IL35574A - Nematic azobenzene and azoxybenezene compounds - Google Patents

Nematic azobenzene and azoxybenezene compounds

Info

Publication number: IL35574A
Authority: IL; Israel
Prior art keywords: formula; compound; specified; azobenzene; butyl
Prior art date: 1970-03-28

Application number

IL35574A

Other languages

English (en)

Other versions

IL35574A0 (en

Original Assignee

Merck Patent Gmbh

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.)

1970-03-28

Filing date

1970-11-03

Publication date

1973-11-28

1970-11-03 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

1971-01-28 Publication of IL35574A0 publication Critical patent/IL35574A0/xx

1973-11-28 Publication of IL35574A publication Critical patent/IL35574A/en

Links

150000001875 compounds Chemical class 0.000 title claims description 58
DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 title description 6
239000000203 mixture Substances 0.000 claims description 49
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 33
238000000034 method Methods 0.000 claims description 21
125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 claims description 18
230000008569 process Effects 0.000 claims description 15
238000002360 preparation method Methods 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 13
150000001412 amines Chemical class 0.000 claims description 10
GAUZCKBSTZFWCT-UHFFFAOYSA-N azoxybenzene Chemical compound C=1C=CC=CC=1[N+]([O-])=NC1=CC=CC=C1 GAUZCKBSTZFWCT-UHFFFAOYSA-N 0.000 claims description 6
150000002832 nitroso derivatives Chemical class 0.000 claims description 6
NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 5
230000008878 coupling Effects 0.000 claims description 5
238000010168 coupling process Methods 0.000 claims description 5
238000005859 coupling reaction Methods 0.000 claims description 5
150000002828 nitro derivatives Chemical class 0.000 claims description 3
230000011987 methylation Effects 0.000 claims description 2
238000007069 methylation reaction Methods 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
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
239000003989 dielectric material Substances 0.000 claims 1
-1 azoxy phenols Chemical class 0.000 description 39
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 38
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
239000000243 solution Substances 0.000 description 30
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
239000002904 solvent Substances 0.000 description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
239000002253 acid Substances 0.000 description 14
238000013019 agitation Methods 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
235000011121 sodium hydroxide Nutrition 0.000 description 12
125000000751 azo group Chemical group [*]N=N[*] 0.000 description 11
125000004432 carbon atom Chemical group C* 0.000 description 11
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
238000005804 alkylation reaction Methods 0.000 description 9
238000007254 oxidation reaction Methods 0.000 description 9
239000012071 phase Substances 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
230000029936 alkylation Effects 0.000 description 8
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 7
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
229960000583 acetic acid Drugs 0.000 description 7
230000003647 oxidation Effects 0.000 description 7
239000008096 xylene Substances 0.000 description 7
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
230000032050 esterification Effects 0.000 description 6
238000005886 esterification reaction Methods 0.000 description 6
239000007800 oxidant agent Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
150000001298 alcohols Chemical class 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
230000007935 neutral effect Effects 0.000 description 5
235000011118 potassium hydroxide Nutrition 0.000 description 5
230000035484 reaction time Effects 0.000 description 5
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
OGIQUQKNJJTLSZ-UHFFFAOYSA-N 4-butylaniline Chemical compound CCCCC1=CC=C(N)C=C1 OGIQUQKNJJTLSZ-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000002585 base Substances 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
238000001816 cooling Methods 0.000 description 4
UCVODTZQZHMTPN-UHFFFAOYSA-N heptanoyl chloride Chemical compound CCCCCCC(Cl)=O UCVODTZQZHMTPN-UHFFFAOYSA-N 0.000 description 4
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
239000002609 medium Substances 0.000 description 4
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 4
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 3
230000010933 acylation Effects 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
150000001989 diazonium salts Chemical class 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
235000011181 potassium carbonates Nutrition 0.000 description 3
239000000047 product Substances 0.000 description 3
235000019260 propionic acid Nutrition 0.000 description 3
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
230000009467 reduction Effects 0.000 description 3
238000006722 reduction reaction Methods 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
238000004611 spectroscopical analysis Methods 0.000 description 3
JZRBCNLSIDKBMG-UHFFFAOYSA-N 1-butyl-4-nitrobenzene Chemical compound CCCCC1=CC=C([N+]([O-])=O)C=C1 JZRBCNLSIDKBMG-UHFFFAOYSA-N 0.000 description 2
BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
WCMGWOJHPKFPPP-UHFFFAOYSA-N 1-methoxy-1,2-diphenylhydrazine Chemical compound C=1C=CC=CC=1N(OC)NC1=CC=CC=C1 WCMGWOJHPKFPPP-UHFFFAOYSA-N 0.000 description 2
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
PXKHNRMAKNHKDZ-UHFFFAOYSA-N CCCCC1(C=CC=CC1)[N+]([O-])=NC1=CC=CC=C1 Chemical compound CCCCC1(C=CC=CC1)[N+]([O-])=NC1=CC=CC=C1 PXKHNRMAKNHKDZ-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
BNUHAJGCKIQFGE-UHFFFAOYSA-N Nitroanisol Chemical compound COC1=CC=C([N+]([O-])=O)C=C1 BNUHAJGCKIQFGE-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
150000008041 alkali metal carbonates Chemical class 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
239000004327 boric acid Substances 0.000 description 2
150000001649 bromium compounds Chemical class 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
150000001805 chlorine compounds Chemical class 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
238000004587 chromatography analysis Methods 0.000 description 2
150000001851 cinnamic acid derivatives Chemical class 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 2
239000012954 diazonium Substances 0.000 description 2
YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 2
230000005684 electric field Effects 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
238000006266 etherification reaction Methods 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
DAPZDAPTZFJZTO-UHFFFAOYSA-N heptanoyl heptanoate Chemical compound CCCCCCC(=O)OC(=O)CCCCCC DAPZDAPTZFJZTO-UHFFFAOYSA-N 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000011133 lead Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000004973 liquid crystal related substance Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
239000012418 sodium perborate tetrahydrate Substances 0.000 description 2
IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 2
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 2
229940005605 valeric acid Drugs 0.000 description 2
239000011701 zinc Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
XPKBEMRQGZHRTE-UHFFFAOYSA-N (1-methoxycyclohexa-2,4-dien-1-yl)-phenyldiazene Chemical compound COC1(CC=CC=C1)N=NC1=CC=CC=C1 XPKBEMRQGZHRTE-UHFFFAOYSA-N 0.000 description 1
OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 description 1
CKZZENMFYRVBIE-UHFFFAOYSA-N (4-acetyloxyphenyl)imino-(4-methoxyphenyl)-oxidoazanium Chemical compound COC1=CC=C(C=C1)[N+]([O-])=NC1=CC=C(C=C1)OC(C)=O CKZZENMFYRVBIE-UHFFFAOYSA-N 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
CWLGEPSKQDNHIO-JOBJLJCHSA-N (e)-n-[(e)-benzylideneamino]-1-phenylmethanimine Chemical compound C=1C=CC=CC=1/C=N/N=C/C1=CC=CC=C1 CWLGEPSKQDNHIO-JOBJLJCHSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
XFDALNVZYFHILZ-UHFFFAOYSA-N 1-butyl-4-nitrosobenzene Chemical compound CCCCC1=CC=C(N=O)C=C1 XFDALNVZYFHILZ-UHFFFAOYSA-N 0.000 description 1
LAHFBMSKRXEQFS-CMDGGOBGSA-N 1-ethyl-4-[(e)-2-(4-methoxyphenyl)ethenyl]benzene Chemical compound C1=CC(CC)=CC=C1\C=C\C1=CC=C(OC)C=C1 LAHFBMSKRXEQFS-CMDGGOBGSA-N 0.000 description 1
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
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WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 1
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150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
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238000004440 column chromatography Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
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CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
238000000804 electron spin resonance spectroscopy Methods 0.000 description 1
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150000002148 esters Chemical class 0.000 description 1
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239000008103 glucose Substances 0.000 description 1
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150000002561 ketenes Chemical class 0.000 description 1
ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 1
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FEIWNULTQYHCDN-UHFFFAOYSA-N mbba Chemical compound C1=CC(CCCC)=CC=C1N=CC1=CC=C(OC)C=C1 FEIWNULTQYHCDN-UHFFFAOYSA-N 0.000 description 1
238000005259 measurement Methods 0.000 description 1
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VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
CZXGXYBOQYQXQD-UHFFFAOYSA-N methyl benzenesulfonate Chemical compound COS(=O)(=O)C1=CC=CC=C1 CZXGXYBOQYQXQD-UHFFFAOYSA-N 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
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239000011707 mineral Substances 0.000 description 1
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LKHMZCUKGPUKEA-UHFFFAOYSA-N n-(4-methoxyphenyl)-1-phenylmethanimine Chemical compound C1=CC(OC)=CC=C1N=CC1=CC=CC=C1 LKHMZCUKGPUKEA-UHFFFAOYSA-N 0.000 description 1
GNRWGOKACXCAMH-UHFFFAOYSA-N n-[(4-methylphenyl)sulfonylmethyl]nitrous amide Chemical compound CC1=CC=C(S(=O)(=O)CNN=O)C=C1 GNRWGOKACXCAMH-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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150000007530 organic bases Chemical class 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
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235000011056 potassium acetate Nutrition 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
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230000002441 reversible effect Effects 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910001023 sodium amalgam Inorganic materials 0.000 description 1
PTLRDCMBXHILCL-UHFFFAOYSA-M sodium arsenite Chemical compound [Na+].[O-][As]=O PTLRDCMBXHILCL-UHFFFAOYSA-M 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol 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)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 description 1
229940032091 stigmasterol Drugs 0.000 description 1
BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 description 1
235000016831 stigmasterol Nutrition 0.000 description 1
235000021286 stilbenes Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 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
- C09K19/08—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
- C09K19/24—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing nitrogen-to-nitrogen bonds
- C09K19/26—Azoxy compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
- C07C245/06—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings
- C07C245/08—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings with the two nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings, e.g. azobenzene
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/06—Preparation of azo dyes from other azo compounds by oxidation
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/28—Preparation of azo dyes from other azo compounds by etherification of hydroxyl 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
- C09K19/08—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
- C09K19/24—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing nitrogen-to-nitrogen bonds
- G—PHYSICS
- G01—MEASURING; TESTING
- G01R—MEASURING ELECTRIC VARIABLES; MEASURING MAGNETIC VARIABLES
- G01R33/00—Arrangements or instruments for measuring magnetic variables
- G01R33/20—Arrangements or instruments for measuring magnetic variables involving magnetic resonance
- G01R33/28—Details of apparatus provided for in groups G01R33/44 - G01R33/64
- G01R33/281—Means for the use of in vitro contrast agents
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Physics & Mathematics (AREA)
Crystallography & Structural Chemistry (AREA)
Nonlinear Science (AREA)
Materials Engineering (AREA)
Engineering & Computer Science (AREA)
General Physics & Mathematics (AREA)
Optics & Photonics (AREA)
Condensed Matter Physics & Semiconductors (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Liquid Crystal Substances (AREA)
Inks, Pencil-Leads, Or Crayons (AREA)

IL35574A 1970-03-28 1970-11-03 Nematic azobenzene and azoxybenezene compounds IL35574A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2014989A DE2014989C3 (de)	1970-03-28	1970-03-28	Azoxybenzole

Publications (2)

Publication Number	Publication Date
IL35574A0 IL35574A0 (en)	1971-01-28
IL35574A true IL35574A (en)	1973-11-28

Family

ID=5766555

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL35574A IL35574A (en)	1970-03-28	1970-11-03	Nematic azobenzene and azoxybenezene compounds

Country Status (10)

Country	Link
US (1)	US3773747A (fr)
JP (2)	JPS5136257B1 (fr)
BE (1)	BE758449A (fr)
CH (1)	CH549223A (fr)
DE (1)	DE2014989C3 (fr)
FR (1)	FR2083840A5 (fr)
GB (1)	GB1285388A (fr)
IL (1)	IL35574A (fr)
NL (1)	NL7016152A (fr)
SU (1)	SU433697A3 (fr)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3853785A (en) *	1971-10-14	1974-12-10	Univ Temple	Stable liquid crystal mixtures including anil-type nematic compounds
FR2184512B1 (fr) *	1972-05-19	1975-11-28	Thomson Csf
US4011173A (en) *	1972-08-03	1977-03-08	Merck Patent Gesellschaft Mit Beschrankter Haftung	Modified nematic mixtures with positive dielectric anisotropy
GB1433130A (en) *	1972-11-09	1976-04-22	Secr Defence	Substituted biphenyl and polyphenyl compounds and liquid crystal materials and devices containing them
JPS564596B2 (fr) *	1972-12-06	1981-01-30
JPS562115B2 (fr) *	1973-03-13	1981-01-17
JPS605630B2 (ja) *	1973-07-06	1985-02-13	セイコーエプソン株式会社	表示装置
JPS5023385A (fr) *	1973-07-06	1975-03-13
US3932298A (en) *	1973-07-19	1976-01-13	Temple University	Nematic liquid crystals with charge-transfer acceptors as dopants
DE2441296C3 (de) *	1973-08-31	1978-11-02	Dai Nippon Toryo K.K., Osaka (Japan)	Nematische Flüssigkristallmassen und deren Verwendung
US3979320A (en) *	1973-09-22	1976-09-07	Hodogaya Chemical Co., Ltd.	Liquid crystal composition
US3926834A (en) *	1973-10-01	1975-12-16	Rockwell International Corp	Low melting point disubstituted-p,p'-phenyl cinnamate liquid crystals
NL174720C (nl) *	1973-12-13	1984-08-01	Philips Nv	Beeldweergeefcel en methode voor de vervaardiging van een vloeibaar kristallijn p-n.butyl-p'-alkoxyazobenzeen.
US4097120A (en) *	1973-12-13	1978-06-27	U.S. Philips Corporation	Liquid crystalline compounds and mixtures
US4020002A (en) *	1974-02-28	1977-04-26	Beckman Instruments, Inc.	Non-schiff base field effect liquid crystal composition
DE2504564B2 (de) *	1974-06-07	1977-11-24		(+)p-alkoxy-p'-(2-methylbutyl)azoxybenzole und ein diese enthaltendes cholesterinisches fluessigkristallgemisch
US3975286A (en) *	1974-09-03	1976-08-17	Beckman Instruments, Inc.	Low voltage actuated field effect liquid crystals compositions and method of synthesis
US4066567A (en) *	1976-02-04	1978-01-03	Temple University	Liquid crystal cumulative dosimeter
DE2836644A1 (de) *	1978-08-22	1980-03-06	Boehringer Mannheim Gmbh	Diagnostisches mittel zum nachweis von leukozyten in koerperfluessigkeiten und dafuer geeignete chromogene
JPS5973555A (ja) *	1982-10-20	1984-04-25	Seiko Epson Corp	エステル−アゾキシ化合物
JPS59126492A (ja) *	1982-12-24	1984-07-21	Fujitsu Ltd	液晶組成物
EP0292139A1 (fr) *	1987-05-05	1988-11-23	Imperial Chemical Industries Plc	Composés azoiques
CN104710812B (zh) *	2013-12-16	2017-02-22	上海安诺其集团股份有限公司	一种可碱性染色的分散染料的制备方法
CN106893356A (zh) *	2017-01-10	2017-06-27	泉州市希姆色彩研究院有限公司	一种高水牢度的分散橙染料及其制备方法
CN113149861B (zh) *	2021-05-13	2023-01-31	郑州大学	对羟甲基苯甲酸（烷基酯）-4-偶氮苯及其制备方法和应用

0
- BE BE758449D patent/BE758449A/fr unknown
1970
- 1970-03-28 DE DE2014989A patent/DE2014989C3/de not_active Expired
- 1970-11-02 GB GB52048/70A patent/GB1285388A/en not_active Expired
- 1970-11-03 IL IL35574A patent/IL35574A/en unknown
- 1970-11-03 CH CH1626570A patent/CH549223A/xx not_active IP Right Cessation
- 1970-11-04 NL NL7016152A patent/NL7016152A/xx unknown
- 1970-11-05 JP JP45096948A patent/JPS5136257B1/ja active Pending
- 1970-11-20 US US00091522A patent/US3773747A/en not_active Expired - Lifetime
- 1970-12-18 FR FR7045783A patent/FR2083840A5/fr not_active Expired
1971
- 1971-04-08 SU SU1644189A patent/SU433697A3/ru active
1972
- 1972-12-19 JP JP47126848A patent/JPS5137838B1/ja active Pending

Also Published As

Publication number	Publication date
DE2014989B2 (de)	1974-04-11
BE758449A (fr)	1971-04-16
FR2083840A5 (fr)	1971-12-17
GB1285388A (en)	1972-08-16
CH549223A (de)	1974-05-15
JPS5136257B1 (fr)	1976-10-07
DE2014989C3 (de)	1974-11-14
US3773747A (en)	1973-11-20
SU433697A3 (ru)	1974-06-25
JPS5137838B1 (fr)	1976-10-18
DE2014989A1 (de)	1971-10-21
IL35574A0 (en)	1971-01-28
NL7016152A (fr)	1971-09-30

Publication	Publication Date	Title
IL35574A (en)	1973-11-28	Nematic azobenzene and azoxybenezene compounds
US4002670A (en)	1977-01-11	Nematic compounds and mixtures
US4001137A (en)	1977-01-04	Nematic compounds and mixtures
US4181625A (en)	1980-01-01	Liquid crystalline cyclohexylcyclohexanes
KR900003432B1 (ko)	1990-05-18	액정 유전체의 제조 공정
HK22184A (en)	1984-03-23	Cyclohexane derivatives, liquid crystal dielectrics containing them and their use as constituents of liquid crystal dielectrics
US4871472A (en)	1989-10-03	Esters in ferroelectric mixtures
Reddy et al.	2002	Ferroelectric properties exhibited by mesophases of compounds composed of achiral banana-shaped molecules
US4029594A (en)	1977-06-14	Novel liquid crystal compounds and electro-optic devices incorporating them
Rondeau et al.	1972	Central linkage influence upon mesomorphic and electrooptical behavior of diaryl nematics. General proton magnetic resonance method employing a lanthanide shift reagent for analysis of isomeric azoxybenzenes
US4871470A (en)	1989-10-03	Cyclohexane derivatives
US3893994A (en)	1975-07-08	4-(Alkyl)-4{40 -(alkoxy or alkylcarbonyloxy)-1,1{40 -azobene
US3925237A (en)	1975-12-09	Novel liquid crystal electro-optic devices
JPS58121248A (ja)	1983-07-19	４−フルオロビフエニル誘導体、それらの製造方法、それらを含有する誘電体および電子光学表示要素
JPH0764829B2 (ja)	1995-07-12	液晶化合物
US4719032A (en)	1988-01-12	Cyclohexane derivatives
Gray et al.	1974	Stable, low melting nematogens of positive dielectric anisotropy for display devices
US4012434A (en)	1977-03-15	Nematic compounds and mixtures
US4970023A (en)	1990-11-13	Biphenyl compounds, method of producing the same as well as liquid crystal compositions and light switch elements each containing the same
US4877220A (en)	1989-10-31	Hexasubstituted cyclohexane compounds
JPS6217987B2 (fr)	1987-04-21
US3391186A (en)	1968-07-02	Benzoic acids
CN117778029B (zh)	2026-01-06	一种反式十氢化萘吲哚类液晶化合物及其制备方法
CN102816454B (zh)	2013-11-20	一类含酯基的1,8-萘酰亚胺类荧光二向性染料、其制备方法及应用
EP0315701A1 (fr)	1989-05-17	Compose de biphenyle