JPH036133B2 - - Google Patents
Info
- Publication number
- JPH036133B2 JPH036133B2 JP57078737A JP7873782A JPH036133B2 JP H036133 B2 JPH036133 B2 JP H036133B2 JP 57078737 A JP57078737 A JP 57078737A JP 7873782 A JP7873782 A JP 7873782A JP H036133 B2 JPH036133 B2 JP H036133B2
- Authority
- JP
- Japan
- Prior art keywords
- trans
- liquid crystal
- compound
- water
- 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 - Lifetime
Links
- 239000004973 liquid crystal related substance Substances 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 15
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 235000010233 benzoic acid Nutrition 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 26
- 150000001875 compounds Chemical class 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 235000019441 ethanol Nutrition 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 9
- -1 biphenyl type Chemical class 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- RJUNDCRSFNELHE-UHFFFAOYSA-N 4-[4-(methoxymethyl)cyclohexyl]benzoic acid Chemical compound C1CC(COC)CCC1C1=CC=C(C(O)=O)C=C1 RJUNDCRSFNELHE-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- SBIUNXPEIHYSQC-JOCQHMNTSA-N CCOC[C@H]1CC[C@@H](CC1)c1ccc(cc1)C(O)=O Chemical compound CCOC[C@H]1CC[C@@H](CC1)c1ccc(cc1)C(O)=O SBIUNXPEIHYSQC-JOCQHMNTSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- DUYCNDMGJORWPS-UHFFFAOYSA-N (4-phenylcyclohexyl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1CCC(C=2C=CC=CC=2)CC1 DUYCNDMGJORWPS-UHFFFAOYSA-N 0.000 description 1
- LGORKSSOIBSSJH-UHFFFAOYSA-N 4-(4-pentylcyclohexyl)cyclohexan-1-ol Chemical compound C1CC(CCCCC)CCC1C1CCC(O)CC1 LGORKSSOIBSSJH-UHFFFAOYSA-N 0.000 description 1
- WBQSLPCFNYMITM-UHFFFAOYSA-N 4-[4-(methoxymethyl)cyclohexyl]benzonitrile Chemical compound C1CC(COC)CCC1C1=CC=C(C#N)C=C1 WBQSLPCFNYMITM-UHFFFAOYSA-N 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- AVGOGVDPWQSBIM-HDRKRICHSA-N C(C)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)O Chemical compound C(C)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)O AVGOGVDPWQSBIM-HDRKRICHSA-N 0.000 description 1
- HLNIDPMUKHLOAE-BIAGXBKMSA-N CCCC[C@H]1CC[C@@H](CC1)[C@H]1CC[C@H](O)CC1 Chemical compound CCCC[C@H]1CC[C@@H](CC1)[C@H]1CC[C@H](O)CC1 HLNIDPMUKHLOAE-BIAGXBKMSA-N 0.000 description 1
- HHYPJFMVDNEYHS-HDJSIYSDSA-N CCCOC[C@H]1CC[C@@H](CC1)c1ccc(cc1)C(O)=O Chemical compound CCCOC[C@H]1CC[C@@H](CC1)c1ccc(cc1)C(O)=O HHYPJFMVDNEYHS-HDJSIYSDSA-N 0.000 description 1
- LTDOGFZSKALWMM-HAQNSBGRSA-N COC[C@@H]1CC[C@H](CC1)C1=CC=C(C(=O)Cl)C=C1 Chemical compound COC[C@@H]1CC[C@H](CC1)C1=CC=C(C(=O)Cl)C=C1 LTDOGFZSKALWMM-HAQNSBGRSA-N 0.000 description 1
- ZXJJNDCOZIXUOU-HAQNSBGRSA-N COC[C@H]1CC[C@@H](CC1)c1ccc(I)cc1 Chemical compound COC[C@H]1CC[C@@H](CC1)c1ccc(I)cc1 ZXJJNDCOZIXUOU-HAQNSBGRSA-N 0.000 description 1
- OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229910010082 LiAlH Inorganic materials 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
- NMRUTZHKRXABQM-UHFFFAOYSA-N [4-(methoxymethyl)cyclohexyl]benzene Chemical compound C1CC(COC)CCC1C1=CC=CC=C1 NMRUTZHKRXABQM-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=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
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- MCYYJHPHBOPLMH-UHFFFAOYSA-L disodium;dioxido-oxo-sulfanylidene-$l^{6}-sulfane;hydrate Chemical compound O.[Na+].[Na+].[O-]S([O-])(=O)=S MCYYJHPHBOPLMH-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 1
- SGCPKFJYODXFOZ-UHFFFAOYSA-N methyl 1-phenylcyclohexane-1-carboxylate Chemical compound C=1C=CC=CC=1C1(C(=O)OC)CCCCC1 SGCPKFJYODXFOZ-UHFFFAOYSA-N 0.000 description 1
- APZUMPUMIRTOSP-UHFFFAOYSA-N methyl 4-phenylcyclohexane-1-carboxylate Chemical compound C1CC(C(=O)OC)CCC1C1=CC=CC=C1 APZUMPUMIRTOSP-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/34—Monohydroxylic alcohols containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/164—Unsaturated ethers containing six-membered aromatic rings
- C07C43/168—Unsaturated ethers containing six-membered aromatic rings containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/17—Unsaturated ethers containing halogen
- C07C43/174—Unsaturated ethers containing halogen containing six-membered aromatic rings
- C07C43/1747—Unsaturated ethers containing halogen containing six-membered aromatic rings containing six membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
- C07C65/26—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic containing rings other than six-membered aromatic rings
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57078737A JPS58194841A (ja) | 1982-05-11 | 1982-05-11 | ４−（トランス−４′−アルキルオキシメチルシクロヘキシル）安息香酸のエステル類 |
| DE8383302510T DE3362256D1 (en) | 1982-05-11 | 1983-05-04 | 4-(trans-4'-alkyloxymethylcyclohexyl) benzoic acid esters |
| EP83302510A EP0094198B1 (en) | 1982-05-11 | 1983-05-04 | 4-(trans-4'-alkyloxymethylcyclohexyl) benzoic acid esters |
| US06/493,288 US4452719A (en) | 1982-05-11 | 1983-05-10 | 4-(Trans-4'-alkyloxymethylcyclohexyl)benzoic acid esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57078737A JPS58194841A (ja) | 1982-05-11 | 1982-05-11 | ４−（トランス−４′−アルキルオキシメチルシクロヘキシル）安息香酸のエステル類 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58194841A JPS58194841A (ja) | 1983-11-12 |
| JPH036133B2 true JPH036133B2 (en]) | 1991-01-29 |
Family
ID=13670197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57078737A Granted JPS58194841A (ja) | 1982-05-11 | 1982-05-11 | ４−（トランス−４′−アルキルオキシメチルシクロヘキシル）安息香酸のエステル類 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4452719A (en]) |
| EP (1) | EP0094198B1 (en]) |
| JP (1) | JPS58194841A (en]) |
| DE (1) | DE3362256D1 (en]) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3268611D1 (en) * | 1981-02-25 | 1986-03-06 | Hitachi Ltd | Colorless liquid crystalline compounds |
| DE3206269A1 (de) * | 1982-02-20 | 1983-09-01 | Merck Patent Gmbh, 6100 Darmstadt | Bicyclohexylderivate |
| EP0090548B1 (en) * | 1982-03-26 | 1987-11-11 | Chisso Corporation | Liquid-crystalline compounds |
| JPS58219137A (ja) * | 1982-06-12 | 1983-12-20 | Chisso Corp | ４−（トランス−４−アルキルオキシメチルシクロヘキシル）−４′−（トランス−４−アルキルシクロヘキシル）ビフエニル類 |
| US4550981A (en) * | 1982-09-30 | 1985-11-05 | Hoffmann-La Roche Inc. | Liquid crystalline esters and mixtures |
| US4661283A (en) * | 1984-03-02 | 1987-04-28 | Chisso Corporation | Benzoate derivatives having a large positive dielectric anisotropy value and liquid crystal compositions containing same |
| GB2162515B (en) * | 1984-07-04 | 1988-05-18 | Secr Defence | Liquid crystal esters |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2800553A1 (de) * | 1978-01-07 | 1979-07-12 | Merck Patent Gmbh | Cyclohexanderivate |
| ATE1993T1 (de) * | 1979-07-20 | 1982-12-15 | Bbc Aktiengesellschaft Brown, Boveri & Cie. | Anisotrope carbonsaeure-4-cyclohexylphenylester und sie enthaltende fluessigkristallmischungen. |
| CH645876A5 (de) * | 1980-01-25 | 1984-10-31 | Chisso Corp | Halogenierte esterderivate mit positiver anisotropie und diese verbindungen enthaltende fluessigkristallmischungen. |
| JPS5721359A (en) * | 1980-07-15 | 1982-02-04 | Chisso Corp | 4'''-cyano-4"-biphenylyl 4-(trans-4'-alkylcyclohexyl)benzoate |
| DE3268611D1 (en) * | 1981-02-25 | 1986-03-06 | Hitachi Ltd | Colorless liquid crystalline compounds |
-
1982
- 1982-05-11 JP JP57078737A patent/JPS58194841A/ja active Granted
-
1983
- 1983-05-04 EP EP83302510A patent/EP0094198B1/en not_active Expired
- 1983-05-04 DE DE8383302510T patent/DE3362256D1/de not_active Expired
- 1983-05-10 US US06/493,288 patent/US4452719A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0094198B1 (en) | 1986-02-26 |
| JPS58194841A (ja) | 1983-11-12 |
| EP0094198A2 (en) | 1983-11-16 |
| US4452719A (en) | 1984-06-05 |
| DE3362256D1 (en) | 1986-04-03 |
| EP0094198A3 (en) | 1984-03-21 |
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