WO2003027119A1 - Isosorbide derivatives - Google Patents
Isosorbide derivatives Download PDFInfo
- Publication number
- WO2003027119A1 WO2003027119A1 PCT/IB2002/003700 IB0203700W WO03027119A1 WO 2003027119 A1 WO2003027119 A1 WO 2003027119A1 IB 0203700 W IB0203700 W IB 0203700W WO 03027119 A1 WO03027119 A1 WO 03027119A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- isosorbide
- group
- derivative
- photo
- hydroxy
- Prior art date
Links
- 0 *c1ccc(C=Cc2ccc(CCl)cc2)cc1 Chemical compound *c1ccc(C=Cc2ccc(CCl)cc2)cc1 0.000 description 5
- CNBHBZZWRUQPTN-GDPLYGHDSA-N O[C@@H](CO[C@H]12)[C@@H]1OC[C@H]2OC1OCCCC1 Chemical compound O[C@@H](CO[C@H]12)[C@@H]1OC[C@H]2OC1OCCCC1 CNBHBZZWRUQPTN-GDPLYGHDSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- 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
- C09K19/58—Dopants or charge transfer agents
- C09K19/586—Optically active dopants; chiral dopants
-
- 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
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
- C09K2019/3408—Five-membered ring with oxygen(s) in fused, bridged or spiro ring systems
-
- 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
Definitions
- the invention pertains to an isosorbide derivative having at least one polymerizable group, to a method for the preparation thereof, to a cholesteric composition and an optical element comprising said isosorbide derivative, and to the use of the isosorbide derivative in optical elements.
- Isosorbide derivatives having a polymerizable group are known in the art.
- chiral dopants comprising an isosorbide moiety and ester groups.
- these chiral dopants are used to induce or enhance the helical twist of the molecules of a liquid crystalline medium, which can be used to make cholesteric color filters (CCF's).
- Such filters are made by applying a solution of a mixture of nematic compounds, for instance diacrylates, a photosensitive chiral compound, and a photo-initiator onto a substrate by using a coating technique such as spin coating.
- a coating technique such as spin coating.
- the pitch p of the molecular helix depends on the concentration of the chiral dopant and is proportional to a factor that is called the helical twisting power (HTP).
- the pitch of the helix and the direction of the helix determine the wavelength at which light reflects from the cholesteric liquid crystals and whether the reflected light is polarized right or left handed.
- High HTP values are required to allow the use of low concentrations of chiral dopant, which is important since these dopants are expensive and difficult to make. It is further explained that a short pitch is sometimes demanded, whereas for other applications a long pitch is required. This can be realized by adapting the concentration of the chiral dopant. For instance, by using sites with different concentrations or with different extents of dopant photo-isomerization, concentration gradient of free monomers could be formed during the isomerization process by using locations with high and low radiation intensity.
- This method was improved by the introduction of a photo- isomerizable chiral compound, preferably a chiral acrylate.
- the degree of conversion is determined by the radiation intensity, and the pitch of the cholesterically ordered material is determined by the unconverted or converted state of the photo-isomerizable compound.
- a specific chiral dopant that satisfies these conditions was disclosed to be a menthone derivative, which is a benzene derivative with an ether group separated by a spacer from an acrylic moiety and at the para position having an ester group comprising a photo- isomerizable cyclohexylidene moiety.
- the photo-isomerizable menthone derivative as used is far from ideal since it possess low twisting powers, requiring relatively high concentrations thereof, and more importantly, having only limited thermal stability. Since heating steps are necessary to make LCD's (liquid crystalline displays) color filters comprising these menthone derivatives lose their optical performance. Furthermore, it is desirable to improve the alignment capability of the prior art menthone derivatives.
- isosorbide derivatives can be provided with photo-convertible groups to give derivatives with extremely good thermal stability, high HTP values, and excellent alignment capability.
- the invention therefore relates to isosorbide derivatives having at least one polymerizable group, characterized in that the isosorbide derivative further comprises at least one photo-convertible group suitable for adjusting the helical twisting power of the isosorbide derivative.
- the photo-convertible group can be a group that is cyclized, cleaved, or rearranged upon irradiation.
- the photo-convertible group is a photo- isomerizable group.
- Suitable photo-isomerizable groups comprise an olephinic moiety that can undergo cis-trans isomerization upon irradiation. Examples of such groups are derived from styrene- and stilbene-like compounds.
- the isosorbide derivatives of the invention further comprise a polymerizable group.
- a suitable polymerizable group is the (meth)acrylate group.
- the isosorbide molecule contains two hydroxy groups, at least one thereof being esterified or etherified with a substituent.
- the substituents comprise the photo- convertible and photo-isomerizable groups.
- the photo-convertible and photo-isomerizable groups may be contained in the same or in different substituents.
- the different substituents comprise the same or different photo-convertible and/or photo- isomerizable groups, or that the photo-convertible and photo-isomerizable groups are contained in only one of the ester or ether substituents, whereas the other hydroxy group of the isosorbide is a free hydroxy group or is esterified or etherified with a substituent that does not comprise a photo-convertible and/or photo-isomerizable group.
- a preferred isosorbide derivative was found to have the formula
- A stands for a bond or a p-phenylene group
- Q and Q' are independently selected from H, C1-C3 alkyl, C1-C3 alkoxy, halogen, and CN; n is an integer from 1 to 3; and m is an integer from 0 to 2.
- C1-C3 alkyl means an alkyl group with 1 to 3 carbon atoms, i.e. methyl, ethyl, propyl, and isopropyl.
- C1-C3 alkoxy means an alkoxy group with these alkyl groups.
- halogen means a halogen atom, such as fluorine, chlorine, bromine, and iodine.
- A stands for a bond or a p-phenylene group
- Q is selected from H, C1-C3 alkyl, C1-C3 alkoxy, halogen, and CN; and m is an integer from 0 to 2. From a synthetic point of view it is preferred that in these compounds both 2- and 5-hydroxy substituents are the same. To prevent crystallization prior to polymerization, it is preferred to use compounds wherein the two substituents are different, i.e. wherein A, B, P, Q, o, and/or m are differently selected for the two substituents. When both substituents are the same, the synthesis can be simplified by using a direct etherification or esterification of isosorbide, without first selectively protecting the 5-hydroxy group.
- isosorbide derivatives according to this invention are:
- the isosorbide derivatives according to the invention may be used as a cholesteric composition mixed with other chiral compounds, for instance such as with a non- isomerizable isosorbide derivative (isosorbide C) of the formula:
- the isosorbide derivatives of the invention can be prepared in a manner, which is a modification of that as described in EP-Al -980,868 on page 7.
- the present modified synthesis enables to make isosorbides that selectively have different substituents at their 2- and 5-hydroxy groups.
- an additional temporary protection step is added, i.e. a step of selectively temporarily protecting the 2- hydroxy group, after which the 5-hydroxy group can selectively be etherified.
- the present method therefore comprises the steps of a) the synthesis of a 5-hydroxy ether-protected isosorbide from i) esterification of the 2-hydroxy group of isosorbide with a lower organic acid to an isosorbide 2-carboxylate, ii) etherification of the 5-hydroxy group of the isosorbide 2-carboxylate with an ether-protecting group, and iii) saponification of the 2-carboxylate group from the 5-hydroxy ether-protected isosorbide 2-carboxylate, b) followed by an etherification or esterification step of the 2-hydroxy group of the 5-hydroxy ether-protected isosorbide with an alcohol (or derivative thereof) or acid, respectively, optionally comprising polymerizable and/or photo-convertible groups, c) then a cleavage step of the ether-protective group to obtain an isosorbide derivative with a free 5-hydroxy group, and optionally d) an esterification step of the free 5-hydroxy group with an acid which optional
- This modified method has the advantage that no separation is necessary of the 5-hydroxy ether-protected isosorbide from the 2-hydroxy ether-protected, 2,5-dihydroxy ether-protected, and unprotected isosorbides.
- the ether-protecting group can be any common group that is know in the art for the protection of hydroxy groups through an ether linkage.
- Preferred ether-protective groups are the THP (tetrahydropyranyl) ether and the ethoxyethyl ether groups that are formed when a hydroxy group is reacted with 3,4-dihydro-2H-pyran and ethylvinylether, respectively, and which can easily cleaved under acidic conditions to release the hydroxy group.
- the a lower organic acid that is used in step i) of the above method preferably is acetic acid or halo-substituted acetic acid.
- the isosorbide derivatives of the invention exhibit a larger HTP than the prior art menthone derivatives of WO 00/34808, thus less material is required to obtain a blue reflective layer.
- the alignment of the CCF based on these isosorbide derivatives and therefore the reflection intensity is also significantly improved.
- the thermal stability is much higher than that of the menthone derivative based CCF's.
- a red layer is then obtained after a certain period of irradiation.
- a photo-convertible and a non-photo-convertible chiral dopant are used, e.g. isosorbides A or B together with C, and the concentrations are chosen properly, a layer can be obtained that reflects blue before irradiation and red in the photostationary state. This means that only the formation of a green color depends on the total UV dose, thus making the manufacture of a mask for pixelated irradiation very simple. This makes the isosorbide derivatives suitable for use in optical elements, preferably in optical color filters.
- Fig. 1A shows the transmission spectrum of a cholester color filter in accordance with the invention before heating and after heating at 200°C in air for the indicated times
- Fig. IB shows the transmission spectrum of a cholester color filter not in accordance before heating and after heating at 200°C in air for the indicated times.
- the aqueous layer was extracted again with dichloromethane (500ml).
- the combined organic layers were passed through filter paper, dried over magnesium sulfate and the solvent was evaporated to leave 154 g of a yellow viscous oil (yield 94%).
- Example 12 In a manner analogous to that of Example 11 a color filter reflecting at 450 nm (blue) before irradiation and 650 nm (red) after irradiation was made with a mixture of
- Example 12 was repeated with a mixture of
- Fig. 1A shows the transmission spectra of the CCF of Example 12 (according to the invention) before heating and after heating at 200°C in air for the indicated times.
- Fig. IB shows the transmission spectra of the CCF of Example 13 (comparative example) before heating and after heating at 200°C in air for the indicated times.
- the reflection band i.e. the minimum of transmission
- the intensity of the reflection band is large (minimum transmission 5%), and the transmission in wavelength regions other than the reflection band is high (-90%).
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2004-7004171A KR20040035864A (en) | 2001-09-24 | 2002-09-18 | Isosorbide derivatives |
JP2003530707A JP2005505577A (en) | 2001-09-24 | 2002-09-18 | Isosorbide derivatives |
US10/490,723 US7311948B2 (en) | 2001-09-24 | 2002-09-18 | Isosorbide derivatives |
EP02799442A EP1432716A1 (en) | 2001-09-24 | 2002-09-18 | Isosorbide derivatives |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP01203609.1 | 2001-09-24 | ||
EP01203609 | 2001-09-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2003027119A1 true WO2003027119A1 (en) | 2003-04-03 |
Family
ID=8180961
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IB2002/003700 WO2003027119A1 (en) | 2001-09-24 | 2002-09-18 | Isosorbide derivatives |
Country Status (6)
Country | Link |
---|---|
US (1) | US7311948B2 (en) |
EP (1) | EP1432716A1 (en) |
JP (1) | JP2005505577A (en) |
KR (1) | KR20040035864A (en) |
CN (1) | CN1556812A (en) |
WO (1) | WO2003027119A1 (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1298765C (en) * | 2005-07-01 | 2007-02-07 | 清华大学 | Poly(ester-amide) containing isosorbide unit and process for preparing same |
CN100497441C (en) * | 2004-09-29 | 2009-06-10 | 清华大学 | Polyimide containing isoscrbierite unit and its preparing method |
WO2010007758A1 (en) | 2008-07-14 | 2010-01-21 | 富士フイルム株式会社 | Optical anisotropic film, process for producing optical anisotropic film, substrate for liquid crystal cell, and liquid crystal display device |
KR101298371B1 (en) | 2008-10-01 | 2013-08-20 | 제온 코포레이션 | Polymerizable chiral compound, polymerizable liquid crystal composition, liquid crystal polymer and optically anisotropic body |
WO2023237572A1 (en) * | 2022-06-10 | 2023-12-14 | Merck Patent Gmbh | Polymerisable liquid crystal medium and polymerised liquid crystal film |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4188058B2 (en) * | 2002-11-05 | 2008-11-26 | ダイセル化学工業株式会社 | Polymer compound for photoresist and resin composition for photoresist |
JP2007176870A (en) * | 2005-12-28 | 2007-07-12 | Nippon Zeon Co Ltd | Chiral agent |
US20070189990A1 (en) * | 2006-02-16 | 2007-08-16 | Anthony East | Ultraviolet absorber for cosmetics and polymeric materials |
TWI429404B (en) * | 2008-03-03 | 2014-03-11 | Senomyx Inc | Isosorbide derivatives and their use as flavor modifiers, tastants, and taste enhancers |
EP2301941B1 (en) * | 2009-09-10 | 2013-06-19 | Cognis IP Management GmbH | Isosorbide glyceryl ether derivatives and their use in household applications |
JP5270510B2 (en) * | 2009-10-19 | 2013-08-21 | 第一工業製薬株式会社 | Cyclic (meth) acrylate compound, method for producing the same, and resin composition |
TWI410424B (en) * | 2009-11-12 | 2013-10-01 | Ind Tech Res Inst | Chiral compound and liquid crystal composition containing the same |
CN102093377B (en) * | 2009-12-10 | 2012-11-28 | 财团法人工业技术研究院 | Chiral compound and liquid crystal composition containing same |
TWI414527B (en) | 2010-10-06 | 2013-11-11 | Ind Tech Res Inst | Isosorbide derivatives and liquid crystal displays comprising the same |
US8613507B2 (en) | 2010-10-18 | 2013-12-24 | Xerox Corporation | Curable phase change inks containing functionalized isosorbides |
JP5594243B2 (en) * | 2011-07-14 | 2014-09-24 | 信越化学工業株式会社 | Polymerizable ester compound, polymer compound, resist material, and pattern forming method |
US9441164B2 (en) | 2013-07-31 | 2016-09-13 | Semiconductor Energy Laboratory Co., Ltd. | Isosorbide derivative, liquid crystal composition, liquid crystal element, and liquid crystal display device |
BR112016014276A2 (en) * | 2013-12-20 | 2017-08-08 | Archer Daniels Midland Co | METHOD OF ALKYLATION OF AN ANHYDRO-SUGAR COMPOUND; ETHER COMPOUND; ISOHEXIDE ALKYLATED COMPOUND; AND CARBONATE COMPOUND |
KR101959994B1 (en) | 2017-07-25 | 2019-03-21 | 순천대학교 산학협력단 | Antimicrobial isosorbide derivatives and antimicrobial composition comprising the same |
CN109535170A (en) * | 2018-11-30 | 2019-03-29 | 先尼科化工(上海)有限公司 | A kind of synthetic method of chiral dopant H |
CN113881417B (en) * | 2020-07-01 | 2023-04-07 | 中国石油化工股份有限公司 | Chemical agent composition containing sorbitan polyether carboxylate, preparation method thereof and CO reduction method thereof 2 Method for driving out minimum miscible pressure |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995016007A1 (en) * | 1993-12-11 | 1995-06-15 | Basf Aktiengesellschaft | Polymerizable chiral compounds and their use |
EP0773250A1 (en) * | 1995-11-09 | 1997-05-14 | Consortium für elektrochemische Industrie GmbH | Chiral dianhydro hexite derivative containing liquid-crystalline organosiloxanes |
WO1998000428A1 (en) * | 1996-07-01 | 1998-01-08 | Merck Patent Gmbh | Chiral dopants |
JPH10158268A (en) * | 1996-10-02 | 1998-06-16 | Nitto Denko Corp | Optically active monomer, liquid crystal polymer and optical element |
EP0885945A1 (en) * | 1997-06-19 | 1998-12-23 | Consortium für elektrochemische Industrie GmbH | Method for broadening the cholesteric reflexion bands of photopolymerised cholesteric liquid crystals and optical elements made according to this method |
EP0980868A1 (en) * | 1997-04-28 | 2000-02-23 | Nitto Denko Corporation | Optically active monomer, liquid crystalline polymer, and optical element |
JP2001323266A (en) * | 2000-05-19 | 2001-11-22 | Nitto Denko Corp | Cholesteric liquid crystal composition, oriented film and multicolor reflecting plate |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19520704A1 (en) * | 1995-06-09 | 1996-12-12 | Basf Ag | Polymerizable chiral compounds and their use |
DE19913604A1 (en) * | 1999-03-25 | 2000-09-28 | Basf Ag | Chiral compounds and their use as chiral dopants for the production of cholesteric liquid-crystalline compositions |
GB9930557D0 (en) * | 1999-12-23 | 2000-02-16 | Rolic Ag | Optically active materials |
US6589445B2 (en) * | 2000-06-27 | 2003-07-08 | Fuji Photo Film Co., Ltd. | Light-reaction type optically active compound, light-reaction type chiral agent, liquid crystal composition, liquid crystal color filter, optical film, recording medium, and method of changing twist structure of liquid crystal |
TW555837B (en) * | 2001-07-02 | 2003-10-01 | Merck Patent Gmbh | Chiral compounds |
US6902687B2 (en) * | 2002-04-18 | 2005-06-07 | Fuji Photo Film Co., Ltd. | Optically active isosorbide derivative and optically active isomannide derivative, production methods thereof, photo-reactive chiral agent, liquid crystal composition, liquid crystal color filter, optical film and recording medium, method for changing helical structure of liquid crystal and method for fixing helical structure of liquid crystal |
-
2002
- 2002-09-18 US US10/490,723 patent/US7311948B2/en not_active Expired - Fee Related
- 2002-09-18 WO PCT/IB2002/003700 patent/WO2003027119A1/en active Application Filing
- 2002-09-18 CN CNA028186419A patent/CN1556812A/en active Pending
- 2002-09-18 JP JP2003530707A patent/JP2005505577A/en active Pending
- 2002-09-18 KR KR10-2004-7004171A patent/KR20040035864A/en not_active Application Discontinuation
- 2002-09-18 EP EP02799442A patent/EP1432716A1/en not_active Ceased
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995016007A1 (en) * | 1993-12-11 | 1995-06-15 | Basf Aktiengesellschaft | Polymerizable chiral compounds and their use |
EP0773250A1 (en) * | 1995-11-09 | 1997-05-14 | Consortium für elektrochemische Industrie GmbH | Chiral dianhydro hexite derivative containing liquid-crystalline organosiloxanes |
WO1998000428A1 (en) * | 1996-07-01 | 1998-01-08 | Merck Patent Gmbh | Chiral dopants |
JPH10158268A (en) * | 1996-10-02 | 1998-06-16 | Nitto Denko Corp | Optically active monomer, liquid crystal polymer and optical element |
EP0980868A1 (en) * | 1997-04-28 | 2000-02-23 | Nitto Denko Corporation | Optically active monomer, liquid crystalline polymer, and optical element |
EP0885945A1 (en) * | 1997-06-19 | 1998-12-23 | Consortium für elektrochemische Industrie GmbH | Method for broadening the cholesteric reflexion bands of photopolymerised cholesteric liquid crystals and optical elements made according to this method |
JP2001323266A (en) * | 2000-05-19 | 2001-11-22 | Nitto Denko Corp | Cholesteric liquid crystal composition, oriented film and multicolor reflecting plate |
Non-Patent Citations (2)
Title |
---|
PATENT ABSTRACTS OF JAPAN vol. 1998, no. 11 30 September 1998 (1998-09-30) * |
PATENT ABSTRACTS OF JAPAN vol. 2002, no. 03 3 April 2002 (2002-04-03) * |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100497441C (en) * | 2004-09-29 | 2009-06-10 | 清华大学 | Polyimide containing isoscrbierite unit and its preparing method |
CN1298765C (en) * | 2005-07-01 | 2007-02-07 | 清华大学 | Poly(ester-amide) containing isosorbide unit and process for preparing same |
WO2010007758A1 (en) | 2008-07-14 | 2010-01-21 | 富士フイルム株式会社 | Optical anisotropic film, process for producing optical anisotropic film, substrate for liquid crystal cell, and liquid crystal display device |
KR101298371B1 (en) | 2008-10-01 | 2013-08-20 | 제온 코포레이션 | Polymerizable chiral compound, polymerizable liquid crystal composition, liquid crystal polymer and optically anisotropic body |
WO2023237572A1 (en) * | 2022-06-10 | 2023-12-14 | Merck Patent Gmbh | Polymerisable liquid crystal medium and polymerised liquid crystal film |
Also Published As
Publication number | Publication date |
---|---|
EP1432716A1 (en) | 2004-06-30 |
JP2005505577A (en) | 2005-02-24 |
US7311948B2 (en) | 2007-12-25 |
US20040232383A1 (en) | 2004-11-25 |
CN1556812A (en) | 2004-12-22 |
KR20040035864A (en) | 2004-04-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US7311948B2 (en) | Isosorbide derivatives | |
EP2001974B1 (en) | Liquid crystal compositions, polymer networks derived therefrom and process for making the same | |
KR20020005004A (en) | Liquid crystal compounds | |
KR20080108581A (en) | Chiral diole compounds, liquid crystal compositions and polymer networks derived therefrom | |
US6733690B1 (en) | Laterally substituted curable liquid crystals | |
KR100619468B1 (en) | Liquid crystal compounds, and a LCP mixture, a LCP network and an optical or electro-optical device comprising the same | |
US6673267B2 (en) | Phenylacetylene compound, liquid crystal composition, polymer, optically anisotropic product, and liquid crystal or optical element | |
KR20020079589A (en) | Polymerizable liquid crystal compound and optical film | |
KR100794481B1 (en) | Liquid crystalline compounds, and polymer network and liquid crystalline polymer film comprising the same | |
EP2179007B1 (en) | Alkaloid monomers, liquid crystal compositions and polymer networks derived therefrom | |
US7910021B2 (en) | Polymerizable optical active compound and polymerizable composition containing the same | |
KR20020062767A (en) | Optically active materials | |
KR20100057034A (en) | Chiral compounds, liquid crystal compositions and polymer networks derived therefrom | |
KR100405930B1 (en) | Photo-crosslinkable naphthalene derivative | |
Lub et al. | Synthesis and properties of photoisomerizable derivatives of isosorbide and their use in cholesteric filters | |
US7261836B2 (en) | Chiral dopant with phenylethanediol functionality | |
EP1093454B1 (en) | Chiral compounds and their use as doping agents in liquid crystals | |
KR20050024409A (en) | Chiral dopant with phenylethanediol functionality | |
Yoon et al. | Syntheses and Optical Properties of Cholesteric Liquid Crystal Polymers Utilizing p-Phenylene Bis-(p-(3-acryloxy-2-methylpropyloxy) benzoate |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): CN JP KR |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): AT BE BG CH CY CZ DE DK EE ES FR GB GR IE IT LU MC NL PT SE SK TR |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2003530707 Country of ref document: JP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2002799442 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1020047004171 Country of ref document: KR |
|
WWE | Wipo information: entry into national phase |
Ref document number: 20028186419 Country of ref document: CN |
|
WWE | Wipo information: entry into national phase |
Ref document number: 10490723 Country of ref document: US |
|
WWP | Wipo information: published in national office |
Ref document number: 2002799442 Country of ref document: EP |