JPS6251257B2 - - Google Patents
Info
- Publication number
- JPS6251257B2 JPS6251257B2 JP55024865A JP2486580A JPS6251257B2 JP S6251257 B2 JPS6251257 B2 JP S6251257B2 JP 55024865 A JP55024865 A JP 55024865A JP 2486580 A JP2486580 A JP 2486580A JP S6251257 B2 JPS6251257 B2 JP S6251257B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- formula
- carbon atom
- cholesteric
- asymmetric carbon
- 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 24
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- CCLVGHDFLATNLC-UHFFFAOYSA-N 4-[4-(2-methylbutyl)phenyl]benzoic acid Chemical compound C1=CC(CC(C)CC)=CC=C1C1=CC=C(C(O)=O)C=C1 CCLVGHDFLATNLC-UHFFFAOYSA-N 0.000 claims description 6
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 claims description 6
- 239000004988 Nematic liquid crystal Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 230000003098 cholesteric effect Effects 0.000 description 11
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000007704 transition Effects 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
- JJLWOHRZGKBRSG-UHFFFAOYSA-N 1-(2-methylbutyl)-4-phenylcyclohexa-2,4-diene-1-carboxylic acid Chemical compound C1=CC(CC(C)CC)(C(O)=O)CC=C1C1=CC=CC=C1 JJLWOHRZGKBRSG-UHFFFAOYSA-N 0.000 description 2
- VHWGPISIUNUREA-UHFFFAOYSA-N 4-pentylcyclohexan-1-ol Chemical compound CCCCCC1CCC(O)CC1 VHWGPISIUNUREA-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- -1 (butyl)-4′-biphenylcarboxylic acid Chemical compound 0.000 description 1
- VTWWIMHDYYPURZ-UHFFFAOYSA-N 3-butyl-4-phenylbenzoic acid Chemical compound CCCCC1=CC(C(O)=O)=CC=C1C1=CC=CC=C1 VTWWIMHDYYPURZ-UHFFFAOYSA-N 0.000 description 1
- OYTSIQCCOOVUOB-UHFFFAOYSA-N 4-ethyldecan-1-ol Chemical compound CCCCCCC(CC)CCCO OYTSIQCCOOVUOB-UHFFFAOYSA-N 0.000 description 1
- KBAGHZBLGCSVEN-UHFFFAOYSA-N 4-hexylcyclohexan-1-ol Chemical compound CCCCCCC1CCC(O)CC1 KBAGHZBLGCSVEN-UHFFFAOYSA-N 0.000 description 1
- ZNPSUQQXTRRSBM-UHFFFAOYSA-N 4-n-Pentylphenol Chemical compound CCCCCC1=CC=C(O)C=C1 ZNPSUQQXTRRSBM-UHFFFAOYSA-N 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
Classifications
-
- 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
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
- C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
-
- 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
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2486580A JPS56122334A (en) | 1980-02-29 | 1980-02-29 | Liquid crystal 4-alkylcyclohexyl ester |
| DE8181101066T DE3161461D1 (en) | 1980-02-29 | 1981-02-16 | Trans-4"-alkylcyclohexyl esters of 4'-(2-methylbutyl)-4-biphenylcarboxylic acid and liquid crystal compositions containing same |
| EP81101066A EP0035155B1 (en) | 1980-02-29 | 1981-02-16 | Trans-4"-alkylcyclohexyl esters of 4'-(2-methylbutyl)-4-biphenylcarboxylic acid and liquid crystal compositions containing same |
| US06/238,209 US4341653A (en) | 1980-02-29 | 1981-02-26 | Liquid-crystalline 4-alkylcyclohexyl esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2486580A JPS56122334A (en) | 1980-02-29 | 1980-02-29 | Liquid crystal 4-alkylcyclohexyl ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56122334A JPS56122334A (en) | 1981-09-25 |
| JPS6251257B2 true JPS6251257B2 (US08088816-20120103-C00036.png) | 1987-10-29 |
Family
ID=12150100
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2486580A Granted JPS56122334A (en) | 1980-02-29 | 1980-02-29 | Liquid crystal 4-alkylcyclohexyl ester |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4341653A (US08088816-20120103-C00036.png) |
| EP (1) | EP0035155B1 (US08088816-20120103-C00036.png) |
| JP (1) | JPS56122334A (US08088816-20120103-C00036.png) |
| DE (1) | DE3161461D1 (US08088816-20120103-C00036.png) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03110347U (US08088816-20120103-C00036.png) * | 1990-02-28 | 1991-11-12 | ||
| JPH03115838U (US08088816-20120103-C00036.png) * | 1990-03-12 | 1991-12-02 |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57195219A (en) * | 1981-05-25 | 1982-11-30 | Matsushita Electric Ind Co Ltd | Liquid crystal color display panel |
| JPS58103578A (ja) * | 1981-12-16 | 1983-06-20 | Alps Electric Co Ltd | カラ−液晶表示素子 |
| DE3208089A1 (de) * | 1982-03-06 | 1983-09-08 | Merck Patent Gmbh, 6100 Darmstadt | Halogenbiphenylderivate |
| EP0110299B2 (en) * | 1982-11-26 | 1993-06-09 | Hitachi, Ltd. | Smectic liquid crystal compounds and liquid crystal compositions |
| DE3373193D1 (en) * | 1983-01-06 | 1987-10-01 | Chisso Corp | Liquid crystalline compounds and mixtures thereof |
| EP0168043B1 (de) * | 1984-07-11 | 1990-11-07 | MERCK PATENT GmbH | Flüssigkristall-Phase |
| JPS6160782A (ja) * | 1984-08-31 | 1986-03-28 | Fujitsu Ltd | 蓄積型液晶組成物 |
| JPS6289645A (ja) * | 1985-09-18 | 1987-04-24 | Chisso Corp | 強誘電性液晶エステル化合物及び液晶組成物 |
| EP0247466B1 (de) * | 1986-05-22 | 1993-11-24 | F. Hoffmann-La Roche Ag | Flüssigkristalline Derivate von Phenylbenzoat |
| JPH0832673B2 (ja) * | 1987-03-20 | 1996-03-29 | チッソ株式会社 | オルト−シアノ−ベンゼン骨格を含む光学活性液晶化合物 |
| DE3887569T2 (de) * | 1987-06-04 | 1994-08-04 | Canon Kk | Flüssigkristallzusammensetzung und Flüssigkristall-Vorrichtung, die diese enthält. |
| JP4918979B2 (ja) * | 2005-10-25 | 2012-04-18 | 井関農機株式会社 | 植物抜根機 |
| RU2563133C2 (ru) * | 2009-08-28 | 2015-09-20 | Геркулес Инкорпорейтед | Пленкообразующая композиция для нанесения покрытий на основе твердых порошкообразных соединений |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2288732A1 (fr) * | 1974-10-22 | 1976-05-21 | Merck Patent Gmbh | Nouveaux esters biphenyliques, procede pour leur preparation et application comme constituants de cristaux liquides |
| JPS5257139A (en) * | 1975-11-06 | 1977-05-11 | Dainippon Toryo Kk | Production of cairal nematic compound and liquid crystal composition |
| GB1592161A (en) * | 1976-08-13 | 1981-07-01 | Secr Defence | Biphenyl carboxylic esters and their use as liquid crystal materials |
| US4113647A (en) * | 1976-08-13 | 1978-09-12 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Liquid crystalline materials |
| GB1596012A (en) * | 1976-08-16 | 1981-08-19 | Secr Defence | Optically active liquid crystal materials and liquid crystal devices containing them |
| FR2415133A2 (fr) * | 1978-01-24 | 1979-08-17 | Thomson Csf | Nouvelle famille de cristaux liquides a grande anisotropie dielectrique negative, et dispositifs utilisant de tels cristaux |
| GB1603076A (en) * | 1977-04-05 | 1981-11-18 | Secr Defence | Esters of (+)-4-(2'-methylbutyl)phenol and their use as liquid crystal materials |
| DE2800553A1 (de) * | 1978-01-07 | 1979-07-12 | Merck Patent Gmbh | Cyclohexanderivate |
| US4293434A (en) * | 1978-08-08 | 1981-10-06 | VEB Werk fur Fernsehelektronik Berlin im VEB Kombinat Mikroelektronik | Liquid crystal compounds |
-
1980
- 1980-02-29 JP JP2486580A patent/JPS56122334A/ja active Granted
-
1981
- 1981-02-16 DE DE8181101066T patent/DE3161461D1/de not_active Expired
- 1981-02-16 EP EP81101066A patent/EP0035155B1/en not_active Expired
- 1981-02-26 US US06/238,209 patent/US4341653A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03110347U (US08088816-20120103-C00036.png) * | 1990-02-28 | 1991-11-12 | ||
| JPH03115838U (US08088816-20120103-C00036.png) * | 1990-03-12 | 1991-12-02 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0035155A1 (en) | 1981-09-09 |
| US4341653A (en) | 1982-07-27 |
| DE3161461D1 (en) | 1983-12-29 |
| JPS56122334A (en) | 1981-09-25 |
| EP0035155B1 (en) | 1983-11-23 |
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