JPH0424336B2 - - Google Patents
Info
- Publication number
- JPH0424336B2 JPH0424336B2 JP60232886A JP23288685A JPH0424336B2 JP H0424336 B2 JPH0424336 B2 JP H0424336B2 JP 60232886 A JP60232886 A JP 60232886A JP 23288685 A JP23288685 A JP 23288685A JP H0424336 B2 JPH0424336 B2 JP H0424336B2
- Authority
- JP
- Japan
- Prior art keywords
- optically active
- liquid crystal
- fluoro
- general formula
- alkanol
- 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
- 239000004973 liquid crystal related substance Substances 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 3
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 238000007259 addition reaction Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 14
- 230000003287 optical effect Effects 0.000 description 13
- 239000013543 active substance Substances 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- 239000004990 Smectic liquid crystal Substances 0.000 description 6
- 239000008204 material by function Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 230000010287 polarization Effects 0.000 description 5
- 230000002269 spontaneous effect Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 230000002441 reversible effect Effects 0.000 description 4
- 239000004988 Nematic liquid crystal Substances 0.000 description 3
- 150000003862 amino acid derivatives Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001841 cholesterols Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- UEBHTEIKXIPNGN-UHFFFAOYSA-N 2-fluoroheptan-1-ol Chemical compound CCCCCC(F)CO UEBHTEIKXIPNGN-UHFFFAOYSA-N 0.000 description 2
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical group OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 239000004986 Cholesteric liquid crystals (ChLC) 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
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- LZRIYTFPVMKAIR-UHFFFAOYSA-N 1-fluoroheptan-1-ol Chemical compound CCCCCCC(O)F LZRIYTFPVMKAIR-UHFFFAOYSA-N 0.000 description 1
- ICEBAZPURYIURB-UHFFFAOYSA-N 2-(2-methylbutyl)benzoic acid Chemical compound CCC(C)CC1=CC=CC=C1C(O)=O ICEBAZPURYIURB-UHFFFAOYSA-N 0.000 description 1
- LRKCNYYCJZXSHR-UHFFFAOYSA-N 2-fluorononan-1-ol Chemical compound CCCCCCCC(F)CO LRKCNYYCJZXSHR-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
- NMOFYYYCFRVWBK-UHFFFAOYSA-N 2-pentyloxirane Chemical compound CCCCCC1CO1 NMOFYYYCFRVWBK-UHFFFAOYSA-N 0.000 description 1
- 238000000023 Kugelrohr distillation Methods 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
- 230000002411 adverse Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Liquid Crystal (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60232886A JPS6293248A (ja) | 1985-10-18 | 1985-10-18 | 光学活性物質、その製造方法およびそれを含む液晶組成物 |
| US06/919,376 US4798680A (en) | 1985-10-18 | 1986-10-16 | Optically active compound, process for producing same and liquid crystal composition containing same |
| US07/112,936 US4873018A (en) | 1985-10-18 | 1987-10-27 | Optically active compound, process for producing same and liquid crystal composition containing same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60232886A JPS6293248A (ja) | 1985-10-18 | 1985-10-18 | 光学活性物質、その製造方法およびそれを含む液晶組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6293248A JPS6293248A (ja) | 1987-04-28 |
| JPH0424336B2 true JPH0424336B2 (enrdf_load_stackoverflow) | 1992-04-24 |
Family
ID=16946378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60232886A Granted JPS6293248A (ja) | 1985-10-18 | 1985-10-18 | 光学活性物質、その製造方法およびそれを含む液晶組成物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6293248A (enrdf_load_stackoverflow) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62111939A (ja) * | 1985-07-23 | 1987-05-22 | Ajinomoto Co Inc | 光学活性β−フルオロヒドリン化合物 |
| JP2582289B2 (ja) * | 1988-09-22 | 1997-02-19 | 株式会社ジャパンエナジー | 光学活性を有する２―フルオロ―１―アルカノール類の製造方法 |
| JP2582288B2 (ja) * | 1988-10-12 | 1997-02-19 | 株式会社ジャパンエナジー | 光学活性な１―フルオロ―２―アルカノール類及びその製造方法 |
| 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 |
| US5785890A (en) * | 1995-10-12 | 1998-07-28 | Canon Kabushiki Kaisha | Liquid crystal composition, liquid crystal device, and liquid crystal display apparatus using same |
| GB2582364A (en) * | 2019-03-21 | 2020-09-23 | Mexichem Fluor Sa De Cv | Methods |
-
1985
- 1985-10-18 JP JP60232886A patent/JPS6293248A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6293248A (ja) | 1987-04-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4798680A (en) | Optically active compound, process for producing same and liquid crystal composition containing same | |
| US4876027A (en) | Optically active composition, mesomorphic compound and liquid crystal device | |
| KR950013094B1 (ko) | 다수의 비대칭 탄소 원자를 함유하는 신규의 광학적 활성 화합물 | |
| US5034152A (en) | Optically active compound and liquid crystal composition containing same | |
| US4917817A (en) | Optical active compound, process for producing same and liquid crystal composition containing same | |
| EP0217354B1 (en) | Novel optically active tolan derivative | |
| JPH0533943B2 (enrdf_load_stackoverflow) | ||
| JPH0424336B2 (enrdf_load_stackoverflow) | ||
| JP2843624B2 (ja) | ２，５―ジ置換ヘテロ環状化合物および液晶相 | |
| EP0280419B1 (en) | Optically active-2-substituted-propyl ether and liquid crystal composition | |
| JPH0588696B2 (enrdf_load_stackoverflow) | ||
| EP0270244B1 (en) | Optically active alcohols | |
| JPH0541615B2 (enrdf_load_stackoverflow) | ||
| EP0312210B1 (en) | Optically active liquid crystalline compounds and compositions containing them | |
| US5166391A (en) | Optically-active aliphatic α-halogen substituted carboxylic acid 4'-(alkoxybenzyloxy)biphenyl thioester compounds | |
| JPS63243059A (ja) | 光学活性な２―フルオロアルカン酸およびそれを含む液晶組成物 | |
| JPH01311051A (ja) | 新規な乳酸誘導体、これを含む液晶組成物及び光スイッチング素子 | |
| US5336436A (en) | Optically active oxirane derivatives, and their use as dopes in liquid-crystal mixtures | |
| JPH0420422B2 (enrdf_load_stackoverflow) | ||
| JP2568247B2 (ja) | 光学活性物質、その製造方法およびそれを含有する液晶組成物 | |
| JPS62174047A (ja) | アルカンニトリル誘導体 | |
| EP0409234A2 (en) | Alpha-hydroxyketone derivatives, liquid crystal compositions containing said derivatives, and liquid crystal devices using said compositions | |
| JPS60199867A (ja) | α−メチル−β−（４−置換フエニル）プロピオン酸のシアノフエニルエステル誘導体 | |
| JPS62106048A (ja) | 乳酸誘導体 | |
| JPH05163204A (ja) | 光学活性なエステル誘導体及びこれを含む液晶組成物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |