JPS6126901B2 - - Google Patents
Info
- Publication number
- JPS6126901B2 JPS6126901B2 JP991779A JP991779A JPS6126901B2 JP S6126901 B2 JPS6126901 B2 JP S6126901B2 JP 991779 A JP991779 A JP 991779A JP 991779 A JP991779 A JP 991779A JP S6126901 B2 JPS6126901 B2 JP S6126901B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- trans
- phthalonitrile
- compound
- propyloxy
- 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 52
- 229920006391 phthalonitrile polymer Polymers 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 19
- 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 10
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- BZWJDKJBAVXCMH-UHFFFAOYSA-N 1-diazopropane Chemical compound CCC=[N+]=[N-] BZWJDKJBAVXCMH-UHFFFAOYSA-N 0.000 claims description 2
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 claims description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N Cyclohexanecarboxylic acid Natural products OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 1
- 238000013329 compounding Methods 0.000 claims 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000463 material Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 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
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000013213 extrapolation Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- FEIWNULTQYHCDN-UHFFFAOYSA-N mbba Chemical compound C1=CC(CCCC)=CC=C1N=CC1=CC=C(OC)C=C1 FEIWNULTQYHCDN-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 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 2
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- -1 p-hexyloxybenzoic acid p-n-pentylphenyl ester Trans-4-n-butylcyclohexanecarboxylic acid Chemical compound 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- HBQUXMZZODHFMJ-UHFFFAOYSA-N 4-hexoxybenzoic acid Chemical compound CCCCCCOC1=CC=C(C(O)=O)C=C1 HBQUXMZZODHFMJ-UHFFFAOYSA-N 0.000 description 1
- KIIIPQXXLVCCQP-UHFFFAOYSA-N 4-propoxyphenol Chemical compound CCCOC1=CC=C(O)C=C1 KIIIPQXXLVCCQP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- NJBHSLCRSWEKRV-UHFFFAOYSA-N [N+](=[N-])=C=CC Chemical compound [N+](=[N-])=C=CC NJBHSLCRSWEKRV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000001000 anthraquinone dye Substances 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
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 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
- 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 1
- KOUCTZDKTJGHSS-UHFFFAOYSA-N pentyl 4-methylbenzenesulfonate Chemical compound CCCCCOS(=O)(=O)C1=CC=C(C)C=C1 KOUCTZDKTJGHSS-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
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- JTTWNTXHFYNETH-UHFFFAOYSA-N propyl 4-methylbenzenesulfonate Chemical compound CCCOS(=O)(=O)C1=CC=C(C)C=C1 JTTWNTXHFYNETH-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP991779A JPS55102550A (en) | 1979-01-31 | 1979-01-31 | 3-propyloxy-6-cyclohexanecarboxy-phthalonitrile |
| US06/074,655 US4279770A (en) | 1978-09-20 | 1979-09-12 | Liquid crystal 2,3-dicyano-hydroquinone derivatives |
| CA335,840A CA1131655A (en) | 1978-09-20 | 1979-09-18 | 2,3-dicyano-hydroquinone derivatives |
| DE2937700A DE2937700C2 (de) | 1978-09-20 | 1979-09-18 | 2,3-Dicyano-hydrochinon-Derivate und Flüssigkristallmaterialien, die diese Derivate enthalten |
| CH845579A CH642345A5 (de) | 1978-09-20 | 1979-09-19 | 2,3-dicyano-hydrochinon derivate. |
| FR7923469A FR2436777A1 (fr) | 1978-09-20 | 1979-09-20 | Derive de la 2,3-dicyano-hydroquinone et leur application aux liquides |
| GB7932598A GB2035303B (en) | 1978-09-20 | 1979-09-20 | 2,3-dicyano-hydroquinone derivatives |
| DD79215670A DD146187A5 (de) | 1978-09-20 | 1979-09-20 | Verfahren zur herstellung von 2-chlor-6-nitroanilinen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP991779A JPS55102550A (en) | 1979-01-31 | 1979-01-31 | 3-propyloxy-6-cyclohexanecarboxy-phthalonitrile |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55102550A JPS55102550A (en) | 1980-08-05 |
| JPS6126901B2 true JPS6126901B2 (enrdf_load_stackoverflow) | 1986-06-23 |
Family
ID=11733438
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP991779A Granted JPS55102550A (en) | 1978-09-20 | 1979-01-31 | 3-propyloxy-6-cyclohexanecarboxy-phthalonitrile |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55102550A (enrdf_load_stackoverflow) |
-
1979
- 1979-01-31 JP JP991779A patent/JPS55102550A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55102550A (en) | 1980-08-05 |