DE3149139C2 - - Google Patents
Info
- Publication number
- DE3149139C2 DE3149139C2 DE19813149139 DE3149139A DE3149139C2 DE 3149139 C2 DE3149139 C2 DE 3149139C2 DE 19813149139 DE19813149139 DE 19813149139 DE 3149139 A DE3149139 A DE 3149139A DE 3149139 C2 DE3149139 C2 DE 3149139C2
- Authority
- DE
- Germany
- Prior art keywords
- trans
- compounds
- nitrile
- atoms
- groups
- 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 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- ZETPYKRXIXPMQA-UHFFFAOYSA-N cyclohexylmethoxybenzene Chemical compound C1CCCCC1COC1=CC=CC=C1 ZETPYKRXIXPMQA-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000005699 methyleneoxy group Chemical group [H]C([H])([*:1])O[*:2] 0.000 claims description 3
- 239000004973 liquid crystal related substance Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- -1 alkyl radical Chemical group 0.000 description 36
- 150000002825 nitriles Chemical group 0.000 description 5
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 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 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000004990 Smectic liquid crystal Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 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 3
- HJTSPRADKFAWLL-WGSAOQKQSA-N C(CC)[C@@H]1CC[C@H](CC1)COCCCCOC1=CC=CC=C1 Chemical compound C(CC)[C@@H]1CC[C@H](CC1)COCCCCOC1=CC=CC=C1 HJTSPRADKFAWLL-WGSAOQKQSA-N 0.000 description 2
- AHRBWIMPHQPYBY-MXVIHJGJSA-N C(CCCC)[C@@H]1CC[C@H](CC1)COC1=CC=C(C=C1)CCC Chemical compound C(CCCC)[C@@H]1CC[C@H](CC1)COC1=CC=C(C=C1)CCC AHRBWIMPHQPYBY-MXVIHJGJSA-N 0.000 description 2
- YXFJUJFYYAPINJ-IYARVYRRSA-N C(CCCC)[C@@H]1CC[C@H](CC1)COC1=CC=C(C=C1)NCC Chemical compound C(CCCC)[C@@H]1CC[C@H](CC1)COC1=CC=C(C=C1)NCC YXFJUJFYYAPINJ-IYARVYRRSA-N 0.000 description 2
- KEXBXUAWXSOHEK-MEMLXQNLSA-N C(CCCC)[C@@H]1CC[C@H](CC1)COCCCCNC1=CC=CC=C1 Chemical compound C(CCCC)[C@@H]1CC[C@H](CC1)COCCCCNC1=CC=CC=C1 KEXBXUAWXSOHEK-MEMLXQNLSA-N 0.000 description 2
- GGAOIHAVCMLVCM-VHCLGDRQSA-N C1(=C(C=CC=C1)[C@@H]1CC[C@H](CC1)COC(CCCC1=CC=CC=C1)CCC)C Chemical compound C1(=C(C=CC=C1)[C@@H]1CC[C@H](CC1)COC(CCCC1=CC=CC=C1)CCC)C GGAOIHAVCMLVCM-VHCLGDRQSA-N 0.000 description 2
- WDMNRIZGTFBZML-MEMLXQNLSA-N C1(=C(C=CC=C1)[C@@H]1CC[C@H](CC1)COC1=CC=C(C=C1)CCC)C Chemical compound C1(=C(C=CC=C1)[C@@H]1CC[C@H](CC1)COC1=CC=C(C=C1)CCC)C WDMNRIZGTFBZML-MEMLXQNLSA-N 0.000 description 2
- YSLKMIUBCXOOQC-RSBROLRWSA-N CCC(CCCNC1=CC=CC=C1)OC[C@H]1CC[C@H](C)CC1 Chemical compound CCC(CCCNC1=CC=CC=C1)OC[C@H]1CC[C@H](C)CC1 YSLKMIUBCXOOQC-RSBROLRWSA-N 0.000 description 2
- WWTMINJBNZOCBM-HDJSIYSDSA-N C[C@@H]1CC[C@H](CC1)COC1=CC=C(C=C1)NCC Chemical compound C[C@@H]1CC[C@H](CC1)COC1=CC=C(C=C1)NCC WWTMINJBNZOCBM-HDJSIYSDSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- AIRBBFPZJFJYAK-OIFYPAEGSA-N C(CC)[C@@H]1CC[C@H](CC1)COC(CCCC1=CC=CC=C1)C Chemical compound C(CC)[C@@H]1CC[C@H](CC1)COC(CCCC1=CC=CC=C1)C AIRBBFPZJFJYAK-OIFYPAEGSA-N 0.000 description 1
- NSIOLAARWVBEDY-WKILWMFISA-N C(CC)[C@@H]1CC[C@H](CC1)COC1=CC=C(C=C1)OCC Chemical compound C(CC)[C@@H]1CC[C@H](CC1)COC1=CC=C(C=C1)OCC NSIOLAARWVBEDY-WKILWMFISA-N 0.000 description 1
- FNUWTRXUMODLEK-MGCOHNPYSA-N CCC[C@H]1CC[C@H](CBr)CC1 Chemical compound CCC[C@H]1CC[C@H](CBr)CC1 FNUWTRXUMODLEK-MGCOHNPYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/21—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring 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
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH65681A CH644392A5 (de) | 1981-02-02 | 1981-02-02 | Anisotrope cyclohexylmethylphenylaether. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3149139A1 DE3149139A1 (de) | 1982-08-26 |
| DE3149139C2 true DE3149139C2 (enrdf_load_stackoverflow) | 1989-11-09 |
Family
ID=4192085
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813149139 Granted DE3149139A1 (de) | 1981-02-02 | 1981-12-11 | "anisotrope cyclohexylmethylphenylaether" |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS57146729A (enrdf_load_stackoverflow) |
| CH (1) | CH644392A5 (enrdf_load_stackoverflow) |
| DE (1) | DE3149139A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2092576B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8811374D0 (en) * | 1988-05-13 | 1988-06-15 | Merck Patent Gmbh | Thermochromic esters |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56161339A (en) * | 1980-01-30 | 1981-12-11 | Secr Defence Brit | Liquid crystal compound, liquid crystal material and device containing said compound |
| DE3040632A1 (de) * | 1980-10-29 | 1982-05-27 | Merck Patent Gmbh, 6100 Darmstadt | Cyclohexylphenylderivate, diese enthaltende dielektrika und elektrooptisches anzeigeelement |
-
1981
- 1981-02-02 CH CH65681A patent/CH644392A5/de not_active IP Right Cessation
- 1981-12-11 DE DE19813149139 patent/DE3149139A1/de active Granted
-
1982
- 1982-02-01 GB GB8202751A patent/GB2092576B/en not_active Expired
- 1982-02-01 JP JP1342582A patent/JPS57146729A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CH644392A5 (de) | 1984-07-31 |
| GB2092576B (en) | 1985-04-17 |
| DE3149139A1 (de) | 1982-08-26 |
| JPS57146729A (en) | 1982-09-10 |
| GB2092576A (en) | 1982-08-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: MERCK PATENT GMBH, 6100 DARMSTADT, DE |
|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |