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 (en, 2012) | 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 (en, 2012) |
| EP (1) | EP0004489B1 (en, 2012) |
| JP (1) | JPS54130489A (en, 2012) |
| DE (1) | DE2961732D1 (en, 2012) |
| FR (1) | FR2419966A1 (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3050545A1 (de) * | 1980-08-22 | 1982-09-23 | S Belyaev | 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 inversion 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 (en, 2012) * | 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 |
| 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 |
| 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 |
| 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 |
|---|---|
| FR2419966A1 (fr) | 1979-10-12 |
| JPS54130489A (en) | 1979-10-09 |
| FR2419966B1 (en, 2012) | 1981-08-14 |
| DE2961732D1 (en) | 1982-02-25 |
| EP0004489B1 (fr) | 1982-01-06 |
| US4257910A (en) | 1981-03-24 |
| EP0004489A1 (fr) | 1979-10-03 |
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