en) * | 2001-01-23 | 2006-12-12 | Southwest Research Institute | Selective ether cleavage synthesis of liquid crystals |
| US20040199004A1 (en) * | 2001-01-23 | 2004-10-07 | Southwest Research Institute | Novel mesogens |
| DE60207838T2 (de) * | 2001-03-07 | 2006-07-06 | The University Of Texas System, Austin | Verbundharze mit ultraniedriger schrumpfung auf grundlage von mischungen nematischer flüssigkristallmonomere |
| JP4223394B2 (ja) * | 2001-07-09 | 2009-02-12 | サウスウェスト リサーチ インスティテュート | 新規メソゲン及びそれらの合成及び使用 |
| TW563654U (en) | 2002-03-07 | 2003-11-21 | Link Treasure Ltd | Two-way safety lock structure for single-hand trolley collapsing |
-
2002
- 2002-01-23 DE DE60235748T patent/DE60235748D1/de not_active Expired - Lifetime
- 2002-01-23 AU AU2002243644A patent/AU2002243644A1/en not_active Abandoned
- 2002-01-23 EP EP02709143A patent/EP1366133B1/en not_active Expired - Lifetime
- 2002-01-23 US US10/057,548 patent/US7041234B2/en not_active Expired - Lifetime
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Also Published As
| Publication number | Publication date |
|---|---|
| AU2002243644A1 (en) | 2002-08-06 |
| JP2004526816A (ja) | 2004-09-02 |
| ATE461986T1 (de) | 2010-04-15 |
| EP1366133B1 (en) | 2010-03-24 |
| WO2002059553A3 (en) | 2002-09-19 |
| CA2435644A1 (en) | 2002-08-01 |
| US7108801B2 (en) | 2006-09-19 |
| EP1366133A4 (en) | 2004-04-14 |
| US20020177727A1 (en) | 2002-11-28 |
| WO2002059553A2 (en) | 2002-08-01 |
| DE60235748D1 (de) | 2010-05-06 |
| CA2435644C (en) | 2010-06-01 |
| US20030036609A1 (en) | 2003-02-20 |
| WO2002059553A8 (en) | 2002-11-07 |
| EP1366133A2 (en) | 2003-12-03 |
| US7041234B2 (en) | 2006-05-09 |
| US20030055280A1 (en) | 2003-03-20 |
| US7238831B2 (en) | 2007-07-03 |
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