JPS6348260B2 - - Google Patents

Info

Publication number

JPS6348260B2

JPS6348260B2 JP369281A JP369281A JPS6348260B2 JP S6348260 B2 JPS6348260 B2 JP S6348260B2 JP 369281 A JP369281 A JP 369281A JP 369281 A JP369281 A JP 369281A JP S6348260 B2 JPS6348260 B2 JP S6348260B2

Authority

JP

Japan

Prior art keywords

liquid crystal

nematic

acid

present

toluene

Prior art date

1981-01-13

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

• Espacenet
• Global Dossier
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• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
• 239000004973 liquid crystal related substance Substances 0.000 description 16
• 150000001875 compounds Chemical class 0.000 description 13
• 239000000203 mixture Substances 0.000 description 11
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
• BBYDXOIZLAWGSL-UHFFFAOYSA-N 4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C=C1 BBYDXOIZLAWGSL-UHFFFAOYSA-N 0.000 description 5
• -1 phenyl ester Chemical class 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
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• 239000013078 crystal Substances 0.000 description 4
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 239000000463 material Substances 0.000 description 3
• 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 2
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
• OACHBIGUVRUHBJ-UHFFFAOYSA-N 4-(4-butylphenyl)phenol Chemical compound C1=CC(CCCC)=CC=C1C1=CC=C(O)C=C1 OACHBIGUVRUHBJ-UHFFFAOYSA-N 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
• 239000002253 acid Substances 0.000 description 2
• 125000000217 alkyl group Chemical group 0.000 description 2
• 125000004432 carbon atom Chemical group C* 0.000 description 2
• 239000003054 catalyst Substances 0.000 description 2
• 238000004519 manufacturing process Methods 0.000 description 2
• 238000002844 melting Methods 0.000 description 2
• 230000008018 melting Effects 0.000 description 2
• 238000002156 mixing Methods 0.000 description 2
• 230000007935 neutral effect Effects 0.000 description 2
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
• 238000003756 stirring Methods 0.000 description 2
• 239000000126 substance Substances 0.000 description 2
• CUMYUHCDOGNXFX-UHFFFAOYSA-N 1-butyl-4-(4-methoxyphenyl)benzene Chemical group C1=CC(CCCC)=CC=C1C1=CC=C(OC)C=C1 CUMYUHCDOGNXFX-UHFFFAOYSA-N 0.000 description 1
• CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 1
• XXUSEPRYHRDKFV-CTYIDZIISA-N C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(C#N)C=C1 XXUSEPRYHRDKFV-CTYIDZIISA-N 0.000 description 1
• FURZYCFZFBYJBT-JCNLHEQBSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 FURZYCFZFBYJBT-JCNLHEQBSA-N 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 239000004988 Nematic liquid crystal Substances 0.000 description 1
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
• 239000008186 active pharmaceutical agent Substances 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 125000002723 alicyclic group Chemical group 0.000 description 1
• 125000001931 aliphatic group Chemical group 0.000 description 1
• 150000001412 amines Chemical class 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical group [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 229910052791 calcium Inorganic materials 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 238000006243 chemical reaction Methods 0.000 description 1
• 230000003098 cholesteric effect Effects 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 125000004802 cyanophenyl group Chemical group 0.000 description 1
• 230000003247 decreasing effect Effects 0.000 description 1
• 230000001747 exhibiting effect Effects 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 239000012467 final product Substances 0.000 description 1
• 239000007789 gas Substances 0.000 description 1
• 125000005843 halogen group Chemical group 0.000 description 1
• 229910052739 hydrogen Inorganic materials 0.000 description 1
• 239000001257 hydrogen Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
• 238000000034 method Methods 0.000 description 1
• 230000003287 optical effect Effects 0.000 description 1
• 230000000704 physical effect Effects 0.000 description 1
• 239000000047 product Substances 0.000 description 1
• 229920006395 saturated elastomer Polymers 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 239000002904 solvent Substances 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1
• 230000007704 transition Effects 0.000 description 1