DD146187A5 - Verfahren zur herstellung von 2-chlor-6-nitroanilinen - Google Patents

Verfahren zur herstellung von 2-chlor-6-nitroanilinen Download PDF

Info

Publication number: DD146187A5
Authority: DD; German Democratic Republic
Prior art keywords: liquid crystal; compounds; meaning; point; crystal compositions
Prior art date: 1978-09-20

Application number

DD79215670A

Other languages

German (de)

English (en)

Inventor

Wolfang Dr Buck

Richard Dr Sehring

Gerbert Dr Linden

Sigmund Dr Lust

Original Assignee

Celamerck Gmbh & Co Kg

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.)

1978-09-20

Filing date

1979-09-20

Publication date

1981-01-28

1978-09-20 Priority claimed from JP11559178A external-priority patent/JPS5543016A/ja

1978-11-15 Priority claimed from JP14071078A external-priority patent/JPS5566556A/ja

1978-11-25 Priority claimed from JP14550878A external-priority patent/JPS5572156A/ja

1979-01-31 Priority claimed from JP991779A external-priority patent/JPS55102550A/ja

1979-03-24 Priority claimed from JP3454579A external-priority patent/JPS5822146B2/ja

1979-08-27 Priority claimed from JP10897879A external-priority patent/JPS5632446A/ja

1979-09-20 Application filed by Celamerck Gmbh & Co Kg filed Critical Celamerck Gmbh & Co Kg

1981-01-28 Publication of DD146187A5 publication Critical patent/DD146187A5/de

Links

238000002360 preparation method Methods 0.000 title description 5
238000000034 method Methods 0.000 title description 3
239000004973 liquid crystal related substance Substances 0.000 claims abstract description 92
150000001875 compounds Chemical class 0.000 claims abstract description 79
239000000463 material Substances 0.000 claims abstract description 29
125000000217 alkyl group Chemical group 0.000 claims abstract description 6
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
239000000203 mixture Substances 0.000 claims description 54
230000000694 effects Effects 0.000 claims description 8
101100242909 Streptococcus pneumoniae (strain ATCC BAA-255 / R6) pbpA gene Proteins 0.000 abstract 1
101100269618 Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) aliA gene Proteins 0.000 abstract 1
101100439974 Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) clpE gene Proteins 0.000 abstract 1
101150109310 msrAB1 gene Proteins 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
239000013078 crystal Substances 0.000 description 17
239000000975 dye Substances 0.000 description 17
239000000126 substance Substances 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
MPAIWVOBMLSHQA-UHFFFAOYSA-N 3,6-dihydroxybenzene-1,2-dicarbonitrile Chemical compound OC1=CC=C(O)C(C#N)=C1C#N MPAIWVOBMLSHQA-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
238000003756 stirring Methods 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000000470 constituent Substances 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
-1 methoxybenzylidene butyl Chemical group 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000004990 Smectic liquid crystal Substances 0.000 description 6
210000004027 cell Anatomy 0.000 description 5
238000001816 cooling Methods 0.000 description 5
239000007788 liquid Substances 0.000 description 5
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
BALGERHMIXFENA-MGCOHNPYSA-N CCCC[C@H]1CC[C@H](C(O)=O)CC1 Chemical compound CCCC[C@H]1CC[C@H](C(O)=O)CC1 BALGERHMIXFENA-MGCOHNPYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
239000002253 acid Substances 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
230000004044 response Effects 0.000 description 4
238000005406 washing Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
239000004988 Nematic liquid crystal Substances 0.000 description 3
238000000862 absorption spectrum Methods 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
239000010410 layer Substances 0.000 description 3
FEIWNULTQYHCDN-UHFFFAOYSA-N mbba Chemical compound C1=CC(CCCC)=CC=C1N=CC1=CC=C(OC)C=C1 FEIWNULTQYHCDN-UHFFFAOYSA-N 0.000 description 3
238000005259 measurement Methods 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
230000007704 transition Effects 0.000 description 3
238000002834 transmittance Methods 0.000 description 3
HSIXZGAHLLBZIH-UHFFFAOYSA-N 1-diazopentane Chemical compound CCCCC=[N+]=[N-] HSIXZGAHLLBZIH-UHFFFAOYSA-N 0.000 description 2
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
101150065749 Churc1 gene Proteins 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
102100038239 Protein Churchill Human genes 0.000 description 2
239000001000 anthraquinone dye Substances 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
150000001983 dialkylethers Chemical class 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 2
229920006391 phthalonitrile polymer Polymers 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
150000003459 sulfonic acid esters Chemical class 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
UISXVYOLBGBYCV-UHFFFAOYSA-N (4-pentylphenyl) 4-methoxybenzoate Chemical compound C1=CC(CCCCC)=CC=C1OC(=O)C1=CC=C(OC)C=C1 UISXVYOLBGBYCV-UHFFFAOYSA-N 0.000 description 1
XBWZMEWGBMUVMK-UHFFFAOYSA-N 1-(4-ethylnonoxy)-2-phenylbenzene Chemical group CCCCCC(CC)CCCOC1=CC=CC=C1C1=CC=CC=C1 XBWZMEWGBMUVMK-UHFFFAOYSA-N 0.000 description 1
KOAUFWIBJVYJHF-UHFFFAOYSA-N 1-ethoxy-4-(4-pentylphenyl)benzene Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(OCC)C=C1 KOAUFWIBJVYJHF-UHFFFAOYSA-N 0.000 description 1
SJSJFFGLDGAYIC-UHFFFAOYSA-N 3-hydroxy-6-pentoxybenzene-1,2-dicarbonitrile Chemical compound CCCCCOC1=CC=C(O)C(C#N)=C1C#N SJSJFFGLDGAYIC-UHFFFAOYSA-N 0.000 description 1
JFKUBRAOUZEZSL-UHFFFAOYSA-N 4-butylbenzoic acid Chemical compound CCCCC1=CC=C(C(O)=O)C=C1 JFKUBRAOUZEZSL-UHFFFAOYSA-N 0.000 description 1
NVXIJHWKTUUWCT-UHFFFAOYSA-N 4-hexanoyloxybenzoic acid Chemical compound CCCCCC(=O)OC1=CC=C(C(O)=O)C=C1 NVXIJHWKTUUWCT-UHFFFAOYSA-N 0.000 description 1
ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 1
GXZUFBKHCCQHLU-PCYFZWJMSA-N C(#N)C1=C(C=CC(=C1C#N)C(=O)O[C@@H]1CC[C@H](CC1)CCCCCC)C(=O)O[C@@H]1CC[C@H](CC1)CCCCCC Chemical compound C(#N)C1=C(C=CC(=C1C#N)C(=O)O[C@@H]1CC[C@H](CC1)CCCCCC)C(=O)O[C@@H]1CC[C@H](CC1)CCCCCC GXZUFBKHCCQHLU-PCYFZWJMSA-N 0.000 description 1
RVLAXPQGTRTHEV-XYPYZODXSA-N CCCCC[C@H]1CC[C@H](C(O)=O)CC1 Chemical compound CCCCC[C@H]1CC[C@H](C(O)=O)CC1 RVLAXPQGTRTHEV-XYPYZODXSA-N 0.000 description 1
KEIWXKBPBNHMFN-UHFFFAOYSA-N COC1=CC=C(C(=O)OC2(CC=CC=C2)CCCCC)C=C1 Chemical compound COC1=CC=C(C(=O)OC2(CC=CC=C2)CCCCC)C=C1 KEIWXKBPBNHMFN-UHFFFAOYSA-N 0.000 description 1
101100493710 Caenorhabditis elegans bath-40 gene Proteins 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
WZWRHKQSYZLFDM-UHFFFAOYSA-N N-ethoxy-N-(5-phenylpent-4-enyl)aniline Chemical compound C(C)ON(C1=CC=CC=C1)CCCC=CC1=CC=CC=C1 WZWRHKQSYZLFDM-UHFFFAOYSA-N 0.000 description 1
230000032900 absorption of visible light Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
238000000149 argon plasma sintering Methods 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
230000008859 change Effects 0.000 description 1
210000002858 crystal cell Anatomy 0.000 description 1
150000005690 diesters Chemical group 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000013213 extrapolation Methods 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
DBOAVDSSZWDGTH-UHFFFAOYSA-N n-(4-butylphenyl)-1-(4-ethoxyphenyl)methanimine Chemical compound C1=CC(CCCC)=CC=C1N=CC1=CC=C(OCC)C=C1 DBOAVDSSZWDGTH-UHFFFAOYSA-N 0.000 description 1
KMVXENDYYJFUGZ-UHFFFAOYSA-N n-methoxy-n-(5-phenylpent-4-enyl)aniline Chemical compound C=1C=CC=CC=1N(OC)CCCC=CC1=CC=CC=C1 KMVXENDYYJFUGZ-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
KOUCTZDKTJGHSS-UHFFFAOYSA-N pentyl 4-methylbenzenesulfonate Chemical compound CCCCCOS(=O)(=O)C1=CC=C(C)C=C1 KOUCTZDKTJGHSS-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
230000000704 physical effect Effects 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
238000001556 precipitation Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
239000004065 semiconductor Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
230000001052 transient effect Effects 0.000 description 1
230000000007 visual effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/18—Nitro compounds
- A01N33/20—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group
- A01N33/22—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group having at least one oxygen or sulfur atom and at least one nitro group directly attached to the same aromatic ring system
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
- C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
- C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Crystallography & Structural Chemistry (AREA)
Materials Engineering (AREA)
Plant Pathology (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Health & Medical Sciences (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Liquid Crystal Substances (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Liquid Crystal (AREA)

DD79215670A 1978-09-20 1979-09-20 Verfahren zur herstellung von 2-chlor-6-nitroanilinen DD146187A5 (de)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
JP11559178A JPS5543016A (en)	1978-09-20	1978-09-20	Dicyanohydroquinonecyclohexanecarboxylic ester
JP14071078A JPS5566556A (en)	1978-11-15	1978-11-15	3-pentyloxy-6-cyclohexanecarboxy-phthalonitrile
JP14550878A JPS5572156A (en)	1978-11-25	1978-11-25	3-butoxy-6-cyclohexanecarboxy-phthalonitriles
JP991779A JPS55102550A (en)	1979-01-31	1979-01-31	3-propyloxy-6-cyclohexanecarboxy-phthalonitrile
JP3454579A JPS5822146B2 (ja)	1979-03-24	1979-03-24	３↓−アルキルオキシ↓−６↓−ヒドロキシ↓−フタロニトリルの４↓−（４′↓−トランス↓−アルキルシクロヘキシル）安息香酸エステル類
JP10897879A JPS5632446A (en)	1979-08-27	1979-08-27	3-alkyloxy-6-(trans-4'-alkyloxycyclohexanecarboxy)- phthalonitrile

Publications (1)

Publication Number	Publication Date
DD146187A5 true DD146187A5 (de)	1981-01-28

Family

ID=27548237

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79215670A DD146187A5 (de)	1978-09-20	1979-09-20	Verfahren zur herstellung von 2-chlor-6-nitroanilinen

Country Status (7)

Country	Link
US (1)	US4279770A (fr)
CA (1)	CA1131655A (fr)
CH (1)	CH642345A5 (fr)
DD (1)	DD146187A5 (fr)
DE (1)	DE2937700C2 (fr)
FR (1)	FR2436777A1 (fr)
GB (1)	GB2035303B (fr)

Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2967129D1 (en) *	1979-05-28	1984-08-30	Merck Patent Gmbh	Liquid-crystal compositions
DE2933563A1 (de) *	1979-07-18	1981-02-05	Bbc Brown Boveri & Cie	Anisotrope verbindungen mit negativer dk-anisotropie
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1979
- 1979-09-12 US US06/074,655 patent/US4279770A/en not_active Expired - Lifetime
- 1979-09-18 DE DE2937700A patent/DE2937700C2/de not_active Expired
- 1979-09-18 CA CA335,840A patent/CA1131655A/fr not_active Expired
- 1979-09-19 CH CH845579A patent/CH642345A5/de not_active IP Right Cessation
- 1979-09-20 FR FR7923469A patent/FR2436777A1/fr active Granted
- 1979-09-20 GB GB7932598A patent/GB2035303B/en not_active Expired
- 1979-09-20 DD DD79215670A patent/DD146187A5/de unknown

Also Published As

Publication number	Publication date
CH642345A5 (de)	1984-04-13
US4279770A (en)	1981-07-21
FR2436777B1 (fr)	1984-04-27
CA1131655A (fr)	1982-09-14
DE2937700A1 (de)	1980-04-17
GB2035303A (en)	1980-06-18
GB2035303B (en)	1983-01-06
DE2937700C2 (de)	1984-08-30
FR2436777A1 (fr)	1980-04-18

Publication	Publication Date	Title
DD146187A5 (de)	1981-01-28	Verfahren zur herstellung von 2-chlor-6-nitroanilinen
DE2139628C3 (de)	1981-12-24	4-Benzolyloxybenzoesäurephenylester und diese enthaltende nematische Gemische
DE68917013T2 (de)	1994-12-01	Naphthalen-Verbindung und dieselbe enthaltende flüssigkristalline Zusammensetzung.
EP0056501B1 (fr)	1984-05-02	Mélange de cristaux liquides
EP0019665B1 (fr)	1984-07-25	Composés de cristaux liquides
DE2617593A1 (de)	1976-11-11	Diphenylderivate und ihre verwendung
DE3447359A1 (de)	1986-07-03	Fluessigkristalline phase
DE2639838A1 (de)	1977-03-17	Optisch aktive cyanodiphenylverbindungen, fluessigkristallmaterialien und fluessigkristallvorrichtungen
DD241263A5 (de)	1986-12-03	Fluessigkristalline phase
DE2853728A1 (de)	1980-07-17	Fluessigkristalline carbonsaeureester, verfahren zu ihrer herstellung, diese enthaltende dielektrika und elektrooptisches anzeigeelement
DD209205A5 (de)	1984-04-25	Fluessigkristallines dielektrikum fuer elektrooptische anzeigeelemente
DE4027981A1 (de)	1992-04-30	Matrix-fluessigkristallanzeige
DE3037303C2 (fr)	1990-05-03
EP0063713A1 (fr)	1982-11-03	Colorants anthraquinoniques dichroiques, des diélectriques de cristaux liquides les contenant et des dispositifs d'affichage électro-optiques
DE2613293C3 (de)	1982-02-18	Cyanosubstituierte Biphenylverbindungen, Verfahren zu deren Herstellung und diese Verbindungen enthaltende flüssigkristalline Dielektrika
CH649766A5 (de)	1985-06-14	Substituierte benzoesaeurephenylester, fluessigkristallmischungen diese enthaltend und verwendung derselben in anzeigeeinheiten.
EP0258349B1 (fr)	1990-05-23	Element d'affichage electro-optique
DE3324774C2 (de)	1985-03-07	Cyclohexancarbonsäure-biphenylester und Benzoyloxybenzoesäurephenylester und deren Verwendung
DE3318533A1 (de)	1984-01-05	Nematische fluessigkristalline verbindungen
DE3141309A1 (de)	1982-06-16	"fluessigkristall-zubereitung und verfahren zur verbesserung der farbe von dichroitischen farbstoffen in fluessigkristall-anzeigen"
DE3510733A1 (de)	1986-09-25	Fluessigkristallphase
CH653006A5 (de)	1985-12-13	Kristallin-fluessige alkylcyclohexancarbonsaeure- bzw. substituierte benzoesaeure-alkylcyclohexylester, ihre herstellung und verwendung.
DE69004188T2 (de)	1994-03-31	Carboxylatverbindungen, diese Verbindungen enthaltende flüssigkristalline Zusammensetzungen und flüssigkristalliner Bauteil.
DD244351A5 (de)	1987-04-01	Verbindungen fuer ferroelektrische fluessigkristallvorrichtungen
DE4307049A1 (de)	1994-09-15	Diskotische Flüssigkristalle