JPH0122260B2 - - Google Patents

Info

Publication number

JPH0122260B2

JPH0122260B2 JP13233581A JP13233581A JPH0122260B2 JP H0122260 B2 JPH0122260 B2 JP H0122260B2 JP 13233581 A JP13233581 A JP 13233581A JP 13233581 A JP13233581 A JP 13233581A JP H0122260 B2 JPH0122260 B2 JP H0122260B2

Authority

JP

Japan

Prior art keywords

trans

liquid crystal

phenylcarbonyloxy

compound

pentylcyclohexyl

Prior art date

1981-08-24

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

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• 239000004973 liquid crystal related substance Substances 0.000 claims description 20
• 150000001875 compounds Chemical class 0.000 claims description 15
• 125000000217 alkyl group Chemical group 0.000 claims 1
• 125000004432 carbon atom Chemical group C* 0.000 claims 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 9
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
• 239000000203 mixture Substances 0.000 description 8
• 239000000463 material Substances 0.000 description 7
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
• 239000005711 Benzoic acid Substances 0.000 description 5
• 235000010233 benzoic acid Nutrition 0.000 description 5
• 239000013078 crystal Substances 0.000 description 5
• 235000013399 edible fruits Nutrition 0.000 description 5
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
• 238000006243 chemical reaction Methods 0.000 description 4
• 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 description 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
• 238000000862 absorption spectrum Methods 0.000 description 3
• PTHRGNKLKBVZGA-UHFFFAOYSA-N (2,3-dicyano-4-hydroxyphenyl) pentanoate Chemical compound CCCCC(=O)OC1=CC=C(O)C(C#N)=C1C#N PTHRGNKLKBVZGA-UHFFFAOYSA-N 0.000 description 2
• LDCKYCPBTBCBQF-UHFFFAOYSA-N 4-(4-pentylcyclohexyl)benzoyl chloride Chemical compound C1CC(CCCCC)CCC1C1=CC=C(C(Cl)=O)C=C1 LDCKYCPBTBCBQF-UHFFFAOYSA-N 0.000 description 2
• 239000004988 Nematic liquid crystal Substances 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• 238000009835 boiling Methods 0.000 description 2
• 239000003054 catalyst Substances 0.000 description 2
• 239000000975 dye Substances 0.000 description 2
• 150000002148 esters Chemical class 0.000 description 2
• -1 n-pentylcyclohexyl Chemical group 0.000 description 2
• XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
• 238000010992 reflux Methods 0.000 description 2
• 238000003756 stirring Methods 0.000 description 2
• 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 1
• FURZYCFZFBYJBT-UHFFFAOYSA-N 4-(4-pentylcyclohexyl)benzonitrile Chemical compound C1CC(CCCCC)CCC1C1=CC=C(C#N)C=C1 FURZYCFZFBYJBT-UHFFFAOYSA-N 0.000 description 1
• QCNUKEGGHOLBES-UHFFFAOYSA-N 4-propylcyclohexane-1-carboxylic acid Chemical compound CCCC1CCC(C(O)=O)CC1 QCNUKEGGHOLBES-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
• 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
• 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 1
• 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 1
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
• 230000005540 biological transmission Effects 0.000 description 1
• 239000003795 chemical substances by application Substances 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 210000002858 crystal cell Anatomy 0.000 description 1
• 125000004093 cyano group Chemical group *C#N 0.000 description 1
• 238000000354 decomposition reaction Methods 0.000 description 1
• 238000010586 diagram Methods 0.000 description 1
• 239000006185 dispersion Substances 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 239000011159 matrix material Substances 0.000 description 1
• 238000000034 method Methods 0.000 description 1
• XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 239000000047 product Substances 0.000 description 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• 239000011541 reaction mixture Substances 0.000 description 1
• 239000002904 solvent Substances 0.000 description 1
• 230000007704 transition Effects 0.000 description 1
• 238000005406 washing Methods 0.000 description 1