JPH0148891B2 - - Google Patents
Info
- Publication number
- JPH0148891B2 JPH0148891B2 JP14137581A JP14137581A JPH0148891B2 JP H0148891 B2 JPH0148891 B2 JP H0148891B2 JP 14137581 A JP14137581 A JP 14137581A JP 14137581 A JP14137581 A JP 14137581A JP H0148891 B2 JPH0148891 B2 JP H0148891B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- liquid crystal
- trans
- acid
- formula
- 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
- 239000004973 liquid crystal related substance Substances 0.000 claims description 45
- 150000002148 esters Chemical class 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 12
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 5
- MPAIWVOBMLSHQA-UHFFFAOYSA-N 3,6-dihydroxybenzene-1,2-dicarbonitrile Chemical compound OC1=CC=C(O)C(C#N)=C1C#N MPAIWVOBMLSHQA-UHFFFAOYSA-N 0.000 claims description 4
- 244000028419 Styrax benzoin Species 0.000 claims description 4
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 4
- 235000008411 Sumatra benzointree Nutrition 0.000 claims description 4
- 229960002130 benzoin Drugs 0.000 claims description 4
- 235000019382 gum benzoic Nutrition 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 57
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- BALGERHMIXFENA-MGCOHNPYSA-N CCCC[C@H]1CC[C@H](C(O)=O)CC1 Chemical compound CCCC[C@H]1CC[C@H](C(O)=O)CC1 BALGERHMIXFENA-MGCOHNPYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- RVLAXPQGTRTHEV-XYPYZODXSA-N CCCCC[C@H]1CC[C@H](C(O)=O)CC1 Chemical compound CCCCC[C@H]1CC[C@H](C(O)=O)CC1 RVLAXPQGTRTHEV-XYPYZODXSA-N 0.000 description 4
- QCNUKEGGHOLBES-KYZUINATSA-N CCC[C@H]1CC[C@H](C(O)=O)CC1 Chemical compound CCC[C@H]1CC[C@H](C(O)=O)CC1 QCNUKEGGHOLBES-KYZUINATSA-N 0.000 description 4
- -1 phenyl ester Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- RVLAXPQGTRTHEV-UHFFFAOYSA-N 4-pentylcyclohexane-1-carboxylic acid Chemical compound CCCCCC1CCC(C(O)=O)CC1 RVLAXPQGTRTHEV-UHFFFAOYSA-N 0.000 description 2
- QCNUKEGGHOLBES-UHFFFAOYSA-N 4-propylcyclohexane-1-carboxylic acid Chemical compound CCCC1CCC(C(O)=O)CC1 QCNUKEGGHOLBES-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- FEIWNULTQYHCDN-UHFFFAOYSA-N mbba Chemical compound C1=CC(CCCC)=CC=C1N=CC1=CC=C(OC)C=C1 FEIWNULTQYHCDN-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- KMVXENDYYJFUGZ-UHFFFAOYSA-N n-methoxy-n-(5-phenylpent-4-enyl)aniline Chemical compound C=1C=CC=CC=1N(OC)CCCC=CC1=CC=CC=C1 KMVXENDYYJFUGZ-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- SQQBGYGZHHXUPZ-UHFFFAOYSA-N 1-butylcyclohexane-1-carboxylic acid Chemical compound CCCCC1(C(O)=O)CCCCC1 SQQBGYGZHHXUPZ-UHFFFAOYSA-N 0.000 description 1
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 1
- YXKKMVGGPRVHIL-SHTZXODSSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C(O)=O)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C(O)=O)C=C1 YXKKMVGGPRVHIL-SHTZXODSSA-N 0.000 description 1
- UMPSXOXLNGYHLJ-WKILWMFISA-N CCCCC[C@H]1CC[C@@H](CC1)c1ccccc1C#N Chemical compound CCCCC[C@H]1CC[C@@H](CC1)c1ccccc1C#N UMPSXOXLNGYHLJ-WKILWMFISA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- WZWRHKQSYZLFDM-UHFFFAOYSA-N N-ethoxy-N-(5-phenylpent-4-enyl)aniline Chemical compound C(C)ON(C1=CC=CC=C1)CCCC=CC1=CC=CC=C1 WZWRHKQSYZLFDM-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 238000000149 argon plasma sintering 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
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 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 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-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
- 230000000704 physical effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- FZMJEGJVKFTGMU-UHFFFAOYSA-N triethoxy(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC FZMJEGJVKFTGMU-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
- Liquid Crystal (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14137581A JPS5841853A (ja) | 1981-09-08 | 1981-09-08 | ４―（トランス―４′―アルキルシクロヘキシル）安息香酸２，３―ジシアノ―４―アルキルオキシフェニルエステル類 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14137581A JPS5841853A (ja) | 1981-09-08 | 1981-09-08 | ４―（トランス―４′―アルキルシクロヘキシル）安息香酸２，３―ジシアノ―４―アルキルオキシフェニルエステル類 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5841853A JPS5841853A (ja) | 1983-03-11 |
| JPH0148891B2 true JPH0148891B2 (enrdf_load_html_response) | 1989-10-20 |
Family
ID=15290528
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14137581A Granted JPS5841853A (ja) | 1981-09-08 | 1981-09-08 | ４―（トランス―４′―アルキルシクロヘキシル）安息香酸２，３―ジシアノ―４―アルキルオキシフェニルエステル類 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5841853A (enrdf_load_html_response) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8414344D0 (en) * | 1984-06-05 | 1984-07-11 | Showell A W Sugicraft Ltd | Surgical element |
-
1981
- 1981-09-08 JP JP14137581A patent/JPS5841853A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5841853A (ja) | 1983-03-11 |
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