DD140755A5 - Fluessigkristallmischungen - Google Patents

Fluessigkristallmischungen Download PDF

Info

Publication number: DD140755A5
Authority: DD; German Democratic Republic
Prior art keywords: carbon atoms; straight; cyanophenyl; pyrimidine; chain
Prior art date: 1977-06-03

Application number

DD78205686A

Other languages

German (de)

English (en)

Inventor

Arthur Boller

Alfred Germann

Martin Schadt

Hanspeter Scherrer

Original Assignee

Hoffmann La Roche

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.)

1977-06-03

Filing date

1978-05-31

Publication date

1980-03-26

1977-06-03 Priority claimed from CH686377A external-priority patent/CH633310A5/de

1978-05-31 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1980-03-26 Publication of DD140755A5 publication Critical patent/DD140755A5/de

Links

125000004432 carbon atom Chemical group C* 0.000 claims description 76
239000000203 mixture Substances 0.000 claims description 63
150000001875 compounds Chemical class 0.000 claims description 48
239000004973 liquid crystal related substance Substances 0.000 claims description 40
125000000217 alkyl group Chemical group 0.000 claims description 33
-1 propylcyclohexyl Chemical group 0.000 claims description 24
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
125000003545 alkoxy group Chemical group 0.000 claims description 15
125000004423 acyloxy group Chemical group 0.000 claims description 10
125000005910 alkyl carbonate group Chemical group 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 9
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
RGONNDWSVOCREF-UHFFFAOYSA-N 4-(5-pentylpyrimidin-2-yl)benzonitrile Chemical compound N1=CC(CCCCC)=CN=C1C1=CC=C(C#N)C=C1 RGONNDWSVOCREF-UHFFFAOYSA-N 0.000 claims description 7
239000002019 doping agent Substances 0.000 claims description 7
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 claims description 6
239000000463 material Substances 0.000 claims description 6
VSNGFYYRBATOTN-UHFFFAOYSA-N 4-(5-heptylpyrimidin-2-yl)benzonitrile Chemical compound N1=CC(CCCCCCC)=CN=C1C1=CC=C(C#N)C=C1 VSNGFYYRBATOTN-UHFFFAOYSA-N 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
102100040141 Aminopeptidase O Human genes 0.000 claims description 4
108050008333 Aminopeptidase O Proteins 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
239000003791 organic solvent mixture Substances 0.000 claims description 4
ZVVKBAKPLNVTNG-UHFFFAOYSA-N 1-cyclohexyl-4-hexylbenzene Chemical compound C1=CC(CCCCCC)=CC=C1C1CCCCC1 ZVVKBAKPLNVTNG-UHFFFAOYSA-N 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
125000004802 cyanophenyl group Chemical group 0.000 claims 2
WMWOAQARUZYORF-UHFFFAOYSA-N (4-butylcyclohexyl)benzene Chemical compound C1CC(CCCC)CCC1C1=CC=CC=C1 WMWOAQARUZYORF-UHFFFAOYSA-N 0.000 claims 1
VXAPTJFPJNYKQT-UHFFFAOYSA-N 1-(4-butylcyclohexyl)-4-ethylbenzene Chemical compound C1CC(CCCC)CCC1C1=CC=C(CC)C=C1 VXAPTJFPJNYKQT-UHFFFAOYSA-N 0.000 claims 1
SMNNDVUKAKPGDD-UHFFFAOYSA-N 2-butylbenzoic acid Chemical compound CCCCC1=CC=CC=C1C(O)=O SMNNDVUKAKPGDD-UHFFFAOYSA-N 0.000 claims 1
YNFUGQHDAKFMGG-UHFFFAOYSA-N 2-heptylbenzoic acid Chemical compound CCCCCCCC1=CC=CC=C1C(O)=O YNFUGQHDAKFMGG-UHFFFAOYSA-N 0.000 claims 1
JFKUBRAOUZEZSL-UHFFFAOYSA-N 4-butylbenzoic acid Chemical compound CCCCC1=CC=C(C(O)=O)C=C1 JFKUBRAOUZEZSL-UHFFFAOYSA-N 0.000 claims 1
CWYNKKGQJYAHQG-UHFFFAOYSA-N 4-pentylbenzoic acid Chemical compound CCCCCC1=CC=C(C(O)=O)C=C1 CWYNKKGQJYAHQG-UHFFFAOYSA-N 0.000 claims 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
239000004305 biphenyl Substances 0.000 claims 1
UMFTYCUYCNMERS-UHFFFAOYSA-N heptyl benzoate Chemical compound CCCCCCCOC(=O)C1=CC=CC=C1 UMFTYCUYCNMERS-UHFFFAOYSA-N 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 18
239000002904 solvent Substances 0.000 description 16
239000004594 Masterbatch (MB) Substances 0.000 description 15
238000005352 clarification Methods 0.000 description 14
239000003054 catalyst Substances 0.000 description 13
239000012230 colorless oil Substances 0.000 description 12
239000007789 gas Substances 0.000 description 12
238000004821 distillation Methods 0.000 description 11
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 11
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000011877 solvent mixture Substances 0.000 description 7
LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 6
239000007858 starting material Substances 0.000 description 6
238000003747 Grignard reaction Methods 0.000 description 5
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
238000000746 purification Methods 0.000 description 5
ZGBOHJUSTPZQPL-UHFFFAOYSA-N 1-methyl-4-(4-pentylphenyl)benzene Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(C)C=C1 ZGBOHJUSTPZQPL-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
239000003990 capacitor Substances 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
CKUNTDNDGXPOPB-UHFFFAOYSA-N 4-butylcyclohexan-1-one Chemical compound CCCCC1CCC(=O)CC1 CKUNTDNDGXPOPB-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000009835 boiling Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000013078 crystal Substances 0.000 description 3
150000001983 dialkylethers Chemical class 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000000446 fuel Substances 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
ZBKKHIUKTPWMNV-UHFFFAOYSA-N 1-(4-cyclohexylphenyl)butan-1-one Chemical compound C1=CC(C(=O)CCC)=CC=C1C1CCCCC1 ZBKKHIUKTPWMNV-UHFFFAOYSA-N 0.000 description 2
LBNXAWYDQUGHGX-UHFFFAOYSA-N 1-Phenylheptane Chemical compound CCCCCCCC1=CC=CC=C1 LBNXAWYDQUGHGX-UHFFFAOYSA-N 0.000 description 2
MMZRCTBETQZXRV-UHFFFAOYSA-N 1-butyl-4-cyclohexylbenzene Chemical compound C1=CC(CCCC)=CC=C1C1CCCCC1 MMZRCTBETQZXRV-UHFFFAOYSA-N 0.000 description 2
BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 2
SGVYKUFIHHTIFL-UHFFFAOYSA-N 2-methylnonane Chemical compound CCCCCCCC(C)C SGVYKUFIHHTIFL-UHFFFAOYSA-N 0.000 description 2
RDISTOCQRJJICR-UHFFFAOYSA-N 4-(4-pentoxyphenyl)benzonitrile Chemical group C1=CC(OCCCCC)=CC=C1C1=CC=C(C#N)C=C1 RDISTOCQRJJICR-UHFFFAOYSA-N 0.000 description 2
AITQOXOBSMXBRV-UHFFFAOYSA-N 4-[4-(4-pentylphenyl)phenyl]benzonitrile Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 AITQOXOBSMXBRV-UHFFFAOYSA-N 0.000 description 2
HHPCNRKYVYWYAU-UHFFFAOYSA-N 4-cyano-4'-pentylbiphenyl Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(C#N)C=C1 HHPCNRKYVYWYAU-UHFFFAOYSA-N 0.000 description 2
VXAPTJFPJNYKQT-SAABIXHNSA-N C(C)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCC Chemical compound C(C)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCC VXAPTJFPJNYKQT-SAABIXHNSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
VLOUAKPIQASFDS-UHFFFAOYSA-M [Br-].CCC1=CC=C([Mg+])C=C1 Chemical compound [Br-].CCC1=CC=C([Mg+])C=C1 VLOUAKPIQASFDS-UHFFFAOYSA-M 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
150000001350 alkyl halides Chemical class 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 2
ZAJNGDIORYACQU-UHFFFAOYSA-N decan-2-one Chemical compound CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 description 2
JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
230000003993 interaction Effects 0.000 description 2
239000011159 matrix material Substances 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
CFNJLPHOBMVMNS-UHFFFAOYSA-N pentyl butyrate Chemical compound CCCCCOC(=O)CCC CFNJLPHOBMVMNS-UHFFFAOYSA-N 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
HUAZGNHGCJGYNP-UHFFFAOYSA-N propyl butyrate Chemical compound CCCOC(=O)CCC HUAZGNHGCJGYNP-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
235000015096 spirit Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
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 1
WCCDNUMASFDPFO-UHFFFAOYSA-N (4-cyanophenyl) 4-pentylbenzoate Chemical compound C1=CC(CCCCC)=CC=C1C(=O)OC1=CC=C(C#N)C=C1 WCCDNUMASFDPFO-UHFFFAOYSA-N 0.000 description 1
UURSXESKOOOTOV-MDZDMXLPSA-N (e)-dec-5-ene Chemical compound CCCC\C=C\CCCC UURSXESKOOOTOV-MDZDMXLPSA-N 0.000 description 1
IRUCBBFNLDIMIK-BQYQJAHWSA-N (e)-oct-4-ene Chemical compound CCC\C=C\CCC IRUCBBFNLDIMIK-BQYQJAHWSA-N 0.000 description 1
NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical compound CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 description 1
OVISMSJCKCDOPU-UHFFFAOYSA-N 1,6-dichlorohexane Chemical compound ClCCCCCCCl OVISMSJCKCDOPU-UHFFFAOYSA-N 0.000 description 1
PPLQCJVUEGHONH-UHFFFAOYSA-N 1-(4-butylcyclohexyl)-4-methylbenzene Chemical compound C1CC(CCCC)CCC1C1=CC=C(C)C=C1 PPLQCJVUEGHONH-UHFFFAOYSA-N 0.000 description 1
AQGQFAYRXWDTNS-UHFFFAOYSA-N 1-(4-cyclohexylphenyl)hexan-1-one Chemical compound C1=CC(C(=O)CCCCC)=CC=C1C1CCCCC1 AQGQFAYRXWDTNS-UHFFFAOYSA-N 0.000 description 1
ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 1
PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 1
MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
XONRFFCHOHCERL-UHFFFAOYSA-N 1-pentoxy-4-phenylcyclohexa-2,4-diene-1-carbonitrile Chemical group C1=CC(OCCCCC)(C#N)CC=C1C1=CC=CC=C1 XONRFFCHOHCERL-UHFFFAOYSA-N 0.000 description 1
ADDYVSMEUDGKHR-UHFFFAOYSA-N 1-pentyl-2-(4-phenylphenyl)benzene Chemical group C(CCCC)C1=C(C=CC=C1)C1=CC=C(C=C1)C1=CC=CC=C1 ADDYVSMEUDGKHR-UHFFFAOYSA-N 0.000 description 1
DOYXDCAHTUMXDF-UHFFFAOYSA-N 1-propoxyheptane Chemical compound CCCCCCCOCCC DOYXDCAHTUMXDF-UHFFFAOYSA-N 0.000 description 1
YWSUTIDJJFRSGC-UHFFFAOYSA-N 2-(4-butylphenyl)pyrimidine Chemical compound C1=CC(CCCC)=CC=C1C1=NC=CC=N1 YWSUTIDJJFRSGC-UHFFFAOYSA-N 0.000 description 1
CITFZKZKBVMLJC-UHFFFAOYSA-N 2-(4-ethylphenyl)pyrimidine Chemical compound C1=CC(CC)=CC=C1C1=NC=CC=N1 CITFZKZKBVMLJC-UHFFFAOYSA-N 0.000 description 1
YHLDKXWPUSOTIZ-UHFFFAOYSA-N 2-(4-heptylphenyl)pyrimidine Chemical compound C1=CC(CCCCCCC)=CC=C1C1=NC=CC=N1 YHLDKXWPUSOTIZ-UHFFFAOYSA-N 0.000 description 1
JXNZECXISPFJQO-UHFFFAOYSA-N 2-(4-pentylphenyl)pyrimidine Chemical compound C1=CC(CCCCC)=CC=C1C1=NC=CC=N1 JXNZECXISPFJQO-UHFFFAOYSA-N 0.000 description 1
JIPIOGWIAONPMB-UHFFFAOYSA-N 2-(4-propylphenyl)pyrimidine Chemical compound C1=CC(CCC)=CC=C1C1=NC=CC=N1 JIPIOGWIAONPMB-UHFFFAOYSA-N 0.000 description 1
HLCPWBZNUKCSBN-UHFFFAOYSA-N 2-aminobenzonitrile Chemical compound NC1=CC=CC=C1C#N HLCPWBZNUKCSBN-UHFFFAOYSA-N 0.000 description 1
YQIASAUDDDCAKU-UHFFFAOYSA-N 2-hexylbenzoic acid Chemical compound CCCCCCC1=CC=CC=C1C(O)=O YQIASAUDDDCAKU-UHFFFAOYSA-N 0.000 description 1
LGZVXDCVOZLFAW-UHFFFAOYSA-N 4-(5-butylpyrimidin-2-yl)benzonitrile Chemical compound N1=CC(CCCC)=CN=C1C1=CC=C(C#N)C=C1 LGZVXDCVOZLFAW-UHFFFAOYSA-N 0.000 description 1
SEBTZFGCLRTNBV-UHFFFAOYSA-N 4-(5-octylpyrimidin-2-yl)benzonitrile Chemical compound N1=CC(CCCCCCCC)=CN=C1C1=CC=C(C#N)C=C1 SEBTZFGCLRTNBV-UHFFFAOYSA-N 0.000 description 1
NHQUJEQINIHXMP-UHFFFAOYSA-N 4-(5-propylpyrimidin-2-yl)benzonitrile Chemical compound N1=CC(CCC)=CN=C1C1=CC=C(C#N)C=C1 NHQUJEQINIHXMP-UHFFFAOYSA-N 0.000 description 1
XWUMNFKBSYDPGC-UHFFFAOYSA-N 4-[2-(4-butylphenyl)pyrimidin-5-yl]benzonitrile Chemical compound C1=CC(CCCC)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C#N)C=N1 XWUMNFKBSYDPGC-UHFFFAOYSA-N 0.000 description 1
CBEXHCVSJVGBCO-UHFFFAOYSA-N 4-[2-(4-heptylphenyl)pyrimidin-5-yl]benzonitrile Chemical compound C1=CC(CCCCCCC)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C#N)C=N1 CBEXHCVSJVGBCO-UHFFFAOYSA-N 0.000 description 1
XJLAPYRYCHYFKX-UHFFFAOYSA-N 4-[2-(4-hexylphenyl)pyrimidin-5-yl]benzonitrile Chemical compound C1=CC(CCCCCC)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C#N)C=N1 XJLAPYRYCHYFKX-UHFFFAOYSA-N 0.000 description 1
VKTWVTMDYIPLPB-UHFFFAOYSA-N 4-[2-(4-pentylphenyl)pyrimidin-5-yl]benzonitrile Chemical compound C1=CC(CCCCC)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C#N)C=N1 VKTWVTMDYIPLPB-UHFFFAOYSA-N 0.000 description 1
BHUVGGQKZPXFTP-UHFFFAOYSA-N 4-butyl-1-phenylcyclohexan-1-ol Chemical compound C1CC(CCCC)CCC1(O)C1=CC=CC=C1 BHUVGGQKZPXFTP-UHFFFAOYSA-N 0.000 description 1
125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
KRNAJRBXIMJEFF-UHFFFAOYSA-N 4-hexylbenzaldehyde Chemical compound CCCCCCC1=CC=C(C=O)C=C1 KRNAJRBXIMJEFF-UHFFFAOYSA-N 0.000 description 1
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
NQEDLIZOPMNZMC-UHFFFAOYSA-N 4-propylcyclohexan-1-one Chemical compound CCCC1CCC(=O)CC1 NQEDLIZOPMNZMC-UHFFFAOYSA-N 0.000 description 1
WGCKVXHOTDDNOA-UHFFFAOYSA-N 4-pyrimidin-2-ylbenzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=NC=CC=N1 WGCKVXHOTDDNOA-UHFFFAOYSA-N 0.000 description 1
OYOBZVHPZUVLSF-JCNLHEQBSA-N C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(CC)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(CC)C=C1 OYOBZVHPZUVLSF-JCNLHEQBSA-N 0.000 description 1
ZCLQLQSCISYXDV-SAABIXHNSA-N C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(CCC)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(CCC)C=C1 ZCLQLQSCISYXDV-SAABIXHNSA-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
YCAYVMOKDCQMPX-KOMQPUFPSA-N CC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCC Chemical compound CC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCC YCAYVMOKDCQMPX-KOMQPUFPSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
HFPDWJMICZDKNO-UHFFFAOYSA-M [Br-].CCCC1=CC=C([Mg+])C=C1 Chemical compound [Br-].CCCC1=CC=C([Mg+])C=C1 HFPDWJMICZDKNO-UHFFFAOYSA-M 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
150000001345 alkine derivatives Chemical class 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-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
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
JWBQJUFCNOLNNC-UHFFFAOYSA-N dec-5-yne Chemical compound CCCCC#CCCCC JWBQJUFCNOLNNC-UHFFFAOYSA-N 0.000 description 1
KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 1
DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000005684 electric field Effects 0.000 description 1
238000003487 electrochemical reaction Methods 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
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000005669 field effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
PLZDDPSCZHRBOY-UHFFFAOYSA-N inaktives 3-Methyl-nonan Natural products CCCCCCC(C)CC PLZDDPSCZHRBOY-UHFFFAOYSA-N 0.000 description 1
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
BVUQKCCKUOSAEV-UHFFFAOYSA-M magnesium;methylbenzene;bromide Chemical compound [Mg+2].[Br-].CC1=CC=[C-]C=C1 BVUQKCCKUOSAEV-UHFFFAOYSA-M 0.000 description 1
NKSKNAWLKUQLNY-UHFFFAOYSA-N methyl 4-octylbenzoate Chemical compound CCCCCCCCC1=CC=C(C(=O)OC)C=C1 NKSKNAWLKUQLNY-UHFFFAOYSA-N 0.000 description 1
DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
CMNMHJVRZHGAAK-UHFFFAOYSA-N octyl hexanoate Chemical compound CCCCCCCCOC(=O)CCCCC CMNMHJVRZHGAAK-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
DEDZSLCZHWTGOR-UHFFFAOYSA-N propylcyclohexane Chemical compound CCCC1CCCCC1 DEDZSLCZHWTGOR-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
ULIAPOFMBCCSPE-UHFFFAOYSA-N tridecan-7-one Chemical compound CCCCCCC(=O)CCCCCC ULIAPOFMBCCSPE-UHFFFAOYSA-N 0.000 description 1
238000007514 turning Methods 0.000 description 1
238000009834 vaporization Methods 0.000 description 1
230000008016 vaporization Effects 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
210000000707 wrist Anatomy 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/22—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by reduction
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
- 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
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/792—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic containing rings other than 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
- C09K19/42—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
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/48—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing Schiff bases
- 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
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/58—Dopants or charge transfer agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/18—Carbon
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/44—Palladium
- 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

Landscapes

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

DD78205686A 1977-06-03 1978-05-31 Fluessigkristallmischungen DD140755A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH686377A CH633310A5 (en)	1977-06-03	1977-06-03	Liquid-crystal mixtures
CH386878		1978-04-11

Publications (1)

Publication Number	Publication Date
DD140755A5 true DD140755A5 (de)	1980-03-26

Family

ID=25694048

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD78205686A DD140755A5 (de)	1977-06-03	1978-05-31	Fluessigkristallmischungen

Country Status (9)

Country	Link
US (1)	US4198130A (it)
JP (1)	JPS542283A (it)
DD (1)	DD140755A5 (it)
DE (1)	DE2823909C2 (it)
FR (1)	FR2393046A1 (it)
GB (1)	GB1597990A (it)
HK (1)	HK11382A (it)
IT (1)	IT1094950B (it)
NL (1)	NL7805785A (it)

Families Citing this family (34)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4337999A (en) *	1977-08-29	1982-07-06	Sharp Corporation	Fluorescent liquid crystal display compositions and devices
JPS5478383A (en) *	1977-12-05	1979-06-22	Toshiba Corp	Liquid crystal display element
DE2822504A1 (de) *	1978-05-23	1979-11-29	Siegfried Ag	Verfahren zur herstellung von trans-4-alkyl-cyanoarylcyclohexanen
EP0008956B1 (en) *	1978-09-13	1983-10-12	The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and	Improvements in or relating to liquid crystal materials and devices
DE2944905A1 (de) *	1978-12-13	1980-10-23	Werk Fernsehelektronik Veb	Kristallin-fluessige substituierte 1,3-dioxane und diese enthaltende gemische
CA1120478A (en) *	1979-02-05	1982-03-23	Arthur Boller	Cyclohexyl pyrimidines
DE2907332A1 (de) *	1979-02-24	1980-09-18	Merck Patent Gmbh	Fluorphenylcyclohexane, verfahren zu ihrer herstellung und ihre verwendung als komponenten fluessigkristalliner dielektrika
DE2927277A1 (de) *	1979-07-06	1981-01-08	Merck Patent Gmbh	Cyclohexylbiphenyle, verfahren zu ihrer herstellung, diese enthaltende dielektrika und elektrooptisches anzeigeelement
US4293193A (en) *	1979-08-15	1981-10-06	Temple University	Amine-substituted liquid crystal compositions
US4364838A (en) *	1979-11-14	1982-12-21	Hoffmann-La Roche Inc.	Liquid crystal mixtures
DE2948836A1 (de) *	1979-12-05	1981-06-11	Merck Patent Gmbh, 6100 Darmstadt	Partiell hydrierte oligo-1,4-phenylene, diese enthaltende dielektrika und elektrooptisches anzeigeelement
DE2949080A1 (de) *	1979-12-06	1981-06-11	Merck Patent Gmbh, 6100 Darmstadt	Naphthalinderivate, diese enthaltende dielektrika und elektrooptisches anzeigeelement
US4335011A (en) *	1980-03-28	1982-06-15	Timex Corporation	Cyclohexyl-dioxane liquid crystalline compounds
DE3023989A1 (de) *	1980-06-26	1982-01-21	Merck Patent Gmbh, 6100 Darmstadt	Fluessigkristallines dielektrikum
JPS5734176A (en) *	1980-08-08	1982-02-24	Hitachi Ltd	Liquid crystal composition
DE3201721A1 (de) *	1981-01-30	1982-08-19	F. Hoffmann-La Roche & Co. AG, 4002 Basel	Disubstituierte aethane
DE3268611D1 (en) *	1981-02-25	1986-03-06	Hitachi Ltd	Colorless liquid crystalline compounds
DE3266741D1 (en) *	1981-03-13	1985-11-14	Secr Defence Brit	Liquid crystal compositions
US4422951A (en) *	1981-04-02	1983-12-27	Chisso Corporation	Liquid crystal benzene derivatives
JPS588778A (ja) *	1981-07-08	1983-01-18	Hitachi Ltd	液晶組成物
JPS588779A (ja) *	1981-07-08	1983-01-18	Hitachi Ltd	液晶表示装置
JPS588780A (ja) *	1981-07-08	1983-01-18	Hitachi Ltd	液晶組成物
US4482472A (en) *	1981-08-06	1984-11-13	The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britian And Northern Ireland	Liquid crystal materials
EP0090548B1 (en) *	1982-03-26	1987-11-11	Chisso Corporation	Liquid-crystalline compounds
JPS58225179A (ja) *	1982-06-21	1983-12-27	Sharp Corp	液晶組成物
GB8302395D0 (en) *	1983-01-28	1983-03-02	Secr Defence	Liquid crystal materials
JPS6055078A (ja) *	1983-08-30	1985-03-29	シャープ株式会社	液晶組成物
JPS59221376A (ja) *	1983-05-31	1984-12-12	Sharp Corp	液晶組成物
DE3321373A1 (de) *	1983-06-14	1984-12-20	Merck Patent Gmbh, 6100 Darmstadt	Bicyclohexyle
JPH0629426B2 (ja) *	1984-07-09	1994-04-20	カシオ計算機株式会社	液晶組成物
DD234278A1 (de) *	1985-01-28	1986-03-26	Univ Halle Wittenberg	Schaltzeitverkuerzende dotierungen fuer kristallin-fluessige gemische
US4879061A (en) *	1986-09-29	1989-11-07	Crystaloid Electronics Co.	Liquid crystalline materials and method of making same
JPH02221485A (ja) *	1989-02-23	1990-09-04	Mitsui Petrochem Ind Ltd	低濾水性パルプの製法
JP5655341B2 (ja) *	2010-03-29	2015-01-21	Dic株式会社	シクロヘキサン化合物

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1393216A (en) *	1972-10-05	1975-05-07	Werk Fernsehelektronik Veb	Liquid crystalline nematic substance comprising diesters of 2-substituted hydroquinone and applications thereof
DD105701A1 (it) *	1973-07-02	1974-05-05
US4000084A (en) *	1973-12-17	1976-12-28	Hughes Aircraft Company	Liquid crystal mixtures for electro-optical display devices
JPS5235183A (en) *	1975-09-12	1977-03-17	Hitachi Ltd	Liquid crystal composition for electoric field effect type display
US4062798A (en) *	1975-09-19	1977-12-13	Hoffmann-La Roche Inc.	Phenylpyrimidine derivatives
DE2548360C2 (de) *	1975-10-29	1983-12-08	Merck Patent Gmbh, 6100 Darmstadt	Flüssigkristalline Materialien mit verminderter Viskosität
DE2557267A1 (de) *	1975-12-19	1977-06-30	Bbc Brown Boveri & Cie	Fluessigkristallsubstanz
NL7701750A (nl) *	1976-02-26	1977-08-30	Hoffmann La Roche	Mengsels van vloeibare kristallen.
DE2636684C3 (de) *	1976-08-14	1980-06-19	Merck Patent Gmbh, 6100 Darmstadt	Phenylcyclohexanderivate und ihre Verwendung in flüssigkristallinen Dielektrika
US4029595A (en) *	1976-09-17	1977-06-14	Rca Corporation	Novel liquid crystal compounds and electro-optic devices incorporating them
DE2701591C3 (de) *	1977-01-15	1979-12-20	Merck Patent Gmbh, 6100 Darmstadt	Hexahydroterphenylderivate und deren Verwendung in flüssigkristallinen Dielektrika

1978
- 1978-05-22 US US05/907,961 patent/US4198130A/en not_active Expired - Lifetime
- 1978-05-25 GB GB22498/78A patent/GB1597990A/en not_active Expired
- 1978-05-26 NL NL7805785A patent/NL7805785A/xx not_active Application Discontinuation
- 1978-05-31 DE DE2823909A patent/DE2823909C2/de not_active Expired
- 1978-05-31 DD DD78205686A patent/DD140755A5/de unknown
- 1978-06-01 FR FR7816467A patent/FR2393046A1/fr active Granted
- 1978-06-01 JP JP6500978A patent/JPS542283A/ja active Granted
- 1978-06-02 IT IT24162/78A patent/IT1094950B/it active
1982
- 1982-03-11 HK HK113/82A patent/HK11382A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
FR2393046B1 (it)	1980-04-04
DE2823909C2 (de)	1986-01-30
FR2393046A1 (fr)	1978-12-29
JPS6123839B2 (it)	1986-06-07
US4198130A (en)	1980-04-15
HK11382A (en)	1982-03-19
DE2823909A1 (de)	1978-12-07
IT1094950B (it)	1985-08-10
NL7805785A (nl)	1978-12-05
GB1597990A (en)	1981-09-16
JPS542283A (en)	1979-01-09
IT7824162A0 (it)	1978-06-02

Publication	Publication Date	Title
DE2823909C2 (de)	1986-01-30	Flüssigkristallmischungen
EP0030277B1 (de)	1983-07-27	Partiell hydrierte Oligo-1,4-phenylene, diese enthaltende Dielektrika und elektrooptisches Anzeigeelement
EP0051738B1 (de)	1984-07-25	Fluorhaltige Cyclohexylbiphenylderivate, diese enthaltende Dielektrika und elektrooptisches Anzeigeelement
EP0014885B1 (de)	1983-06-15	Cyclohexylpyrimidine, deren Herstellung und Verwendung, sowie flüssigkristalline Gemische und elektro-optische Vorrichtungen, die solche Verbindungen enthalten, und deren Herstellung
EP0264435B1 (de)	1992-03-04	Smektische flüssigkristalline phasen
DE3201721C2 (it)	1990-07-26
EP0064193B1 (de)	1984-07-25	Fluorhaltige 4,4'-Bis-(cyclohexyl)-biphenylderivate, diese enthaltende Dielektrika und elektrooptisches Anzeigeelement
EP0281611B1 (de)	1993-11-24	Flüssigkristalline phasen für elektrooptische anzeigeelemente basierend auf dem ecb-effekt
DE2701591B2 (de)	1979-05-03	Hexahydroterphenylderivate und deren Verwendung in fliissigkristallinen Dielektrika
EP0209622A1 (de)	1987-01-28	Hydroterphenyle
DE3524489A1 (de)	1986-01-23	2-phenylpyridinderivate und verfahren zu ihrer herstellung
EP0438575B1 (de)	1994-10-26	Benzolderivate und flüssigkristallines medium
DE4107120A1 (de)	1991-09-19	4,4'disubstituierte 2',3-difluorphenyle und fluessigkristallines medium
EP0445274B1 (de)	1995-01-18	Flüssigkristallines medium
DE2708276A1 (de)	1977-09-01	Fluessigkristallmischungen
DE69008544T2 (de)	1994-11-24	Flüssigkristallverbindungen mit hoher optischer Anisotropie.
DE4027923A1 (de)	1991-03-07	Phenylcyclohexane und fluessigkristallines medium
EP0478740A1 (de)	1992-04-08	Phenylcyclohexane und flüssigkristallines medium
DE4428766A1 (de)	1995-03-02	Benzolderivate und flüssigkristallines Medium
DE69018065T2 (de)	1995-08-31	Flüssigkristalline eigenschaften besitzende phenylnaphthalene.
WO1986005799A1 (fr)	1986-10-09	Phase cristalline liquide
EP1223210A1 (de)	2002-07-17	Mehrfach fluorierte Fluorene und ihre Verwendung in Flüssigkristallmischungen
EP0482157B1 (de)	1999-11-17	1,3-dioxanderivate und flüssigkristallines medium
DE3150761A1 (de)	1982-10-07	Fluessigkristallmaterial
DE4016130C2 (de)	2000-06-21	Phenylcyclohexane und flüssigkristallines Medium