FR2473538A1 - Melange en cristaux liquides de l'ester du 4-(2,2-dicyan-ethenyl)-phenol et procede pour leur fabrication - Google Patents
Melange en cristaux liquides de l'ester du 4-(2,2-dicyan-ethenyl)-phenol et procede pour leur fabrication Download PDFInfo
- Publication number
- FR2473538A1 FR2473538A1 FR8022717A FR8022717A FR2473538A1 FR 2473538 A1 FR2473538 A1 FR 2473538A1 FR 8022717 A FR8022717 A FR 8022717A FR 8022717 A FR8022717 A FR 8022717A FR 2473538 A1 FR2473538 A1 FR 2473538A1
- Authority
- FR
- France
- Prior art keywords
- coo
- formula
- nematic liquid
- acid
- liquid crystalline
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 29
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title claims abstract description 10
- 239000004973 liquid crystal related substance Substances 0.000 title abstract description 4
- 239000007788 liquid Substances 0.000 claims abstract description 26
- -1 4- (2,2-dicyan-ethenyl) -phenol ester Chemical class 0.000 claims abstract description 14
- 150000002148 esters Chemical class 0.000 claims abstract description 10
- FNCOVSWSZZVFBQ-UHFFFAOYSA-N 2-[(4-hydroxyphenyl)methylidene]propanedinitrile Chemical compound OC1=CC=C(C=C(C#N)C#N)C=C1 FNCOVSWSZZVFBQ-UHFFFAOYSA-N 0.000 claims abstract description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- SSYVIRDHEJGVCM-UHFFFAOYSA-N (4-carbonochloridoylphenyl) heptanoate Chemical compound CCCCCCC(=O)OC1=CC=C(C(Cl)=O)C=C1 SSYVIRDHEJGVCM-UHFFFAOYSA-N 0.000 claims description 2
- HBQUXMZZODHFMJ-UHFFFAOYSA-N 4-hexoxybenzoic acid Chemical compound CCCCCCOC1=CC=C(C(O)=O)C=C1 HBQUXMZZODHFMJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 abstract 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000006000 Knoevenagel condensation reaction Methods 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- OIBFRBIJSBWAHB-UHFFFAOYSA-N (2-butoxyphenyl) 2-hexylbenzoate Chemical compound CCCCCCC1=CC=CC=C1C(=O)OC1=CC=CC=C1OCCCC OIBFRBIJSBWAHB-UHFFFAOYSA-N 0.000 description 1
- BADVPHQPIAWXCD-UHFFFAOYSA-N (2-octoxyphenyl) 2-pentoxybenzoate Chemical compound CCCCCCCCOC1=CC=CC=C1OC(=O)C1=CC=CC=C1OCCCCC BADVPHQPIAWXCD-UHFFFAOYSA-N 0.000 description 1
- GVRJUQNXOBRHEU-UHFFFAOYSA-N (4-formylphenyl) 4-hexoxybenzoate Chemical compound C1=CC(OCCCCCC)=CC=C1C(=O)OC1=CC=C(C=O)C=C1 GVRJUQNXOBRHEU-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
- BXSMMAVTEURRGG-UHFFFAOYSA-N 3-chlorohexane Chemical compound CCCC(Cl)CC BXSMMAVTEURRGG-UHFFFAOYSA-N 0.000 description 1
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 1
- 102000002322 Egg Proteins Human genes 0.000 description 1
- 108010000912 Egg Proteins Proteins 0.000 description 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940052296 esters of benzoic acid for local anesthesia Drugs 0.000 description 1
- ILUJQPXNXACGAN-UHFFFAOYSA-N ortho-methoxybenzoic acid Natural products COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 1
- 210000004681 ovum Anatomy 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD21841180 | 1980-01-11 | ||
| DD21841080A DD158177A3 (de) | 1980-01-11 | 1980-01-11 | Kristallin-fluessige nematische gemische |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2473538A1 true FR2473538A1 (fr) | 1981-07-17 |
| FR2473538B1 FR2473538B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1983-11-25 |
Family
ID=25747678
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8022717A Granted FR2473538A1 (fr) | 1980-01-11 | 1980-10-23 | Melange en cristaux liquides de l'ester du 4-(2,2-dicyan-ethenyl)-phenol et procede pour leur fabrication |
Country Status (5)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3221462A1 (de) * | 1981-06-18 | 1983-01-05 | F. Hoffmann-La Roche & Co AG, 4002 Basel | Fluessigkristallines gemisch |
| US4528114A (en) * | 1981-12-18 | 1985-07-09 | Hoffmann-La Roche Inc. | Acetylenes |
| US4512636A (en) * | 1982-06-15 | 1985-04-23 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdon Of Great Britian And Northern Ireland Of Whitehall | Liquid crystal compounds |
| EP0122389B1 (de) * | 1983-03-16 | 1987-08-05 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Flüssigkristallkomponenten mit einer Alkenylseitenkette |
| US5252252A (en) * | 1983-09-10 | 1993-10-12 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Anisotropic compounds and liquid crystal mixtures |
| DE3332692A1 (de) * | 1983-09-10 | 1985-03-28 | Merck Patent Gmbh, 6100 Darmstadt | Anisotrope verbindungen und fluessigkristallmischungen |
| EP0167912B1 (de) * | 1984-07-12 | 1990-01-03 | F. Hoffmann-La Roche Ag | Flüssigkristalline Gemische enthaltend Komponenten mit einer 4-Alkenyl- oder 2Z-Alkenyl-Seitenkette |
| US5238602A (en) * | 1984-07-16 | 1993-08-24 | Hoffmann La Roche Inc. | Liquid crystals |
| CA1336441C (en) * | 1987-12-28 | 1995-07-25 | Manabu Uchida | Liquid crystal composition |
| JPH08283226A (ja) * | 1995-04-14 | 1996-10-29 | Chisso Corp | アクリロニトリル誘導体、液晶組成物および液晶表示素子 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2544577A1 (de) * | 1974-10-30 | 1976-05-06 | Werk Fernsehelektronik Veb | Kristallin-fluessige nematische substanzen |
| FR2377441A1 (fr) * | 1977-01-14 | 1978-08-11 | Thomson Csf | Nouvelle famille de cristaux liquides de proprietes ameliorees, et dispositifs utilisant de tels cristaux liquides |
-
1980
- 1980-10-03 US US06/202,958 patent/US4363767A/en not_active Expired - Lifetime
- 1980-10-23 CH CH7895/80A patent/CH648339A5/de not_active IP Right Cessation
- 1980-10-23 FR FR8022717A patent/FR2473538A1/fr active Granted
- 1980-12-04 GB GB8038882A patent/GB2067188B/en not_active Expired
- 1980-12-12 DE DE19803046872 patent/DE3046872A1/de active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2544577A1 (de) * | 1974-10-30 | 1976-05-06 | Werk Fernsehelektronik Veb | Kristallin-fluessige nematische substanzen |
| FR2377441A1 (fr) * | 1977-01-14 | 1978-08-11 | Thomson Csf | Nouvelle famille de cristaux liquides de proprietes ameliorees, et dispositifs utilisant de tels cristaux liquides |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3046872A1 (de) | 1981-09-17 |
| DE3046872C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-06-01 |
| FR2473538B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1983-11-25 |
| GB2067188A (en) | 1981-07-22 |
| US4363767A (en) | 1982-12-14 |
| GB2067188B (en) | 1984-02-29 |
| CH648339A5 (de) | 1985-03-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |