JPS6321657B2 - - Google Patents
Info
- Publication number
- JPS6321657B2 JPS6321657B2 JP55122681A JP12268180A JPS6321657B2 JP S6321657 B2 JPS6321657 B2 JP S6321657B2 JP 55122681 A JP55122681 A JP 55122681A JP 12268180 A JP12268180 A JP 12268180A JP S6321657 B2 JPS6321657 B2 JP S6321657B2
- Authority
- JP
- Japan
- Prior art keywords
- cyanobiphenyl
- liquid crystal
- formula
- compound
- point
- 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
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 19
- 239000004973 liquid crystal related substance Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- PGSCYBVRPKEFIQ-UHFFFAOYSA-N 4-[4-(2-propoxyethoxy)phenyl]benzonitrile Chemical group C1=CC(OCCOCCC)=CC=C1C1=CC=C(C#N)C=C1 PGSCYBVRPKEFIQ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- HHPCNRKYVYWYAU-UHFFFAOYSA-N 4-cyano-4'-pentylbiphenyl Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(C#N)C=C1 HHPCNRKYVYWYAU-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- BQYZDMNAARQHKR-UHFFFAOYSA-N 1-(2-bromoethoxy)propane Chemical compound CCCOCCBr BQYZDMNAARQHKR-UHFFFAOYSA-N 0.000 description 2
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 2
- KAFCJMNPFYAAGY-UHFFFAOYSA-N 4-[4-(2-methoxyethoxy)phenyl]benzonitrile Chemical group C1=CC(OCCOC)=CC=C1C1=CC=C(C#N)C=C1 KAFCJMNPFYAAGY-UHFFFAOYSA-N 0.000 description 2
- BALGERHMIXFENA-UHFFFAOYSA-N 4-butylcyclohexane-1-carboxylic acid Chemical compound CCCCC1CCC(C(O)=O)CC1 BALGERHMIXFENA-UHFFFAOYSA-N 0.000 description 2
- QCNUKEGGHOLBES-UHFFFAOYSA-N 4-propylcyclohexane-1-carboxylic acid Chemical compound CCCC1CCC(C(O)=O)CC1 QCNUKEGGHOLBES-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-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
- 238000009835 boiling Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- -1 ester Ester Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229940044631 ferric chloride hexahydrate Drugs 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- NQXWGWZJXJUMQB-UHFFFAOYSA-K iron trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].Cl[Fe+]Cl NQXWGWZJXJUMQB-UHFFFAOYSA-K 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WOLUYEFMPZAHNN-UHFFFAOYSA-N 1-(2-bromoethoxy)butane Chemical group CCCCOCCBr WOLUYEFMPZAHNN-UHFFFAOYSA-N 0.000 description 1
- QOZKHOIGOQWTRS-UHFFFAOYSA-N 1-(2-bromoethoxy)hexane Chemical group CCCCCCOCCBr QOZKHOIGOQWTRS-UHFFFAOYSA-N 0.000 description 1
- NLSQTAPVYFQSHD-UHFFFAOYSA-N 1-(2-bromoethoxy)pentane Chemical group CCCCCOCCBr NLSQTAPVYFQSHD-UHFFFAOYSA-N 0.000 description 1
- MMYKTRPLXXWLBC-UHFFFAOYSA-N 1-bromo-2-ethoxyethane Chemical group CCOCCBr MMYKTRPLXXWLBC-UHFFFAOYSA-N 0.000 description 1
- YGAFPDUUNJQCQP-UHFFFAOYSA-N 1-bromo-4-[4-(2-propoxyethoxy)phenyl]benzene Chemical group C1=CC(OCCOCCC)=CC=C1C1=CC=C(Br)C=C1 YGAFPDUUNJQCQP-UHFFFAOYSA-N 0.000 description 1
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
- XVRYDCKPOBZQSJ-UHFFFAOYSA-N 2-(4-heptylcyclohexyl)benzonitrile Chemical compound C1CC(CCCCCCC)CCC1C1=CC=CC=C1C#N XVRYDCKPOBZQSJ-UHFFFAOYSA-N 0.000 description 1
- UMPSXOXLNGYHLJ-UHFFFAOYSA-N 2-(4-pentylcyclohexyl)benzonitrile Chemical compound C1CC(CCCCC)CCC1C1=CC=CC=C1C#N UMPSXOXLNGYHLJ-UHFFFAOYSA-N 0.000 description 1
- OXDUBUKGEAQLQL-UHFFFAOYSA-N 2-(4-propylcyclohexyl)benzonitrile Chemical compound C1CC(CCC)CCC1C1=CC=CC=C1C#N OXDUBUKGEAQLQL-UHFFFAOYSA-N 0.000 description 1
- WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 description 1
- SLCDMYPZGHPEPA-UHFFFAOYSA-N 3-pentyl-4-phenylbenzonitrile Chemical group CCCCCC1=CC(C#N)=CC=C1C1=CC=CC=C1 SLCDMYPZGHPEPA-UHFFFAOYSA-N 0.000 description 1
- ARUBXNBYMCVENE-UHFFFAOYSA-N 4-(4-bromophenyl)phenol Chemical group C1=CC(O)=CC=C1C1=CC=C(Br)C=C1 ARUBXNBYMCVENE-UHFFFAOYSA-N 0.000 description 1
- ZRMIETZFPZGBEB-UHFFFAOYSA-N 4-(4-hydroxyphenyl)benzonitrile Chemical group C1=CC(O)=CC=C1C1=CC=C(C#N)C=C1 ZRMIETZFPZGBEB-UHFFFAOYSA-N 0.000 description 1
- ZQVKTHRQIXSMGY-UHFFFAOYSA-N 4-Ethylbenzoic acid Chemical compound CCC1=CC=C(C(O)=O)C=C1 ZQVKTHRQIXSMGY-UHFFFAOYSA-N 0.000 description 1
- BIKMBOVFDFUCLV-UHFFFAOYSA-N 4-[4-(2-butoxyethoxy)phenyl]benzonitrile Chemical group C1=CC(OCCOCCCC)=CC=C1C1=CC=C(C#N)C=C1 BIKMBOVFDFUCLV-UHFFFAOYSA-N 0.000 description 1
- LPYBLZNRQFKEFR-UHFFFAOYSA-N 4-[4-(2-ethoxyethoxy)phenyl]benzonitrile Chemical group C1=CC(OCCOCC)=CC=C1C1=CC=C(C#N)C=C1 LPYBLZNRQFKEFR-UHFFFAOYSA-N 0.000 description 1
- LEHPDVBBXPOFJZ-UHFFFAOYSA-N 4-[4-(2-hexoxyethoxy)phenyl]benzonitrile Chemical group C1=CC(OCCOCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 LEHPDVBBXPOFJZ-UHFFFAOYSA-N 0.000 description 1
- VIHCWPXLDVGLFE-UHFFFAOYSA-N 4-[4-(2-pentoxyethoxy)phenyl]benzonitrile Chemical group C1=CC(OCCOCCCCC)=CC=C1C1=CC=C(C#N)C=C1 VIHCWPXLDVGLFE-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 101000713575 Homo sapiens Tubulin beta-3 chain Proteins 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 102100036790 Tubulin beta-3 chain Human genes 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55122681A JPS5746952A (en) | 1980-09-04 | 1980-09-04 | 4'-(beta-alkyloxyethoxy)-4-cyanobiphenyl |
| EP81106745A EP0047453B1 (en) | 1980-09-04 | 1981-08-28 | 4'-(beta-alkyloxyethoxy)-4-cyanobiphenyl |
| DE8181106745T DE3162179D1 (de) | 1980-09-04 | 1981-08-28 | 4'-(beta-alkyloxyethoxy)-4-cyanobiphenyl |
| US06/298,769 US4374748A (en) | 1980-09-04 | 1981-09-02 | 4'-(β-Alkyloxyethoxy)-4-cyanobiphenyl |
| DD81233017A DD201604A5 (de) | 1980-09-04 | 1981-09-03 | Nematisches fluessigkristallmaterial |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55122681A JPS5746952A (en) | 1980-09-04 | 1980-09-04 | 4'-(beta-alkyloxyethoxy)-4-cyanobiphenyl |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5746952A JPS5746952A (en) | 1982-03-17 |
| JPS6321657B2 true JPS6321657B2 (en]) | 1988-05-09 |
Family
ID=14841986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55122681A Granted JPS5746952A (en) | 1980-09-04 | 1980-09-04 | 4'-(beta-alkyloxyethoxy)-4-cyanobiphenyl |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4374748A (en]) |
| EP (1) | EP0047453B1 (en]) |
| JP (1) | JPS5746952A (en]) |
| DD (1) | DD201604A5 (en]) |
| DE (1) | DE3162179D1 (en]) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3268611D1 (en) * | 1981-02-25 | 1986-03-06 | Hitachi Ltd | Colorless liquid crystalline compounds |
| US4556727A (en) * | 1984-07-18 | 1985-12-03 | University Patents, Inc. | Ferroelectric smectic liquid crystals |
| US4654162A (en) * | 1984-08-13 | 1987-03-31 | Chisso Corporation | Alcohol derivatives |
| JP2676508B2 (ja) * | 1986-09-12 | 1997-11-17 | コニカ株式会社 | 液晶表示装置 |
| JP2594266B2 (ja) * | 1987-02-05 | 1997-03-26 | チッソ株式会社 | 光学活性−２−アルコキシ−プロピルエーテル類および液晶組成物 |
| WO1988008870A1 (en) * | 1987-05-13 | 1988-11-17 | The General Electric Company, P.L.C. | Liquid crystal material |
| JP2627629B2 (ja) * | 1987-12-07 | 1997-07-09 | チッソ株式会社 | 液晶組成物 |
| US4844836A (en) * | 1988-11-23 | 1989-07-04 | Adeka Argus Chemical Co., Ltd. | Optically active cyanobiphenyl compound |
| US5178794A (en) * | 1989-03-01 | 1993-01-12 | Dainippon Ink And Chemicals, Inc. | Alkylene glycol derivative and liquid crystal mixture containing the same |
| JP2605249B2 (ja) * | 1993-07-23 | 1997-04-30 | 大日本インキ化学工業株式会社 | 液晶組成物及び液晶表示装置 |
| FR2759696B1 (fr) * | 1997-02-18 | 1999-04-16 | Expansia Sa | Preparation du 4-cyano-4'-hydroxy biphenyle |
| GB0202201D0 (en) * | 2002-01-31 | 2002-03-20 | Qinetiq Ltd | Liquid crystal compounds |
| KR101108738B1 (ko) * | 2008-10-14 | 2012-03-14 | 웅진코웨이주식회사 | 분쇄 스크류, 분쇄통 및 이를 구비하는 음식물 처리기의 분쇄로 |
| CN109575945B (zh) * | 2017-09-28 | 2022-06-17 | 江苏和成显示科技有限公司 | 液晶组合物及其液晶显示器件 |
| CN109575948B (zh) * | 2017-09-28 | 2022-06-17 | 江苏和成显示科技有限公司 | 一种液晶组合物及其液晶显示器件 |
| CN108717239B (zh) * | 2017-11-20 | 2021-02-19 | 山东蓝贝易书信息科技有限公司 | 易热擦除型液晶膜写字板及制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4005064A (en) * | 1971-05-18 | 1977-01-25 | Owens-Illinois, Inc. | Liquid crystal or mesomorphic 4-methoxyalkoxy-4'-alkyl azoxybenzene compounds |
| GB1433130A (en) * | 1972-11-09 | 1976-04-22 | Secr Defence | Substituted biphenyl and polyphenyl compounds and liquid crystal materials and devices containing them |
| NL7414352A (nl) * | 1973-11-19 | 1975-05-21 | Hoffmann La Roche | Vloeibaarkristallijne bifenylen. |
| GB1556994A (en) * | 1975-09-03 | 1979-12-05 | Secr Defence | Optically active cyanobiphenyl compounds and liquid crystal materials and devices containing them |
| JPS5365846A (en) * | 1976-11-26 | 1978-06-12 | Chisso Corp | P-(beta-alkoxy)ethoxybenzoic acid p'-cyanophenylesters |
-
1980
- 1980-09-04 JP JP55122681A patent/JPS5746952A/ja active Granted
-
1981
- 1981-08-28 EP EP81106745A patent/EP0047453B1/en not_active Expired
- 1981-08-28 DE DE8181106745T patent/DE3162179D1/de not_active Expired
- 1981-09-02 US US06/298,769 patent/US4374748A/en not_active Expired - Lifetime
- 1981-09-03 DD DD81233017A patent/DD201604A5/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DD201604A5 (de) | 1983-07-27 |
| US4374748A (en) | 1983-02-22 |
| EP0047453A1 (en) | 1982-03-17 |
| DE3162179D1 (de) | 1984-03-15 |
| EP0047453B1 (en) | 1984-02-08 |
| JPS5746952A (en) | 1982-03-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR920004141B1 (ko) | 스멕틱 액정조성물 | |
| KR100333020B1 (ko) | 액정화합물,이러한화합물을함유하는액정조성물및이러한조성물을사용하여제조된액정표시소자 | |
| US3951846A (en) | Novel liquid crystal electro-optic devices | |
| JP2722195B2 (ja) | スメクテイツク液晶相 | |
| JPS6321657B2 (en]) | ||
| US5308542A (en) | 4,4'-disubstituted 2',3-difluorobisphenyls and a liquid-crystalline medium | |
| EP0099099B1 (en) | High temperature liquid crystal substances having four rings and liquid crystal compositions containing the same | |
| JPS6144863B2 (en]) | ||
| US4623477A (en) | Ester compounds having a pyrimidine ring | |
| JP2746711B2 (ja) | フッ素化４″― シアノ置換ターフェニル | |
| KR0140529B1 (ko) | 시아노-측면 치환된 테르페닐 | |
| JP3783248B2 (ja) | ４−（２−シクロヘキシル）プロピル−ｐ−テルフェニル誘導体 | |
| US5122297A (en) | Tetracyclic benzene derivatives and liquid-crystalline media | |
| JP2927957B2 (ja) | フェニルシクロヘキサン類および液晶媒体 | |
| EP0390329B1 (en) | Pyrimidine derivative | |
| JPS6324507B2 (en]) | ||
| EP0452274A2 (en) | Phenylcyclohexyldioxane derivatives having an ether bond for electro-optical displays | |
| JP4193077B2 (ja) | １，３−フェニレン誘導体 | |
| JP3065094B2 (ja) | エーテル結合を有するハロゲン化フェニルシクロヘキシルジオキサン | |
| JP2745073B2 (ja) | フェニルアセチレン化合物 | |
| JP3797436B2 (ja) | 光学活性化合物 | |
| JPH0132216B2 (en]) | ||
| JPS6261017B2 (en]) | ||
| JPS642114B2 (en]) | ||
| JP2929677B2 (ja) | エーテル系化合物 |