DE3034222A1 - Kristallin-fluessige subst.-trans-n-alkylcyclohexane bzw. subst.-3-subst.-benzoyloxy-(trans-4-n-alkylcyclohexane) - Google Patents
Kristallin-fluessige subst.-trans-n-alkylcyclohexane bzw. subst.-3-subst.-benzoyloxy-(trans-4-n-alkylcyclohexane)Info
- Publication number
- DE3034222A1 DE3034222A1 DE19803034222 DE3034222A DE3034222A1 DE 3034222 A1 DE3034222 A1 DE 3034222A1 DE 19803034222 DE19803034222 DE 19803034222 DE 3034222 A DE3034222 A DE 3034222A DE 3034222 A1 DE3034222 A1 DE 3034222A1
- Authority
- DE
- Germany
- Prior art keywords
- trans
- subst
- crystalline
- liquid
- alkylcyclohexane
- 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- Withdrawn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
- 239000007788 liquid Substances 0.000 title claims abstract description 50
- 239000000126 substance Substances 0.000 claims abstract description 33
- 239000000975 dye Substances 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 9
- 239000005711 Benzoic acid Substances 0.000 claims description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 150000001805 chlorine compounds Chemical class 0.000 claims description 3
- -1 substituted-3-substituted-benzoyloxy Chemical group 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 150000001934 cyclohexanes Chemical class 0.000 claims 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 2
- ZOSBAYFWABIRBV-UHFFFAOYSA-N 1-pentylcyclohexane-1-carboxylic acid Chemical compound CCCCCC1(C(O)=O)CCCCC1 ZOSBAYFWABIRBV-UHFFFAOYSA-N 0.000 claims 1
- ZVBMXGLAFRTOJS-UHFFFAOYSA-N 1-propylcyclohexane-1-carboxylic acid Chemical compound CCCC1(C(O)=O)CCCCC1 ZVBMXGLAFRTOJS-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 7
- 238000004611 spectroscopical analysis Methods 0.000 abstract description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 4
- 238000004817 gas chromatography Methods 0.000 abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- NUANGSLQWFBVEH-UHFFFAOYSA-N 4-butylcyclohexan-1-ol Chemical compound CCCCC1CCC(O)CC1 NUANGSLQWFBVEH-UHFFFAOYSA-N 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- ZHJCVLQOKPGYDJ-MGCOHNPYSA-N CCCC[C@H]1CC[C@@H](CC1)C(Cl)=O Chemical compound CCCC[C@H]1CC[C@@H](CC1)C(Cl)=O ZHJCVLQOKPGYDJ-MGCOHNPYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004990 Smectic 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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000003935 benzaldehydes Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 235000015243 ice cream Nutrition 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- RBJMHPPHRYOTPB-UHFFFAOYSA-N (1-butylcyclobutyl) 1-propylcyclohexane-1-carboxylate Chemical compound C1CCCCC1(CCC)C(=O)OC1(CCCC)CCC1 RBJMHPPHRYOTPB-UHFFFAOYSA-N 0.000 description 1
- DNEFXLDIYGSPBK-UHFFFAOYSA-N (4-cyanophenyl) 1-pentylcyclohexane-1-carboxylate Chemical compound C=1C=C(C#N)C=CC=1OC(=O)C1(CCCCC)CCCCC1 DNEFXLDIYGSPBK-UHFFFAOYSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- 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 description 1
- NNOHXABAQAGKRZ-UHFFFAOYSA-N 3,5-dinitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC(C(Cl)=O)=CC([N+]([O-])=O)=C1 NNOHXABAQAGKRZ-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
- CYYZDBDROVLTJU-UHFFFAOYSA-N 4-n-Butylphenol Chemical compound CCCCC1=CC=C(O)C=C1 CYYZDBDROVLTJU-UHFFFAOYSA-N 0.000 description 1
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 102000002322 Egg Proteins Human genes 0.000 description 1
- 108010000912 Egg Proteins Proteins 0.000 description 1
- 241000238558 Eucarida Species 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- WGMXHGLHSLDTLY-UHFFFAOYSA-N benzene-1,4-diol;benzoic acid Chemical class OC1=CC=C(O)C=C1.OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WGMXHGLHSLDTLY-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical class CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 210000004681 ovum Anatomy 0.000 description 1
- LIDDQKAMUXHIQD-UHFFFAOYSA-N phenyl 2-benzoyloxybenzoate Chemical class C=1C=CC=CC=1C(=O)OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 LIDDQKAMUXHIQD-UHFFFAOYSA-N 0.000 description 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical class C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-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
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000009466 transformation Effects 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
- 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
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
-
- 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
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/19—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds in six-membered aromatic rings
- C07C29/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds in six-membered aromatic rings in a non-condensed rings substituted with hydroxy groups
-
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/88—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound
- C07C29/92—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound by a consecutive conversion and reconstruction
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD21574379A DD146041A1 (de) | 1979-09-24 | 1979-09-24 | Verfahren zur herstellung von kristallin-fluessigen 4-eckige klammer auf trans-4-n-alkylcyclohexanoyloxy eckige klammer zu-trans-n-alkylcyclohexanen bzw.4-eckige klammer auf trans-4-n-alkylcyclohexanoyloxy eckige klammer zu-3-subst.-benzoyloxy- eckige klammer auf trans-4-n-alkylcyclohexanen eckige klammer zu |
| DD21574279 | 1979-09-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3034222A1 true DE3034222A1 (de) | 1981-04-02 |
Family
ID=25747663
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803034222 Withdrawn DE3034222A1 (de) | 1979-09-24 | 1980-09-11 | Kristallin-fluessige subst.-trans-n-alkylcyclohexane bzw. subst.-3-subst.-benzoyloxy-(trans-4-n-alkylcyclohexane) |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4490278A (enExample) |
| CH (1) | CH653006A5 (enExample) |
| DE (1) | DE3034222A1 (enExample) |
| FR (1) | FR2465707A1 (enExample) |
| GB (1) | GB2061924B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4510069A (en) * | 1982-08-26 | 1985-04-09 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Cyclohexane derivatives |
| US4528114A (en) * | 1981-12-18 | 1985-07-09 | Hoffmann-La Roche Inc. | Acetylenes |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4406814A (en) * | 1981-04-10 | 1983-09-27 | Eaton Corporation | Liquid crystalline materials and optical displays utilizing same |
| DD245869A1 (de) * | 1983-10-28 | 1987-05-20 | Dietrich Demus | Verfahren zur herstellung von estern der 4- (4-alkyl-cyclohexyl)-methyl -cyclohexancarbonsaeuren und 4- (4-alkyl-cyclohexyl)-methyl -benzoesaeuren |
| CA1285643C (en) * | 1986-10-06 | 1991-07-02 | Christopher Simon Winter | Optical switching devices |
| US5637135A (en) * | 1995-06-26 | 1997-06-10 | Capillary Technology Corporation | Chromatographic stationary phases and adsorbents from hybrid organic-inorganic sol-gels |
| US6413448B1 (en) * | 1999-04-26 | 2002-07-02 | Displaytech, Inc. | Cyclohexyl- and cyclohexenyl-substituted liquid crystals with low birefringence |
| US7195719B1 (en) | 2001-01-03 | 2007-03-27 | Displaytech, Inc. | High polarization ferroelectric liquid crystal compositions |
| US6838128B1 (en) | 2002-02-05 | 2005-01-04 | Displaytech, Inc. | High polarization dopants for ferroelectric liquid crystal compositions |
| USD771907S1 (en) * | 2015-12-17 | 2016-11-22 | Prana Living, Llc | Wetsuit bottom |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD105701A1 (enExample) * | 1973-07-02 | 1974-05-05 | ||
| DE2636684C3 (de) * | 1976-08-14 | 1980-06-19 | Merck Patent Gmbh, 6100 Darmstadt | Phenylcyclohexanderivate und ihre Verwendung in flüssigkristallinen Dielektrika |
| DE2702598C2 (de) * | 1977-01-22 | 1984-10-25 | Merck Patent Gmbh, 6100 Darmstadt | Cyclohexylcyclohexane und diese enthaltende Dielektrika |
| DE2800553A1 (de) * | 1978-01-07 | 1979-07-12 | Merck Patent Gmbh | Cyclohexanderivate |
| US4293434A (en) * | 1978-08-08 | 1981-10-06 | VEB Werk fur Fernsehelektronik Berlin im VEB Kombinat Mikroelektronik | Liquid crystal compounds |
| DE2933611A1 (de) * | 1979-07-18 | 1981-02-12 | Bbc Brown Boveri & Cie | Cyclohexylcyclohexanoate |
| DE2933563A1 (de) * | 1979-07-18 | 1981-02-05 | Bbc Brown Boveri & Cie | Anisotrope verbindungen mit negativer dk-anisotropie |
| JPS5683449A (en) * | 1979-12-12 | 1981-07-08 | Chisso Corp | Cyclohexanecarboxylic acid cyclohexyl ester derivative |
| JPS56125342A (en) * | 1980-03-07 | 1981-10-01 | Kanto Kagaku Kk | Preparation of ee-type mono-substituted cyclohexane-1- carboxylic acid ester |
| JPS56125318A (en) * | 1980-03-07 | 1981-10-01 | Kanto Kagaku Kk | Preparation of ee type monosubstituted cycloheaxane-1- carbonyl compound |
| JPS56129287A (en) * | 1980-03-14 | 1981-10-09 | Hitachi Ltd | Nematic liquid crystal composition |
| JPS5748945A (en) * | 1980-09-09 | 1982-03-20 | Dainippon Ink & Chem Inc | Novel nematic liquid crystal compound |
| JPS5799557A (en) * | 1980-12-15 | 1982-06-21 | Chisso Corp | Trans-1,4-di-(4'-trans-alkylcyclohexylcarbonyloxy) cyclohexane |
| DE3100142A1 (de) * | 1981-01-07 | 1982-08-12 | Merck Patent Gmbh, 6100 Darmstadt | Cyclohexylcarbonitrilderivate, diese enthaltende dielektrika und elektrooptisches anzeigeelement |
-
1980
- 1980-09-11 DE DE19803034222 patent/DE3034222A1/de not_active Withdrawn
- 1980-09-18 CH CH6985/80A patent/CH653006A5/de not_active IP Right Cessation
- 1980-09-22 GB GB8030510A patent/GB2061924B/en not_active Expired
- 1980-09-22 US US06/189,542 patent/US4490278A/en not_active Expired - Lifetime
- 1980-09-24 FR FR8020521A patent/FR2465707A1/fr active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4528114A (en) * | 1981-12-18 | 1985-07-09 | Hoffmann-La Roche Inc. | Acetylenes |
| US4510069A (en) * | 1982-08-26 | 1985-04-09 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Cyclohexane derivatives |
| US5108652A (en) * | 1982-08-26 | 1992-04-28 | Merck patent Gesellschaft mit beschrankter Haftung Darmstadt | Cyclohexane derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2465707B1 (enExample) | 1984-05-25 |
| GB2061924A (en) | 1981-05-20 |
| CH653006A5 (de) | 1985-12-13 |
| GB2061924B (en) | 1983-09-28 |
| US4490278A (en) | 1984-12-25 |
| FR2465707A1 (fr) | 1981-03-27 |
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| Publication | Publication Date | Title |
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