DD264451A5 - Fluessigkristalline kompositionen - Google Patents

Fluessigkristalline kompositionen Download PDF

Info

Publication number: DD264451A5
Authority: DD; German Democratic Republic
Prior art keywords: ring; ethane; substituted; trans; isothiocyanatophenyl
Prior art date: 1985-12-16

Application number

DD86297632A

Other languages

German (de)

English (en)

Inventor

Roman Dabrowski

Jerzy Dziaduszek

Tomasz Szczucinski

Witold Drzewinski

Zofia Stolarz

Jozef Zmija

Janusz Parka

Bozena Sosnowska

Original Assignee

��@��@��@��K@��@��k��

��@��@ ��`�� k��@��@��k��

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.)

1985-12-16

Filing date

1986-12-15

Publication date

1989-02-01

1986-12-15 Application filed by ��@��@��@��K@��@��k��, ��@��@ ��`�� k��@��@��k�� filed Critical ��@��@��@��K@��@��k��

1989-02-01 Publication of DD264451A5 publication Critical patent/DD264451A5/de

Links

239000000203 mixture Substances 0.000 title claims abstract description 81
239000007788 liquid Substances 0.000 title abstract description 32
150000001875 compounds Chemical class 0.000 claims abstract description 89
239000000975 dye Substances 0.000 claims abstract description 9
-1 5-substituted pyrimidine ring Chemical group 0.000 abstract description 77
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 26
125000000217 alkyl group Chemical group 0.000 abstract description 13
VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical group C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 abstract description 12
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 10
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical group CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 abstract description 10
125000003545 alkoxy group Chemical group 0.000 abstract description 8
125000000714 pyrimidinyl group Chemical class 0.000 abstract description 4
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 88
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 35
238000000034 method Methods 0.000 description 29
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
239000010410 layer Substances 0.000 description 20
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 18
238000002844 melting Methods 0.000 description 16
230000008018 melting Effects 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
230000008569 process Effects 0.000 description 12
150000001555 benzenes Chemical class 0.000 description 10
239000012071 phase Substances 0.000 description 10
230000007704 transition Effects 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
235000010290 biphenyl Nutrition 0.000 description 9
239000004305 biphenyl Substances 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
239000002178 crystalline material Substances 0.000 description 8
230000000694 effects Effects 0.000 description 8
150000003230 pyrimidines Chemical class 0.000 description 8
230000002349 favourable effect Effects 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
230000003287 optical effect Effects 0.000 description 7
239000007787 solid Substances 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
125000004093 cyano group Chemical group *C#N 0.000 description 6
150000001934 cyclohexanes Chemical class 0.000 description 6
239000004973 liquid crystal related substance Substances 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
239000000463 material Substances 0.000 description 5
239000000758 substrate Substances 0.000 description 5
WPYSJFXXQNITBC-UHFFFAOYSA-N 1-isothiocyanato-4-phenylbenzene Chemical group C1=CC(N=C=S)=CC=C1C1=CC=CC=C1 WPYSJFXXQNITBC-UHFFFAOYSA-N 0.000 description 4
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical group C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 description 4
125000001810 isothiocyanato group Chemical group *N=C=S 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000011084 recovery Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000007868 Raney catalyst Substances 0.000 description 3
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
229910000564 Raney nickel Inorganic materials 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000002131 composite material Substances 0.000 description 3
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 3
230000001419 dependent effect Effects 0.000 description 3
125000000532 dioxanyl group Chemical group 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
238000007429 general method Methods 0.000 description 3
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 3
230000009467 reduction Effects 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
150000003512 tertiary amines Chemical class 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
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
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
239000002585 base Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000001720 carbohydrates Chemical class 0.000 description 2
235000014633 carbohydrates Nutrition 0.000 description 2
230000008859 change Effects 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
235000019256 formaldehyde Nutrition 0.000 description 2
229960004279 formaldehyde Drugs 0.000 description 2
238000003384 imaging method Methods 0.000 description 2
GRWIABMEEKERFV-UHFFFAOYSA-N methanol;oxolane Chemical compound OC.C1CCOC1 GRWIABMEEKERFV-UHFFFAOYSA-N 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000002243 precursor Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
230000008707 rearrangement Effects 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000007858 starting material Substances 0.000 description 2
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
MLGSMOZSPAWDIL-UHFFFAOYSA-N (4-heptylcyclohexyl)benzene Chemical compound C1CC(CCCCCCC)CCC1C1=CC=CC=C1 MLGSMOZSPAWDIL-UHFFFAOYSA-N 0.000 description 1
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
XRPVQXPWEVJKTN-UHFFFAOYSA-N 1-hexyl-4-phenylbenzene Chemical group C1=CC(CCCCCC)=CC=C1C1=CC=CC=C1 XRPVQXPWEVJKTN-UHFFFAOYSA-N 0.000 description 1
OAYSYSIGKCDBKZ-UHFFFAOYSA-N 1-isothiocyanato-2-phenylbenzene Chemical group S=C=NC1=CC=CC=C1C1=CC=CC=C1 OAYSYSIGKCDBKZ-UHFFFAOYSA-N 0.000 description 1
CVPRIERKONBZQY-UHFFFAOYSA-N 1-isothiocyanato-4-(4-pentylphenyl)benzene Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(N=C=S)C=C1 CVPRIERKONBZQY-UHFFFAOYSA-N 0.000 description 1
AHPBUSLCEMEERH-UHFFFAOYSA-N 1-isothiocyanato-4-(4-propylphenyl)benzene Chemical group C1=CC(CCC)=CC=C1C1=CC=C(N=C=S)C=C1 AHPBUSLCEMEERH-UHFFFAOYSA-N 0.000 description 1
YWPABLWXCWUIIT-UHFFFAOYSA-N 2-(2-phenylphenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1C1=CC=CC=C1 YWPABLWXCWUIIT-UHFFFAOYSA-N 0.000 description 1
FYXZTVPBFJQFBO-UHFFFAOYSA-N 2-(4-nitrophenyl)acetyl chloride Chemical compound [O-][N+](=O)C1=CC=C(CC(Cl)=O)C=C1 FYXZTVPBFJQFBO-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
HRXZRAXKKNUKRF-UHFFFAOYSA-N 4-ethylaniline Chemical compound CCC1=CC=C(N)C=C1 HRXZRAXKKNUKRF-UHFFFAOYSA-N 0.000 description 1
BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
101100533567 Leptosphaeria maculans sirH gene Proteins 0.000 description 1
241000220317 Rosa Species 0.000 description 1
230000009471 action Effects 0.000 description 1
125000005910 alkyl carbonate group Chemical group 0.000 description 1
150000001409 amidines Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
GAUZCKBSTZFWCT-UHFFFAOYSA-N azoxybenzene Chemical compound C=1C=CC=CC=1[N+]([O-])=NC1=CC=CC=C1 GAUZCKBSTZFWCT-UHFFFAOYSA-N 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
244000309464 bull Species 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
230000003098 cholesteric effect Effects 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
238000010276 construction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 1
238000011161 development Methods 0.000 description 1
230000005684 electric field Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229960000192 felbinac Drugs 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000000446 fuel Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000006872 improvement Effects 0.000 description 1
101150057984 isdB gene Proteins 0.000 description 1
150000002540 isothiocyanates Chemical class 0.000 description 1
239000000155 melt Substances 0.000 description 1
AGJSNMGHAVDLRQ-IWFBPKFRSA-N methyl (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-IWFBPKFRSA-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
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
RUOPINZRYMFPBF-UHFFFAOYSA-N pentane-1,3-diol Chemical compound CCC(O)CCO RUOPINZRYMFPBF-UHFFFAOYSA-N 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
239000011734 sodium Substances 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
239000012265 solid product Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
230000003068 static effect Effects 0.000 description 1
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
230000008719 thickening Effects 0.000 description 1
125000000858 thiocyanato group Chemical group *SC#N 0.000 description 1
239000012485 toluene extract Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
229940049591 zoderm Drugs 0.000 description 1

Classifications

- 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
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- 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
- 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
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
- 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
- C09K19/3028—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon single bonds
- 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
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/321—Compounds containing a bicyclo [2,2,2] octane ring
- 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
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Crystallography & Structural Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Liquid Crystal Substances (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

DD86297632A 1985-12-16 1986-12-15 Fluessigkristalline kompositionen DD264451A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PL1985256832A PL147864B1 (en)	1985-12-16	1985-12-16	A method of liquid crystal compounds with a terminal izotiocyanate group getting

Publications (1)

Publication Number	Publication Date
DD264451A5 true DD264451A5 (de)	1989-02-01

Family

ID=20029516

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86297632A DD264451A5 (de)	1985-12-16	1986-12-15	Fluessigkristalline kompositionen

Country Status (8)

Country	Link
US (1)	US4849130A (pl)
EP (1)	EP0227004B1 (pl)
JP (1)	JPS62167758A (pl)
DD (1)	DD264451A5 (pl)
DE (1)	DE3670287D1 (pl)
HU (1)	HU202265B (pl)
PL (1)	PL147864B1 (pl)
SU (2)	SU1766252A3 (pl)

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DE3561395D1 (de) *	1984-05-25	1988-02-18	Hoffmann La Roche	Phenylisothiocyanates
DE3545345A1 (de) *	1985-12-20	1987-07-02	Merck Patent Gmbh	Fluessigkristalline senfoele
EP0242716B1 (de) *	1986-04-22	1991-03-20	F. Hoffmann-La Roche Ag	Flüssigkristalline Pyridinderivate
PL151370B1 (en) *	1986-12-24	1990-08-31		Liquidcrystalline cyclohexylbenzene derivatives their manufacturing and novel nematic admixtures containing same.
DE3709549A1 (de) *	1987-03-24	1988-10-06	Hoechst Ag	Verwendung von 5-phenyl-pyrimidinderivaten als komponenten in smektischen fluessigkristallmischungen
PL151894B1 (en) *	1987-09-25	1990-10-31		Liquid crystal composition
US5292838A (en) *	1988-07-15	1994-03-08	Fina Technology, Inc.	Process and catalyst for producing syndiotactic polymers
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GB8912339D0 (en) *	1989-05-30	1989-07-12	Merck Patent Gmbh	Fluorinated biphenyl derivatives
DE3928267A1 (de) *	1989-08-26	1991-02-28	Merck Patent Gmbh	5-oxy-2-phenylpyrimidine und fluessigkristallines medium
JP3144801B2 (ja) *	1990-04-02	2001-03-12	メルクパテントゲゼルシャフトミットベシュレンクテルハフトング	ネマチック液晶混合物類およびマトリックス液晶ディスプレイ
DE69106966T2 (de) *	1990-07-26	1995-08-24	Asahi Glass Co Ltd	Flüssigkristallanzeigeelement sowie Flüssigkristall-Projektionsanzeigevorrichtung mit einer aktiven Matrix.
ES2142426T3 (es) *	1994-06-13	2000-04-16	Targor Gmbh	Compuestos de metales de transicion.
US6403772B1 (en) *	1995-09-11	2002-06-11	Montell Technology Company, Bv	Open-pentadienyl metallocenes, precursors thereof and polymerization catalysts therefrom
US6025407A (en) *	1997-10-30	2000-02-15	Occidental Chemical Corporation	Photo-polymerization of vinyl chloride using metallocene catalysts
JP4341092B2 (ja) *	1998-12-25	2009-10-07	チッソ株式会社	ジアミノ化合物およびその製造方法
JP2001134221A (ja) *	1999-09-13	2001-05-18	Asulab Sa	２つの重なり合った表示装置を含む表示アセンブリ
JP2002012868A (ja) *	2000-05-08	2002-01-15	Merck Patent Gmbh	液晶媒体
EP1334139A2 (en)	2000-11-07	2003-08-13	Symyx Technologies, Inc.	Substituted pyridyl amine ligands, complexes and catalysts therefrom. processes for producing polyolefins therewith
TWI356073B (en)	2003-09-26	2012-01-11	Lubrizol Advanced Mat Inc	A transparent thermoplastic blend of a cycloolefin
FR2867195A1 (fr) *	2004-03-04	2005-09-09	Optogone Sa	Compose a base de cristaux liquides pour la realisation de composants optoelectroniques et procede de fabrication correspondant
GB0411119D0 (en)	2004-05-19	2004-06-23	Exxonmobil Chem Patents Inc	Modifiers for thermoplastic alloys produced using such modifiers
JP6718657B2 (ja)	2015-02-27	2020-07-08	住友化学株式会社	組成物
KR102676388B1 (ko)	2015-07-24	2024-06-18	스미또모 가가꾸 가부시끼가이샤	조성물, 조성물을 함유하는 광학 필름, 광학 필름의 제조 방법
CN116332800B (zh) *	2021-12-24	2025-02-11	西安近代化学研究所	一种具有超低介电损耗的液晶化合物、组合物和高频组件

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DE3462602D1 (en) *	1983-03-30	1987-04-16	Wojskowa Akad Tech	Liquid crystalline cyclohexylbenzene derivatives, their preparation and the liquid crystal compositions containing them
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JPS60136555A (ja) *	1983-12-26	1985-07-20	Chisso Corp	４−イソチオシアナ−トフエノ−ルのエステル類
JPS60146868A (ja) *	1984-01-06	1985-08-02	Chisso Corp	４−置換フエニルイソチオシアナ−ト類
DE3401320A1 (de) *	1984-01-17	1985-07-25	Merck Patent Gmbh, 6100 Darmstadt	Ethanderivate
JPS60204781A (ja) *	1984-03-28	1985-10-16	Chisso Corp	トランス−２−（ｐ−イソチオシアナ−トフエニル）−５−アルキル−ｍ−ジオキサン類
JPS60222458A (ja) *	1984-04-17	1985-11-07	Chisso Corp	ｐ−置換フエニルイソチオシアネ−ト類
DE3561395D1 (de) *	1984-05-25	1988-02-18	Hoffmann La Roche	Phenylisothiocyanates
US4676924A (en) *	1984-07-02	1987-06-30	Wojskowa Akademia Techniczna	Liquid crystalline isothiocyanates with dioxane ring and liquid crystalline admixtures containing same
DE3575158D1 (de) *	1984-07-12	1990-02-08	Hoffmann La Roche	Fluessigkristalline gemische enthaltend komponenten mit einer 4-alkenyl- oder 2z-alkenyl-seitenkette.
DE3447359A1 (de) *	1984-12-24	1986-07-03	Merck Patent Gmbh, 6100 Darmstadt	Fluessigkristalline phase
JPS61158957A (ja) *	1984-12-28	1986-07-18	Chisso Corp	ベンゾイルイソチオシアナ−ト誘導体
JPS61189263A (ja) *	1985-02-18	1986-08-22	Kawasaki Kagaku Kogyo Kk	液晶化合物及びその製造方法並びに液晶組成物
DE3667170D1 (de) *	1985-03-26	1990-01-04	Hoffmann La Roche	Alkenylsubstituierte phenylisothiocyanate und benzonitrile.
DE3545345A1 (de) *	1985-12-20	1987-07-02	Merck Patent Gmbh	Fluessigkristalline senfoele
DE3628088A1 (de) *	1986-08-19	1988-02-25	Bat Cigarettenfab Gmbh	Einrichtung zur optischen ueberpruefung der oberflaeche von stabfoermigen rauchartikeln und/oder filterstaeben fuer die tabakindustrie
JPH06143172A (ja) *	1992-10-30	1994-05-24	Fujitsu Ltd	冗長マニピュレータの制御方式

1985
- 1985-12-16 PL PL1985256832A patent/PL147864B1/pl unknown
1986
- 1986-12-15 DD DD86297632A patent/DD264451A5/de not_active IP Right Cessation
- 1986-12-15 SU SU864028651A patent/SU1766252A3/ru active
- 1986-12-16 HU HU865230A patent/HU202265B/hu not_active IP Right Cessation
- 1986-12-16 DE DE8686117465T patent/DE3670287D1/de not_active Expired - Fee Related
- 1986-12-16 JP JP61301133A patent/JPS62167758A/ja active Pending
- 1986-12-16 EP EP86117465A patent/EP0227004B1/en not_active Expired - Lifetime
1987
- 1987-06-12 SU SU874202716A patent/SU1655962A1/ru active
1988
- 1988-03-31 US US07/176,253 patent/US4849130A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP0227004A1 (en)	1987-07-01
SU1766252A3 (ru)	1992-09-30
HUT44597A (en)	1988-03-28
PL147864B1 (en)	1989-08-31
EP0227004B1 (en)	1990-04-11
US4849130A (en)	1989-07-18
HU202265B (en)	1991-02-28
PL256832A1 (en)	1988-07-21
JPS62167758A (ja)	1987-07-24
DE3670287D1 (de)	1990-05-17
SU1655962A1 (ru)	1991-06-15

Legal Events

Date	Code	Title	Description
1995-09-14	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD264451A5 (de)	1989-02-01	Fluessigkristalline kompositionen
DE2937700C2 (de)	1984-08-30	2,3-Dicyano-hydrochinon-Derivate und Flüssigkristallmaterialien, die diese Derivate enthalten
DE69101807T2 (de)	1994-11-24	Dichroitische Azofarbstoffe.
EP0051738B1 (de)	1984-07-25	Fluorhaltige Cyclohexylbiphenylderivate, diese enthaltende Dielektrika und elektrooptisches Anzeigeelement
DE3782913T2 (de)	1993-06-09	Fluessigkristallverbindungen, gemische und anordnungen.
DE2922236C2 (de)	1986-09-25	Flüssigkristalline Cyclohexanderivate, diese enthaltende flüssigkristalline Materialien und deren Verwendung
EP0056501B1 (de)	1984-05-02	Flüssigkristallmischung
EP0474062B1 (de)	1995-12-13	Matrix-Flüssigkristallanzeige
EP0085335B1 (de)	1986-04-02	Flüssigkristallines Dielektrikum, neue Farbstoffe, Verfahren zu ihrer Herstellung und elektrooptisches Anzeigeelement
DE2617593A1 (de)	1976-11-11	Diphenylderivate und ihre verwendung
CH647252A5 (de)	1985-01-15	Dichroitische anthrachinonfarbstoffe und deren verwendung in fluessigkristallinen dielektrika fuer elektrooptisches anzeigeelement.
DE3227916C2 (pl)	1989-08-03
DE102015107966A1 (de)	2016-06-16	Cyclopropyl-enthaltende Flüssigkristallverbindungen sowie Flüssigkristallmischung
DE2823909A1 (de)	1978-12-07	Fluessigkristallmischungen
EP0063713A1 (de)	1982-11-03	Dichroitische Anthrachinonfarbstoffe, diese enthaltende flüssigkristalline Dielektrika und elektrooptisches Anzeigeelement
CH649766A5 (de)	1985-06-14	Substituierte benzoesaeurephenylester, fluessigkristallmischungen diese enthaltend und verwendung derselben in anzeigeeinheiten.
CH645104A5 (de)	1984-09-14	Nematische fluessig-kristalline 5-cyan-2-(4-acyloxy-phenyl)-pyrimidine und diese enthaltende gemische.
DE69414574T2 (de)	1999-04-15	Flüssigkristallmaterialien, -mischungen und -vorrichtungen
DE3590260T1 (de)	1986-08-07	Pyrimidinester
DE3606787A1 (de)	1987-09-03	Elektrooptisches anzeigeelement
DD274040A5 (de)	1989-12-06	Fluessig-kristallines gemisch, welches zur verwendung in der vorrichtung fuer die verbildlichung von informationen bestimmt ist
DD219497A5 (de)	1985-03-06	Fluessig-kristalline gemische
DE4024190A1 (de)	1991-02-07	Fluessigkristallmischung und fluessigkristallvorrichtung, bei der sie verwendet wird
DE69018065T2 (de)	1995-08-31	Flüssigkristalline eigenschaften besitzende phenylnaphthalene.
DE3510733A1 (de)	1986-09-25	Fluessigkristallphase