NO872039L - Nitrogenholdige heterocykliske forbindelser. - Google Patents
Nitrogenholdige heterocykliske forbindelser.Info
- Publication number
- NO872039L NO872039L NO872039A NO872039A NO872039L NO 872039 L NO872039 L NO 872039L NO 872039 A NO872039 A NO 872039A NO 872039 A NO872039 A NO 872039A NO 872039 L NO872039 L NO 872039L
- Authority
- NO
- Norway
- Prior art keywords
- cyano
- cis
- cyclohexane
- phenyl
- ester
- Prior art date
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 36
- -1 biphenylyl Chemical group 0.000 claims description 23
- 239000004990 Smectic liquid crystal Substances 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 125000004955 1,4-cyclohexylene group Chemical class [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 6
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004959 2,6-naphthylene group Chemical group [H]C1=C([H])C2=C([H])C([*:1])=C([H])C([H])=C2C([H])=C1[*:2] 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 239000012071 phase Substances 0.000 description 49
- 239000000203 mixture Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 230000010287 polarization Effects 0.000 description 6
- 230000002269 spontaneous effect Effects 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- KQDQEDGPZKEHMH-UHFFFAOYSA-N (4-cyano-4-heptylcyclohexyl) 4-(5-butoxypyrimidin-2-yl)benzoate Chemical compound C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(OCCCC)=CN=2)C=C1 KQDQEDGPZKEHMH-UHFFFAOYSA-N 0.000 description 1
- OTXGJXSAPGNWQC-UHFFFAOYSA-N (4-cyano-4-heptylcyclohexyl) 4-(5-decoxypyrimidin-2-yl)benzoate Chemical compound N1=CC(OCCCCCCCCCC)=CN=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 OTXGJXSAPGNWQC-UHFFFAOYSA-N 0.000 description 1
- KBJZHEXPTSMENQ-UHFFFAOYSA-N (4-cyano-4-heptylcyclohexyl) 4-(5-heptoxypyridin-2-yl)benzoate Chemical compound N1=CC(OCCCCCCC)=CC=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 KBJZHEXPTSMENQ-UHFFFAOYSA-N 0.000 description 1
- KMRSRDRDLDLNPG-UHFFFAOYSA-N (4-cyano-4-heptylcyclohexyl) 4-(5-heptoxypyrimidin-2-yl)benzoate Chemical compound N1=CC(OCCCCCCC)=CN=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 KMRSRDRDLDLNPG-UHFFFAOYSA-N 0.000 description 1
- XMGXEUUNKRFEDG-UHFFFAOYSA-N (4-cyano-4-heptylcyclohexyl) 4-(5-hexoxypyridin-2-yl)benzoate Chemical compound C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(OCCCCCC)=CC=2)C=C1 XMGXEUUNKRFEDG-UHFFFAOYSA-N 0.000 description 1
- GWRJGKNKBYMRAI-UHFFFAOYSA-N (4-cyano-4-heptylcyclohexyl) 4-(5-hexoxypyrimidin-2-yl)benzoate Chemical compound C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(OCCCCCC)=CN=2)C=C1 GWRJGKNKBYMRAI-UHFFFAOYSA-N 0.000 description 1
- STRLIZRTQMIALP-UHFFFAOYSA-N (4-cyano-4-heptylcyclohexyl) 4-(5-nonoxypyrimidin-2-yl)benzoate Chemical compound N1=CC(OCCCCCCCCC)=CN=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 STRLIZRTQMIALP-UHFFFAOYSA-N 0.000 description 1
- DVTMUCVVXCVVLT-UHFFFAOYSA-N (4-cyano-4-heptylcyclohexyl) 4-(5-octoxypyridin-2-yl)benzoate Chemical compound N1=CC(OCCCCCCCC)=CC=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 DVTMUCVVXCVVLT-UHFFFAOYSA-N 0.000 description 1
- CVEMWLFBFXZQGX-UHFFFAOYSA-N (4-cyano-4-heptylcyclohexyl) 4-(5-pentoxypyridin-2-yl)benzoate Chemical compound C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(OCCCCC)=CC=2)C=C1 CVEMWLFBFXZQGX-UHFFFAOYSA-N 0.000 description 1
- JDTITCZSRLYJGI-UHFFFAOYSA-N (4-cyano-4-heptylcyclohexyl) 4-(5-pentoxypyrimidin-2-yl)benzoate Chemical compound C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(OCCCCC)=CN=2)C=C1 JDTITCZSRLYJGI-UHFFFAOYSA-N 0.000 description 1
- GWCGGAJXRWVMFZ-UHFFFAOYSA-N (4-cyano-4-heptylcyclohexyl) 4-(5-propylpyrimidin-2-yl)benzoate Chemical compound C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(CCC)=CN=2)C=C1 GWCGGAJXRWVMFZ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LSXKDWGTSHCFPP-UHFFFAOYSA-N 1-bromoheptane Chemical compound CCCCCCCBr LSXKDWGTSHCFPP-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- KRUVEFPHPNUUQC-UHFFFAOYSA-N 1-heptyl-4-(iodomethyl)cyclohexane-1-carbonitrile Chemical compound CCCCCCCC1(C#N)CCC(CI)CC1 KRUVEFPHPNUUQC-UHFFFAOYSA-N 0.000 description 1
- BWSJCIQVGWVVPG-UHFFFAOYSA-N 2-(ethoxymethylidene)heptanal Chemical compound CCCCCC(C=O)=COCC BWSJCIQVGWVVPG-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- TWLNIMGLDJVXLL-UHFFFAOYSA-N 4-(4-cyano-4-hexylcyclohexyl)benzenecarboximidamide;hydrochloride Chemical compound Cl.C1CC(CCCCCC)(C#N)CCC1C1=CC=C(C(N)=N)C=C1 TWLNIMGLDJVXLL-UHFFFAOYSA-N 0.000 description 1
- RFJRBHWPACFFMC-UHFFFAOYSA-N 4-(5-hexylpyrimidin-2-yl)phenol Chemical compound N1=CC(CCCCCC)=CN=C1C1=CC=C(O)C=C1 RFJRBHWPACFFMC-UHFFFAOYSA-N 0.000 description 1
- ZUEPHMIGLCURNA-UHFFFAOYSA-N 4-[[(4-cyanophenyl)-[4-(5-nonylpyrimidin-2-yl)phenyl]methoxy]-[4-(5-nonylpyrimidin-2-yl)phenyl]methyl]benzonitrile Chemical compound N1=CC(CCCCCCCCC)=CN=C1C1=CC=C(C(OC(C=2C=CC(=CC=2)C#N)C=2C=CC(=CC=2)C=2N=CC(CCCCCCCCC)=CN=2)C=2C=CC(=CC=2)C#N)C=C1 ZUEPHMIGLCURNA-UHFFFAOYSA-N 0.000 description 1
- VTIPXAAINIQCCN-UHFFFAOYSA-N 4-cyano-4-heptylcyclohexane-1-carboxylic acid Chemical compound CCCCCCCC1(C#N)CCC(C(O)=O)CC1 VTIPXAAINIQCCN-UHFFFAOYSA-N 0.000 description 1
- KJZWYCAIEUYAIW-UHFFFAOYSA-N 4-cyanocyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCC(C#N)CC1 KJZWYCAIEUYAIW-UHFFFAOYSA-N 0.000 description 1
- XXOUHKWIQVEQIH-UHFFFAOYSA-N 5-butoxypyridine-2-carboxylic acid Chemical compound CCCCOC1=CC=C(C(O)=O)N=C1 XXOUHKWIQVEQIH-UHFFFAOYSA-N 0.000 description 1
- JDGWQKJGGFDZIM-UHFFFAOYSA-N 5-decoxypyridine-2-carboxylic acid Chemical compound CCCCCCCCCCOC1=CC=C(C(O)=O)N=C1 JDGWQKJGGFDZIM-UHFFFAOYSA-N 0.000 description 1
- BHBVZTPSMXMHTQ-UHFFFAOYSA-N 5-heptoxypyridine-2-carboxylic acid Chemical compound CCCCCCCOC1=CC=C(C(O)=O)N=C1 BHBVZTPSMXMHTQ-UHFFFAOYSA-N 0.000 description 1
- DUKKMMYQNBPJKS-UHFFFAOYSA-N 5-heptyl-2-(4-methoxyphenyl)pyridine Chemical compound N1=CC(CCCCCCC)=CC=C1C1=CC=C(OC)C=C1 DUKKMMYQNBPJKS-UHFFFAOYSA-N 0.000 description 1
- FWUKUCZPNKFOKT-UHFFFAOYSA-N 5-heptyl-2-[4-[[[4-(5-heptylpyrimidin-2-yl)phenyl]-(4-hexylphenyl)methoxy]-(4-hexylphenyl)methyl]phenyl]pyrimidine Chemical compound N1=CC(CCCCCCC)=CN=C1C1=CC=C(C(OC(C=2C=CC(CCCCCC)=CC=2)C=2C=CC(=CC=2)C=2N=CC(CCCCCCC)=CN=2)C=2C=CC(CCCCCC)=CC=2)C=C1 FWUKUCZPNKFOKT-UHFFFAOYSA-N 0.000 description 1
- ZQTCISOMXPYKMJ-UHFFFAOYSA-N 5-hexoxypyridine-2-carboxylic acid Chemical compound CCCCCCOC1=CC=C(C(O)=O)N=C1 ZQTCISOMXPYKMJ-UHFFFAOYSA-N 0.000 description 1
- IEOSDPQVDNLLKP-UHFFFAOYSA-N 5-hexyl-2-[4-[[[4-(5-hexylpyrimidin-2-yl)phenyl]-(4-pentylphenyl)methoxy]-(4-pentylphenyl)methyl]phenyl]pyrimidine Chemical compound N1=CC(CCCCCC)=CN=C1C1=CC=C(C(OC(C=2C=CC(CCCCC)=CC=2)C=2C=CC(=CC=2)C=2N=CC(CCCCCC)=CN=2)C=2C=CC(CCCCC)=CC=2)C=C1 IEOSDPQVDNLLKP-UHFFFAOYSA-N 0.000 description 1
- LRVWMFHQTPNPJY-UHFFFAOYSA-N 5-hexylpyridine-2-carboxylic acid Chemical compound CCCCCCC1=CC=C(C(O)=O)N=C1 LRVWMFHQTPNPJY-UHFFFAOYSA-N 0.000 description 1
- REUXMHILPWSNAZ-UHFFFAOYSA-N 5-nonoxypyridine-2-carboxylic acid Chemical compound CCCCCCCCCOC1=CC=C(C(O)=O)N=C1 REUXMHILPWSNAZ-UHFFFAOYSA-N 0.000 description 1
- UQIHAPCKXFURLU-UHFFFAOYSA-N 5-nonyl-2-[4-[[[4-(5-nonylpyrimidin-2-yl)phenyl]-(4-propylphenyl)methoxy]-(4-propylphenyl)methyl]phenyl]pyrimidine Chemical compound N1=CC(CCCCCCCCC)=CN=C1C1=CC=C(C(OC(C=2C=CC(CCC)=CC=2)C=2C=CC(=CC=2)C=2N=CC(CCCCCCCCC)=CN=2)C=2C=CC(CCC)=CC=2)C=C1 UQIHAPCKXFURLU-UHFFFAOYSA-N 0.000 description 1
- TYFOIKIYYXHTOV-UHFFFAOYSA-N 5-octoxypyridine-2-carboxylic acid Chemical compound CCCCCCCCOC1=CC=C(C(O)=O)N=C1 TYFOIKIYYXHTOV-UHFFFAOYSA-N 0.000 description 1
- DPCYKLNMNFPPKK-UHFFFAOYSA-N 5-pentoxypyridine-2-carboxylic acid Chemical compound CCCCCOC1=CC=C(C(O)=O)N=C1 DPCYKLNMNFPPKK-UHFFFAOYSA-N 0.000 description 1
- BOHRWPVFCVAKKS-UHFFFAOYSA-N 5-pentylpyridine-2-carboxylic acid Chemical compound CCCCCC1=CC=C(C(O)=O)N=C1 BOHRWPVFCVAKKS-UHFFFAOYSA-N 0.000 description 1
- RAQLHHNBGLJEAK-UHFFFAOYSA-N 5-propyl-2-pyridinecarboxylic acid Chemical compound CCCC1=CC=C(C(O)=O)N=C1 RAQLHHNBGLJEAK-UHFFFAOYSA-N 0.000 description 1
- KYZLWBKEIIMVQV-UHFFFAOYSA-N 6-butoxypyridine-3-carboxylic acid Chemical compound CCCCOC1=CC=C(C(O)=O)C=N1 KYZLWBKEIIMVQV-UHFFFAOYSA-N 0.000 description 1
- QKXKSQXNSFZTLA-UHFFFAOYSA-N 6-heptoxypyridine-3-carboxylic acid Chemical compound CCCCCCCOC1=CC=C(C(O)=O)C=N1 QKXKSQXNSFZTLA-UHFFFAOYSA-N 0.000 description 1
- KJWAYJXNAIDFNV-UHFFFAOYSA-N 6-hexoxypyridine-3-carboxylic acid Chemical compound CCCCCCOC1=CC=C(C(O)=O)C=N1 KJWAYJXNAIDFNV-UHFFFAOYSA-N 0.000 description 1
- YXVRTHPEKWLVJI-UHFFFAOYSA-N 6-nonoxypyridine-3-carboxylic acid Chemical compound CCCCCCCCCOC1=CC=C(C(O)=O)C=N1 YXVRTHPEKWLVJI-UHFFFAOYSA-N 0.000 description 1
- YJRUFYZSTYLKOR-UHFFFAOYSA-N 6-nonylpyridine-3-carboxylic acid Chemical compound CCCCCCCCCC1=CC=C(C(O)=O)C=N1 YJRUFYZSTYLKOR-UHFFFAOYSA-N 0.000 description 1
- QJVMDTYBBWGZLQ-UHFFFAOYSA-N 6-octoxypyridine-3-carboxylic acid Chemical compound CCCCCCCCOC1=CC=C(C(O)=O)C=N1 QJVMDTYBBWGZLQ-UHFFFAOYSA-N 0.000 description 1
- RARWYXSDTKTTAU-UHFFFAOYSA-N 6-pentoxypyridine-3-carboxylic acid Chemical compound CCCCCOC1=CC=C(C(O)=O)C=N1 RARWYXSDTKTTAU-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- MISUIWKANNDPPL-AQYVVDRMSA-N C1=CC(CCCCCCC)=CC=C1C1=CN=C([C@@H]2CC[C@H](CC2)C#N)N=C1 Chemical compound C1=CC(CCCCCCC)=CC=C1C1=CN=C([C@@H]2CC[C@H](CC2)C#N)N=C1 MISUIWKANNDPPL-AQYVVDRMSA-N 0.000 description 1
- CTLMPSCHACFQQF-UHFFFAOYSA-N C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(CCCC)=CN=2)C=C1 Chemical compound C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(CCCC)=CN=2)C=C1 CTLMPSCHACFQQF-UHFFFAOYSA-N 0.000 description 1
- NTQZLBKLTIBLDQ-UHFFFAOYSA-N C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(CCCCC)=CC=2)C=C1 Chemical compound C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(CCCCC)=CC=2)C=C1 NTQZLBKLTIBLDQ-UHFFFAOYSA-N 0.000 description 1
- KNUZFPACILFMSY-UHFFFAOYSA-N C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(CCCCC)=CN=2)C=C1 Chemical compound C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(CCCCC)=CN=2)C=C1 KNUZFPACILFMSY-UHFFFAOYSA-N 0.000 description 1
- QWIRKOISOKYTBS-UHFFFAOYSA-N C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(CCCCCC)=CC=2)C=C1 Chemical compound C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(CCCCCC)=CC=2)C=C1 QWIRKOISOKYTBS-UHFFFAOYSA-N 0.000 description 1
- XKPYDCLBMAJDAP-UHFFFAOYSA-N C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(CCCCCC)=CN=2)C=C1 Chemical compound C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(CCCCCC)=CN=2)C=C1 XKPYDCLBMAJDAP-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- DGMPVYSXXIOGJY-UHFFFAOYSA-N Fusaric acid Chemical compound CCCCC1=CC=C(C(O)=O)N=C1 DGMPVYSXXIOGJY-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- IHSRFCVMRMPZGC-UHFFFAOYSA-N N1=CC(CCCCCCC)=CN=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 Chemical compound N1=CC(CCCCCCC)=CN=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 IHSRFCVMRMPZGC-UHFFFAOYSA-N 0.000 description 1
- ZZBIREGOWWUZBT-UHFFFAOYSA-N N1=CC(CCCCCCCC)=CC=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 Chemical compound N1=CC(CCCCCCCC)=CC=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 ZZBIREGOWWUZBT-UHFFFAOYSA-N 0.000 description 1
- AIEAHMWNQZPSRU-UHFFFAOYSA-N N1=CC(CCCCCCCC)=CN=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 Chemical compound N1=CC(CCCCCCCC)=CN=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 AIEAHMWNQZPSRU-UHFFFAOYSA-N 0.000 description 1
- NEPZDBQTTBKDJO-UHFFFAOYSA-N N1=CC(CCCCCCCCC)=CN=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 Chemical compound N1=CC(CCCCCCCCC)=CN=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 NEPZDBQTTBKDJO-UHFFFAOYSA-N 0.000 description 1
- WNBUFVVGENCYFE-UHFFFAOYSA-N N1=CC(CCCCCCCCCC)=CN=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 Chemical compound N1=CC(CCCCCCCCCC)=CN=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 WNBUFVVGENCYFE-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 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
- JZFVMTKUEHVOSZ-UHFFFAOYSA-N chembl1536636 Chemical compound N1=CC(CCCCCCC)=CC=C1C1=CC=C(O)C=C1 JZFVMTKUEHVOSZ-UHFFFAOYSA-N 0.000 description 1
- VBWIZSYFQSOUFQ-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#CC1CCCCC1 VBWIZSYFQSOUFQ-UHFFFAOYSA-N 0.000 description 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 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
- 238000005661 deetherification reaction Methods 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 229940043279 diisopropylamine Drugs 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
- 230000005684 electric field Effects 0.000 description 1
- BBBQVCMVHFUKMI-UHFFFAOYSA-N ethyl 4-cyano-4-heptylcyclohexane-1-carboxylate Chemical compound CCCCCCCC1(C#N)CCC(C(=O)OCC)CC1 BBBQVCMVHFUKMI-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 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
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- DWNRISLZVCBTRN-UHFFFAOYSA-N lithium;piperidin-1-ide Chemical compound [Li]N1CCCCC1 DWNRISLZVCBTRN-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 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
- 239000012074 organic phase Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000017105 transposition Effects 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
- 150000003672 ureas Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
-
- 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
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
- C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
-
- 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
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
-
- 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
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/3444—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine
-
- 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
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
- C09K19/3452—Pyrazine
-
- 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
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
- C09K19/3455—Pyridazine
-
- 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
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
- C09K19/3458—Uncondensed pyrimidines
-
- 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
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
-
- 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
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
- C09K2019/325—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring containing a tetrahydronaphthalene, e.g. -2,6-diyl (tetralin)
-
- 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
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
- C09K2019/326—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring containing a decahydronaphthalene, e.g. -2,6-diyl (decalin)
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)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853533333 DE3533333A1 (de) | 1985-09-18 | 1985-09-18 | Smektische fluessigkristalline phasen |
| PCT/EP1986/000530 WO1987001701A2 (fr) | 1985-09-18 | 1986-09-15 | Composes heterocycliques contenant de l'azote |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO872039D0 NO872039D0 (no) | 1987-05-15 |
| NO872039L true NO872039L (no) | 1987-05-15 |
Family
ID=6281320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO872039A NO872039L (no) | 1985-09-18 | 1987-05-15 | Nitrogenholdige heterocykliske forbindelser. |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5002694A (fr) |
| EP (1) | EP0238576B1 (fr) |
| JP (2) | JP2777885B2 (fr) |
| KR (1) | KR870700610A (fr) |
| DD (2) | DD252196A5 (fr) |
| DE (2) | DE3533333A1 (fr) |
| NO (1) | NO872039L (fr) |
| WO (1) | WO1987001701A2 (fr) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3764044D1 (de) * | 1986-02-17 | 1990-09-06 | Merck Patent Gmbh | Chirale verbindungen. |
| US5180521A (en) * | 1986-02-17 | 1993-01-19 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Chiral compounds |
| DE3614778A1 (de) * | 1986-05-02 | 1987-11-05 | Merck Patent Gmbh | Smektische fluessigkristalline phasen |
| DE3621581A1 (de) * | 1986-06-27 | 1988-01-07 | Merck Patent Gmbh | Polymerisierbare fluessigkristallmaterialien |
| DE3788276D1 (de) * | 1986-09-16 | 1994-01-05 | Merck Patent Gmbh | Flüssigkristalline phasen für elektrooptische anzeigeelemente basierend auf dem ecb-effekt. |
| DE3787253D1 (de) * | 1986-11-20 | 1993-10-07 | Hoffmann La Roche | Ferroelektrische Flüssigkristalle. |
| US5232625A (en) * | 1986-12-08 | 1993-08-03 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Cyano-alicyclic esters in liquid crystal compositions |
| GB8629322D0 (en) * | 1986-12-08 | 1987-01-14 | Secr Defence | Cyano-terpenoid esters |
| DE3852422T2 (de) * | 1987-04-27 | 1995-05-04 | Chisso Corp | Optisch aktive 2-Biphenylpyrimidinderivate und diese enthaltende Flüssigkristallmischungen. |
| GB8712464D0 (en) * | 1987-05-27 | 1987-07-01 | Merck Patent Gmbh | Liquid crystal phase |
| DE3731639A1 (de) * | 1987-09-19 | 1989-03-30 | Hoechst Ag | Fluessigkristalline phenylpyrimidin-cyclohexancarbonsaeureester, verfahren zu ihrer herstellung und ihre verwendung in fluessigkristallmischungen |
| GB8724458D0 (en) * | 1987-10-19 | 1987-11-25 | Secr Defence | Lateral cyano terphenyls |
| CA1336441C (fr) * | 1987-12-28 | 1995-07-25 | Manabu Uchida | Composition de cristal liquide |
| JPH0312480A (ja) * | 1989-06-09 | 1991-01-21 | Canon Inc | 強誘電性カイラルスメクチック液晶組成物およびこれを含む液晶素子 |
| JPH0312477A (ja) * | 1989-06-09 | 1991-01-21 | Canon Inc | 強誘電性カイラルスメクチック液晶組成物およびこれを含む液晶素子 |
| JPH0312484A (ja) * | 1989-06-09 | 1991-01-21 | Canon Inc | 強誘電性カイラルスメクチック液晶組成物おこよびこれを含む液晶素子 |
| JP2763339B2 (ja) * | 1989-07-31 | 1998-06-11 | キヤノン株式会社 | 液晶組成物およびこれを使用した液晶素子 |
| GB9002830D0 (en) * | 1990-02-08 | 1990-04-04 | Secr Defence | L.c.cyanoalkenes & alkenes |
| JP2796753B2 (ja) * | 1990-05-09 | 1998-09-10 | キヤノン株式会社 | カイラルスメクチック液晶組成物およびそれを使用した液晶素子 |
| US5128061A (en) * | 1990-08-14 | 1992-07-07 | Optical Shields, Inc. | Phenyl-pyrimidine liquid crystal materials |
| JP3015998B2 (ja) * | 1993-08-31 | 2000-03-06 | キヤノン株式会社 | 液晶性化合物、それを含む液晶組成物、該液晶組成物を用いた液晶素子、液晶装置、並びに表示方法 |
| US6824707B2 (en) * | 2001-10-23 | 2004-11-30 | Clariant International Ltd. | Active matrix liquid crystal device and smectic liquid crystal mixture |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3382646D1 (de) * | 1982-08-26 | 1993-01-28 | Merck Patent Gmbh | Cyclohexanderivate und ihre verwendung als komponenten fluessigkristalliner-dielektrika. |
| JPS5939876A (ja) * | 1982-08-26 | 1984-03-05 | Chisso Corp | ピリミジン誘導体 |
| EP0111695A3 (fr) * | 1982-11-19 | 1985-08-21 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Dérivés de pyridazine |
| DE3377219D1 (en) * | 1982-11-26 | 1988-08-04 | Hitachi Ltd | Smectic liquid crystal compounds and liquid crystal compositions |
| DE3325727A1 (de) * | 1983-07-16 | 1985-01-24 | Merck Patent Gmbh, 6100 Darmstadt | Fluessigkristalline verbindungen |
| DE3332692A1 (de) * | 1983-09-10 | 1985-03-28 | Merck Patent Gmbh, 6100 Darmstadt | Anisotrope verbindungen und fluessigkristallmischungen |
| DE3332691A1 (de) * | 1983-09-10 | 1985-03-28 | Merck Patent Gmbh, 6100 Darmstadt | Anisotrope verbindungen und fluessigkristallmischungen |
| GB8400665D0 (en) * | 1984-01-11 | 1984-02-15 | Secr Defence | Disubstituted ethanes |
| DE3404116A1 (de) * | 1984-02-07 | 1985-08-08 | Merck Patent Gmbh, 6100 Darmstadt | Stickstoffhaltige heterocyclen |
| EP0158252B1 (fr) * | 1984-04-07 | 1988-12-21 | MERCK PATENT GmbH | Phase liquide cristalline |
| EP0191860B1 (fr) * | 1984-06-07 | 1990-04-18 | Seiko Instruments Inc. | Compose de cristaux liquides |
| EP0172360B1 (fr) * | 1984-06-29 | 1988-11-09 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Cyclohexanecarbonitriles et leur application comme composants de cristaux liquides |
| GB8428653D0 (en) * | 1984-11-13 | 1984-12-19 | Secr Defence | Diesters |
| DE3500909A1 (de) * | 1985-01-12 | 1986-07-17 | Merck Patent Gmbh, 6100 Darmstadt | Pyrimidine |
| DE3506446A1 (de) * | 1985-02-23 | 1986-08-28 | Merck Patent Gmbh, 6100 Darmstadt | Pyrimidinderivate |
| DE3510434A1 (de) * | 1985-03-22 | 1986-09-25 | Merck Patent Gmbh, 6100 Darmstadt | Cyclohexanderivate |
| DE3515374C2 (de) * | 1985-04-27 | 1998-02-26 | Hoechst Ag | Chirale getilte smektische flüssigkristalline Phasen und deren Verwendung in elektrooptischen Anzeigeelementen |
| DE3515373A1 (de) * | 1985-04-27 | 1986-11-06 | Merck Patent Gmbh, 6100 Darmstadt | Stickstoffhaltige heterocyclen |
| DE3518734A1 (de) * | 1985-05-24 | 1986-11-27 | Merck Patent Gmbh, 6100 Darmstadt | Smektische fluessigkristalline phasen |
| DD240385A1 (de) * | 1985-08-26 | 1986-10-29 | Univ Halle Wittenberg | Anwendung ferroelektrischer fluessigkristalle |
| DE3600052A1 (de) * | 1986-01-03 | 1987-07-09 | Merck Patent Gmbh | Heterocyclische verbindungen |
| ATE82952T1 (de) * | 1986-02-21 | 1992-12-15 | Secr Defence Brit | Fluessigkristallverbindungen, gemische und anordnungen. |
| DE3706766A1 (de) * | 1986-03-14 | 1987-09-17 | Merck Patent Gmbh | Smektische fluessigkristalline phasen |
| DE3788243D1 (de) * | 1986-05-22 | 1994-01-05 | Hoffmann La Roche | Flüssigkristalline Derivate von Phenylbenzoat. |
| EP0248335B1 (fr) * | 1986-05-30 | 1990-10-31 | Hoechst Aktiengesellschaft | Esters chiraux d'acides carboxyliques alpha substitués et pyrimidine-5-yl-phenols hydroxyles mésogènes et leur utilisation comme dopants dans des phases liquides cristallines |
| US4777280A (en) * | 1986-07-01 | 1988-10-11 | University Patents, Inc. | Phenylbenzoate 1-cyanoalkoxy compounds |
-
1985
- 1985-09-18 DE DE19853533333 patent/DE3533333A1/de not_active Withdrawn
-
1986
- 1986-09-15 US US07/071,226 patent/US5002694A/en not_active Expired - Lifetime
- 1986-09-15 DE DE8686905780T patent/DE3685213D1/de not_active Expired - Fee Related
- 1986-09-15 EP EP86905780A patent/EP0238576B1/fr not_active Expired - Lifetime
- 1986-09-15 JP JP61504895A patent/JP2777885B2/ja not_active Expired - Fee Related
- 1986-09-15 WO PCT/EP1986/000530 patent/WO1987001701A2/fr active IP Right Grant
- 1986-09-15 JP JP61505361A patent/JPS63500945A/ja active Pending
- 1986-09-18 DD DD86294525A patent/DD252196A5/de unknown
- 1986-09-18 DD DD86294527A patent/DD252197A5/de not_active IP Right Cessation
-
1987
- 1987-05-15 KR KR870700426A patent/KR870700610A/ko not_active Application Discontinuation
- 1987-05-15 NO NO872039A patent/NO872039L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE3685213D1 (de) | 1992-06-11 |
| NO872039D0 (no) | 1987-05-15 |
| WO1987001701A3 (fr) | 1987-06-18 |
| US5002694A (en) | 1991-03-26 |
| KR870700610A (ko) | 1987-12-30 |
| DD252197A5 (de) | 1987-12-09 |
| DD252196A5 (de) | 1987-12-09 |
| JPS63500948A (ja) | 1988-04-07 |
| WO1987001701A2 (fr) | 1987-03-26 |
| DE3533333A1 (de) | 1987-03-26 |
| EP0238576A1 (fr) | 1987-09-30 |
| JP2777885B2 (ja) | 1998-07-23 |
| JPS63500945A (ja) | 1988-04-07 |
| EP0238576B1 (fr) | 1992-05-06 |
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