JPH0458461B2 - - Google Patents
Info
- Publication number
- JPH0458461B2 JPH0458461B2 JP59185148A JP18514884A JPH0458461B2 JP H0458461 B2 JPH0458461 B2 JP H0458461B2 JP 59185148 A JP59185148 A JP 59185148A JP 18514884 A JP18514884 A JP 18514884A JP H0458461 B2 JPH0458461 B2 JP H0458461B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- phase
- liquid crystal
- compound
- optically active
- 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
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 239000012071 phase Substances 0.000 description 39
- 239000004973 liquid crystal related substance Substances 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- -1 1-methylheptyl group Chemical group 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000047 product Substances 0.000 description 9
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 239000004990 Smectic liquid crystal Substances 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 230000004044 response Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000004988 Nematic liquid crystal Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000001747 exhibiting effect Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- NZAJDUYRCYEQPE-UHFFFAOYSA-N (4-carbonochloridoylphenyl) octanoate Chemical compound CCCCCCCC(=O)OC1=CC=C(C(Cl)=O)C=C1 NZAJDUYRCYEQPE-UHFFFAOYSA-N 0.000 description 3
- DVRCNPGZGBUBQO-UHFFFAOYSA-N (4-hydroxyphenyl) 2-methylbutyl carbonate Chemical compound CCC(C)COC(=O)OC1=CC=C(O)C=C1 DVRCNPGZGBUBQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- GSXKSPKHWYOXNZ-UHFFFAOYSA-N [4-(4-hydroxyphenyl)phenyl] 2-methylbutyl carbonate Chemical group C1=CC(OC(=O)OCC(C)CC)=CC=C1C1=CC=C(O)C=C1 GSXKSPKHWYOXNZ-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 210000002858 crystal cell Anatomy 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 230000010287 polarization Effects 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WDOIAMUGUNVXHW-UHFFFAOYSA-N (4-carbonochloridoylphenyl) octyl carbonate Chemical compound CCCCCCCCOC(=O)OC1=CC=C(C(Cl)=O)C=C1 WDOIAMUGUNVXHW-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000003098 cholesteric effect Effects 0.000 description 2
- 229940117975 chromium trioxide Drugs 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- CRNAPIOANHRWDJ-UHFFFAOYSA-N (4-formylphenyl) octanoate Chemical compound CCCCCCCC(=O)OC1=CC=C(C=O)C=C1 CRNAPIOANHRWDJ-UHFFFAOYSA-N 0.000 description 1
- PQJXLQYHNPVRIO-UHFFFAOYSA-N (4-formylphenyl) octyl carbonate Chemical compound CCCCCCCCOC(=O)OC1=CC=C(C=O)C=C1 PQJXLQYHNPVRIO-UHFFFAOYSA-N 0.000 description 1
- GBSJRDFAVZTVSI-UHFFFAOYSA-N 2-[4-(2-methylbutoxycarbonyloxy)phenyl]-4-octanoyloxybenzoic acid Chemical compound CCCCCCCC(=O)OC1=CC=C(C(O)=O)C(C=2C=CC(OC(=O)OCC(C)CC)=CC=2)=C1 GBSJRDFAVZTVSI-UHFFFAOYSA-N 0.000 description 1
- MQNLOOJFAVAAKD-UHFFFAOYSA-N 2-methylbutyl carbonochloridate Chemical compound CCC(C)COC(Cl)=O MQNLOOJFAVAAKD-UHFFFAOYSA-N 0.000 description 1
- GCQBIYCSSJYFJX-UHFFFAOYSA-N 4-(2-methylbutoxy)phenol Chemical compound CCC(C)COC1=CC=C(O)C=C1 GCQBIYCSSJYFJX-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
- HXBKPYIEQLLNBK-UHFFFAOYSA-N 4-(4-octylphenyl)benzoic acid Chemical compound C1=CC(CCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 HXBKPYIEQLLNBK-UHFFFAOYSA-N 0.000 description 1
- LNZLKYDXPBRIOA-UHFFFAOYSA-N 4-(4-octylphenyl)benzoyl chloride Chemical compound C1=CC(CCCCCCCC)=CC=C1C1=CC=C(C(Cl)=O)C=C1 LNZLKYDXPBRIOA-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
- POKXFVOZMZUBQN-UHFFFAOYSA-N 4-octoxycarbonyloxybenzoic acid Chemical compound CCCCCCCCOC(=O)OC1=CC=C(C(O)=O)C=C1 POKXFVOZMZUBQN-UHFFFAOYSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ODRRZCIOSQUOFW-UHFFFAOYSA-N [4-(2-methylbutoxycarbonyloxy)phenyl] 4-(4-octylphenyl)benzoate Chemical compound C1=CC(CCCCCCCC)=CC=C1C1=CC=C(C(=O)OC=2C=CC(OC(=O)OCC(C)CC)=CC=2)C=C1 ODRRZCIOSQUOFW-UHFFFAOYSA-N 0.000 description 1
- UUHWYBCAHOFQHS-UHFFFAOYSA-N [4-[4-(2-methylbutoxycarbonyloxy)phenyl]phenyl] 2-methylbutyl carbonate Chemical group C1=CC(OC(=O)OCC(C)CC)=CC=C1C1=CC=C(OC(=O)OCC(C)CC)C=C1 UUHWYBCAHOFQHS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000003446 memory effect Effects 0.000 description 1
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
- VFXVAXFIFHSGNR-UHFFFAOYSA-N octyl carbonochloridate Chemical compound CCCCCCCCOC(Cl)=O VFXVAXFIFHSGNR-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 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 (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59185148A JPS6163638A (ja) | 1984-09-04 | 1984-09-04 | 炭酸エステル液晶及びその組成物 |
| US06/692,164 US4647398A (en) | 1984-02-03 | 1985-01-17 | Liquid-crystalline carbonic acid esters and liquid crystal compositions containing same |
| DE8585300550T DE3579330D1 (de) | 1984-02-03 | 1985-01-28 | Fluessigkristallcarbonsaeureester und diese enthaltende fluessigkristallkompositionen. |
| EP85300550A EP0152217B1 (en) | 1984-02-03 | 1985-01-28 | Liquid crystalline carbonic acid esters and liquid crystal compositions containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59185148A JPS6163638A (ja) | 1984-09-04 | 1984-09-04 | 炭酸エステル液晶及びその組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6163638A JPS6163638A (ja) | 1986-04-01 |
| JPH0458461B2 true JPH0458461B2 (nl) | 1992-09-17 |
Family
ID=16165698
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59185148A Granted JPS6163638A (ja) | 1984-02-03 | 1984-09-04 | 炭酸エステル液晶及びその組成物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6163638A (nl) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6187777A (ja) * | 1984-10-05 | 1986-05-06 | Ajinomoto Co Inc | 液晶組成物 |
-
1984
- 1984-09-04 JP JP59185148A patent/JPS6163638A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6163638A (ja) | 1986-04-01 |
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