DE2519659C3 - p-n-Alkyl-p'-cyanoazoxybenzole, Verfahren zu deren Herstellung und diese enthaltende Zusammensetzungen - Google Patents
p-n-Alkyl-p'-cyanoazoxybenzole, Verfahren zu deren Herstellung und diese enthaltende ZusammensetzungenInfo
- Publication number
- DE2519659C3 DE2519659C3 DE19752519659 DE2519659A DE2519659C3 DE 2519659 C3 DE2519659 C3 DE 2519659C3 DE 19752519659 DE19752519659 DE 19752519659 DE 2519659 A DE2519659 A DE 2519659A DE 2519659 C3 DE2519659 C3 DE 2519659C3
- Authority
- DE
- Germany
- Prior art keywords
- liquid crystal
- mesomorphic
- weight
- cyanoazoxybenzene
- 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 description 133
- 238000000034 method Methods 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 4
- 230000008569 process Effects 0.000 title description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 105
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 47
- 150000001875 compounds Chemical class 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- 238000002156 mixing Methods 0.000 description 31
- 229960000583 acetic acid Drugs 0.000 description 19
- 239000012153 distilled water Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 description 12
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 11
- 238000001816 cooling Methods 0.000 description 10
- 239000012362 glacial acetic acid Substances 0.000 description 10
- 238000010587 phase diagram Methods 0.000 description 10
- 239000004988 Nematic liquid crystal Substances 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- 238000000862 absorption spectrum Methods 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 7
- 238000001819 mass spectrum Methods 0.000 description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
- 239000002262 Schiff base Substances 0.000 description 6
- 150000004753 Schiff bases Chemical class 0.000 description 6
- -1 n-octyl group Chemical group 0.000 description 6
- 238000001256 steam distillation Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000006482 condensation reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000005684 electric field Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 230000008859 change Effects 0.000 description 3
- 238000007710 freezing Methods 0.000 description 3
- 230000008014 freezing Effects 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- HQYQXJJGHURQSU-UHFFFAOYSA-N 1-butyl-2-nitrosobenzene Chemical compound CCCCC1=CC=CC=C1N=O HQYQXJJGHURQSU-UHFFFAOYSA-N 0.000 description 1
- QHYPBLILCYMWPE-UHFFFAOYSA-N 1-hexyl-4-nitrosobenzene Chemical compound C(CCCCC)C1=CC=C(C=C1)N=O QHYPBLILCYMWPE-UHFFFAOYSA-N 0.000 description 1
- VHYMAUCXAKKEMG-UHFFFAOYSA-N CCCCCC(C=CC=C1)=C1N=O Chemical compound CCCCCC(C=CC=C1)=C1N=O VHYMAUCXAKKEMG-UHFFFAOYSA-N 0.000 description 1
- 102100035861 Cytosolic 5'-nucleotidase 1A Human genes 0.000 description 1
- 101000802744 Homo sapiens Cytosolic 5'-nucleotidase 1A Proteins 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000005685 electric field effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 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 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000009466 transformation Effects 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 (3)
| Publication Number | Publication Date |
|---|---|
| DE2519659A1 DE2519659A1 (de) | 1976-07-01 |
| DE2519659B2 DE2519659B2 (de) | 1978-03-16 |
| DE2519659C3 true DE2519659C3 (de) | 1978-11-09 |
Family
ID=27472604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752519659 Expired DE2519659C3 (de) | 1974-12-19 | 1975-05-02 | p-n-Alkyl-p'-cyanoazoxybenzole, Verfahren zu deren Herstellung und diese enthaltende Zusammensetzungen |
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 |
| CA1051421A (en) | 1979-03-27 |
| FR2295112A1 (fr) | 1976-07-16 |
| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |