FR2461697A1 - 3-cyano-4-alcoxybenzoate de 2-chloro-4-alcoylphenyle et son utilisation dans une composition de cristaux liquides - Google Patents
3-cyano-4-alcoxybenzoate de 2-chloro-4-alcoylphenyle et son utilisation dans une composition de cristaux liquides Download PDFInfo
- Publication number
- FR2461697A1 FR2461697A1 FR8015053A FR8015053A FR2461697A1 FR 2461697 A1 FR2461697 A1 FR 2461697A1 FR 8015053 A FR8015053 A FR 8015053A FR 8015053 A FR8015053 A FR 8015053A FR 2461697 A1 FR2461697 A1 FR 2461697A1
- Authority
- FR
- France
- Prior art keywords
- liquid crystal
- chloro
- coo
- crystal composition
- cyano
- 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.)
- Granted
Links
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 47
- 239000000203 mixture Substances 0.000 title claims abstract description 22
- 150000002148 esters Chemical class 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 description 25
- 150000001875 compounds Chemical class 0.000 description 19
- 230000005284 excitation Effects 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- XMEQDAIDOBVHEK-UHFFFAOYSA-N 3-bromo-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(Br)=C1 XMEQDAIDOBVHEK-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000011159 matrix material Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
- 210000002858 crystal cell Anatomy 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- LSXKDWGTSHCFPP-UHFFFAOYSA-N 1-bromoheptane Chemical compound CCCCCCCBr LSXKDWGTSHCFPP-UHFFFAOYSA-N 0.000 description 1
- OKJBADUDDQPCLG-UHFFFAOYSA-N 3-bromo-4-heptoxybenzoic acid Chemical compound CCCCCCCOC1=CC=C(C(O)=O)C=C1Br OKJBADUDDQPCLG-UHFFFAOYSA-N 0.000 description 1
- AQKLCFDPMZXVRO-UHFFFAOYSA-N 3-bromo-4-heptoxybenzoyl chloride Chemical compound CCCCCCCOC1=CC=C(C(Cl)=O)C=C1Br AQKLCFDPMZXVRO-UHFFFAOYSA-N 0.000 description 1
- DFPHFPFAZFPZDC-UHFFFAOYSA-N 3-cyano-4-hexoxybenzoic acid Chemical compound CCCCCCOC1=CC=C(C(O)=O)C=C1C#N DFPHFPFAZFPZDC-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- PCUMSUHMEMDETN-UHFFFAOYSA-N CCCCCCCOC1=C(C=C(C=C1)C(O)=O)C#N Chemical compound CCCCCCCOC1=C(C=C(C=C1)C(O)=O)C#N PCUMSUHMEMDETN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 229940044631 ferric chloride hexahydrate Drugs 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NQXWGWZJXJUMQB-UHFFFAOYSA-K iron trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].Cl[Fe+]Cl NQXWGWZJXJUMQB-UHFFFAOYSA-K 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
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
- C09K19/04—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
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
- C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9308279A JPS5616447A (en) | 1979-07-20 | 1979-07-20 | Ester compound |
| JP17181979A JPS5695978A (en) | 1979-12-28 | 1979-12-28 | Liquid crystal composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2461697A1 true FR2461697A1 (fr) | 1981-02-06 |
| FR2461697B1 FR2461697B1 (enExample) | 1985-03-15 |
Family
ID=26434526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8015053A Granted FR2461697A1 (fr) | 1979-07-20 | 1980-07-07 | 3-cyano-4-alcoxybenzoate de 2-chloro-4-alcoylphenyle et son utilisation dans une composition de cristaux liquides |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4341652A (enExample) |
| CH (1) | CH643819A5 (enExample) |
| DE (1) | DE3026965C2 (enExample) |
| FR (1) | FR2461697A1 (enExample) |
| GB (1) | GB2058050B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3164750D1 (en) * | 1980-10-13 | 1984-08-16 | Secr Defence Brit | Liquid crystal devices |
| US4406814A (en) * | 1981-04-10 | 1983-09-27 | Eaton Corporation | Liquid crystalline materials and optical displays utilizing same |
| DE3221462A1 (de) * | 1981-06-18 | 1983-01-05 | F. Hoffmann-La Roche & Co AG, 4002 Basel | Fluessigkristallines gemisch |
| US4729639A (en) * | 1982-03-29 | 1988-03-08 | Tektronix, Inc. | Dual frequency addressable liquid crystals and methods of use |
| US4550981A (en) * | 1982-09-30 | 1985-11-05 | Hoffmann-La Roche Inc. | Liquid crystalline esters and mixtures |
| JP2554473B2 (ja) * | 1986-08-18 | 1996-11-13 | チッソ株式会社 | シアノ基を有する新規光学活性液晶化合物 |
| US5356561A (en) * | 1989-12-07 | 1994-10-18 | Mitsui Petrochemical Industries, Ltd. | Carboxylate compounds, liquid crystal compositions and liquid crystal elements containing said compounds and method of optical modulation using said elements |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2618609A1 (de) * | 1975-04-30 | 1976-12-02 | Thomson Csf | Organische verbindungen mit starker negativer dielektrischer anisotropie, verfahren zu ihrer herstellung sowie diese verbindungen enthaltendes mesomorphes gemisch fuer elektrooptische zwecke |
| US4198312A (en) * | 1977-11-18 | 1980-04-15 | Dainippon Inc. & Chemicals, Inc. | 3'-Chloro-4'-cyanophenyl 4-n-alkylbenzoates |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5755744B2 (enExample) * | 1972-01-13 | 1982-11-26 | ||
| GB1393216A (en) * | 1972-10-05 | 1975-05-07 | Werk Fernsehelektronik Veb | Liquid crystalline nematic substance comprising diesters of 2-substituted hydroquinone and applications thereof |
| US4009934A (en) * | 1974-01-11 | 1977-03-01 | Eastman Kodak Company | Electro-optic display devices and methods |
| US4173545A (en) * | 1976-04-06 | 1979-11-06 | Thomson-Csf | Liquid crystal with high negative dielectric anisotropy and mixtures of the same with nematic liquid crystals for improving dynamic scattering in electro-optic devices |
| JPS52142683A (en) * | 1976-05-25 | 1977-11-28 | Citizen Watch Co Ltd | Liquid crystal composite |
| US4113647A (en) * | 1976-08-13 | 1978-09-12 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Liquid crystalline materials |
| US4235736A (en) * | 1977-02-11 | 1980-11-25 | Thomson-Csf | Diphenylic esters exhibiting mesomorphic phases |
| GB2003864B (en) * | 1977-08-17 | 1982-02-17 | Thomson Csf | Liquid crystals |
| FR2400546A1 (fr) * | 1977-08-17 | 1979-03-16 | Thomson Csf | Famille de cristaux liquides de type " diester disubstitue " et dispositif electro-optique utilisant de tels cristaux liquides |
| JPS5521429A (en) * | 1978-07-31 | 1980-02-15 | Seiko Epson Corp | Liquid crystal composition |
| US4293434A (en) * | 1978-08-08 | 1981-10-06 | VEB Werk fur Fernsehelektronik Berlin im VEB Kombinat Mikroelektronik | Liquid crystal compounds |
| JPS5529545A (en) * | 1978-08-22 | 1980-03-01 | Seiko Epson Corp | Liquid crystal composition |
| US4279770A (en) * | 1978-09-20 | 1981-07-21 | Chisso Corporation | Liquid crystal 2,3-dicyano-hydroquinone derivatives |
| JPS5584385A (en) * | 1978-12-20 | 1980-06-25 | Seiko Epson Corp | Liquid crystal composition |
| GB2046731B (en) * | 1979-01-26 | 1983-04-20 | Suwa Seikosha Kk | (2'-cyano-4'-alkyl-)phenyl 3-chloro-4alkoxybenzoates theirpreparation and use in liquid crystal compositions |
| GB2053193B (en) * | 1979-05-01 | 1983-05-05 | Suwa Seikosha Kk | 2'-cyano-4'-n-alkylphenyl 3-cyano-4-n-alkoxybenzoates |
-
1980
- 1980-07-07 FR FR8015053A patent/FR2461697A1/fr active Granted
- 1980-07-16 GB GB8023286A patent/GB2058050B/en not_active Expired
- 1980-07-16 DE DE3026965A patent/DE3026965C2/de not_active Expired
- 1980-07-18 CH CH553780A patent/CH643819A5/de not_active IP Right Cessation
- 1980-07-18 US US06/171,938 patent/US4341652A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2618609A1 (de) * | 1975-04-30 | 1976-12-02 | Thomson Csf | Organische verbindungen mit starker negativer dielektrischer anisotropie, verfahren zu ihrer herstellung sowie diese verbindungen enthaltendes mesomorphes gemisch fuer elektrooptische zwecke |
| US4198312A (en) * | 1977-11-18 | 1980-04-15 | Dainippon Inc. & Chemicals, Inc. | 3'-Chloro-4'-cyanophenyl 4-n-alkylbenzoates |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2058050B (en) | 1983-05-11 |
| US4341652A (en) | 1982-07-27 |
| GB2058050A (en) | 1981-04-08 |
| DE3026965A1 (de) | 1981-02-12 |
| DE3026965C2 (de) | 1985-09-19 |
| CH643819A5 (de) | 1984-06-29 |
| FR2461697B1 (enExample) | 1985-03-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |