DE3152228C1 - 2,2'-Azoimidazolderivate,Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung eines fluessigkristallinen Materials - Google Patents
2,2'-Azoimidazolderivate,Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung eines fluessigkristallinen MaterialsInfo
- Publication number
- DE3152228C1 DE3152228C1 DE3152228A DE3152228A DE3152228C1 DE 3152228 C1 DE3152228 C1 DE 3152228C1 DE 3152228 A DE3152228 A DE 3152228A DE 3152228 A DE3152228 A DE 3152228A DE 3152228 C1 DE3152228 C1 DE 3152228C1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- alkyl group
- general formula
- liquid
- hydrogen atom
- 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
- 239000002178 crystalline material Substances 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000007788 liquid Substances 0.000 title description 16
- MJKDQDZHUIFGLN-UHFFFAOYSA-N bis(1H-imidazol-2-yl)diazene Chemical class C1=CNC(N=NC=2NC=CN=2)=N1 MJKDQDZHUIFGLN-UHFFFAOYSA-N 0.000 title description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- -1 aminoguanidine hydrazone Chemical class 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims description 2
- 238000010792 warming Methods 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 description 25
- 239000000975 dye Substances 0.000 description 23
- 239000011159 matrix material Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 238000001429 visible spectrum Methods 0.000 description 12
- 239000000126 substance Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000004973 liquid crystal related substance Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 238000003384 imaging method Methods 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- OTVRYZXVVMZHHW-FNOPAARDSA-N (8s,9s,10r,13r,14s,17r)-3-chloro-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1C=C2CC(Cl)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 OTVRYZXVVMZHHW-FNOPAARDSA-N 0.000 description 2
- UBDZFAGVPPMTIT-UHFFFAOYSA-N 2-aminoguanidine;hydron;chloride Chemical compound [Cl-].NC(N)=N[NH3+] UBDZFAGVPPMTIT-UHFFFAOYSA-N 0.000 description 2
- JRHHJNMASOIRDS-UHFFFAOYSA-N 4-ethoxybenzaldehyde Chemical compound CCOC1=CC=C(C=O)C=C1 JRHHJNMASOIRDS-UHFFFAOYSA-N 0.000 description 2
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-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
- 241000394567 Viola pubescens Species 0.000 description 2
- 159000000032 aromatic acids Chemical class 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 239000001045 blue dye Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 239000001046 green dye Substances 0.000 description 2
- 230000010365 information processing Effects 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 150000002696 manganese Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- OYHFBAQMPKCVEB-UHFFFAOYSA-N 1-(benzylideneamino)imidazol-2-amine Chemical compound Nc1nccn1N=Cc1ccccc1 OYHFBAQMPKCVEB-UHFFFAOYSA-N 0.000 description 1
- WNPXUCYRKHVMAD-UHFFFAOYSA-N 2-(benzylideneamino)guanidine Chemical compound NC(N)=NN=CC1=CC=CC=C1 WNPXUCYRKHVMAD-UHFFFAOYSA-N 0.000 description 1
- IKNNMFOQCUXFSC-UHFFFAOYSA-N 2-bromo-1-[4-(4-octylphenyl)phenyl]ethanone Chemical group C1=CC(CCCCCCCC)=CC=C1C1=CC=C(C(=O)CBr)C=C1 IKNNMFOQCUXFSC-UHFFFAOYSA-N 0.000 description 1
- PLXMOAALOJOTIY-FPTXNFDTSA-N Aesculin Natural products OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)[C@H]1Oc2cc3C=CC(=O)Oc3cc2O PLXMOAALOJOTIY-FPTXNFDTSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- GAUZCKBSTZFWCT-UHFFFAOYSA-N azoxybenzene Chemical compound C=1C=CC=CC=1[N+]([O-])=NC1=CC=CC=C1 GAUZCKBSTZFWCT-UHFFFAOYSA-N 0.000 description 1
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol group Chemical group [C@@H]1(CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@H](C)CCCC(C)C HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002265 electronic spectrum Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- VZUGBLTVBZJZOE-KRWDZBQOSA-N n-[3-[(4s)-2-amino-1,4-dimethyl-6-oxo-5h-pyrimidin-4-yl]phenyl]-5-chloropyrimidine-2-carboxamide Chemical compound N1=C(N)N(C)C(=O)C[C@@]1(C)C1=CC=CC(NC(=O)C=2N=CC(Cl)=CN=2)=C1 VZUGBLTVBZJZOE-KRWDZBQOSA-N 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical class C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 150000004905 tetrazines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/88—Nitrogen atoms, e.g. allantoin
-
- 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
- C09K19/3477—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a five-membered aromatic ring containing at least one nitrogen atom
- C09K19/348—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a five-membered aromatic ring containing at least one nitrogen atom containing at least two nitrogen atoms
-
- 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
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/60—Pleochroic dyes
-
- 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
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/60—Pleochroic dyes
- C09K19/601—Azoic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
- Liquid Crystal Substances (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU2967311 | 1980-07-31 | ||
| SU802967844A SU951856A1 (ru) | 1980-07-31 | 1980-07-31 | Жидкокристаллический материал |
| SU802967265A SU946186A1 (ru) | 1980-07-31 | 1980-07-31 | Производные 2,2-азоимидазола как дихроичные красители дл жидких кристаллов |
| SU802967803A SU944323A1 (ru) | 1980-07-31 | 1980-07-31 | Дихроичный краситель дл жидкокристаллического материала |
| PCT/SU1981/000059 WO1982000472A1 (en) | 1980-07-31 | 1981-06-25 | Derivatives of 2,2-azoimidazole,method for the preparation thereof,liquid crystal material and electro-optical device |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3152228C1 true DE3152228C1 (de) | 1985-07-18 |
Family
ID=27484903
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3152228A Expired DE3152228C1 (de) | 1980-07-31 | 1981-06-25 | 2,2'-Azoimidazolderivate,Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung eines fluessigkristallinen Materials |
| DE813152228T Pending DE3152228A1 (de) | 1980-07-31 | 1981-06-25 | Derivatives of 2,2-azoimidazole,method for the preparation thereof,liquid crystal material and electro-optical device |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE813152228T Pending DE3152228A1 (de) | 1980-07-31 | 1981-06-25 | Derivatives of 2,2-azoimidazole,method for the preparation thereof,liquid crystal material and electro-optical device |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4457859A (enExample) |
| JP (1) | JPS57501238A (enExample) |
| CH (1) | CH651844A5 (enExample) |
| DE (2) | DE3152228C1 (enExample) |
| FR (1) | FR2487830A1 (enExample) |
| GB (1) | GB2095273B (enExample) |
| NL (1) | NL8120400A (enExample) |
| WO (1) | WO1982000472A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK59888A (da) * | 1987-03-20 | 1988-09-21 | Hoffmann La Roche | Imidazolderivater |
| US5289301A (en) * | 1992-06-12 | 1994-02-22 | Boit, Inc. | Liquid crystal color modulation displays with dyes of different orders and circuitry for providing modulated AC excitation voltage |
| GB2393185B (en) * | 2002-09-17 | 2005-10-12 | Generics | A novel process for the preparation of 3,3'-azo-bis(6-hydroxybenzoic acid) and its derivatives |
| GB2396154B (en) * | 2002-10-15 | 2007-02-28 | Merck Patent Gmbh | 4,5-Dicyanoimidazole derivatives and their use in liquid crystal media and liquid crystal devices |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE564813C (de) * | 1930-06-04 | 1932-11-23 | Siemens Schuckertwerke Akt Ges | Buerstenabhebevorrichtung fuer Buerstenhalter elektrischer Maschinen |
| FR966395A (fr) * | 1948-05-12 | 1950-10-09 | Prod De Chimie Organique De La | Procédé de préparation de composés de la série des thio-hydantoïnes et produits nouveaux de cette série |
| CH507241A (de) * | 1968-01-31 | 1971-05-15 | Bayer Ag | Verfahren zur Herstellung von 3,5-disubstituierten Pyridinen neben 2-substituierten 2-Aminomethyl-1,3-propandiolen |
| CH564813A5 (enExample) * | 1973-11-12 | 1975-07-31 | Bbc Brown Boveri & Cie | |
| EP0002104B1 (en) * | 1977-10-14 | 1982-10-20 | BDH Chemicals Limited | Pleochroic dyes suitable for use in solution with liquid crystal materials for electro-optic device applications |
| DD137242B1 (de) * | 1978-06-16 | 1980-10-29 | Dietrich Demus | Nematische kristallin-fluessige mischungen |
| CH641828A5 (fr) * | 1979-08-17 | 1984-03-15 | Ebauches Sa | Composition a base de cristal liquide pour dispositif electro-optique. |
-
1981
- 1981-06-25 JP JP56503486A patent/JPS57501238A/ja active Pending
- 1981-06-25 DE DE3152228A patent/DE3152228C1/de not_active Expired
- 1981-06-25 DE DE813152228T patent/DE3152228A1/de active Pending
- 1981-06-25 US US06/364,848 patent/US4457859A/en not_active Expired - Fee Related
- 1981-06-25 GB GB8208525A patent/GB2095273B/en not_active Expired
- 1981-06-25 WO PCT/SU1981/000059 patent/WO1982000472A1/ru not_active Ceased
- 1981-06-25 NL NL8120400A patent/NL8120400A/nl unknown
- 1981-06-25 CH CH2063/82A patent/CH651844A5/de not_active IP Right Cessation
- 1981-07-30 FR FR8114888A patent/FR2487830A1/fr active Granted
Non-Patent Citations (1)
| Title |
|---|
| Chem.Ber., 101, 1968, S. 3151-3162 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1982000472A1 (en) | 1982-02-18 |
| FR2487830A1 (fr) | 1982-02-05 |
| CH651844A5 (de) | 1985-10-15 |
| US4457859A (en) | 1984-07-03 |
| JPS57501238A (enExample) | 1982-07-15 |
| GB2095273A (en) | 1982-09-29 |
| NL8120400A (enExample) | 1982-06-01 |
| FR2487830B1 (enExample) | 1983-01-28 |
| DE3152228A1 (de) | 1983-01-13 |
| GB2095273B (en) | 1984-09-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8100 | Publication of the examined application without publication of unexamined application | ||
| D1 | Grant (no unexamined application published) patent law 81 | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |