JPH0248534B2 - - Google Patents
Info
- Publication number
- JPH0248534B2 JPH0248534B2 JP60245709A JP24570985A JPH0248534B2 JP H0248534 B2 JPH0248534 B2 JP H0248534B2 JP 60245709 A JP60245709 A JP 60245709A JP 24570985 A JP24570985 A JP 24570985A JP H0248534 B2 JPH0248534 B2 JP H0248534B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- derivatives
- optically active
- lactic acid
- general formula
- 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 - Lifetime
Links
- 239000004973 liquid crystal related substance Substances 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 25
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 230000003287 optical effect Effects 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 18
- 239000000543 intermediate Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000004990 Smectic liquid crystal Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000008204 material by function Substances 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 230000010287 polarization Effects 0.000 description 6
- -1 polycyclic hydrocarbon Chemical class 0.000 description 6
- 230000002441 reversible effect Effects 0.000 description 5
- 230000002269 spontaneous effect Effects 0.000 description 5
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- 239000004988 Nematic liquid crystal Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- UKCFWUCWNZTUPT-UHFFFAOYSA-N 2-dodecoxypropan-1-ol Chemical compound CCCCCCCCCCCCOC(C)CO UKCFWUCWNZTUPT-UHFFFAOYSA-N 0.000 description 3
- 150000003862 amino acid derivatives Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001841 cholesterols Chemical class 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000004043 responsiveness Effects 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- DEDUBNVYPMOFDR-UHFFFAOYSA-N 2-ethoxypropan-1-ol Chemical compound CCOC(C)CO DEDUBNVYPMOFDR-UHFFFAOYSA-N 0.000 description 2
- MULOYHAWVKRCKQ-UHFFFAOYSA-N 2-ethoxypropyl 4-methylbenzenesulfonate Chemical compound CCOC(C)COS(=O)(=O)C1=CC=C(C)C=C1 MULOYHAWVKRCKQ-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
- SCSPMWDAVWKKMU-UHFFFAOYSA-N 4-(3-hexadecan-2-yloxypropoxy)benzoic acid Chemical compound CCCCCCCCCCCCCCC(C)OCCCOC1=CC=C(C(O)=O)C=C1 SCSPMWDAVWKKMU-UHFFFAOYSA-N 0.000 description 2
- 229940090248 4-hydroxybenzoic acid Drugs 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
- GPFWCOGWPCSZBO-UHFFFAOYSA-N 5-(3-dodecan-2-yloxypropoxy)-2-phenylbenzoic acid Chemical compound OC(=O)C1=CC(OCCCOC(C)CCCCCCCCCC)=CC=C1C1=CC=CC=C1 GPFWCOGWPCSZBO-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 125000001165 hydrophobic group Chemical group 0.000 description 2
- 150000003903 lactic acid esters Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- MPZIBALFBLXPKH-UHFFFAOYSA-N (4-nonoxyphenyl) 4-(4-octoxyphenyl)benzoate Chemical compound C1=CC(OCCCCCCCCC)=CC=C1OC(=O)C1=CC=C(C=2C=CC(OCCCCCCCC)=CC=2)C=C1 MPZIBALFBLXPKH-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- SKIDNYUZJPMKFC-UHFFFAOYSA-N 1-iododecane Chemical compound CCCCCCCCCCI SKIDNYUZJPMKFC-UHFFFAOYSA-N 0.000 description 1
- GCDPERPXPREHJF-UHFFFAOYSA-N 1-iodododecane Chemical compound CCCCCCCCCCCCI GCDPERPXPREHJF-UHFFFAOYSA-N 0.000 description 1
- LMHCYRULPLGEEZ-UHFFFAOYSA-N 1-iodoheptane Chemical compound CCCCCCCI LMHCYRULPLGEEZ-UHFFFAOYSA-N 0.000 description 1
- KMWHQYDMBYABKL-UHFFFAOYSA-N 1-iodohexadecane Chemical compound CCCCCCCCCCCCCCCCI KMWHQYDMBYABKL-UHFFFAOYSA-N 0.000 description 1
- ANOOTOPTCJRUPK-UHFFFAOYSA-N 1-iodohexane Chemical compound CCCCCCI ANOOTOPTCJRUPK-UHFFFAOYSA-N 0.000 description 1
- OGSJMFCWOUHXHN-UHFFFAOYSA-N 1-iodononane Chemical compound CCCCCCCCCI OGSJMFCWOUHXHN-UHFFFAOYSA-N 0.000 description 1
- UWLHSHAHTBJTBA-UHFFFAOYSA-N 1-iodooctane Chemical compound CCCCCCCCI UWLHSHAHTBJTBA-UHFFFAOYSA-N 0.000 description 1
- HHXJMIXXUWDKIA-UHFFFAOYSA-N 1-iodopentadecane Chemical compound CCCCCCCCCCCCCCCI HHXJMIXXUWDKIA-UHFFFAOYSA-N 0.000 description 1
- BLXSFCHWMBESKV-UHFFFAOYSA-N 1-iodopentane Chemical compound CCCCCI BLXSFCHWMBESKV-UHFFFAOYSA-N 0.000 description 1
- XGAMQNYEIPCUIZ-UHFFFAOYSA-N 1-iodotridecane Chemical compound CCCCCCCCCCCCCI XGAMQNYEIPCUIZ-UHFFFAOYSA-N 0.000 description 1
- FKUQOQPBCHJHAP-UHFFFAOYSA-N 1-iodoundecane Chemical compound CCCCCCCCCCCI FKUQOQPBCHJHAP-UHFFFAOYSA-N 0.000 description 1
- FALHGBIGXAGVGI-UHFFFAOYSA-N 2,5-bis(4-hexoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCC)=CC=C1C1=CN=C(C=2C=CC(OCCCCCC)=CC=2)N=C1 FALHGBIGXAGVGI-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
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- LCDPGWAEBCUYHP-UHFFFAOYSA-N 2-methyloctadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCC(C)CO LCDPGWAEBCUYHP-UHFFFAOYSA-N 0.000 description 1
- FWFAVISHBVXODB-UHFFFAOYSA-N 2-octoxypropan-1-ol Chemical compound CCCCCCCCOC(C)CO FWFAVISHBVXODB-UHFFFAOYSA-N 0.000 description 1
- JTZLOANPENMPIP-UHFFFAOYSA-N 2-pentoxypropan-1-ol Chemical compound CCCCCOC(C)CO JTZLOANPENMPIP-UHFFFAOYSA-N 0.000 description 1
- VCFRVGVFFZAYOH-UHFFFAOYSA-N 4-(2-propoxyphenyl)benzoic acid Chemical compound CCCOc1ccccc1-c1ccc(cc1)C(O)=O VCFRVGVFFZAYOH-UHFFFAOYSA-N 0.000 description 1
- DVDMLGMLYBBANS-UHFFFAOYSA-N 4-(3-dodecan-2-yloxypropoxy)benzoic acid Chemical compound CCCCCCCCCCC(C)OCCCOC1=CC=C(C(O)=O)C=C1 DVDMLGMLYBBANS-UHFFFAOYSA-N 0.000 description 1
- ZPCIKAYNHZRQAN-UHFFFAOYSA-N 4-(3-ethoxypropoxy)benzoic acid Chemical compound CCOCCCOC1=CC=C(C(O)=O)C=C1 ZPCIKAYNHZRQAN-UHFFFAOYSA-N 0.000 description 1
- JTGCXYYDAVPSFD-UHFFFAOYSA-N 4-(4-hydroxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(O)C=C1 JTGCXYYDAVPSFD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FMCGFINLOXSJPV-UHFFFAOYSA-N 5-nonyl-2-(4-octoxyphenyl)pyrimidine Chemical compound N1=CC(CCCCCCCCC)=CN=C1C1=CC=C(OCCCCCCCC)C=C1 FMCGFINLOXSJPV-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- ZGUGWUXLJSTTMA-UHFFFAOYSA-N Promazinum Chemical class C1=CC=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZGUGWUXLJSTTMA-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical class C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- GAUZCKBSTZFWCT-UHFFFAOYSA-N azoxybenzene Chemical class C=1C=CC=CC=1[N+]([O-])=NC1=CC=CC=C1 GAUZCKBSTZFWCT-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical class C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 150000001788 chalcone derivatives Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical class C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical class C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000007070 tosylation reaction Methods 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60245709A JPS62106048A (ja) | 1985-11-01 | 1985-11-01 | 乳酸誘導体 |
| US06/922,308 US4812259A (en) | 1985-11-01 | 1986-10-23 | Lactic acid derivative, liquid crystal composition containing same and liquid crystal device |
| GB8625958A GB2184116B (en) | 1985-11-01 | 1986-10-30 | Lactic acid derivative, liquid crystal composition containing same and liquid crystal device |
| DE19863637084 DE3637084A1 (de) | 1985-11-01 | 1986-10-31 | Propylenglykoldiether-derivate, fluessigkristallmischung und fluessigkristallvorrichtung |
| US07/292,953 US4880560A (en) | 1985-11-01 | 1989-01-03 | Lactic acid derivative, liquid crystal composition containing same and liquid crystal device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60245709A JPS62106048A (ja) | 1985-11-01 | 1985-11-01 | 乳酸誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62106048A JPS62106048A (ja) | 1987-05-16 |
| JPH0248534B2 true JPH0248534B2 (enrdf_load_stackoverflow) | 1990-10-25 |
Family
ID=17137639
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60245709A Granted JPS62106048A (ja) | 1985-11-01 | 1985-11-01 | 乳酸誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62106048A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1216473B (it) * | 1988-02-29 | 1990-03-08 | Montefibre Spa | Derivati poliossialchilen_etere_terminati di acidi organici, loro esteri alchilici e loro sali alcalini e alcalino terrosi. |
-
1985
- 1985-11-01 JP JP60245709A patent/JPS62106048A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62106048A (ja) | 1987-05-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4880560A (en) | Lactic acid derivative, liquid crystal composition containing same and liquid crystal device | |
| US5114613A (en) | Lactic acid derivative and liquid crystal composition containing same | |
| US4876027A (en) | Optically active composition, mesomorphic compound and liquid crystal device | |
| EP0302875B1 (en) | Optically active naphthalene compounds and liquid crystal compositions containing them | |
| 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 | |
| EP0301511A1 (en) | Optically active compound and liquid crystal composition containing same | |
| EP0217354B1 (en) | Novel optically active tolan derivative | |
| KR960000076B1 (ko) | 키랄성 에스테르의 제조방법 | |
| JPH0533943B2 (enrdf_load_stackoverflow) | ||
| JP2740347B2 (ja) | 液晶用キラルドーピング剤として用いられる光学活性化合物及びその製法 | |
| US5059345A (en) | Optically active compound and chiral liquid crystal composition containing the same | |
| JPH0651657B2 (ja) | フルオロアルカン誘導体、それを含む液晶組成物および液晶素子 | |
| EP0244129A2 (en) | Optically active compound and liquid crystalline composition | |
| JPH0436145B2 (enrdf_load_stackoverflow) | ||
| JP2856362B2 (ja) | フルオロフェニルピリミジン化合物 | |
| JPH0248534B2 (enrdf_load_stackoverflow) | ||
| JP2524341B2 (ja) | 光学活性液晶化合物および組成物 | |
| JPH0533942B2 (enrdf_load_stackoverflow) | ||
| JPH0430938B2 (enrdf_load_stackoverflow) | ||
| JPS63502756A (ja) | ネマチツク液晶相 | |
| JP2848471B2 (ja) | 光学活性化合物およびそれを含む液晶組成物 | |
| JPS62142131A (ja) | 液晶中間体 | |
| EP0256307B1 (en) | Optically active compounds having biphenyl skeleton, liquid crystal composition and switching element containing them | |
| JP2579810B2 (ja) | アルキルチオ安息香酸誘導体 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |