JPS6312056B2 - - Google Patents
Info
- Publication number
- JPS6312056B2 JPS6312056B2 JP10897879A JP10897879A JPS6312056B2 JP S6312056 B2 JPS6312056 B2 JP S6312056B2 JP 10897879 A JP10897879 A JP 10897879A JP 10897879 A JP10897879 A JP 10897879A JP S6312056 B2 JPS6312056 B2 JP S6312056B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- trans
- phthalonitrile
- acid
- hydroquinone
- 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 57
- 229920006391 phthalonitrile polymer Polymers 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 22
- 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 15
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
- 150000001875 compounds Chemical class 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000000463 material Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 235000011121 sodium hydroxide Nutrition 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000004988 Nematic liquid crystal Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-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
- -1 3-n-propyl Chemical group 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
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 3
- 239000004990 Smectic liquid crystal Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000001816 cooling 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
- 239000000155 melt Substances 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
- BALGERHMIXFENA-UHFFFAOYSA-N 4-butylcyclohexane-1-carboxylic acid Chemical compound CCCCC1CCC(C(O)=O)CC1 BALGERHMIXFENA-UHFFFAOYSA-N 0.000 description 2
- HBQUXMZZODHFMJ-UHFFFAOYSA-N 4-hexoxybenzoic acid Chemical compound CCCCCCOC1=CC=C(C(O)=O)C=C1 HBQUXMZZODHFMJ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000000921 elemental analysis 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
- 238000005406 washing Methods 0.000 description 2
- IRMSQSDYVDQMKE-UHFFFAOYSA-N (4-pentylphenyl) 4-hexoxybenzoate Chemical compound C1=CC(OCCCCCC)=CC=C1C(=O)OC1=CC=C(CCCCC)C=C1 IRMSQSDYVDQMKE-UHFFFAOYSA-N 0.000 description 1
- UISXVYOLBGBYCV-UHFFFAOYSA-N (4-pentylphenyl) 4-methoxybenzoate Chemical compound C1=CC(CCCCC)=CC=C1OC(=O)C1=CC=C(OC)C=C1 UISXVYOLBGBYCV-UHFFFAOYSA-N 0.000 description 1
- SQQBGYGZHHXUPZ-UHFFFAOYSA-N 1-butylcyclohexane-1-carboxylic acid Chemical compound CCCCC1(C(O)=O)CCCCC1 SQQBGYGZHHXUPZ-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- JAYBMJPZPJBTQZ-WKILWMFISA-N C1C[C@@H](CCCC)CC[C@@H]1C(=O)OC1=CC=C(OCC)C=C1 Chemical compound C1C[C@@H](CCCC)CC[C@@H]1C(=O)OC1=CC=C(OCC)C=C1 JAYBMJPZPJBTQZ-WKILWMFISA-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
- 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
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 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
- 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
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- QYJXDIUNDMRLAO-UHFFFAOYSA-N butyl 4-methylbenzenesulfonate Chemical compound CCCCOS(=O)(=O)C1=CC=C(C)C=C1 QYJXDIUNDMRLAO-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000013213 extrapolation 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
- 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
- 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
- 230000000704 physical effect Effects 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
- 239000002994 raw material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000002834 transmittance Methods 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)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10897879A JPS5632446A (en) | 1979-08-27 | 1979-08-27 | 3-alkyloxy-6-(trans-4'-alkyloxycyclohexanecarboxy)- 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. |
| DD79215670A DD146187A5 (de) | 1978-09-20 | 1979-09-20 | Verfahren zur herstellung von 2-chlor-6-nitroanilinen |
| GB7932598A GB2035303B (en) | 1978-09-20 | 1979-09-20 | 2,3-dicyano-hydroquinone derivatives |
| FR7923469A FR2436777A1 (fr) | 1978-09-20 | 1979-09-20 | Derive de la 2,3-dicyano-hydroquinone et leur application aux liquides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10897879A JPS5632446A (en) | 1979-08-27 | 1979-08-27 | 3-alkyloxy-6-(trans-4'-alkyloxycyclohexanecarboxy)- phthalonitrile |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5632446A JPS5632446A (en) | 1981-04-01 |
| JPS6312056B2 true JPS6312056B2 (en]) | 1988-03-17 |
Family
ID=14498467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10897879A Granted JPS5632446A (en) | 1978-09-20 | 1979-08-27 | 3-alkyloxy-6-(trans-4'-alkyloxycyclohexanecarboxy)- phthalonitrile |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5632446A (en]) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102492430A (zh) * | 2011-11-28 | 2012-06-13 | 江苏和成化学材料有限公司 | 液晶组合物和包含该液晶组合物的液晶显示元件 |
-
1979
- 1979-08-27 JP JP10897879A patent/JPS5632446A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5632446A (en) | 1981-04-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1131655A (en) | 2,3-dicyano-hydroquinone derivatives | |
| JPH0568520B2 (en]) | ||
| EP0162437A2 (en) | Liquid crystal compound and liquid crystal composition including the same | |
| JPS6126899B2 (en]) | ||
| JPH0466857B2 (en]) | ||
| JPS6312056B2 (en]) | ||
| JP3007441B2 (ja) | ケイ素液晶化合物 | |
| JPS6126900B2 (en]) | ||
| JPS59141540A (ja) | 三環カルボン酸エステル誘導体 | |
| JPS6126898B2 (en]) | ||
| JPH0717905B2 (ja) | 液晶組成物 | |
| JP2887693B2 (ja) | 小員環化合物 | |
| JP3257006B2 (ja) | 不飽和エステル類 | |
| JPS5982382A (ja) | 含ハロゲンメタジオキサンエステル | |
| JP2822083B2 (ja) | アルキンオキシフエニルビシクロヘキサン類化合物 | |
| JPS6126901B2 (en]) | ||
| JPS6312057B2 (en]) | ||
| JP2001316347A (ja) | ナフタレン誘導体 | |
| JP2761909B2 (ja) | フツ素置換フエニルピリミジンのアルケニルエステル誘導体 | |
| JP2956946B2 (ja) | トリフルオロメチル化合物 | |
| JP2514395B2 (ja) | 側鎖にアルキル基を有する液晶性化合物 | |
| JP2822079B2 (ja) | シクロプロパン誘導体 | |
| JP2516395B2 (ja) | １，１−ジハロゲノシクロヘキサン誘導体 | |
| JP2822080B2 (ja) | シクロヘキシルメチルオキシアリル誘導体ベンゼン | |
| JP2907993B2 (ja) | 液晶組成物およびその用途 |