JPS6350342B2 - - Google Patents

Info

Publication number: JPS6350342B2
Authority: JP; Japan
Prior art keywords: trans; isothiocyanatobenzene; weight; liquid crystal; alkyl
Prior art date: 1983-03-30
Legal status (The legal status 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 status listed.): Expired

Application number

JP6504084A

Other languages

English (en)

Japanese (ja)

Other versions

JPS60120858A (ja

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wojskowa Akad Tech

Original Assignee

Wojskowa Akad Tech

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.)

1983-03-30

Filing date

1984-03-30

Publication date

1988-10-07

1984-03-30 Application filed by Wojskowa Akad Tech filed Critical Wojskowa Akad Tech

1985-06-28 Publication of JPS60120858A publication Critical patent/JPS60120858A/ja

1988-10-07 Publication of JPS6350342B2 publication Critical patent/JPS6350342B2/ja

Status Granted legal-status Critical Current

Links

239000000203 mixture Substances 0.000 claims description 61
150000001875 compounds Chemical class 0.000 claims description 30
239000004973 liquid crystal related substance Substances 0.000 claims description 30
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 15
-1 alkyl chloroformate Chemical compound 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 6
150000003512 tertiary amines Chemical class 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 5
239000000047 product Substances 0.000 claims 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 claims description 4
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical group ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 3
239000002262 Schiff base Substances 0.000 claims description 2
150000004753 Schiff bases Chemical class 0.000 claims description 2
239000012467 final product Substances 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims 2
238000002955 isolation Methods 0.000 claims 1
239000012071 phase Substances 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
230000008018 melting Effects 0.000 description 12
238000002844 melting Methods 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
238000009472 formulation Methods 0.000 description 8
238000000034 method Methods 0.000 description 7
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 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
239000004990 Smectic liquid crystal Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
125000004093 cyano group Chemical group *C#N 0.000 description 5
239000000374 eutectic mixture Substances 0.000 description 5
230000007704 transition Effects 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
230000003287 optical effect Effects 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 3
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 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical class S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 3
239000007787 solid Substances 0.000 description 3
WBUQBWQWNDKJJR-UHFFFAOYSA-N 4-[4-(2-methylbutoxy)phenyl]benzonitrile Chemical group C1=CC(OCC(C)CC)=CC=C1C1=CC=C(C#N)C=C1 WBUQBWQWNDKJJR-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
239000013078 crystal Substances 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
WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
239000012990 dithiocarbamate Substances 0.000 description 2
150000002540 isothiocyanates Chemical class 0.000 description 2
239000000463 material Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
JFMJIOVWGSCZGB-UHFFFAOYSA-N 1-[4-(4-pentylphenyl)phenyl]pentan-1-one Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(C(=O)CCCC)C=C1 JFMJIOVWGSCZGB-UHFFFAOYSA-N 0.000 description 1
VXJTWTJULLKDPY-UHFFFAOYSA-N 1-bromo-4-(4-pentylphenyl)benzene Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(Br)C=C1 VXJTWTJULLKDPY-UHFFFAOYSA-N 0.000 description 1
DZQBXEUCFFUIBR-UHFFFAOYSA-N 1-pentyl-4-(4-pentylphenyl)benzene Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(CCCCC)C=C1 DZQBXEUCFFUIBR-UHFFFAOYSA-N 0.000 description 1
DLLIPJSMDJCZRF-UHFFFAOYSA-N 4-(4-ethylphenyl)benzonitrile Chemical group C1=CC(CC)=CC=C1C1=CC=C(C#N)C=C1 DLLIPJSMDJCZRF-UHFFFAOYSA-N 0.000 description 1
ZGOWXOZNUNZPAV-UHFFFAOYSA-N 4-(4-heptylphenyl)benzonitrile Chemical group C1=CC(CCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 ZGOWXOZNUNZPAV-UHFFFAOYSA-N 0.000 description 1
YUYXUPYNSOFWFV-UHFFFAOYSA-N 4-(4-hexoxyphenyl)benzonitrile Chemical group C1=CC(OCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 YUYXUPYNSOFWFV-UHFFFAOYSA-N 0.000 description 1
GPGGNNIMKOVSAG-UHFFFAOYSA-N 4-(4-octoxyphenyl)benzonitrile Chemical group C1=CC(OCCCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 GPGGNNIMKOVSAG-UHFFFAOYSA-N 0.000 description 1
PBMCTXQDYLSLTP-UHFFFAOYSA-N 4-(4-pentylphenyl)-3-phenylbenzonitrile Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(C#N)C=C1C1=CC=CC=C1 PBMCTXQDYLSLTP-UHFFFAOYSA-N 0.000 description 1
RZCQJZFWJZHMPK-UHFFFAOYSA-N 4-(4-propoxyphenyl)benzonitrile Chemical group C1=CC(OCCC)=CC=C1C1=CC=C(C#N)C=C1 RZCQJZFWJZHMPK-UHFFFAOYSA-N 0.000 description 1
VFOPSGNFWHESOK-UHFFFAOYSA-N N=C=S.C1=CC=CC=C1C1=CC=CC=C1 Chemical class N=C=S.C1=CC=CC=C1C1=CC=CC=C1 VFOPSGNFWHESOK-UHFFFAOYSA-N 0.000 description 1
239000004988 Nematic liquid crystal Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000000751 azo group Chemical class [*]N=N[*] 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
QPHMMPRFMVERHL-UHFFFAOYSA-N carbamodithioic acid;n,n-diethylethanamine Chemical compound NC([S-])=S.CC[NH+](CC)CC QPHMMPRFMVERHL-UHFFFAOYSA-N 0.000 description 1
VNWKTOKETHGBQD-AKLPVKDBSA-N carbane Chemical compound [15CH4] VNWKTOKETHGBQD-AKLPVKDBSA-N 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
150000004659 dithiocarbamates Chemical class 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001810 isothiocyanato group Chemical group *N=C=S 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
230000017105 transposition Effects 0.000 description 1
125000005208 trialkylammonium group Chemical group 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
- C09K19/30—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
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- 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
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3009—Cy-Ph

Landscapes

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

JP6504084A 1983-03-30 1984-03-30 液晶シクロヘキシルベンゼン誘導体、その製法およびそれを含む液晶組成物 Granted JPS60120858A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
PL24128683A PL138287B1 (en)	1983-03-30	1983-03-30	Method of obtaining novel liquid crystal derivatives of 4-/trans-4-n-alkyl-cyclohexyl/-1-isothiocyanatebenzenes
PL241286		1983-03-30
PL241288		1983-03-30

Publications (2)

Publication Number	Publication Date
JPS60120858A JPS60120858A (ja)	1985-06-28
JPS6350342B2 true JPS6350342B2 (fr)	1988-10-07

Family

ID=20016456

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP6504084A Granted JPS60120858A (ja)	1983-03-30	1984-03-30	液晶シクロヘキシルベンゼン誘導体、その製法およびそれを含む液晶組成物

Country Status (2)

Country	Link
JP (1)	JPS60120858A (fr)
PL (1)	PL138287B1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR100544104B1 (ko) *	1998-05-26	2006-03-23	삼성에스디아이 주식회사	네마틱 액정조성물 및 이를 이용한 액정표시소자
US8252201B1 (en)	2008-11-09	2012-08-28	Military University of Technology	Liquid crystalline medium

1983
- 1983-03-30 PL PL24128683A patent/PL138287B1/pl unknown
1984
- 1984-03-30 JP JP6504084A patent/JPS60120858A/ja active Granted

Also Published As

Publication number	Publication date
PL241286A1 (en)	1984-10-08
JPS60120858A (ja)	1985-06-28
PL138287B1 (en)	1986-08-30

Publication	Publication Date	Title
JPH0662603B2 (ja)	1994-08-17	シクロヘキサンカルボニトリル誘導体
EP0126883B1 (fr)	1987-03-11	Dérivés cristallins liquides de cyclohexylbenzène, leur préparation et compositions cristallines liquides les contenant
DE3627964C2 (de)	2000-11-02	Ferroelektrische kristallin-flüssige Derivate verzweigter acyclischer chiraler alpha-Chlorcarbonsäuren, Verfahren zu ihrer Herstellung und ihre Verwendung in Gemischen für schnell schaltende Displays in der Optoelektronik
JPH0437062B2 (fr)	1992-06-18
KR100510617B1 (ko)	2006-01-27	비스알케닐비사이클로헥산및액정매질
EP0044759B1 (fr)	1984-03-21	Cristal liquide smectique de type A présentant une anisotropie diélectrique positive
EP0276067B1 (fr)	1990-12-27	Cristal liquide du type tolane
EP0170082A2 (fr)	1986-02-05	Cristaux liquides d'isothiocyanates comportant un noyau dioxane et mélanges liquides cristallins les contenant
JPS6350342B2 (fr)	1988-10-07
Gray et al.	1974	Stable, low melting nematogens of positive dielectric anisotropy for display devices
Dǎbrowski et al.	1989	New liquid-crystalline isothiocyanates with high clearing points, low viscosities and strong nematic character
CH670639A5 (fr)	1989-06-30
JPS6067477A (ja)	1985-04-17	シクロヘキシルジオキサン化合物
JPH0424336B2 (fr)	1992-04-24
JPS59141527A (ja)	1984-08-14	部分還元されたナフタリン誘導体
JPH04506817A (ja)	1992-11-26	フェニルシクロヘキサン類および液晶媒体
Osman	1982	Mesomorphic Properties of Some 4-Cyclohexyl Phenyl Esters
JPH055821B2 (fr)	1993-01-25
JPH0320378B2 (fr)	1991-03-19
Osman et al.	1983	Stable Liquid Crystals with Large Negative Dielectric Anisotropy. Part IV
JPH01308239A (ja)	1989-12-12	液晶性化合物
JPS6176480A (ja)	1986-04-18	液晶のトランス‐４‐（トランス‐５‐置換‐１，３‐ジオキサン‐２‐イル）‐シクロヘキサンカルボン酸エステル、その製造方法およびその用途
JPH0523254B2 (fr)	1993-04-02
JPS615054A (ja)	1986-01-10	シクロヘキサンカルボン酸フエネチルエステル誘導体
JPS615052A (ja)	1986-01-10	オキシ酢酸エステル誘導体