CH674844A5 - - Google Patents

Download PDF

Info

Publication number: CH674844A5
Authority: CH; Switzerland
Prior art keywords: mol; undecane; dioxaspiro; theory; crystalline
Prior art date: 1987-04-03

Application number

CH75888A

Other languages

German (de)

English (en)

Inventor

Dietrich Prof Dr Demus

Hans-Joachim Prof Dr Deutscher

Roger Dr Frach

Carsten Dr Tschierske

Adelbert Dr Wiegeleben

Horst Prof Dr Zaschke

Original Assignee

Werk Fernsehelektronik Veb

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.)

1987-04-03

Filing date

1988-03-01

Publication date

1990-07-31

1988-03-01 Application filed by Werk Fernsehelektronik Veb filed Critical Werk Fernsehelektronik Veb

1990-07-31 Publication of CH674844A5 publication Critical patent/CH674844A5/de

Links

239000000203 mixture Substances 0.000 claims description 24
239000000126 substance Substances 0.000 claims description 13
239000007788 liquid Substances 0.000 claims description 9
230000005693 optoelectronics Effects 0.000 claims description 6
RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical class CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 5
150000001875 compounds Chemical class 0.000 claims description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
239000002904 solvent Substances 0.000 description 14
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 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
238000001816 cooling Methods 0.000 description 9
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
230000007704 transition Effects 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000012071 phase Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000004973 liquid crystal related substance Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 4
WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 3
CCOLOUQDTJSMSE-UHFFFAOYSA-N 3-nonyl-1,5-dioxaspiro[5.5]undecane-9-carboxylic acid Chemical compound O1CC(CCCCCCCCC)COC11CCC(C(O)=O)CC1 CCOLOUQDTJSMSE-UHFFFAOYSA-N 0.000 description 3
229960000549 4-dimethylaminophenol Drugs 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
VBHVMTNWIGNNMC-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)octanenitrile Chemical compound CCCCCCC(CO)(CO)C#N VBHVMTNWIGNNMC-UHFFFAOYSA-N 0.000 description 2
UFCBBNJJKOMVCZ-UHFFFAOYSA-N 2-nonylpropane-1,3-diol Chemical compound CCCCCCCCCC(CO)CO UFCBBNJJKOMVCZ-UHFFFAOYSA-N 0.000 description 2
-1 3- (4'-n-Butylcyclohexyl) methyl-9-n-pentyl-1,5-dioxaspiro (5,5) undecane Chemical compound 0.000 description 2
ANJHMDIJEPQYAM-UHFFFAOYSA-N 3-hexyl-1,5-dithiaspiro[5.5]undecane-9-carboxylic acid Chemical compound S1CC(CCCCCC)CSC11CCC(C(O)=O)CC1 ANJHMDIJEPQYAM-UHFFFAOYSA-N 0.000 description 2
RUXBKLNRRHCTMU-UHFFFAOYSA-N 4-(4-butylcyclohexyl)-2-methylcyclohexan-1-one Chemical compound C(CCC)C1CCC(CC1)C1CC(C(CC1)=O)C RUXBKLNRRHCTMU-UHFFFAOYSA-N 0.000 description 2
SDZAFEKXYFWXGK-UHFFFAOYSA-N 9-(4-butylcyclohexyl)-4-methyl-1,5-dioxaspiro[5.5]undecane-3-carboxylic acid Chemical compound C(CCC)C1CCC(CC1)C1CCC2(OCC(C(O2)C)C(=O)O)CC1 SDZAFEKXYFWXGK-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000010779 crude oil Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
PPVJDNABSVBXEP-UHFFFAOYSA-N ethyl 3-hexyl-1,5-dithiaspiro[5.5]undecane-9-carboxylate Chemical compound S1CC(CCCCCC)CSC11CCC(C(=O)OCC)CC1 PPVJDNABSVBXEP-UHFFFAOYSA-N 0.000 description 2
239000005457 ice water Substances 0.000 description 2
125000000896 monocarboxylic acid group Chemical group 0.000 description 2
230000003287 optical effect Effects 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
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
LSDTWMHYCLFXBZ-UHFFFAOYSA-N 1,5-dioxaspiro[5.5]undecane Chemical class C1CCCCC21OCCCO2 LSDTWMHYCLFXBZ-UHFFFAOYSA-N 0.000 description 1
MVMZKLKIUWBNCA-UHFFFAOYSA-N 1-(bromomethyl)-4-butylcyclohexane Chemical compound CCCCC1CCC(CBr)CC1 MVMZKLKIUWBNCA-UHFFFAOYSA-N 0.000 description 1
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
VEVRIIXQAGEKEO-UHFFFAOYSA-N 2-(4-butylcyclohexyl)butane-1,3-diol Chemical compound C(CCC)C1CCC(CC1)C(C(O)C)CO VEVRIIXQAGEKEO-UHFFFAOYSA-N 0.000 description 1
ZGCCYZKDEFMHQF-UHFFFAOYSA-N 2-cyanooctanoic acid Chemical compound CCCCCCC(C#N)C(O)=O ZGCCYZKDEFMHQF-UHFFFAOYSA-N 0.000 description 1
RJFPBIZCYTWMPM-UHFFFAOYSA-N 2-hexylpropane-1,3-dithiol Chemical compound CCCCCCC(CS)CS RJFPBIZCYTWMPM-UHFFFAOYSA-N 0.000 description 1
XRTKZOVDATYNAU-UHFFFAOYSA-N 3-cyano-3-hexyl-1,5-dioxaspiro[5.5]undecane-9-carboxylic acid Chemical compound O1CC(CCCCCC)(C#N)COC11CCC(C(O)=O)CC1 XRTKZOVDATYNAU-UHFFFAOYSA-N 0.000 description 1
CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical compound OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 description 1
UKLNPJDLSPMJMQ-UHFFFAOYSA-N 4-pentylcyclohexan-1-one Chemical compound CCCCCC1CCC(=O)CC1 UKLNPJDLSPMJMQ-UHFFFAOYSA-N 0.000 description 1
KPDFZBPBSSBVOB-UHFFFAOYSA-N 9-(4-butylcyclohexyl)-4-methyl-3-nonyl-1,5-dioxaspiro[5.5]undecane Chemical compound C(CCC)C1CCC(CC1)C1CCC2(OCC(C(O2)C)CCCCCCCCC)CC1 KPDFZBPBSSBVOB-UHFFFAOYSA-N 0.000 description 1
VYTDSUWIUHBTML-UHFFFAOYSA-N CCCCCCC1(COC2(CCC(CC2)C(=O)OCC)OC1)C#N Chemical compound CCCCCCC1(COC2(CCC(CC2)C(=O)OCC)OC1)C#N VYTDSUWIUHBTML-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
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000004990 Smectic liquid crystal Substances 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
VEFXTGTZJOWDOF-UHFFFAOYSA-N benzene;hydrate Chemical compound O.C1=CC=CC=C1 VEFXTGTZJOWDOF-UHFFFAOYSA-N 0.000 description 1
OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
238000005352 clarification Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical class OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
WIOHBOKEUIHYIC-UHFFFAOYSA-N diethyl 2,2-bis(hydroxymethyl)propanedioate Chemical compound CCOC(=O)C(CO)(CO)C(=O)OCC WIOHBOKEUIHYIC-UHFFFAOYSA-N 0.000 description 1
GYQCPOQRINUJOF-UHFFFAOYSA-N diethyl 2-(4-butylcyclohexyl)-2-methylpropanedioate Chemical compound C(C)OC(C(C(=O)OCC)(C)C1CCC(CC1)CCCC)=O GYQCPOQRINUJOF-UHFFFAOYSA-N 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000005684 electric field Effects 0.000 description 1
238000005265 energy consumption Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
VZJMHAGKDYPFAG-UHFFFAOYSA-N ethyl 2-cyano-2-(hydroxymethyl)octanoate Chemical compound CCCCCCC(CO)(C#N)C(=O)OCC VZJMHAGKDYPFAG-UHFFFAOYSA-N 0.000 description 1
ABHZULGDLFSHQE-UHFFFAOYSA-N ethyl 2-ethyldecanoate Chemical compound CCCCCCCCC(CC)C(=O)OCC ABHZULGDLFSHQE-UHFFFAOYSA-N 0.000 description 1
ZXYAWONOWHSQRU-UHFFFAOYSA-N ethyl 4-oxocyclohexanecarboxylate Chemical compound CCOC(=O)C1CCC(=O)CC1 ZXYAWONOWHSQRU-UHFFFAOYSA-N 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000000034 method Methods 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
FFNMBRCFFADNAO-UHFFFAOYSA-N pirenzepine hydrochloride Chemical compound [H+].[H+].[Cl-].[Cl-].C1CN(C)CCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=CC=C21 FFNMBRCFFADNAO-UHFFFAOYSA-N 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C—CHEMISTRY; METALLURGY
- 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
- C09K19/3472—Pyrimidine condensed or bridged with another ring system
- 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
- C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur 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
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
- C09K19/3494—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom the heterocyclic ring containing sulfur and oxygen 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
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K2019/327—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems containing a spiro ring system
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
- C09K2019/3425—Six-membered ring with oxygen(s) in fused, bridged or spiro ring systems

Landscapes

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

CH75888A 1987-04-03 1988-03-01 CH674844A5 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DD30146087A DD259873A1 (de)	1987-04-03	1987-04-03	Kristallin-fluessige mischungen

Publications (1)

Publication Number	Publication Date
CH674844A5 true CH674844A5 (fr)	1990-07-31

Family

ID=5587998

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH75888A CH674844A5 (fr)	1987-04-03	1988-03-01

Country Status (5)

Country	Link
JP (1)	JPS6419074A (fr)
CH (1)	CH674844A5 (fr)
DD (1)	DD259873A1 (fr)
DE (1)	DE3806716A1 (fr)
GB (1)	GB2203429B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8827886D0 (en) *	1988-11-30	1989-01-05	Wellcome Found	Novel heterocyclic pesticidal compounds

1987
- 1987-04-03 DD DD30146087A patent/DD259873A1/de not_active IP Right Cessation
1988
- 1988-03-01 CH CH75888A patent/CH674844A5/de not_active IP Right Cessation
- 1988-03-02 DE DE19883806716 patent/DE3806716A1/de not_active Withdrawn
- 1988-03-29 GB GB8807374A patent/GB2203429B/en not_active Expired - Lifetime
- 1988-04-02 JP JP63080268A patent/JPS6419074A/ja active Pending

Also Published As

Publication number	Publication date
GB2203429A (en)	1988-10-19
JPS6419074A (en)	1989-01-23
DD259873A1 (de)	1988-09-07
GB8807374D0 (en)	1988-05-05
DE3806716A1 (de)	1988-10-20
GB2203429B (en)	1992-01-02

Legal Events

Date	Code	Title	Description
1992-11-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2922236C2 (de)	1986-09-25	Flüssigkristalline Cyclohexanderivate, diese enthaltende flüssigkristalline Materialien und deren Verwendung
EP0022183B1 (fr)	1982-06-23	Dérivés de cyclohexylbiphényl, procédé pour leur préparation, diélectriques les contenant et élément indicateur électrooptique
EP0003215B1 (fr)	1981-06-17	Dérivés du cyclohexane, diélectriques à cristaux liquides les contenant et leur utilisation comme composants de diélectriques à cristaux liquides
EP0051738B1 (fr)	1984-07-25	Dérivés de cyclohexyl-biphényle contenant du fluor, diélectriques les contenant et élément indicateur électro-optique
EP0023728B1 (fr)	1983-08-10	Composés anisotropes à anisotropie directe négative ou positive et anisotropie optique limitée et mélange de cristaux liquides les contenant
DE2944905C2 (fr)	1988-12-22
DE3040632C2 (fr)	1989-02-02
EP0154840B1 (fr)	1989-01-25	Composés de cristaux liquides
EP0056113B1 (fr)	1985-05-29	Dérivés de cyclohexylcarbonitrile, diélectriques et élément d'affichage électro-optique les contenant
EP0215800B1 (fr)	1990-04-04	Pyrimidines
EP0182054A2 (fr)	1986-05-28	Composés hétérocycliques
DE3342631A1 (de)	1985-06-05	Thienothiophenderivate
EP0090282A1 (fr)	1983-10-05	Polymères avec des groupes mésogènes et des colorants dans la chaîne latérale
EP0030277A1 (fr)	1981-06-17	Oligo 1,4-phénylènes partiellement hydrogénés, diélectriques les contenant et élément indicateur électro-optique
EP0104327A2 (fr)	1984-04-04	Application de dérivés cycliques comme composants de cristaux liquides
CH645102A5 (de)	1984-09-14	Disubstituierte pyrimidine.
DE3112185A1 (de)	1982-01-14	Fluessigkristallverbindung
CH649768A5 (de)	1985-06-14	Fluessigkristalline verbindung und fluessigkristalline gemische.
DE3237020C2 (de)	1985-10-17	Trans-4-Alkyloxymethyl-1-(4'-cyanophenyl)cyclohexane und trans-4-Alkyloxymethyl-1-(4"-cyano-4'-biphenylyl)cyclohexane, Verfahren zu deren Herstellung und deren Verwendung
EP0087679A2 (fr)	1983-09-07	1-3-Dioxanes
DD274040A5 (de)	1989-12-06	Fluessig-kristallines gemisch, welches zur verwendung in der vorrichtung fuer die verbildlichung von informationen bestimmt ist
DE3889461T2 (de)	1994-09-01	Lateral cyano- und fluorosubstituierte terphenyle.
EP0031021B1 (fr)	1983-05-18	Tétrahydroquinazolines, procédé pour leur préparation, diélectriques à cristaux liquides les contenant et élément d'affichage électro-optique
EP0073378B1 (fr)	1985-06-19	1,3-Dithiannes 2,5-disubstituées, leur procédé de préparation et leur utilisation
CH674844A5 (fr)	1990-07-31