NL8400195A - 2,5-gedisubstitueerde pyridinen, werkwijze voor het bereiden ervan, mesomorf materiaal en elektro-optische inrichting. - Google Patents
2,5-gedisubstitueerde pyridinen, werkwijze voor het bereiden ervan, mesomorf materiaal en elektro-optische inrichting. Download PDFInfo
- Publication number
- NL8400195A NL8400195A NL8400195A NL8400195A NL8400195A NL 8400195 A NL8400195 A NL 8400195A NL 8400195 A NL8400195 A NL 8400195A NL 8400195 A NL8400195 A NL 8400195A NL 8400195 A NL8400195 A NL 8400195A
- Authority
- NL
- Netherlands
- Prior art keywords
- cyanophenyl
- formula
- pyridine
- mesomorphic
- compounds
- Prior art date
Links
- 239000000463 material Substances 0.000 title claims description 63
- 238000000034 method Methods 0.000 title description 21
- -1 2,5-disubstituted pyridines Chemical class 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 8
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 3
- 239000005695 Ammonium acetate Substances 0.000 claims description 3
- 229940043376 ammonium acetate Drugs 0.000 claims description 3
- 235000019257 ammonium acetate Nutrition 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000004020 conductor Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 239000004973 liquid crystal related substance Substances 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- MRGGVAVONGKJHH-UHFFFAOYSA-N 4-(5-hexylpyridin-2-yl)benzonitrile Chemical compound N1=CC(CCCCCC)=CC=C1C1=CC=C(C#N)C=C1 MRGGVAVONGKJHH-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- 238000005352 clarification Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- PANLHJSWXJODQV-UHFFFAOYSA-N 4-(5-pentylpyridin-2-yl)benzonitrile Chemical compound N1=CC(CCCCC)=CC=C1C1=CC=C(C#N)C=C1 PANLHJSWXJODQV-UHFFFAOYSA-N 0.000 description 3
- HYBZAFSPFHNSAB-UHFFFAOYSA-N 4-(5-propylpyridin-2-yl)benzonitrile Chemical compound N1=CC(CCC)=CC=C1C1=CC=C(C#N)C=C1 HYBZAFSPFHNSAB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 2
- WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 description 2
- BKXSBLROUCJNHD-UHFFFAOYSA-N 4-(5-butylpyridin-2-yl)benzonitrile Chemical compound N1=CC(CCCC)=CC=C1C1=CC=C(C#N)C=C1 BKXSBLROUCJNHD-UHFFFAOYSA-N 0.000 description 2
- TUENMDWVPMFBFB-UHFFFAOYSA-N 4-(5-ethylpyridin-2-yl)benzonitrile Chemical compound N1=CC(CC)=CC=C1C1=CC=C(C#N)C=C1 TUENMDWVPMFBFB-UHFFFAOYSA-N 0.000 description 2
- NPMFNFOCVGFNLD-UHFFFAOYSA-N 4-[5-(4-butylphenyl)pyridin-2-yl]benzonitrile Chemical compound C1=CC(CCCC)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C#N)N=C1 NPMFNFOCVGFNLD-UHFFFAOYSA-N 0.000 description 2
- POEBGIQSFIJHAX-UHFFFAOYSA-N 4-hexylcyclohexane-1-carboxylic acid Chemical compound CCCCCCC1CCC(C(O)=O)CC1 POEBGIQSFIJHAX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000002560 nitrile group Chemical group 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- XQRFASOUJIKXRE-UHFFFAOYSA-N (4-cyanophenyl) 4-butylbenzoate Chemical compound C1=CC(CCCC)=CC=C1C(=O)OC1=CC=C(C#N)C=C1 XQRFASOUJIKXRE-UHFFFAOYSA-N 0.000 description 1
- ZWAUTNYPKHVAEZ-UHFFFAOYSA-N (4-cyanophenyl) 4-heptylbenzoate Chemical compound C1=CC(CCCCCCC)=CC=C1C(=O)OC1=CC=C(C#N)C=C1 ZWAUTNYPKHVAEZ-UHFFFAOYSA-N 0.000 description 1
- DEUWEGPRKHPNKB-UHFFFAOYSA-N (4-cyanophenyl) 4-hexylbenzoate Chemical compound C1=CC(CCCCCC)=CC=C1C(=O)OC1=CC=C(C#N)C=C1 DEUWEGPRKHPNKB-UHFFFAOYSA-N 0.000 description 1
- AUXIEQKHXAYAHG-UHFFFAOYSA-N 1-phenylcyclohexane-1-carbonitrile Chemical class C=1C=CC=CC=1C1(C#N)CCCCC1 AUXIEQKHXAYAHG-UHFFFAOYSA-N 0.000 description 1
- ROVMLIKBAVUPPB-UHFFFAOYSA-N 2-(4-butylphenyl)acetic acid Chemical compound CCCCC1=CC=C(CC(O)=O)C=C1 ROVMLIKBAVUPPB-UHFFFAOYSA-N 0.000 description 1
- ZRGPOBYWTUVGAK-UHFFFAOYSA-N 4-(2-pentylphenyl)-3-phenylbenzonitrile Chemical group CCCCCC1=CC=CC=C1C1=CC=C(C#N)C=C1C1=CC=CC=C1 ZRGPOBYWTUVGAK-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
- GPGGNNIMKOVSAG-UHFFFAOYSA-N 4-(4-octoxyphenyl)benzonitrile Chemical group C1=CC(OCCCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 GPGGNNIMKOVSAG-UHFFFAOYSA-N 0.000 description 1
- FURZYCFZFBYJBT-UHFFFAOYSA-N 4-(4-pentylcyclohexyl)benzonitrile Chemical compound C1CC(CCCCC)CCC1C1=CC=C(C#N)C=C1 FURZYCFZFBYJBT-UHFFFAOYSA-N 0.000 description 1
- XXUSEPRYHRDKFV-UHFFFAOYSA-N 4-(4-propylcyclohexyl)benzonitrile Chemical compound C1CC(CCC)CCC1C1=CC=C(C#N)C=C1 XXUSEPRYHRDKFV-UHFFFAOYSA-N 0.000 description 1
- UIGMGAUXSRBGFP-UHFFFAOYSA-N 4-(5-heptylpyridin-2-yl)benzonitrile Chemical compound N1=CC(CCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 UIGMGAUXSRBGFP-UHFFFAOYSA-N 0.000 description 1
- JSDWOOVIJJDUTI-UHFFFAOYSA-N 4-(5-methylpyridin-2-yl)benzonitrile Chemical compound N1=CC(C)=CC=C1C1=CC=C(C#N)C=C1 JSDWOOVIJJDUTI-UHFFFAOYSA-N 0.000 description 1
- JGXCAINREKTOBJ-UHFFFAOYSA-N 4-(5-nonylpyridin-2-yl)benzonitrile Chemical compound N1=CC(CCCCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 JGXCAINREKTOBJ-UHFFFAOYSA-N 0.000 description 1
- YYCXNKVYQRGIJB-UHFFFAOYSA-N 4-[5-(4-hexylphenyl)pyridin-2-yl]benzonitrile Chemical compound C1=CC(CCCCCC)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C#N)N=C1 YYCXNKVYQRGIJB-UHFFFAOYSA-N 0.000 description 1
- DRZOJVUGHWZTMN-UHFFFAOYSA-N 4-[5-(4-octylphenyl)pyridin-2-yl]benzonitrile Chemical compound C1=CC(CCCCCCCC)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C#N)N=C1 DRZOJVUGHWZTMN-UHFFFAOYSA-N 0.000 description 1
- AOJIOUFMDYKZAS-UHFFFAOYSA-N 4-[5-(4-pentylphenyl)pyridin-2-yl]benzonitrile Chemical compound C1=CC(CCCCC)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C#N)N=C1 AOJIOUFMDYKZAS-UHFFFAOYSA-N 0.000 description 1
- NLPHXWGWBKZSJC-UHFFFAOYSA-N 4-acetylbenzonitrile Chemical compound CC(=O)C1=CC=C(C#N)C=C1 NLPHXWGWBKZSJC-UHFFFAOYSA-N 0.000 description 1
- BALGERHMIXFENA-UHFFFAOYSA-N 4-butylcyclohexane-1-carboxylic acid Chemical compound CCCCC1CCC(C(O)=O)CC1 BALGERHMIXFENA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- PVFOHMXILQEIHX-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-bromophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Br PVFOHMXILQEIHX-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 241001331845 Equus asinus x caballus Species 0.000 description 1
- 108010000178 IGF-I-IGFBP-3 complex Proteins 0.000 description 1
- MPCRDALPQLDDFX-UHFFFAOYSA-L Magnesium perchlorate Chemical compound [Mg+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O MPCRDALPQLDDFX-UHFFFAOYSA-L 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/26—Radicals substituted by halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—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
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/3444—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Pyridine Compounds (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8401698 | 1984-01-23 | ||
| GB8401698A GB2153345B (en) | 1984-01-23 | 1984-01-23 | Liquid crystal cyanophenyl-pyridines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8400195A true NL8400195A (nl) | 1985-08-16 |
Family
ID=10555382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8400195A NL8400195A (nl) | 1984-01-23 | 1984-01-20 | 2,5-gedisubstitueerde pyridinen, werkwijze voor het bereiden ervan, mesomorf materiaal en elektro-optische inrichting. |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH660362A5 (enrdf_load_stackoverflow) |
| DE (1) | DE3404055A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2558831B1 (enrdf_load_stackoverflow) |
| GB (1) | GB2153345B (enrdf_load_stackoverflow) |
| NL (1) | NL8400195A (enrdf_load_stackoverflow) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3524489A1 (de) * | 1984-07-12 | 1986-01-23 | Kabushiki Kaisha Suwa Seikosha, Tokio/Tokyo | 2-phenylpyridinderivate und verfahren zu ihrer herstellung |
| DE3600052A1 (de) | 1986-01-03 | 1987-07-09 | Merck Patent Gmbh | Heterocyclische verbindungen |
| JPS62234066A (ja) * | 1986-04-01 | 1987-10-14 | Chisso Corp | フエニルピリジン誘導体 |
| DE3768691D1 (de) * | 1986-04-22 | 1991-04-25 | Hoffmann La Roche | Fluessigkristalline pyridinderivate. |
| US4880936A (en) * | 1987-03-26 | 1989-11-14 | Dainippon Ink And Chemicals, Inc. | Optically active pyridines useful in liquid crystal form for electrical display devices |
| JP2532886B2 (ja) * | 1987-09-08 | 1996-09-11 | チッソ株式会社 | ネマチツク液晶組成物 |
| JP2711546B2 (ja) * | 1988-04-01 | 1998-02-10 | 大日本インキ化学工業株式会社 | 液晶デバイス |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1452826A (en) * | 1973-10-17 | 1976-10-20 | Secr Defence | Liquid crystal compositions |
-
1984
- 1984-01-10 CH CH10384A patent/CH660362A5/de not_active IP Right Cessation
- 1984-01-20 NL NL8400195A patent/NL8400195A/nl not_active Application Discontinuation
- 1984-01-23 GB GB8401698A patent/GB2153345B/en not_active Expired
- 1984-01-31 FR FR8401497A patent/FR2558831B1/fr not_active Expired
- 1984-02-06 DE DE19843404055 patent/DE3404055A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2558831B1 (fr) | 1986-07-11 |
| GB8401698D0 (en) | 1984-02-22 |
| DE3404055A1 (de) | 1985-10-10 |
| GB2153345A (en) | 1985-08-21 |
| CH660362A5 (de) | 1987-04-15 |
| GB2153345B (en) | 1987-11-25 |
| FR2558831A1 (fr) | 1985-08-02 |
| DE3404055C2 (enrdf_load_stackoverflow) | 1989-03-02 |
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