JPH0571580B2 - - Google Patents
Info
- Publication number
- JPH0571580B2 JPH0571580B2 JP61252819A JP25281986A JPH0571580B2 JP H0571580 B2 JPH0571580 B2 JP H0571580B2 JP 61252819 A JP61252819 A JP 61252819A JP 25281986 A JP25281986 A JP 25281986A JP H0571580 B2 JPH0571580 B2 JP H0571580B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- optically active
- formula
- acid
- added
- 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 - Fee Related
Links
- 239000004973 liquid crystal related substance Substances 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 26
- 239000013543 active substance Substances 0.000 claims description 18
- 230000003287 optical effect Effects 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 description 20
- 239000000243 solution Substances 0.000 description 16
- -1 p-toluenesulfonic acid ester Chemical class 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000004990 Smectic liquid crystal Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 6
- QLLONFPNPUFLOC-UHFFFAOYSA-N 4-(2-fluorooctoxy)benzoic acid Chemical compound CCCCCCC(F)COC1=CC=C(C(O)=O)C=C1 QLLONFPNPUFLOC-UHFFFAOYSA-N 0.000 description 6
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 230000005684 electric field Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- VKTKDEVNYHXHAJ-UHFFFAOYSA-N 2-fluorodecyl 4-methylbenzenesulfonate Chemical compound CCCCCCCCC(F)COS(=O)(=O)C1=CC=C(C)C=C1 VKTKDEVNYHXHAJ-UHFFFAOYSA-N 0.000 description 4
- KBGFGXNDULADJJ-UHFFFAOYSA-N 4-(2-fluorodecoxy)benzoic acid Chemical compound CCCCCCCCC(F)COC1=CC=C(C(O)=O)C=C1 KBGFGXNDULADJJ-UHFFFAOYSA-N 0.000 description 4
- USIIPOFQUJCEMJ-UHFFFAOYSA-N 4-(2-fluorooctoxy)benzonitrile Chemical compound FC(COC1=CC=C(C=C1)C#N)CCCCCC USIIPOFQUJCEMJ-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- LPSALLVYIATOKD-UHFFFAOYSA-N 1-bromo-2-fluorooctane Chemical compound CCCCCCC(F)CBr LPSALLVYIATOKD-UHFFFAOYSA-N 0.000 description 3
- CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical compound OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 description 3
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004988 Nematic liquid crystal Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- 230000010287 polarization Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- GYXGVTMWGOMPMB-UHFFFAOYSA-N 1-[4-(2-fluorodecoxy)phenyl]ethanone Chemical compound CCCCCCCCC(F)COC1=CC=C(C(C)=O)C=C1 GYXGVTMWGOMPMB-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- FMRRBUROSXDNJP-UHFFFAOYSA-N 5-hydroxy-2-phenylbenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1C1=CC=CC=C1 FMRRBUROSXDNJP-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Chemical compound Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000008204 material by function Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000004043 responsiveness Effects 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- SJZQQJOIMGMRKP-UHFFFAOYSA-N 2-fluorodecan-1-ol Chemical compound CCCCCCCCC(F)CO SJZQQJOIMGMRKP-UHFFFAOYSA-N 0.000 description 1
- PXUHUAWWMDRECM-UHFFFAOYSA-N 2-fluorooctan-1-ol Chemical compound CCCCCCC(F)CO PXUHUAWWMDRECM-UHFFFAOYSA-N 0.000 description 1
- QISGWQVXVLFKJQ-UHFFFAOYSA-N 4-(2-fluorododecoxy)benzoic acid Chemical compound CCCCCCCCCCC(F)COC1=CC=C(C(O)=O)C=C1 QISGWQVXVLFKJQ-UHFFFAOYSA-N 0.000 description 1
- BJXUDXRKWPVKJW-UHFFFAOYSA-N 4-(2-fluorohexadecoxy)benzoic acid Chemical compound CCCCCCCCCCCCCCC(F)COC1=CC=C(C(O)=O)C=C1 BJXUDXRKWPVKJW-UHFFFAOYSA-N 0.000 description 1
- UTELHNFEZSUQRN-UHFFFAOYSA-N 4-(2-fluorohexoxy)benzoic acid Chemical compound CCCCC(F)COC1=CC=C(C(O)=O)C=C1 UTELHNFEZSUQRN-UHFFFAOYSA-N 0.000 description 1
- MRYFGFMDLOZNOZ-UHFFFAOYSA-N 4-(2-fluorononoxy)benzoic acid Chemical compound CCCCCCCC(F)COC1=CC=C(C(O)=O)C=C1 MRYFGFMDLOZNOZ-UHFFFAOYSA-N 0.000 description 1
- YOXYXOLFLIGQFM-UHFFFAOYSA-N 4-(2-fluorotetradecoxy)benzoic acid Chemical compound CCCCCCCCCCCCC(F)COC1=CC=C(C(O)=O)C=C1 YOXYXOLFLIGQFM-UHFFFAOYSA-N 0.000 description 1
- PBMBSVZKOYMOOF-UHFFFAOYSA-N 4-(2-fluorotridecoxy)benzoic acid Chemical compound CCCCCCCCCCCC(F)COC1=CC=C(C(O)=O)C=C1 PBMBSVZKOYMOOF-UHFFFAOYSA-N 0.000 description 1
- SUTJIOICAMQTMS-UHFFFAOYSA-N 4-[4-(2-fluorooctoxy)phenyl]benzoic acid Chemical compound C1=CC(OCC(F)CCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 SUTJIOICAMQTMS-UHFFFAOYSA-N 0.000 description 1
- NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 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
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 150000003862 amino acid derivatives Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 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
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 150000001841 cholesterols Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61252819A JPS63107951A (ja) | 1986-10-25 | 1986-10-25 | 光学活性物質およびそれを含む液晶組成物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61252819A JPS63107951A (ja) | 1986-10-25 | 1986-10-25 | 光学活性物質およびそれを含む液晶組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63107951A JPS63107951A (ja) | 1988-05-12 |
| JPH0571580B2 true JPH0571580B2 (en]) | 1993-10-07 |
Family
ID=17242648
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61252819A Granted JPS63107951A (ja) | 1986-10-25 | 1986-10-25 | 光学活性物質およびそれを含む液晶組成物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63107951A (en]) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69416057T2 (de) * | 1993-08-31 | 1999-07-01 | Canon K.K., Tokio/Tokyo | Mesomorphe Verbindung, eine diese enthaltene Flüssigkristallzusammensetzung, eine diese Zusammensetzung verwendende Flüssigkristallvorrichtung, Flüssigkristallapparat und Anzeigeverfahren |
| US5641427A (en) * | 1994-07-26 | 1997-06-24 | Canon Kabushiki Kaisha | Liquid crystal composition, liquid crystal device using the composition liquid crystal apparatus and display method |
| DE69618413T2 (de) * | 1995-10-12 | 2002-06-20 | Canon K.K., Tokio/Tokyo | Flüssigkristallzusammensetzung, Flüssigkristallvorrichtung und Flüssigkristallanzeigeapparat |
-
1986
- 1986-10-25 JP JP61252819A patent/JPS63107951A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63107951A (ja) | 1988-05-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |