JPS6246539B2 - - Google Patents
Info
- Publication number
- JPS6246539B2 JPS6246539B2 JP54030521A JP3052179A JPS6246539B2 JP S6246539 B2 JPS6246539 B2 JP S6246539B2 JP 54030521 A JP54030521 A JP 54030521A JP 3052179 A JP3052179 A JP 3052179A JP S6246539 B2 JPS6246539 B2 JP S6246539B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- formula
- reaction
- mol
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 13
- 239000004973 liquid crystal related substance Substances 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 3
- 230000001747 exhibiting effect Effects 0.000 claims description 2
- 150000005690 diesters Chemical class 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000004990 Smectic liquid crystal Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- -1 4-n-pentyl-phenyl-4-hydroxy-2-cyano-benzoate Chemical compound 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- JSPVUXIWYUJILG-UHFFFAOYSA-N 2-chloro-4-hydroxy-3-(4-pentylphenyl)benzoic acid Chemical compound CCCCCC1=CC=C(C=C1)C2=C(C=CC(=C2Cl)C(=O)O)O JSPVUXIWYUJILG-UHFFFAOYSA-N 0.000 description 1
- WIPYZRZPNMUSER-UHFFFAOYSA-N 2-chloro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1Cl WIPYZRZPNMUSER-UHFFFAOYSA-N 0.000 description 1
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
- MEEKGULDSDXFCN-UHFFFAOYSA-N 2-pentylphenol Chemical compound CCCCCC1=CC=CC=C1O MEEKGULDSDXFCN-UHFFFAOYSA-N 0.000 description 1
- NEKGDYGTJYCIRI-UHFFFAOYSA-N 4-octylbenzoyl chloride Chemical compound CCCCCCCCC1=CC=C(C(Cl)=O)C=C1 NEKGDYGTJYCIRI-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- KVSASDOGYIBWTA-UHFFFAOYSA-N chloro benzoate Chemical compound ClOC(=O)C1=CC=CC=C1 KVSASDOGYIBWTA-UHFFFAOYSA-N 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000012800 visualization 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
- C09K19/10—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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7807799A FR2419966A1 (fr) | 1978-03-17 | 1978-03-17 | Cristal liquide de type diester presentant une phase smectique, a basse frequence d'isotropie dielectrique, et dispositif de visualisation utilisant ce cristal |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54130489A JPS54130489A (en) | 1979-10-09 |
| JPS6246539B2 true JPS6246539B2 (cg-RX-API-DMAC7.html) | 1987-10-02 |
Family
ID=9205952
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3052179A Granted JPS54130489A (en) | 1978-03-17 | 1979-03-15 | Diester type liquid crystal |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4257910A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0004489B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPS54130489A (cg-RX-API-DMAC7.html) |
| DE (1) | DE2961732D1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2419966A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2094311A (en) * | 1980-08-22 | 1982-09-15 | Ivaschenko Aleksandr Vasilevic | New derivatives of phenic acid method of obtaining them liquid crystal material with negative dielectric anisotropy method of obtaining that liquid crystal material liquid crystal material with low frequency in version of sign of dielectric anisotropy and method of obtaining that liquid crystal material |
| FR2604440B1 (fr) * | 1986-09-30 | 1988-11-10 | Thomson Csf | Polymeres mesomorphes a chaines laterales derives du 1-(phenyl)-2-(4-cyanophenyl) ethane |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3915883A (en) * | 1972-04-26 | 1975-10-28 | Eastman Kodak Co | Liquid crystalline compounds and compositions |
| CH582229A5 (cg-RX-API-DMAC7.html) * | 1972-08-19 | 1976-11-30 | Merck Patent Gmbh | |
| US3953491A (en) * | 1972-08-19 | 1976-04-27 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Phenyl esters of 4-benzoyloxybenzoic acid |
| US4009934A (en) * | 1974-01-11 | 1977-03-01 | Eastman Kodak Company | Electro-optic display devices and methods |
| US4090975A (en) * | 1974-11-01 | 1978-05-23 | Itek Corporation | Mixtures of nematic liquid crystal materials |
| FR2309509A1 (fr) * | 1975-04-30 | 1976-11-26 | Thomson Csf | Nouveau compose organique, melange mesomorphe a grande diffusion dynamique comportant ledit compose, et procede de fabrication dudit compose |
| DE2613293C3 (de) * | 1976-03-29 | 1982-02-18 | Merck Patent Gmbh, 6100 Darmstadt | Cyanosubstituierte Biphenylverbindungen, Verfahren zu deren Herstellung und diese Verbindungen enthaltende flüssigkristalline Dielektrika |
| FR2347427A1 (fr) * | 1976-04-06 | 1977-11-04 | Thomson Csf | Cristal liquide a grande anisotropie dielectrique negative, et dispositif de visualisation utilisant un tel cristal liquide |
| FR2357625A2 (fr) * | 1976-07-07 | 1978-02-03 | Thomson Csf | Cristal liquide a grande anisotropie dielectrique negative et dispositif de visualisation utilisant un tel cristal liquide |
| GB1537463A (en) * | 1976-04-06 | 1978-12-29 | Thomson Csf | Para-alkyl-phenyl substituted benzoyl oxybenzoates liquid crystal compositions thereof having high dielectric anisotropy and their use in electro-optical devices |
| DE2745050C2 (de) * | 1976-10-06 | 1983-03-10 | Sharp K.K., Osaka | Material aus flüssigen Kristallen |
| DD138473A3 (de) * | 1977-02-11 | 1979-11-07 | Deutscher Hans Joachim | Kristallin-fluessige substanzen |
| FR2400545A1 (fr) * | 1977-08-17 | 1979-03-16 | Thomson Csf | Famille de cristaux liquides de type " diester ", et dispositif electro-optique utilisant de tels cristaux liquides |
| GB2003864B (en) * | 1977-08-17 | 1982-02-17 | Thomson Csf | Liquid crystals |
-
1978
- 1978-03-17 FR FR7807799A patent/FR2419966A1/fr active Granted
-
1979
- 1979-02-27 DE DE7979400123T patent/DE2961732D1/de not_active Expired
- 1979-02-27 EP EP79400123A patent/EP0004489B1/fr not_active Expired
- 1979-03-13 US US06/020,056 patent/US4257910A/en not_active Expired - Lifetime
- 1979-03-15 JP JP3052179A patent/JPS54130489A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0004489A1 (fr) | 1979-10-03 |
| JPS54130489A (en) | 1979-10-09 |
| FR2419966B1 (cg-RX-API-DMAC7.html) | 1981-08-14 |
| EP0004489B1 (fr) | 1982-01-06 |
| DE2961732D1 (en) | 1982-02-25 |
| FR2419966A1 (fr) | 1979-10-12 |
| US4257910A (en) | 1981-03-24 |
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