CA1051421A - Nematic liquid crystal compounds and compositions - Google Patents
Nematic liquid crystal compounds and compositionsInfo
- Publication number
- CA1051421A CA1051421A CA225,703A CA225703A CA1051421A CA 1051421 A CA1051421 A CA 1051421A CA 225703 A CA225703 A CA 225703A CA 1051421 A CA1051421 A CA 1051421A
- Authority
- CA
- Canada
- Prior art keywords
- liquid crystal
- butylaniline
- nematic liquid
- ethoxybenzylidene
- crystal compositions
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 81
- 150000001875 compounds Chemical class 0.000 title claims abstract description 33
- 239000004988 Nematic liquid crystal Substances 0.000 title claims abstract description 28
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 claims abstract description 12
- YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical class NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002262 Schiff base Substances 0.000 claims abstract description 10
- 150000004753 Schiff bases Chemical class 0.000 claims abstract description 10
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims abstract description 6
- -1 n-octyl group Chemical group 0.000 claims abstract description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims abstract description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 230000001590 oxidative effect Effects 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 36
- 238000002156 mixing Methods 0.000 abstract description 31
- 230000000694 effects Effects 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 description 49
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- DBOAVDSSZWDGTH-UHFFFAOYSA-N n-(4-butylphenyl)-1-(4-ethoxyphenyl)methanimine Chemical compound C1=CC(CCCC)=CC=C1N=CC1=CC=C(OCC)C=C1 DBOAVDSSZWDGTH-UHFFFAOYSA-N 0.000 description 18
- 229960000583 acetic acid Drugs 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000000463 material Substances 0.000 description 14
- FEIWNULTQYHCDN-UHFFFAOYSA-N mbba Chemical compound C1=CC(CCCC)=CC=C1N=CC1=CC=C(OC)C=C1 FEIWNULTQYHCDN-UHFFFAOYSA-N 0.000 description 13
- 239000012153 distilled water Substances 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 239000012362 glacial acetic acid Substances 0.000 description 9
- 239000007789 gas Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 230000001747 exhibiting effect Effects 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 4
- 244000228957 Ferula foetida Species 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- FTMPHIRBCCMRCI-UHFFFAOYSA-N 1-heptyl-4-nitrosobenzene Chemical compound C(CCCCCC)C1=CC=C(C=C1)N=O FTMPHIRBCCMRCI-UHFFFAOYSA-N 0.000 description 2
- QHYPBLILCYMWPE-UHFFFAOYSA-N 1-hexyl-4-nitrosobenzene Chemical compound C(CCCCC)C1=CC=C(C=C1)N=O QHYPBLILCYMWPE-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 2
- UOACKFBJUYNSLK-XRKIENNPSA-N Estradiol Cypionate Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H](C4=CC=C(O)C=C4CC3)CC[C@@]21C)C(=O)CCC1CCCC1 UOACKFBJUYNSLK-XRKIENNPSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GPVBTKFBKLGNTC-UHFFFAOYSA-N (2-cyanophenyl)imino-oxido-phenylazanium Chemical compound C=1C=CC=CC=1[N+]([O-])=NC1=CC=CC=C1C#N GPVBTKFBKLGNTC-UHFFFAOYSA-N 0.000 description 1
- ULHFFAFDSSHFDA-UHFFFAOYSA-N 1-amino-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1N ULHFFAFDSSHFDA-UHFFFAOYSA-N 0.000 description 1
- XFDALNVZYFHILZ-UHFFFAOYSA-N 1-butyl-4-nitrosobenzene Chemical compound CCCCC1=CC=C(N=O)C=C1 XFDALNVZYFHILZ-UHFFFAOYSA-N 0.000 description 1
- OYUYQUBADLGZJW-UHFFFAOYSA-N 1-nitroso-4-octylbenzene Chemical compound C(CCCCCCC)C1=CC=C(C=C1)N=O OYUYQUBADLGZJW-UHFFFAOYSA-N 0.000 description 1
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
- 101150034533 ATIC gene Proteins 0.000 description 1
- 241000766754 Agra Species 0.000 description 1
- 101000654316 Centruroides limpidus Beta-toxin Cll2 Proteins 0.000 description 1
- 241000238366 Cephalopoda Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 101150049580 Esam gene Proteins 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- 241000429017 Pectis Species 0.000 description 1
- 241000718541 Tetragastris balsamifera Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000005685 electric field effect Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000010587 phase diagram Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 101150054688 thiM gene Proteins 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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B55/00—Azomethine dyes
- C09B55/001—Azomethine dyes forming a 1,2 complex metal compound, e.g. with Co or Cr, with an other dye, e.g. with an azo or azomethine dye
-
- 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
- C09K19/24—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing nitrogen-to-nitrogen bonds
- C09K19/26—Azoxy compounds
-
- 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
- C09K19/48—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing Schiff bases
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 (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14495474A JPS5171276A (ja) | 1974-12-19 | 1974-12-19 | Nemachitsukuekishososeibutsu |
| JP14495574A JPS5171277A (ja) | 1974-12-19 | 1974-12-19 | Nemachitsukuekishososeibutsu |
| JP14495374A JPS5171275A (ja) | 1974-12-19 | 1974-12-19 | Nemachitsukuekishososeibutsu |
| JP14495274A JPS5175041A (ja) | 1974-12-19 | 1974-12-19 | Nemachitsukuekishokagobutsuno seizohoho |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1051421A true CA1051421A (en) | 1979-03-27 |
Family
ID=27472604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA225,703A Expired CA1051421A (en) | 1974-12-19 | 1975-04-29 | Nematic liquid crystal compounds and compositions |
Country Status (6)
| Country | Link |
|---|---|
| CA (1) | CA1051421A (enrdf_load_stackoverflow) |
| CH (1) | CH607075A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2519659C3 (enrdf_load_stackoverflow) |
| FR (3) | FR2296675A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1462028A (enrdf_load_stackoverflow) |
| NL (1) | NL7504841A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4253740A (en) * | 1977-09-12 | 1981-03-03 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Liquid crystal materials and devices containing them |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5549101B2 (enrdf_load_stackoverflow) * | 1972-10-11 | 1980-12-10 |
-
1975
- 1975-04-23 GB GB1674575A patent/GB1462028A/en not_active Expired
- 1975-04-24 NL NL7504841A patent/NL7504841A/xx not_active Application Discontinuation
- 1975-04-29 CA CA225,703A patent/CA1051421A/en not_active Expired
- 1975-05-02 DE DE19752519659 patent/DE2519659C3/de not_active Expired
- 1975-05-06 FR FR7514173A patent/FR2296675A1/fr active Granted
- 1975-05-07 CH CH591975A patent/CH607075A5/xx not_active IP Right Cessation
- 1975-09-11 FR FR7527857A patent/FR2295111A1/fr active Granted
- 1975-09-11 FR FR7527858A patent/FR2295112A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2295112B1 (enrdf_load_stackoverflow) | 1980-03-14 |
| FR2295111A1 (fr) | 1976-07-16 |
| FR2295112A1 (fr) | 1976-07-16 |
| DE2519659C3 (de) | 1978-11-09 |
| GB1462028A (en) | 1977-01-19 |
| FR2295111B1 (enrdf_load_stackoverflow) | 1978-04-07 |
| FR2296675B1 (enrdf_load_stackoverflow) | 1978-03-17 |
| CH607075A5 (enrdf_load_stackoverflow) | 1978-11-30 |
| DE2519659B2 (de) | 1978-03-16 |
| DE2519659A1 (de) | 1976-07-01 |
| NL7504841A (nl) | 1976-06-22 |
| FR2296675A1 (fr) | 1976-07-30 |
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