DE2933317A1 - 1,4-bis-(4-subst.-benzoyloxy)-2-tert.butyl-benzole und diese enthaltende kristallin-fluessige nematische gemische - Google Patents
1,4-bis-(4-subst.-benzoyloxy)-2-tert.butyl-benzole und diese enthaltende kristallin-fluessige nematische gemischeInfo
- Publication number
- DE2933317A1 DE2933317A1 DE19792933317 DE2933317A DE2933317A1 DE 2933317 A1 DE2933317 A1 DE 2933317A1 DE 19792933317 DE19792933317 DE 19792933317 DE 2933317 A DE2933317 A DE 2933317A DE 2933317 A1 DE2933317 A1 DE 2933317A1
- Authority
- DE
- Germany
- Prior art keywords
- tert
- butyl
- crystalline
- hydroquinone
- liquid
- 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title abstract description 6
- 239000005711 Benzoic acid Substances 0.000 title abstract description 3
- 235000010233 benzoic acid Nutrition 0.000 title abstract description 3
- 150000002148 esters Chemical class 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 238000004611 spectroscopical analysis Methods 0.000 claims description 7
- -1 1,4-bis [4-substituted-benzoyloxy] -2-tert-butylbenzenes Chemical class 0.000 claims description 6
- 238000004817 gas chromatography Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002253 acid Substances 0.000 abstract description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 4
- 239000012442 inert solvent Substances 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000003841 chloride salts Chemical class 0.000 abstract 1
- 239000013078 crystal Substances 0.000 abstract 1
- 239000012024 dehydrating agents Substances 0.000 abstract 1
- 150000004707 phenolate Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 description 15
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 229940044119 2-tert-butylhydroquinone Drugs 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004988 Nematic liquid crystal Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000000149 argon plasma sintering Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DFHWCSVHLVOKND-UHFFFAOYSA-N (4-butoxyphenyl) 4-hexylbenzoate Chemical compound C1=CC(CCCCCC)=CC=C1C(=O)OC1=CC=C(OCCCC)C=C1 DFHWCSVHLVOKND-UHFFFAOYSA-N 0.000 description 1
- JYWUHAZQZQGGAA-UHFFFAOYSA-N (4-heptoxyphenyl) 4-hexoxybenzoate Chemical compound C1=CC(OCCCCCCC)=CC=C1OC(=O)C1=CC=C(OCCCCCC)C=C1 JYWUHAZQZQGGAA-UHFFFAOYSA-N 0.000 description 1
- JJYZUJHGWKCHBQ-UHFFFAOYSA-N (4-hexoxyphenyl) 4-methoxybenzoate Chemical compound C1=CC(OCCCCCC)=CC=C1OC(=O)C1=CC=C(OC)C=C1 JJYZUJHGWKCHBQ-UHFFFAOYSA-N 0.000 description 1
- VDTCVKLVMVTSMC-UHFFFAOYSA-N (4-octoxyphenyl) 4-pentoxybenzoate Chemical compound C1=CC(OCCCCCCCC)=CC=C1OC(=O)C1=CC=C(OCCCCC)C=C1 VDTCVKLVMVTSMC-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- DNPVFBGEPMQKIW-UHFFFAOYSA-N C(CCCCC)OC1=CC=C(C(=O)OC2=C(C=C(C=C2)OC(C2=CC=C(C=C2)OCCCCCC)=O)C(C)(C)C)C=C1 Chemical compound C(CCCCC)OC1=CC=C(C(=O)OC2=C(C=C(C=C2)OC(C2=CC=C(C=C2)OCCCCCC)=O)C(C)(C)C)C=C1 DNPVFBGEPMQKIW-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 238000004435 EPR spectroscopy Methods 0.000 description 1
- 102000002322 Egg Proteins Human genes 0.000 description 1
- 108010000912 Egg Proteins Proteins 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 210000004681 ovum Anatomy 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- PAYGMRRPBHYIMA-UHFFFAOYSA-N sodium;trihydrate Chemical compound O.O.O.[Na] PAYGMRRPBHYIMA-UHFFFAOYSA-N 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 210000002700 urine Anatomy 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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
-
- 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
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (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 |
|---|---|---|---|
| DD20894378A DD139575A1 (de) | 1978-11-08 | 1978-11-08 | Verfahren zur herstellung von 1,4-bis-eckige klammer auf 4-subst.-benzoyloxy eckige klammer zu-2-tert.-butyl-benzolen |
| DD20894278A DD139592A1 (de) | 1978-11-08 | 1978-11-08 | Kristallin-fluessige nematische substanzen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2933317A1 true DE2933317A1 (de) | 1980-05-22 |
| DE2933317C2 DE2933317C2 (enrdf_load_stackoverflow) | 1988-03-31 |
Family
ID=25747626
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792933317 Granted DE2933317A1 (de) | 1978-11-08 | 1979-08-17 | 1,4-bis-(4-subst.-benzoyloxy)-2-tert.butyl-benzole und diese enthaltende kristallin-fluessige nematische gemische |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2933317A1 (enrdf_load_stackoverflow) |
-
1979
- 1979-08-17 DE DE19792933317 patent/DE2933317A1/de active Granted
Non-Patent Citations (1)
| Title |
|---|
| NICHTS ERMITTELT * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2933317C2 (enrdf_load_stackoverflow) | 1988-03-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |