JPH0269443A - フルオロアルキル系化合物及び液晶組成物 - Google Patents
フルオロアルキル系化合物及び液晶組成物Info
- Publication number
- JPH0269443A JPH0269443A JP63220835A JP22083588A JPH0269443A JP H0269443 A JPH0269443 A JP H0269443A JP 63220835 A JP63220835 A JP 63220835A JP 22083588 A JP22083588 A JP 22083588A JP H0269443 A JPH0269443 A JP H0269443A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- liquid crystal
- compound expressed
- compound
- phase
- 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.)
- Granted
Links
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 34
- 239000000203 mixture Substances 0.000 title claims abstract description 31
- 150000001875 compounds Chemical class 0.000 title abstract description 59
- 125000003709 fluoroalkyl group Chemical group 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- -1 fluoroalkyl compound Chemical group 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims 4
- 239000004990 Smectic liquid crystal Substances 0.000 abstract description 31
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract description 22
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract description 8
- 230000001747 exhibiting effect Effects 0.000 abstract description 7
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 abstract description 6
- 239000005711 Benzoic acid Substances 0.000 abstract description 5
- 235000010233 benzoic acid Nutrition 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 4
- 239000000470 constituent Substances 0.000 abstract description 2
- 125000001153 fluoro group Chemical group F* 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 40
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 11
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 239000012046 mixed solvent Substances 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 230000007704 transition Effects 0.000 description 7
- 238000005292 vacuum distillation Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910019213 POCl3 Inorganic materials 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- AMVHMKULOHFQSB-UHFFFAOYSA-N 4-(4-octoxybenzoyl)oxybenzoic acid Chemical compound C1=CC(OCCCCCCCC)=CC=C1C(=O)OC1=CC=C(C(O)=O)C=C1 AMVHMKULOHFQSB-UHFFFAOYSA-N 0.000 description 2
- HFRUPPHPJRZOCM-UHFFFAOYSA-N 4-octoxyphenol Chemical compound CCCCCCCCOC1=CC=C(O)C=C1 HFRUPPHPJRZOCM-UHFFFAOYSA-N 0.000 description 2
- QDOAWUCLBBYAGY-UHFFFAOYSA-N 4-phenylmethoxycarbonylcyclohexane-1-carboxylic acid Chemical compound C1CC(C(=O)O)CCC1C(=O)OCC1=CC=CC=C1 QDOAWUCLBBYAGY-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JTCRQLVSMPPNJI-MXVIHJGJSA-N O=C([C@@H]1CC[C@H](CC1)C(=O)OCC=1C=CC=CC=1)OCC1=CC=CC=C1 Chemical compound O=C([C@@H]1CC[C@H](CC1)C(=O)OCC=1C=CC=CC=1)OCC1=CC=CC=C1 JTCRQLVSMPPNJI-MXVIHJGJSA-N 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 2
- CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical group C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 description 1
- MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 1
- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- WCJLKAOWUBVWSG-UHFFFAOYSA-N 2-octoxybenzoyl chloride Chemical compound CCCCCCCCOC1=CC=CC=C1C(Cl)=O WCJLKAOWUBVWSG-UHFFFAOYSA-N 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- RGRIMQYNCUGNDQ-UHFFFAOYSA-N 4-phenylmethoxycarbonylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)OCC1=CC=CC=C1 RGRIMQYNCUGNDQ-UHFFFAOYSA-N 0.000 description 1
- 102100022096 Acid-sensing ion channel 5 Human genes 0.000 description 1
- MOZDKDIOPSPTBH-UHFFFAOYSA-N Benzyl parahydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)OCC1=CC=CC=C1 MOZDKDIOPSPTBH-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- HXTYZWJVMWWWDK-IZLXSQMJSA-N ClC(=O)[C@H]1CC[C@@H](CC1)C(Cl)=O Chemical compound ClC(=O)[C@H]1CC[C@@H](CC1)C(Cl)=O HXTYZWJVMWWWDK-IZLXSQMJSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 101000901085 Homo sapiens Acid-sensing ion channel 5 Proteins 0.000 description 1
- VWFWJPJMAFRNET-MQWMPURMSA-N IACI Chemical compound C1=CC=C2C([C@@H](O)[C@@H]3CC4CCN3C[C@@H]4CC)=CC=NC2=C1NC(=O)C1=CC([125I])=C(N=[N+]=[N-])C=C1O VWFWJPJMAFRNET-MQWMPURMSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- TUMHNADUCFXBLP-UHFFFAOYSA-N OC(C(C=C1)=CC=C1C(OCC1=CC=CC=C1)=O)=O.Cl Chemical compound OC(C(C=C1)=CC=C1C(OCC1=CC=CC=C1)=O)=O.Cl TUMHNADUCFXBLP-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical group C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical group C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- NJSUFZNXBBXAAC-UHFFFAOYSA-N ethanol;toluene Chemical compound CCO.CC1=CC=CC=C1 NJSUFZNXBBXAAC-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- OOYGSFOGFJDDHP-KMCOLRRFSA-N kanamycin A sulfate Chemical group OS(O)(=O)=O.O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N OOYGSFOGFJDDHP-KMCOLRRFSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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 |
|---|---|---|---|
| JP63220835A JPH0269443A (ja) | 1988-09-02 | 1988-09-02 | フルオロアルキル系化合物及び液晶組成物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63220835A JPH0269443A (ja) | 1988-09-02 | 1988-09-02 | フルオロアルキル系化合物及び液晶組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0269443A true JPH0269443A (ja) | 1990-03-08 |
| JPH0588696B2 JPH0588696B2 (enrdf_load_stackoverflow) | 1993-12-24 |
Family
ID=16757289
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63220835A Granted JPH0269443A (ja) | 1988-09-02 | 1988-09-02 | フルオロアルキル系化合物及び液晶組成物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0269443A (enrdf_load_stackoverflow) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02142753A (ja) * | 1988-09-23 | 1990-05-31 | Minnesota Mining & Mfg Co <3M> | アキラルフツ素含有液晶 |
| US5580488A (en) * | 1993-05-17 | 1996-12-03 | Canon Kabushiki Kaisha | Mesomorphic compound liquid crystal composition containing the compound, liquid crystal device using the composition, display apparatus and display method |
| US5593616A (en) * | 1993-09-17 | 1997-01-14 | Canon Kabushiki Kaisha | Optically inactive, mesomorphic compound, liquid crystal composition containing the compound, liquid crystal device using the composition, liquid crystal apparatus and display method |
| US5658491A (en) * | 1995-10-12 | 1997-08-19 | Minnesota Mining And Manufacturing Company | Process for controlling cone tilt angle in mixtures of smectic liquid crystal compounds |
| US5688437A (en) * | 1994-04-14 | 1997-11-18 | Canon Kabushiki Kaisha | Liquid crystal composition, liquid crystal device using the composition, liquid crystal apparatus and display method |
| US5702637A (en) * | 1995-04-19 | 1997-12-30 | Minnesota Mining And Manufacturing Company | Liquid crystal compounds having a chiral fluorinated terminal portion |
| US5855812A (en) * | 1997-04-11 | 1999-01-05 | Minnesota Mining And Manufacturing Company | Compounds and process for controlling cone tilt angle in mixtures of smectic liquid crystal compounds |
| US6309561B1 (en) | 1997-12-24 | 2001-10-30 | 3M Innovative Properties Company | Liquid crystal compounds having a chiral fluorinated terminal portion |
| US7973194B1 (en) | 2010-03-18 | 2011-07-05 | Eastman Chemical Company | High solvating cyclohexane dicarboxylate diesters plasticizers |
| JP2011231098A (ja) * | 2009-12-01 | 2011-11-17 | Sumitomo Chemical Co Ltd | シクロアルカンジカルボン酸モノエステルの製造方法 |
-
1988
- 1988-09-02 JP JP63220835A patent/JPH0269443A/ja active Granted
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02142753A (ja) * | 1988-09-23 | 1990-05-31 | Minnesota Mining & Mfg Co <3M> | アキラルフツ素含有液晶 |
| US5580488A (en) * | 1993-05-17 | 1996-12-03 | Canon Kabushiki Kaisha | Mesomorphic compound liquid crystal composition containing the compound, liquid crystal device using the composition, display apparatus and display method |
| US5593616A (en) * | 1993-09-17 | 1997-01-14 | Canon Kabushiki Kaisha | Optically inactive, mesomorphic compound, liquid crystal composition containing the compound, liquid crystal device using the composition, liquid crystal apparatus and display method |
| US5688437A (en) * | 1994-04-14 | 1997-11-18 | Canon Kabushiki Kaisha | Liquid crystal composition, liquid crystal device using the composition, liquid crystal apparatus and display method |
| US5702637A (en) * | 1995-04-19 | 1997-12-30 | Minnesota Mining And Manufacturing Company | Liquid crystal compounds having a chiral fluorinated terminal portion |
| US5972241A (en) * | 1995-04-19 | 1999-10-26 | 3M Innovative Properties Company | Liquid crystal compounds having a chiral fluorinated terminal portion |
| US5658491A (en) * | 1995-10-12 | 1997-08-19 | Minnesota Mining And Manufacturing Company | Process for controlling cone tilt angle in mixtures of smectic liquid crystal compounds |
| US5928562A (en) * | 1995-10-12 | 1999-07-27 | Minnesota Mining And Manufacturing Company | Process for controlling cone tilt angle in mixtures of smectic liquid crystal compounds |
| US5855812A (en) * | 1997-04-11 | 1999-01-05 | Minnesota Mining And Manufacturing Company | Compounds and process for controlling cone tilt angle in mixtures of smectic liquid crystal compounds |
| US6309561B1 (en) | 1997-12-24 | 2001-10-30 | 3M Innovative Properties Company | Liquid crystal compounds having a chiral fluorinated terminal portion |
| JP2011231098A (ja) * | 2009-12-01 | 2011-11-17 | Sumitomo Chemical Co Ltd | シクロアルカンジカルボン酸モノエステルの製造方法 |
| US7973194B1 (en) | 2010-03-18 | 2011-07-05 | Eastman Chemical Company | High solvating cyclohexane dicarboxylate diesters plasticizers |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0588696B2 (enrdf_load_stackoverflow) | 1993-12-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2948783B2 (ja) | 強誘電性液晶 | |
| JPH0269443A (ja) | フルオロアルキル系化合物及び液晶組成物 | |
| NO170801B (no) | Chirale estere av alfa-substituerte karboksylsyrer og mesogne hydroksylforbindelser og deres anvendelse som doteringsstoff i vaeskekrystallfaser | |
| JP2843624B2 (ja) | ２，５―ジ置換ヘテロ環状化合物および液晶相 | |
| GB2200912A (en) | Terphenyl derivatives and liquid crystal materials containing them | |
| EP0244129A2 (en) | Optically active compound and liquid crystalline composition | |
| 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 | |
| JPH01230548A (ja) | フルオロアルキル系化合物及び液晶組成物 | |
| JPS6210083A (ja) | ピリミジニルジオキサン誘導体 | |
| JPS63301872A (ja) | スメクチック性液晶化合物 | |
| JP2974824B2 (ja) | 光学活性化合物とその合成中間体、及びそれを 含む強誘電性液晶組成物 | |
| HK2297A (en) | Ferroelectric liquid crystals | |
| JPH0413648A (ja) | 光学活性化合物及びこれを用いた強誘電性液晶組成物 | |
| JPS59157056A (ja) | 光学活性アルコ−ルのエステル | |
| JPH01245089A (ja) | 液晶材料 | |
| JPH02131444A (ja) | 液晶化合物 | |
| JPH11100578A (ja) | 新規エステル化合物、およびこれを含む液晶組成物並びに光スイッチング素子 | |
| JPH024893A (ja) | 液晶材料 | |
| JPH0267252A (ja) | 光学活性化合物 | |
| JPH0236152A (ja) | アルコキシフェニル酢酸誘導体及び液晶組成物 | |
| JPS6028952A (ja) | フエニルシクロヘキサン類 | |
| JPH01233262A (ja) | フルオロアルコキシビフェニルカルボン酸誘導体及び液晶組成物 | |
| JPH0240342A (ja) | アルキルフェニル酢酸誘導体及び液晶組成物 | |
| JPS63190843A (ja) | 光学活性シクロプロパン化合物 | |
| JPH04159255A (ja) | 光学活性化合物及びこれを含む液晶組成物 |