DD274040A5 - Fluessig-kristallines gemisch, welches zur verwendung in der vorrichtung fuer die verbildlichung von informationen bestimmt ist - Google Patents

Fluessig-kristallines gemisch, welches zur verwendung in der vorrichtung fuer die verbildlichung von informationen bestimmt ist Download PDF

Info

Publication number: DD274040A5
Authority: DD; German Democratic Republic
Prior art keywords: compounds; group; chain; trans; mixture
Prior art date: 1986-12-24

Application number

DD87311127A

Other languages

German (de)

English (en)

Inventor

Roman Dabrowski

Tomasz Szczucinski

Jerzy Dziaduszek

Original Assignee

Wojskowa Akademia Techniczna Im. Jaroslawa Dabrowskiego,Pl

Priority date (The priority date 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 date listed.)

1986-12-24

Filing date

1987-12-23

Publication date

1989-12-06

1987-12-23 Application filed by Wojskowa Akademia Techniczna Im. Jaroslawa Dabrowskiego,Pl filed Critical Wojskowa Akademia Techniczna Im. Jaroslawa Dabrowskiego,Pl

1989-12-06 Publication of DD274040A5 publication Critical patent/DD274040A5/de

Links

239000000203 mixture Substances 0.000 title claims abstract description 67
239000007788 liquid Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 104
230000015572 biosynthetic process Effects 0.000 claims description 6
HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical class [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 claims description 5
239000000975 dye Substances 0.000 claims description 4
239000004988 Nematic liquid crystal Substances 0.000 claims 1
-1 trans-1,4-disubstituted cyclohexane rings Chemical group 0.000 abstract description 21
125000000217 alkyl group Chemical group 0.000 abstract description 20
229910052731 fluorine Inorganic materials 0.000 abstract description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 11
238000002360 preparation method Methods 0.000 abstract description 11
125000003545 alkoxy group Chemical group 0.000 abstract description 8
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract description 6
229910052801 chlorine Inorganic materials 0.000 abstract description 3
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 abstract 1
101150065749 Churc1 gene Proteins 0.000 abstract 1
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 abstract 1
102100038239 Protein Churchill Human genes 0.000 abstract 1
238000012800 visualization Methods 0.000 abstract 1
239000012071 phase Substances 0.000 description 23
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000004973 liquid crystal related substance Substances 0.000 description 9
125000001153 fluoro group Chemical group F* 0.000 description 8
229910052740 iodine Inorganic materials 0.000 description 8
238000000034 method Methods 0.000 description 8
230000002349 favourable effect Effects 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
230000000694 effects Effects 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
230000009466 transformation Effects 0.000 description 5
230000007704 transition Effects 0.000 description 5
239000004990 Smectic liquid crystal Substances 0.000 description 4
125000004093 cyano group Chemical group *C#N 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
0 C**C(*)Cc1ccccc1 Chemical compound C**C(*)Cc1ccccc1 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
239000000463 material Substances 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000002904 solvent Substances 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
IPCQSBSEIBDYIY-HDJSIYSDSA-N C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(N=C=S)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(N=C=S)C=C1 IPCQSBSEIBDYIY-HDJSIYSDSA-N 0.000 description 2
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
101000939500 Homo sapiens UBX domain-containing protein 11 Proteins 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
229910020808 NaBF Inorganic materials 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
102100029645 UBX domain-containing protein 11 Human genes 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
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 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
230000004927 fusion Effects 0.000 description 2
238000002156 mixing Methods 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
239000002243 precursor Substances 0.000 description 2
230000008569 process Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
GRZJZRHVJAXMRR-UHFFFAOYSA-N 1-cyclohexyl-2-phenylbenzene Chemical group C1CCCCC1C1=CC=CC=C1C1=CC=CC=C1 GRZJZRHVJAXMRR-UHFFFAOYSA-N 0.000 description 1
HNBJZFPJDFJMLP-UHFFFAOYSA-N 1-cyclohexylethylbenzene Chemical class C=1C=CC=CC=1C(C)C1CCCCC1 HNBJZFPJDFJMLP-UHFFFAOYSA-N 0.000 description 1
WDRUBCBSUBXPSW-UHFFFAOYSA-N 2,4-diphenylpyrimidine Chemical compound C1=CC=CC=C1C1=CC=NC(C=2C=CC=CC=2)=N1 WDRUBCBSUBXPSW-UHFFFAOYSA-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
WLNDDIWESXCXHM-UHFFFAOYSA-N 2-phenyl-1,4-dioxane Chemical class C1OCCOC1C1=CC=CC=C1 WLNDDIWESXCXHM-UHFFFAOYSA-N 0.000 description 1
ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical class OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 description 1
OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical class C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 1
125000005917 3-methylpentyl group Chemical group 0.000 description 1
ZUARBRLWEPUHQB-UHFFFAOYSA-N 4-(4-nitrophenyl)cyclohexane-1-carboxylic acid Chemical compound C1CC(C(=O)O)CCC1C1=CC=C([N+]([O-])=O)C=C1 ZUARBRLWEPUHQB-UHFFFAOYSA-N 0.000 description 1
GQJHPVOLXNKXKB-UHFFFAOYSA-N 4-[5-(4-butylphenyl)pyrimidin-2-yl]benzonitrile Chemical compound C1=CC(CCCC)=CC=C1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 GQJHPVOLXNKXKB-UHFFFAOYSA-N 0.000 description 1
SHOZKBAAQMRSAY-UHFFFAOYSA-N 4-[5-(4-pentylphenyl)pyrimidin-2-yl]benzonitrile Chemical compound C1=CC(CCCCC)=CC=C1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 SHOZKBAAQMRSAY-UHFFFAOYSA-N 0.000 description 1
OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
JTIKLGPZEFXJDL-UOSFBKCJSA-N C(CCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)N Chemical compound C(CCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)N JTIKLGPZEFXJDL-UOSFBKCJSA-N 0.000 description 1
LNZYVJFVMCWSRW-GTZNLPHPSA-N C(CCCCCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)N=C=S.C(CCCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)N=C=S.C(CC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)N=C=S Chemical compound C(CCCCCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)N=C=S.C(CCCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)N=C=S.C(CC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)N=C=S LNZYVJFVMCWSRW-GTZNLPHPSA-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
WMWOAQARUZYORF-KOMQPUFPSA-N C1C[C@@H](CCCC)CC[C@@H]1C1=CC=CC=C1 Chemical compound C1C[C@@H](CCCC)CC[C@@H]1C1=CC=CC=C1 WMWOAQARUZYORF-KOMQPUFPSA-N 0.000 description 1
STLICVZWECVJDT-QAQDUYKDSA-N C1C[C@@H](CCCCCC)CC[C@@H]1C1=CC=C(N=C=S)C=C1 Chemical compound C1C[C@@H](CCCCCC)CC[C@@H]1C1=CC=C(N=C=S)C=C1 STLICVZWECVJDT-QAQDUYKDSA-N 0.000 description 1
NSGMZTNTQKRAFA-UAPYVXQJSA-N C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 NSGMZTNTQKRAFA-UAPYVXQJSA-N 0.000 description 1
LPCYDIMBPIGDDK-WGSAOQKQSA-N C1C[C@@H](CCCCCCCC)CC[C@@H]1C1=CC=C(N=C=S)C=C1 Chemical compound C1C[C@@H](CCCCCCCC)CC[C@@H]1C1=CC=C(N=C=S)C=C1 LPCYDIMBPIGDDK-WGSAOQKQSA-N 0.000 description 1
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
241000766026 Coregonus nasus Species 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
OBCFRUDIAPQLCD-XYPYZODXSA-N [N+](=O)([O-])C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CC(=O)O Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CC(=O)O OBCFRUDIAPQLCD-XYPYZODXSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000001000 anthraquinone dye Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
239000002585 base Substances 0.000 description 1
SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
150000004074 biphenyls Chemical class 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
229910052799 carbon Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000010276 construction Methods 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical class C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000003989 dielectric material Substances 0.000 description 1
238000009826 distribution Methods 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
125000004185 ester group Chemical group 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
ZRSDQBKGDNPFLT-UHFFFAOYSA-N ethanol;oxolane Chemical compound CCO.C1CCOC1 ZRSDQBKGDNPFLT-UHFFFAOYSA-N 0.000 description 1
XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000005496 eutectics Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 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
239000001257 hydrogen Substances 0.000 description 1
230000006872 improvement Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 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
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 1
230000005693 optoelectronics Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical class C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
OPYYWWIJPHKUDZ-UHFFFAOYSA-N phenyl cyclohexanecarboxylate Chemical class C1CCCCC1C(=O)OC1=CC=CC=C1 OPYYWWIJPHKUDZ-UHFFFAOYSA-N 0.000 description 1
QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
238000003892 spreading Methods 0.000 description 1
230000007480 spreading Effects 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
238000002834 transmittance Methods 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

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/19—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups bound to carbon atoms of six-membered aromatic rings and hydroxy groups bound to acyclic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/06—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to carbon atoms of six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/39—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups
- C07C205/42—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/55—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C22/00—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom
- C07C22/02—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings
- C07C22/04—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/50—Halogenated unsaturated alcohols containing six-membered aromatic rings and other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/16—Isothiocyanates
- C07C331/28—Isothiocyanates having isothiocyanate groups bound to carbon atoms of six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Crystallography & Structural Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Liquid Crystal Substances (AREA)
Liquid Crystal (AREA)

DD87311127A 1986-12-24 1987-12-23 Fluessig-kristallines gemisch, welches zur verwendung in der vorrichtung fuer die verbildlichung von informationen bestimmt ist DD274040A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PL1986263243A PL151370B1 (en)	1986-12-24	1986-12-24	Liquidcrystalline cyclohexylbenzene derivatives their manufacturing and novel nematic admixtures containing same.

Publications (1)

Publication Number	Publication Date
DD274040A5 true DD274040A5 (de)	1989-12-06

Family

ID=20034229

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD87311127A DD274040A5 (de)	1986-12-24	1987-12-23	Fluessig-kristallines gemisch, welches zur verwendung in der vorrichtung fuer die verbildlichung von informationen bestimmt ist

Country Status (6)

Country	Link
EP (1)	EP0272580B1 (fr)
JP (1)	JP2511088B2 (fr)
CN (1)	CN1022490C (fr)
DD (1)	DD274040A5 (fr)
DE (1)	DE3750395D1 (fr)
PL (1)	PL151370B1 (fr)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2229438B (en) *	1989-03-18	1993-06-16	Merck Patent Gmbh	Difluoromethylene compounds and liquid crystalline-media containing such compounds
SG26367G (en) *	1989-08-12	1995-09-18	Merck Patent Gmbh	Benzol derivatives and liquid crystalline medium
DE4027315A1 (de) *	1989-08-30	1991-03-07	Merck Patent Gmbh	Halogenierte benzolderivate und fluessigkristallines medium
WO1991015555A2 (fr) *	1990-04-02	1991-10-17	MERCK Patent Gesellschaft mit beschränkter Haftung	Melanges nematiques de cristaux liquides et affichage matriciel a cristaux liquides
DE4111015B4 (de) *	1990-04-13	2010-10-14	Merck Patent Gmbh	Flüssigkristallines Medium und seine Verwendung
EP0481032A1 (fr) *	1990-04-13	1992-04-22	MERCK PATENT GmbH	Milieu de cristaux liquides
WO1991017135A1 (fr) *	1990-04-27	1991-11-14	MERCK Patent Gesellschaft mit beschränkter Haftung	Phenylcyclohexanes et milieu a cristaux liquides
EP0479972A1 (fr) *	1990-04-30	1992-04-15	MERCK PATENT GmbH	Phenylcyclohexanes et milieu de cristaux liquides
DE602005005749T2 (de) *	2004-08-10	2009-04-30	Merck Patent Gmbh	Polymerisierbare mesogene Cyclohexylphenylderivate
US8114310B2 (en)	2007-10-22	2012-02-14	Merck Patent Gmbh	Liquid-crystal display
US8252201B1 (en)	2008-11-09	2012-08-28	Military University of Technology	Liquid crystalline medium
KR101541138B1 (ko) *	2008-12-16	2015-08-03	주식회사 동진쎄미켐	액정 화합물 및 그 제조방법
JP5601494B2 (ja) *	2009-12-11	2014-10-08	Ｄｉｃ株式会社	液晶材料の製造方法
CN104496795B (zh) *	2014-12-12	2016-09-14	重庆博腾制药科技股份有限公司	一种dgat-1抑制剂中间体的制备方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5939835A (ja) *	1982-08-27	1984-03-05	Asahi Glass Co Ltd	１−（トランス−４−アルキルシクロヘキシル）−２−｛トランス−４′−（ｐ−置換フエニル）シクロヘキシル｝エタン
US4630896A (en) *	1983-06-17	1986-12-23	Hoffmann-La Roche Inc.	Benzonitriles
EP0144648B1 (fr) *	1983-11-02	1987-10-21	F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft	Cristaux liquides: dérivés de cyclohexylbenzène et cyclohexylbiphényl
PL147864B1 (en) *	1985-12-16	1989-08-31	Wojskowa Akad Tech	A method of liquid crystal compounds with a terminal izotiocyanate group getting

1986
- 1986-12-24 PL PL1986263243A patent/PL151370B1/pl unknown
1987
- 1987-12-14 EP EP87118518A patent/EP0272580B1/fr not_active Expired - Lifetime
- 1987-12-14 DE DE3750395T patent/DE3750395D1/de not_active Expired - Lifetime
- 1987-12-23 DD DD87311127A patent/DD274040A5/de not_active IP Right Cessation
- 1987-12-24 CN CN87101284A patent/CN1022490C/zh not_active Expired - Fee Related
- 1987-12-24 JP JP62336779A patent/JP2511088B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
JP2511088B2 (ja)	1996-06-26
DE3750395D1 (de)	1994-09-22
EP0272580A2 (fr)	1988-06-29
PL151370B1 (en)	1990-08-31
JPS63185936A (ja)	1988-08-01
CN1022490C (zh)	1993-10-20
PL263243A1 (en)	1989-03-06
EP0272580A3 (en)	1989-05-24
CN87101284A (zh)	1988-12-14
EP0272580B1 (fr)	1994-08-17

Legal Events

Date	Code	Title	Description
1995-12-21	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE2922236C2 (de)	1986-09-25	Flüssigkristalline Cyclohexanderivate, diese enthaltende flüssigkristalline Materialien und deren Verwendung
EP0051738B1 (fr)	1984-07-25	Dérivés de cyclohexyl-biphényle contenant du fluor, diélectriques les contenant et élément indicateur électro-optique
DE2736525C2 (fr)	1990-07-05
EP0056501B1 (fr)	1984-05-02	Mélange de cristaux liquides
DE2823909C2 (de)	1986-01-30	Flüssigkristallmischungen
EP0471813B1 (fr)	1996-05-22	2',3-difluorbiphenyles 4,4'-disubstitues et milieu cristallin liquide
DE3006666A1 (de)	1981-09-17	Phenylcyclohexenderivate, verfahren zu ihrer herstellung, diese enthaltende fluessigkristalline dielektrika und elektrooptisches anzeieelement
DE2853728A1 (de)	1980-07-17	Fluessigkristalline carbonsaeureester, verfahren zu ihrer herstellung, diese enthaltende dielektrika und elektrooptisches anzeigeelement
EP0030277A1 (fr)	1981-06-17	Oligo 1,4-phénylènes partiellement hydrogénés, diélectriques les contenant et élément indicateur électro-optique
EP0134570B1 (fr)	1988-01-13	Composés anisotropes et mélanges des cristaux liquides
CH649766A5 (de)	1985-06-14	Substituierte benzoesaeurephenylester, fluessigkristallmischungen diese enthaltend und verwendung derselben in anzeigeeinheiten.
DE69008544T2 (de)	1994-11-24	Flüssigkristallverbindungen mit hoher optischer Anisotropie.
DE3888036T2 (de)	1994-06-23	Optisch aktive Verbindung, Verfahren zur ihrer Herstellung und sie enthaltende flüssigkristalline Zusammensetzung.
EP0184012B1 (fr)	1988-01-07	Compositions liquides cristallines
DE3237020C2 (de)	1985-10-17	Trans-4-Alkyloxymethyl-1-(4'-cyanophenyl)cyclohexane und trans-4-Alkyloxymethyl-1-(4"-cyano-4'-biphenylyl)cyclohexane, Verfahren zu deren Herstellung und deren Verwendung
DE3324774C2 (de)	1985-03-07	Cyclohexancarbonsäure-biphenylester und Benzoyloxybenzoesäurephenylester und deren Verwendung
DE3318533C2 (de)	1985-03-07	1-[trans-(äquatorial-äquatorial)-4-Alkylcyclohexyl]-2-[trans-(äquatorial-äquatorial)-4-alkylcyclohexancarbonyloxyphenyl]-äthane und deren Verwendung als elektrooptische Anzeigematerialien
DD219497A5 (de)	1985-03-06	Fluessig-kristalline gemische
DE69018065T2 (de)	1995-08-31	Flüssigkristalline eigenschaften besitzende phenylnaphthalene.
CH664558A5 (de)	1988-03-15	1-(subst.-4-acyloxy-cyclohexyl)-2-(4-alkylcyclohexyl)ethane mit fluessigkristallinen eigenschaften.
CH670639A5 (fr)	1989-06-30
DE2951099A1 (de)	1981-06-25	Tetrahydrochinazoline, verfahren zu ihrer herstellung, diese enthaltende fluessigkristalline dielektrika und elektrooptisches anzeigeelement
EP0480008B1 (fr)	1996-08-21	Phenylcyclohexanes et milieu a cristaux liquides
DE60313847T2 (de)	2007-09-20	Flüssigkristalline verbindungen
DE3221941C2 (de)	1984-08-23	1-[trans-(äquatorial-äquatorial)-4-n-Alkylcyclohexyl]-2-[4-trans-(äquatorial-äquatorial)-4'-n-alkylcyclohexylphenyl]-äthane, Verfahren zu deren Herstellung und deren Verwendung