JPH0564134B2 - - Google Patents
Info
- Publication number
- JPH0564134B2 JPH0564134B2 JP58138148A JP13814883A JPH0564134B2 JP H0564134 B2 JPH0564134 B2 JP H0564134B2 JP 58138148 A JP58138148 A JP 58138148A JP 13814883 A JP13814883 A JP 13814883A JP H0564134 B2 JPH0564134 B2 JP H0564134B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- formula
- optically active
- phase
- synthesized
- 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 - Lifetime
Links
- 150000001875 compounds Chemical group 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 31
- 239000004973 liquid crystal related substance Substances 0.000 claims description 25
- 239000004990 Smectic liquid crystal Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000004988 Nematic liquid crystal Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- -1 4-hydroxy-4'-substituted biphenyl Chemical group 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000010287 polarization Effects 0.000 description 5
- MQNLOOJFAVAAKD-UHFFFAOYSA-N 2-methylbutyl carbonochloridate Chemical compound CCC(C)COC(Cl)=O MQNLOOJFAVAAKD-UHFFFAOYSA-N 0.000 description 4
- JZGBNMKIGIXDCL-UHFFFAOYSA-N 4-(4-tetradecoxyphenyl)phenol Chemical group C1=CC(OCCCCCCCCCCCCCC)=CC=C1C1=CC=C(O)C=C1 JZGBNMKIGIXDCL-UHFFFAOYSA-N 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VKMLCPHQDWRURW-UHFFFAOYSA-N 4-(4-octoxyphenyl)phenol Chemical group C1=CC(OCCCCCCCC)=CC=C1C1=CC=C(O)C=C1 VKMLCPHQDWRURW-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical group OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- YSMHTFWPDRJCMN-UHFFFAOYSA-N butan-2-yl carbonochloridate Chemical compound CCC(C)OC(Cl)=O YSMHTFWPDRJCMN-UHFFFAOYSA-N 0.000 description 3
- 230000003098 cholesteric effect Effects 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000002269 spontaneous effect Effects 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- SHFQYSOBHYYRBO-UHFFFAOYSA-N 1-[4-(4-octoxyphenyl)phenyl]ethanone Chemical group C1=CC(OCCCCCCCC)=CC=C1C1=CC=C(C(C)=O)C=C1 SHFQYSOBHYYRBO-UHFFFAOYSA-N 0.000 description 2
- CKSIBFLEDRJUTN-UHFFFAOYSA-N 3-chloropentan-2-one Chemical compound CCC(Cl)C(C)=O CKSIBFLEDRJUTN-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- GNHSLRMCJVPUAO-UHFFFAOYSA-N [4-(4-acetylphenyl)phenyl] acetate Chemical group C1=CC(OC(=O)C)=CC=C1C1=CC=C(C(C)=O)C=C1 GNHSLRMCJVPUAO-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- RSYNHXZMASRGMC-UHFFFAOYSA-N butan-2-yl hydrogen carbonate Chemical compound CCC(C)OC(O)=O RSYNHXZMASRGMC-UHFFFAOYSA-N 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 210000002858 crystal cell Anatomy 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OKUTVLLADIKJLP-UHFFFAOYSA-N 1-[4-(4-tetradecoxyphenyl)phenyl]ethanone Chemical group C1=CC(OCCCCCCCCCCCCCC)=CC=C1C1=CC=C(C(C)=O)C=C1 OKUTVLLADIKJLP-UHFFFAOYSA-N 0.000 description 1
- XKVLZBNEPALHIO-UHFFFAOYSA-N 1-bromo-2-methylbutane Chemical compound CCC(C)CBr XKVLZBNEPALHIO-UHFFFAOYSA-N 0.000 description 1
- SLBTUZZYJLBZQV-UHFFFAOYSA-N 1-chloro-2-methylpentane Chemical compound CCCC(C)CCl SLBTUZZYJLBZQV-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-BYPYZUCNSA-N 2-Methylbutanoic acid Natural products CC[C@H](C)C(O)=O WLAMNBDJUVNPJU-BYPYZUCNSA-N 0.000 description 1
- 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
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- NAJMIVLMDLWNRF-UHFFFAOYSA-N 2-methylbutyl hydrogen carbonate Chemical compound CCC(C)COC(O)=O NAJMIVLMDLWNRF-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
- MFIQXAVMTLKUJR-UHFFFAOYSA-N 2-methylpentanoyl chloride Chemical compound CCCC(C)C(Cl)=O MFIQXAVMTLKUJR-UHFFFAOYSA-N 0.000 description 1
- IGIDLTISMCAULB-UHFFFAOYSA-N 3-methylvaleric acid Chemical compound CCC(C)CC(O)=O IGIDLTISMCAULB-UHFFFAOYSA-N 0.000 description 1
- DLLIPJSMDJCZRF-UHFFFAOYSA-N 4-(4-ethylphenyl)benzonitrile Chemical group C1=CC(CC)=CC=C1C1=CC=C(C#N)C=C1 DLLIPJSMDJCZRF-UHFFFAOYSA-N 0.000 description 1
- GPGGNNIMKOVSAG-UHFFFAOYSA-N 4-(4-octoxyphenyl)benzonitrile Chemical group C1=CC(OCCCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 GPGGNNIMKOVSAG-UHFFFAOYSA-N 0.000 description 1
- PBMCTXQDYLSLTP-UHFFFAOYSA-N 4-(4-pentylphenyl)-3-phenylbenzonitrile Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(C#N)C=C1C1=CC=CC=C1 PBMCTXQDYLSLTP-UHFFFAOYSA-N 0.000 description 1
- HHPCNRKYVYWYAU-UHFFFAOYSA-N 4-cyano-4'-pentylbiphenyl Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(C#N)C=C1 HHPCNRKYVYWYAU-UHFFFAOYSA-N 0.000 description 1
- 241001270131 Agaricus moelleri Species 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 230000018199 S phase Effects 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- PFZAXLFGUSIZRN-MHZLTWQESA-N [4-(4-tetradecoxyphenyl)phenyl] (2s)-2-methylpentanoate Chemical group C1=CC(OCCCCCCCCCCCCCC)=CC=C1C1=CC=C(OC(=O)[C@@H](C)CCC)C=C1 PFZAXLFGUSIZRN-MHZLTWQESA-N 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000003446 memory effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13814883A JPS6051147A (ja) | 1983-07-28 | 1983-07-28 | 液晶物質及び液晶組成物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13814883A JPS6051147A (ja) | 1983-07-28 | 1983-07-28 | 液晶物質及び液晶組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6051147A JPS6051147A (ja) | 1985-03-22 |
| JPH0564134B2 true JPH0564134B2 (nl) | 1993-09-14 |
Family
ID=15215128
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13814883A Granted JPS6051147A (ja) | 1983-07-28 | 1983-07-28 | 液晶物質及び液晶組成物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6051147A (nl) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60218358A (ja) * | 1984-04-13 | 1985-11-01 | Ajinomoto Co Inc | 液晶 |
| JPS6143A (ja) * | 1984-06-11 | 1986-01-06 | Chisso Corp | 強誘電性液晶化合物及び液晶組成物 |
| JPH0717905B2 (ja) * | 1985-05-09 | 1995-03-01 | 旭硝子株式会社 | 液晶組成物 |
| JPS63165345A (ja) * | 1986-12-26 | 1988-07-08 | Chisso Corp | 光学活性−２−メチル−アルカナ−ト類およびその利用物 |
| US5397504A (en) * | 1987-05-29 | 1995-03-14 | Kanto Kagaku Kabushiki Kaisha | Biphenyl compound |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5219641A (en) * | 1975-08-06 | 1977-02-15 | Merck Patent Gmbh | Biphenyl esters |
-
1983
- 1983-07-28 JP JP13814883A patent/JPS6051147A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5219641A (en) * | 1975-08-06 | 1977-02-15 | Merck Patent Gmbh | Biphenyl esters |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6051147A (ja) | 1985-03-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0131373B1 (en) | Liquid crystalline biphenyl derivatives and mixtures thereof | |
| US4737313A (en) | Liquid-crystalline substituted biphenyl esters | |
| JPH0417174B2 (nl) | ||
| JPH0447658B2 (nl) | ||
| JPH0578542B2 (nl) | ||
| JPH0670020B2 (ja) | 置換ピリダジン類 | |
| JPH0623135B2 (ja) | 液晶物質及び液晶組成物 | |
| JPS61267540A (ja) | 新規光学活性化合物及び液晶組成物 | |
| JPH0443898B2 (nl) | ||
| JPH0564134B2 (nl) | ||
| JPH0416454B2 (nl) | ||
| JPH0669988B2 (ja) | エステル化合物及びこれを含む液晶組成物 | |
| JPS63122651A (ja) | フルオロアルカン誘導体、それを含む液晶組成物および液晶素子 | |
| JP2543745B2 (ja) | 光学活性化合物及び液晶組成物 | |
| JP2521126B2 (ja) | 光学活性液晶化合物 | |
| JPH0572380B2 (nl) | ||
| JP4001974B2 (ja) | プロピオン酸エステル化合物、液晶材料、液晶組成物および液晶素子 | |
| JPH05117206A (ja) | エステル化合物及びそれを含有する液晶組成物及びその液晶組成物を用いた液晶表示素子 | |
| JP4053199B2 (ja) | ベンジルエーテル誘導体、液晶材料、液晶組成物、および液晶素子 | |
| JPS60204780A (ja) | ４−（トランス−５−アルキル−１，３−ジオキサ−２−イル）安息香酸誘導体 | |
| JP3095435B2 (ja) | 液晶化合物 | |
| JP2857231B2 (ja) | エステル化合物及びこれを含む液晶組成物 | |
| JPS6163638A (ja) | 炭酸エステル液晶及びその組成物 | |
| JP2596806B2 (ja) | 光学活性化合物及びその用途 | |
| JP2933688B2 (ja) | 液晶素子 |