DE2751403C3 - p'-Cyanophenylester der p-( ß -Alkoxy)äthoxybenzoesSure und diese enthaltende nematische Flüssigkristallzusammensetzungen - Google Patents
p'-Cyanophenylester der p-( ß -Alkoxy)äthoxybenzoesSure und diese enthaltende nematische FlüssigkristallzusammensetzungenInfo
- Publication number
- DE2751403C3 DE2751403C3 DE2751403A DE2751403A DE2751403C3 DE 2751403 C3 DE2751403 C3 DE 2751403C3 DE 2751403 A DE2751403 A DE 2751403A DE 2751403 A DE2751403 A DE 2751403A DE 2751403 C3 DE2751403 C3 DE 2751403C3
- Authority
- DE
- Germany
- Prior art keywords
- liquid crystal
- ethoxybenzoic acid
- alkoxy
- acid
- cyanophenyl ester
- 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
- XDZMPRGFOOFSBL-UHFFFAOYSA-N 2-ethoxybenzoic acid Chemical compound CCOC1=CC=CC=C1C(O)=O XDZMPRGFOOFSBL-UHFFFAOYSA-N 0.000 title claims description 14
- 239000000203 mixture Substances 0.000 title description 12
- 239000004988 Nematic liquid crystal Substances 0.000 title description 6
- 239000004973 liquid crystal related substance Substances 0.000 description 31
- 150000001875 compounds Chemical class 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 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
- 238000000862 absorption spectrum Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 210000002858 crystal cell Anatomy 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JLEQZACKSXNUMB-UHFFFAOYSA-N (4-ethylphenyl)imino-(4-methoxyphenyl)-oxidoazanium Chemical compound C1=CC(CC)=CC=C1N=[N+]([O-])C1=CC=C(OC)C=C1 JLEQZACKSXNUMB-UHFFFAOYSA-N 0.000 description 1
- QKQIDUFDIUHVFF-UHFFFAOYSA-N 2-(2-ethoxyethoxy)benzoic acid Chemical compound CCOCCOC1=CC=CC=C1C(O)=O QKQIDUFDIUHVFF-UHFFFAOYSA-N 0.000 description 1
- SHFGENOBPXWUJF-UHFFFAOYSA-N 2-(2-phenylphenyl)benzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 SHFGENOBPXWUJF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZGOWXOZNUNZPAV-UHFFFAOYSA-N 4-(4-heptylphenyl)benzonitrile Chemical group C1=CC(CCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 ZGOWXOZNUNZPAV-UHFFFAOYSA-N 0.000 description 1
- CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical compound OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000004848 alkoxyethyl group Chemical group 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005406 washing 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
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the 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
- C09K19/06—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
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
- C09K2019/2035—Ph-COO-Ph
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14191776A JPS5365846A (en) | 1976-11-26 | 1976-11-26 | P-(beta-alkoxy)ethoxybenzoic acid p'-cyanophenylesters |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2751403A1 DE2751403A1 (de) | 1978-06-01 |
| DE2751403B2 DE2751403B2 (de) | 1979-08-02 |
| DE2751403C3 true DE2751403C3 (de) | 1980-04-03 |
Family
ID=15303158
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2751403A Expired DE2751403C3 (de) | 1976-11-26 | 1977-11-17 | p'-Cyanophenylester der p-( ß -Alkoxy)äthoxybenzoesSure und diese enthaltende nematische Flüssigkristallzusammensetzungen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4158011A (OSRAM) |
| JP (1) | JPS5365846A (OSRAM) |
| CH (1) | CH631202A5 (OSRAM) |
| DE (1) | DE2751403C3 (OSRAM) |
| GB (1) | GB1556321A (OSRAM) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4309304A (en) * | 1979-11-01 | 1982-01-05 | Exxon Research & Engineering Co. | Liquid crystal compositions for multiplexed displays |
| US4328116A (en) * | 1979-11-01 | 1982-05-04 | Minnesota Mining And Manufacturing Company | Liquid crystal compositions for multiplexed displays |
| JPS5746952A (en) * | 1980-09-04 | 1982-03-17 | Chisso Corp | 4'-(beta-alkyloxyethoxy)-4-cyanobiphenyl |
| EP0058981B1 (en) * | 1981-02-25 | 1986-01-22 | Hitachi, Ltd. | Colorless liquid crystalline compounds |
| US4556727A (en) * | 1984-07-18 | 1985-12-03 | University Patents, Inc. | Ferroelectric smectic liquid crystals |
| JPS6176449A (ja) * | 1984-08-16 | 1986-04-18 | Chisso Corp | アルコキシエトキシ置換エステル誘導体 |
| US4812259A (en) * | 1985-11-01 | 1989-03-14 | Canon Kabushiki Kaisha | Lactic acid derivative, liquid crystal composition containing same and liquid crystal device |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3923857A (en) * | 1972-02-23 | 1975-12-02 | Hoffmann La Roche | Liquid crystal esters |
-
1976
- 1976-11-26 JP JP14191776A patent/JPS5365846A/ja active Granted
-
1977
- 1977-11-09 US US05/849,737 patent/US4158011A/en not_active Expired - Lifetime
- 1977-11-14 GB GB47344/77A patent/GB1556321A/en not_active Expired
- 1977-11-17 DE DE2751403A patent/DE2751403C3/de not_active Expired
- 1977-11-22 CH CH1423777A patent/CH631202A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1556321A (en) | 1979-11-21 |
| US4158011A (en) | 1979-06-12 |
| DE2751403A1 (de) | 1978-06-01 |
| JPS57310B2 (OSRAM) | 1982-01-06 |
| JPS5365846A (en) | 1978-06-12 |
| DE2751403B2 (de) | 1979-08-02 |
| CH631202A5 (de) | 1982-07-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OAP | Request for examination filed | ||
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |