CH670639A5 - - Google Patents
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- Publication number
- CH670639A5 CH670639A5 CH56187A CH56187A CH670639A5 CH 670639 A5 CH670639 A5 CH 670639A5 CH 56187 A CH56187 A CH 56187A CH 56187 A CH56187 A CH 56187A CH 670639 A5 CH670639 A5 CH 670639A5
- Authority
- CH
- Switzerland
- Prior art keywords
- crystalline
- trans
- liquid
- formula
- oxygen atom
- Prior art date
Links
- 239000000203 mixture Substances 0.000 claims description 52
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 8
- 238000005352 clarification Methods 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 238000001640 fractional crystallisation Methods 0.000 claims description 6
- 238000002844 melting Methods 0.000 claims description 6
- 230000008018 melting Effects 0.000 claims description 6
- 239000004990 Smectic liquid crystal Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 230000003098 cholesteric effect Effects 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 2
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical class ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 claims description 2
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000001816 cooling Methods 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- AITBHTAFQQYBHP-UHFFFAOYSA-N benzene;pyridine Chemical compound C1=CC=CC=C1.C1=CC=NC=C1 AITBHTAFQQYBHP-UHFFFAOYSA-N 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- GBKDCKUFKOVLBI-UHFFFAOYSA-N 4-butylcyclohexane-1-carbohydrazide Chemical compound CCCCC1CCC(C(=O)NN)CC1 GBKDCKUFKOVLBI-UHFFFAOYSA-N 0.000 description 3
- -1 4-substituted-phenyl Chemical group 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OYFBUAXJLRAPEW-UBBSCCEASA-N C(CCC)[C@@H]1CC[C@H](CC1)C=1SC(=NN1)[C@@H]1CC[C@H](CC1)CCCC Chemical compound C(CCC)[C@@H]1CC[C@H](CC1)C=1SC(=NN1)[C@@H]1CC[C@H](CC1)CCCC OYFBUAXJLRAPEW-UBBSCCEASA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 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 2
- WNCUHHQSGMACFL-HZCBDIJESA-N BrC=1C=C(C=CC=1OCCCCCCCCC)C=1SC(=NN=1)[C@@H]1CC[C@H](CC1)CCCC Chemical compound BrC=1C=C(C=CC=1OCCCCCCCCC)C=1SC(=NN=1)[C@@H]1CC[C@H](CC1)CCCC WNCUHHQSGMACFL-HZCBDIJESA-N 0.000 description 2
- MSEIDSVWQXZLKB-ZWGSZDQZSA-N C(CCCCC)[C@@H]1CC[C@H](CC1)C=1SC(=NN=1)[C@@H]1CC[C@H](CC1)CCCCCC Chemical compound C(CCCCC)[C@@H]1CC[C@H](CC1)C=1SC(=NN=1)[C@@H]1CC[C@H](CC1)CCCCCC MSEIDSVWQXZLKB-ZWGSZDQZSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- OUOWCSJYDCPVDM-UHFFFAOYSA-N 4-butylbenzoyl chloride Chemical compound CCCCC1=CC=C(C(Cl)=O)C=C1 OUOWCSJYDCPVDM-UHFFFAOYSA-N 0.000 description 1
- ZHJCVLQOKPGYDJ-UHFFFAOYSA-N 4-butylcyclohexane-1-carbonyl chloride Chemical compound CCCCC1CCC(C(Cl)=O)CC1 ZHJCVLQOKPGYDJ-UHFFFAOYSA-N 0.000 description 1
- HPJDDPSWQZSHQH-UHFFFAOYSA-N 4-heptylcyclohexane-1-carbonyl chloride Chemical compound CCCCCCCC1CCC(C(Cl)=O)CC1 HPJDDPSWQZSHQH-UHFFFAOYSA-N 0.000 description 1
- HBQUXMZZODHFMJ-UHFFFAOYSA-N 4-hexoxybenzoic acid Chemical compound CCCCCCOC1=CC=C(C(O)=O)C=C1 HBQUXMZZODHFMJ-UHFFFAOYSA-N 0.000 description 1
- CPEPWESLFZVUEP-UHFFFAOYSA-N 4-hexylbenzoic acid Chemical compound CCCCCCC1=CC=C(C(O)=O)C=C1 CPEPWESLFZVUEP-UHFFFAOYSA-N 0.000 description 1
- POEBGIQSFIJHAX-UHFFFAOYSA-N 4-hexylcyclohexane-1-carboxylic acid Chemical compound CCCCCCC1CCC(C(O)=O)CC1 POEBGIQSFIJHAX-UHFFFAOYSA-N 0.000 description 1
- IBUQBYKNBNUNHO-UHFFFAOYSA-N 4-pentylperoxybenzoic acid Chemical compound CCCCCOOc1ccc(cc1)C(O)=O IBUQBYKNBNUNHO-UHFFFAOYSA-N 0.000 description 1
- NLWNOUGZCBOKFH-AQYVVDRMSA-N C(CCC)C1=CC=C(C=C1)C=1SC(=NN=1)[C@@H]1CC[C@H](CC1)CCCCCC Chemical compound C(CCC)C1=CC=C(C=C1)C=1SC(=NN=1)[C@@H]1CC[C@H](CC1)CCCCCC NLWNOUGZCBOKFH-AQYVVDRMSA-N 0.000 description 1
- SISNREAILCVMAM-KOMQPUFPSA-N C(CCC)[C@@H]1CC[C@H](CC1)C=1SC(=NN=1)C1=CC=C(C=C1)C#N Chemical compound C(CCC)[C@@H]1CC[C@H](CC1)C=1SC(=NN=1)C1=CC=C(C=C1)C#N SISNREAILCVMAM-KOMQPUFPSA-N 0.000 description 1
- KLWGEWUEZXUROR-XUTJKUGGSA-N C(CCC)[C@@H]1CC[C@H](CC1)C=1SC(=NN=1)C1=CC=C(C=C1)CCCCCC Chemical compound C(CCC)[C@@H]1CC[C@H](CC1)C=1SC(=NN=1)C1=CC=C(C=C1)CCCCCC KLWGEWUEZXUROR-XUTJKUGGSA-N 0.000 description 1
- ZAPXYRNJDDXYBJ-KBQPQWKXSA-N C(CCC)[C@@H]1CC[C@H](CC1)C=1SC(=NN=1)[C@@H]1CC[C@H](CC1)CCCCCCC Chemical compound C(CCC)[C@@H]1CC[C@H](CC1)C=1SC(=NN=1)[C@@H]1CC[C@H](CC1)CCCCCCC ZAPXYRNJDDXYBJ-KBQPQWKXSA-N 0.000 description 1
- OLUFGJUJMWBLHH-AQYVVDRMSA-N C(CCCC)[C@@H]1CC[C@H](CC1)C=1SC(=NN=1)C1=CC=C(C=C1)CCCCCC Chemical compound C(CCCC)[C@@H]1CC[C@H](CC1)C=1SC(=NN=1)C1=CC=C(C=C1)CCCCCC OLUFGJUJMWBLHH-AQYVVDRMSA-N 0.000 description 1
- YDDJLBOTDXUNAU-SAABIXHNSA-N C(CCCCC)[C@@H]1CC[C@H](CC1)C=1SC(=NN=1)C1=CC=C(C=C1)C#N Chemical compound C(CCCCC)[C@@H]1CC[C@H](CC1)C=1SC(=NN=1)C1=CC=C(C=C1)C#N YDDJLBOTDXUNAU-SAABIXHNSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
-
- 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
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
- C09K19/3497—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom the heterocyclic ring containing sulfur and nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD28758186A DD247694A1 (de) | 1986-03-05 | 1986-03-05 | Kristallin-fluessige gemische |
| DD28759286A DD247221A1 (de) | 1986-03-05 | 1986-03-05 | Verfahren zur herstellung 2,5-disubstituierter 1,3,4-thiadiazolderivate mit trans-cyclohexanstrukturfragmenten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH670639A5 true CH670639A5 (enrdf_load_html_response) | 1989-06-30 |
Family
ID=25748035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH56187A CH670639A5 (enrdf_load_html_response) | 1986-03-05 | 1987-02-12 |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH670639A5 (enrdf_load_html_response) |
| DE (1) | DE3703651A1 (enrdf_load_html_response) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3730859A1 (de) | 1987-04-16 | 1989-03-30 | Merck Patent Gmbh | Thiazol- und thiadiazol-derivate enthaltende medien mit smektischer fluessigkristalliner phase |
| US5478496A (en) * | 1987-04-16 | 1995-12-26 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Media containing thiazole derivatives and thiadiazole derivatives and having a smectic liquid-crystalline phase |
| DE3712995B4 (de) * | 1987-04-16 | 2004-02-05 | Qinetiq Ltd. | Thiazol- und Thiadiazol-Derivate enthaltende Medien mit smektischer flüssigkristalliner Phase und die Verwendung dieser Medien in elektrooptischen Anzeigeelementen |
| DE3819972C2 (de) * | 1987-07-01 | 1997-04-10 | Samsung Electronic Devices | 2,5-disubstituierte 1,3,4-Thiadiazole mit ausgedehnten smektischen C-Phasen und Verwendung in flüssigkristallinen Mischungen |
| DE3807871A1 (de) * | 1988-03-10 | 1989-09-21 | Merck Patent Gmbh | Heterocyclische derivate des 1,2-difluorbenzols |
| JP2801269B2 (ja) * | 1989-07-10 | 1998-09-21 | キヤノン株式会社 | 化合物およびこれを含む液晶組成物およびこれを使用した液晶素子 |
| US5143642A (en) * | 1990-01-13 | 1992-09-01 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Liquid-crystalline medium for electrooptical display elements based on the ECB effect |
| WO1996020985A1 (fr) * | 1994-12-29 | 1996-07-11 | Chisso Corporation | Composition smectique de cristaux liquides et dispositif a cristaux liquides |
-
1987
- 1987-02-06 DE DE19873703651 patent/DE3703651A1/de not_active Withdrawn
- 1987-02-12 CH CH56187A patent/CH670639A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE3703651A1 (de) | 1987-09-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |