DE3001423A1 - Neue substituierte phenylbenzoate, verfahren zu deren herstellung, und deren verwendung in fluessigkristallzusammensetzungen - Google Patents
Neue substituierte phenylbenzoate, verfahren zu deren herstellung, und deren verwendung in fluessigkristallzusammensetzungenInfo
- Publication number
- DE3001423A1 DE3001423A1 DE19803001423 DE3001423A DE3001423A1 DE 3001423 A1 DE3001423 A1 DE 3001423A1 DE 19803001423 DE19803001423 DE 19803001423 DE 3001423 A DE3001423 A DE 3001423A DE 3001423 A1 DE3001423 A1 DE 3001423A1
- Authority
- DE
- Germany
- Prior art keywords
- liquid crystal
- coo
- compound
- chloro
- compounds
- 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.)
- Withdrawn
Links
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 51
- 239000000203 mixture Substances 0.000 title claims description 39
- 238000000034 method Methods 0.000 title claims description 26
- 238000004519 manufacturing process Methods 0.000 title description 6
- 150000001564 phenyl benzoates Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 67
- 238000002360 preparation method Methods 0.000 claims description 11
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 238000002329 infrared spectrum Methods 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
- 229960000583 acetic acid Drugs 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 8
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- QGNLHMKIGMZKJX-UHFFFAOYSA-N 3-chloro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(Cl)=C1 QGNLHMKIGMZKJX-UHFFFAOYSA-N 0.000 description 5
- -1 chloro-n-butoxybenzoate Chemical compound 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- KJPGAGKKAWEJLB-UHFFFAOYSA-N 3-chloro-4-hexoxybenzoyl chloride Chemical compound CCCCCCOC1=CC=C(C(Cl)=O)C=C1Cl KJPGAGKKAWEJLB-UHFFFAOYSA-N 0.000 description 3
- CYURSYQPPHRSMN-UHFFFAOYSA-N 5-butyl-2-hydroxybenzonitrile Chemical compound CCCCC1=CC=C(O)C(C#N)=C1 CYURSYQPPHRSMN-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 3
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- MJYBXQVLUPBGPR-UHFFFAOYSA-N 2-hydroxy-5-pentylbenzonitrile Chemical compound CCCCCC1=CC=C(O)C(C#N)=C1 MJYBXQVLUPBGPR-UHFFFAOYSA-N 0.000 description 2
- CDZINMJYMBCTCO-UHFFFAOYSA-N 3-chloro-4-hexoxybenzoic acid Chemical compound CCCCCCOC1=CC=C(C(O)=O)C=C1Cl CDZINMJYMBCTCO-UHFFFAOYSA-N 0.000 description 2
- WOBLCPMGDGMEBX-UHFFFAOYSA-N 3-chloro-4-propoxybenzoic acid Chemical compound CCCOC1=CC=C(C(O)=O)C=C1Cl WOBLCPMGDGMEBX-UHFFFAOYSA-N 0.000 description 2
- NRWDQONAZDVAAJ-UHFFFAOYSA-N 3-chloro-4-propoxybenzoyl chloride Chemical compound CCCOC1=CC=C(C(Cl)=O)C=C1Cl NRWDQONAZDVAAJ-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- ARGDYOIRHYLIMT-UHFFFAOYSA-N n,n-dichloro-4-methylbenzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N(Cl)Cl)C=C1 ARGDYOIRHYLIMT-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- ANVGYLDROLBYEZ-UHFFFAOYSA-N (4-pentylphenyl) 3-chloro-4-(4-pentylbenzoyl)oxybenzoate Chemical compound C1=CC(CCCCC)=CC=C1OC(=O)C(C=C1Cl)=CC=C1OC(=O)C1=CC=C(CCCCC)C=C1 ANVGYLDROLBYEZ-UHFFFAOYSA-N 0.000 description 1
- LSXKDWGTSHCFPP-UHFFFAOYSA-N 1-bromoheptane Chemical compound CCCCCCCBr LSXKDWGTSHCFPP-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- UZZDEUNEMHGVDM-UHFFFAOYSA-N 2-bromo-4-butylphenol Chemical compound CCCCC1=CC=C(O)C(Br)=C1 UZZDEUNEMHGVDM-UHFFFAOYSA-N 0.000 description 1
- FJHOKVWQVJTDNL-UHFFFAOYSA-N 2-bromo-4-pentylphenol Chemical compound CCCCCC1=CC=C(O)C(Br)=C1 FJHOKVWQVJTDNL-UHFFFAOYSA-N 0.000 description 1
- UFUBQDNODUUQTD-UHFFFAOYSA-N 2-bromo-4-propylphenol Chemical compound CCCC1=CC=C(O)C(Br)=C1 UFUBQDNODUUQTD-UHFFFAOYSA-N 0.000 description 1
- XRZVFCMTRUVYIK-UHFFFAOYSA-N 2-hydroxy-5-propylbenzonitrile Chemical compound CCCC1=CC=C(O)C(C#N)=C1 XRZVFCMTRUVYIK-UHFFFAOYSA-N 0.000 description 1
- LCHYEKKJCUJAKN-UHFFFAOYSA-N 2-propylphenol Chemical compound CCCC1=CC=CC=C1O LCHYEKKJCUJAKN-UHFFFAOYSA-N 0.000 description 1
- SNQXWMYZQNPWEK-UHFFFAOYSA-N 3-bromo-4-butylphenol Chemical compound CCCCC1=CC=C(O)C=C1Br SNQXWMYZQNPWEK-UHFFFAOYSA-N 0.000 description 1
- JMMIUVVTWBDJLR-UHFFFAOYSA-N 3-chloro-2-hexoxybenzoic acid Chemical compound CCCCCCOc1c(Cl)cccc1C(O)=O JMMIUVVTWBDJLR-UHFFFAOYSA-N 0.000 description 1
- LGQBVNKWUHKURB-UHFFFAOYSA-N 3-chloro-2-propoxybenzoic acid Chemical compound ClC=1C(=C(C(=O)O)C=CC=1)OCCC LGQBVNKWUHKURB-UHFFFAOYSA-N 0.000 description 1
- OYJRRPQYMFCAPX-UHFFFAOYSA-N 3-chloro-4-heptoxybenzoic acid Chemical compound CCCCCCCOC1=CC=C(C(O)=O)C=C1Cl OYJRRPQYMFCAPX-UHFFFAOYSA-N 0.000 description 1
- VCPIASAEGISZQX-UHFFFAOYSA-N 3-chloro-4-heptoxybenzoyl chloride Chemical compound CCCCCCCOC1=CC=C(C(Cl)=O)C=C1Cl VCPIASAEGISZQX-UHFFFAOYSA-N 0.000 description 1
- ZNPSUQQXTRRSBM-UHFFFAOYSA-N 4-n-Pentylphenol Chemical compound CCCCCC1=CC=C(O)C=C1 ZNPSUQQXTRRSBM-UHFFFAOYSA-N 0.000 description 1
- 101100279438 Caenorhabditis elegans egg-3 gene Proteins 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- DFZSTLUBHNQSLD-UHFFFAOYSA-N phenyl 3-chloro-2-pentoxybenzoate Chemical compound C1(=CC=CC=C1)OC(C1=C(C(=CC=C1)Cl)OCCCCC)=O DFZSTLUBHNQSLD-UHFFFAOYSA-N 0.000 description 1
- VANRDZRQIKYGHT-UHFFFAOYSA-N phenyl 3-chloro-4-hexoxybenzoate Chemical compound C1(=CC=CC=C1)OC(C1=CC(=C(C=C1)OCCCCCC)Cl)=O VANRDZRQIKYGHT-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- VITRLXDSBBVNCZ-UHFFFAOYSA-K trichloroiron;hydrate Chemical compound O.Cl[Fe](Cl)Cl VITRLXDSBBVNCZ-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP859079A JPS55100352A (en) | 1979-01-26 | 1979-01-26 | Ester compound and its preparation |
| JP4065979A JPS55133476A (en) | 1979-04-04 | 1979-04-04 | Liquid crystal composition |
| JP13854679A JPS5661345A (en) | 1979-10-26 | 1979-10-26 | Ester compound and its preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3001423A1 true DE3001423A1 (de) | 1980-08-07 |
Family
ID=27278091
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803001423 Withdrawn DE3001423A1 (de) | 1979-01-26 | 1980-01-16 | Neue substituierte phenylbenzoate, verfahren zu deren herstellung, und deren verwendung in fluessigkristallzusammensetzungen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4279771A (enExample) |
| CH (1) | CH641765A5 (enExample) |
| DE (1) | DE3001423A1 (enExample) |
| FR (1) | FR2453139A1 (enExample) |
| GB (1) | GB2046731B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0106588A1 (en) * | 1982-09-27 | 1984-04-25 | Chisso Corporation | 2-Cyano-4-halogenophenyl esters |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0019665B2 (de) * | 1979-05-28 | 1987-12-16 | MERCK PATENT GmbH | Flüssigkristalline Verbindungen |
| FR2461697A1 (fr) * | 1979-07-20 | 1981-02-06 | Suwa Seikosha Kk | 3-cyano-4-alcoxybenzoate de 2-chloro-4-alcoylphenyle et son utilisation dans une composition de cristaux liquides |
| US4400061A (en) * | 1980-01-30 | 1983-08-23 | Her Majesty's Government of the UK. | Liquid crystal ester compounds exhibiting a low or negative dielectric anisotropy and liquid crystal materials and devices incorporating such compounds |
| DE3164750D1 (en) * | 1980-10-13 | 1984-08-16 | Secr Defence Brit | Liquid crystal devices |
| 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 |
| US4838657A (en) * | 1984-11-15 | 1989-06-13 | Seiko Epson Corporation | Liquid crystal shutter |
| US7726829B2 (en) * | 2007-03-30 | 2010-06-01 | Stuhr Darlene K | Lighted background for fish tanks and the like |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| GB1603076A (en) * | 1977-04-05 | 1981-11-18 | Secr Defence | Esters of (+)-4-(2'-methylbutyl)phenol and their use as liquid crystal materials |
| GB2003864B (en) | 1977-08-17 | 1982-02-17 | Thomson Csf | Liquid crystals |
| JPS5490144A (en) * | 1977-11-18 | 1979-07-17 | Dainippon Ink & Chem Inc | 4-n-alkylbenzoxy-3'-chloro-4'-cyanobenzen |
-
1980
- 1980-01-14 GB GB8001115A patent/GB2046731B/en not_active Expired
- 1980-01-16 DE DE19803001423 patent/DE3001423A1/de not_active Withdrawn
- 1980-01-23 US US06/114,775 patent/US4279771A/en not_active Expired - Lifetime
- 1980-01-24 FR FR8001506A patent/FR2453139A1/fr active Granted
- 1980-01-25 CH CH63280A patent/CH641765A5/de not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0106588A1 (en) * | 1982-09-27 | 1984-04-25 | Chisso Corporation | 2-Cyano-4-halogenophenyl esters |
| US4603018A (en) * | 1982-09-27 | 1986-07-29 | Chisso Corporation | 2-cyano-4-halogenophenyl esters |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2453139A1 (fr) | 1980-10-31 |
| FR2453139B1 (enExample) | 1984-04-20 |
| GB2046731A (en) | 1980-11-19 |
| GB2046731B (en) | 1983-04-20 |
| CH641765A5 (de) | 1984-03-15 |
| US4279771A (en) | 1981-07-21 |
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