![]() Derivative of 1,3-dioxane as component of liquid-crystal nematic composition for optronic apparatus
专利摘要:
The invention relates to liquid crystal nematic substances based on new derivatives of 1,3-dioxanes in electro-optical components, which are used, for instance, as displays in electronic clocks and computer systems. The subject of the invention is nematic liquid crystal substances with favorable properties concerning melting and clear temperatures, stability against thermal stress and electrical fields, low viscosity and low threshold voltage. It was found that liquid crystal 2,5-di-substituted cyclohexyl derivatives of 1,3 dioxanes, having the general formula <IMAGE> <IMAGE> <IMAGE> <IMAGE> <IMAGE> <IMAGE> R1=CnH2n+1; CnH2n+1O; CnH2n+1COO; CN; NO2; F; Cl; Br and R2=CnH2n+1 with n+1 to 9 are suitable for use in electro-optical components. 公开号:SU1493651A1 申请号:SU823480179 申请日:1982-02-18 公开日:1989-07-15 发明作者:Демус Дитрих;Зашке Хорст;Дереш Сильвия;Форбродт Ханс-Маттиа 申请人:Феб Верк Фюр Фернзеэлектроник В Феб Комбинат Микроэлектроник (Инопредприятие); IPC主号:
专利说明:
This invention relates to chemicals derived from 1,3-dioxane of the general formula .CN-f | 3 r Cnl4ml where ,,, - С, С5, С-alkyl, which can be used as a component of the liquid crystal mixture. The purpose of the invention is to obtain new derivatives of dioxane, which increase the bleaching temperature of the liquid-crystalline mixture. Example 1.a) Preparation of 4-alkylcyclohexyl malonic acid di-ethyl ester. Out of 28.9 g (1 mol) of sodium and 500 MJ. absolute alcohol is prepared solution of sodium alcoholate. 160 g (1 mol) of malonic acid ester DIETH 0101-0 and then 1.05 mol of 4-alkylcyclohexyl bromide (cis-trans mixture) are added dropwise to the still hot solution of the alcoholate. While stirring, the mixture is heated for 16 hours, after which, under stirring in a weak vacuum, the main „/ The amount of alcohol. After OHLSL.RNII, so many ice were added to the ice that the precipitated salt dissolved, the organic phase separated in a separatory funnel, treated with ether, the combined organic phases dried over and distilled under vacuum for 20 seconds in a Vigro The output of compounds A is presented in table. one . b) Preparation of trans-2- (A-alkylcyclohexyl) propan-1,3-diol. In a three-necked flask with a capacity of 2 liters, 21 g (0.55 mol) of LiAlH are placed in 1 l of absolute ether. While cooling with ice and stirring, a mixture of 0.5 mol of 4-alkylcyclohexyl malonic ester mixed with the same volume of ether was added dropwise. Then it is stirred for 2 hours. After that, the solution is carefully mixed with 10 ml of ice water and the precipitate formed consisting of aluminum and lithium hydroxides is dissolved by adding 700 ml of 10% sulfuric acid. The organic phase is separated and the aqueous layer is extracted twice with ether. After washing with sodium bicarbonate 2.5% and water, dried over, remove the ether in vacuo and recrystallize repeatedly from hexane. The output of compounds B is presented in table. 2 c) Preparation of cyclohexyl-substituted 1-dioxane. The proposed substances are obtained by condensation of 2-substituted propane-1,3-diols (B) with p-cyanbenzaldehyde, respectively, according to the following procedure: 0.01 mol (I) and 0.011 mol (II) after adding 100 mg of p-toluene sulfonic acid while stirring and with azeotropic water separation, they are heated until the end of the reaction (binding the reaction water on suitable molecular sieves added to the reaction mixture results in the same yields as obtained by working with azeotropic distillation of water), Upon completion of the reaction, the cooled reaction, the mixture is washed with a 2% sodium bicarbonate solution and water, dried on NajS04, the solvent is distilled off and the residue is recrystallized from methanol. Outputs and properties of substances are presented in 1pl.Z, Example 2: The substances according to the invention in the viiiiup are better with change in electro-optical elements of the following types: liquid crystal layer is between two glass plates, inside there are transparent electrodes, for example, from SnOj, which are kept at a constant distance of 5-30 / m m by means of holders. or grout in a certain direction) the electrodes first of all become anisotropic and rotate relative to each other by 90. With this arrangement of crossed polarizers, light penetrates. After applying an electric field, the voltage exceeds the threshold voltage 1J, the element becomes opaque. In such an element of the type Dreh7elle no Sehadt / Helf rich the following mixture is introduced with a positive dielectric anisotropic CN 26 mold thirty 14 mol% (A) 60 mol% Characteristics of the mixture at. 20 C. The threshold voltage U is 0.8V / 500 Hz, the layer thickness is d - 1А, 5, 1 - 1А90 (He; .. ,, 170 fw with at you to l Hb tn, 18-19 s; t „, 73 and 7 ° C. The proposed compound is a clarification temperature. So, if compound A is introduced into 45 amount And the formula to the famous Soedis .n 0 which is taken into the mixture has both the pure that well known 82%, 87 ° C, substance has quantity at that time oce 43 C. 55 A mixture consisting of known compounds, mol.%: (T) / -0, 1/4 fn D) S If PMGSY, (OP:) À1PLN M l Cl f; iH4PHHr 25 (IT) (1) ()) B ukl, com.pngchestl g Bringing instead of sorlyium (V I) a derivative of formula (I) in the quantity 25 (III) 5% has Tpl -9 f. T os at Po, Lp 200 (1) 0 at 20 ° C. 00 (lic.i BUT bykd C, H, / - l C9Hi9-0-; - C5Hi3 3.15 (V) 6.8 5 (IV) 10 F (rmula and h. Derivative 1,3-dioxlia-f1) rmula () / Y15 r-n-xt n.), pm Sbn, s q. ..,. . ".. where is C, H ,,, - C„ C ,, C, is alkyl, It has T l-A C, Tpr with as a component of vein-crystalline 1.1 and Cp |, 750 750 (is, cb 20 of a nematic mixture for an element of 280 fU with at 20 C. tomoptic devices. wasp 00 (lic.i BUT bykd () / Th r-n-xt n.), pm nematic mixture tomoptic devices. Table 1 Note: eK: solid crystalline phase, S, - smectic phase, N - nematic phase, I - liquid-isotropic phase. Table 3
权利要求:
Claims (1) [1] Note: K ·; solid crystalline phase, 5 # - smectic phase, N nematic phase, X - liquid-aootropic phase. Compiled by M. Merkulova Editor A. Ogar Tehred L. Oliynyk Proofreader L. Patay. Order 5945 Circulation 631 Subscription VNIIL of the State Committee for Inventions and Discoveries at the Rent of the USSR 113035, Moscow, Zh-35, 4/5 Raushskaya nab. Production and Publishing Combine "Patent" Uzhgorod, st. Gagarin, 101
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同族专利:
公开号 | 公开日 JPS5916886A|1984-01-28| FR2511696A1|1983-02-25| FR2511696B1|1986-12-26| US4486332A|1984-12-04| GB2105717B|1985-11-20| CH653331A5|1985-12-31| GB2105717A|1983-03-30| DE3227916A1|1983-03-10| JPH02355B2|1990-01-08| DD207308A3|1984-02-22| HU192108B|1987-05-28| HUT36112A|1985-08-28| DE3227916C2|1989-08-03|
引用文献:
公开号 | 申请日 | 公开日 | 申请人 | 专利标题 US2307894A|1939-12-14|1943-01-12|Standard Oil Dev Co|Hydrolysis of meta-dioxanes| US4344856A|1979-12-12|1982-08-17|VEB Werk fur Fernsehelektronik Berlin im VEB Kombinat Mikroelektronik|Crystalline-liquid substituted 1,3-dioxanes and mixtures containing them| DD139867B1|1978-12-13|1982-04-28|APPLICATION OF LIQUID CRYSTALS| DD139852B1|1978-12-13|1982-03-10|Horst Zaschke|PROCESS FOR PREPARING CRYSTALLINE-FLUID SUBSTITUTED 1,3-DIOXANES| DE2944905C2|1978-12-13|1988-12-22|Veb Werk Fuer Fernsehelektronik Im Veb Kombinat Mikroelektronik, Ddr 1160 Berlin, Dd| US4273929A|1979-02-05|1981-06-16|Hoffmann-La Roche Inc.|Heterocyclic compounds| FR2450863A1|1979-03-05|1980-10-03|Timex Corp| -2 DIOXANNES-1,3,5-SUBSTITUES USEFUL AS LIQUID CRYSTALS AND ELECTRO-OPTICAL VISUALIZATION DEVICE CONTAINING THEM| US4322354A|1979-03-05|1982-03-30|Timex Corporation|5-Substituted-2--1,3,-dioxanes| GB2067586B|1979-12-28|1984-10-10|Chisso Corp|Nematic liquid crystal compositions for display apparatus| US4298528A|1980-03-28|1981-11-03|Timex Corporation|Cyclohexyl-dioxane liquid crystalline compounds| US4323473A|1980-03-28|1982-04-06|Timex Corporation|Cyclohexyl cyclohexyl dioxane liquid crystalline compounds and admixture containing same| US4323504A|1980-03-28|1982-04-06|Timex Corporation|Cyclohexyl cyclohexyl dioxane liquid crystalline compounds and admixture containing same| JPS642112B2|1980-05-23|1989-01-13|Chisso Corp| US4356104A|1980-12-03|1982-10-26|Timex Corporation|4-Substituted phenyl 4-benzoates| US4325830A|1980-12-24|1982-04-20|Timex Corporation|Three ring dioxane liquid crystalline compounds| EP0056501B1|1981-01-19|1984-05-02|MERCK PATENT GmbH|Liquid crystal mixture|DE2944905C2|1978-12-13|1988-12-22|Veb Werk Fuer Fernsehelektronik Im Veb Kombinat Mikroelektronik, Ddr 1160 Berlin, Dd| CH655502B|1982-02-17|1986-04-30| DE3207114A1|1982-02-27|1983-09-08|Merck Patent Gmbh, 6100 Darmstadt|1,3-DIOXANES| EP0107759B1|1982-08-26|1992-12-16|MERCK PATENT GmbH|Cyclohexane derivatives and their use as components for liquid crystals| DE3306960A1|1983-02-28|1984-08-30|Merck Patent Gmbh, 6100 Darmstadt|TETRAHYDROPYRANE| EP0122389B1|1983-03-16|1987-08-05|F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft|Liquid crystal components having an alkenyl chain| US4565425A|1983-03-16|1986-01-21|Hoffmann-La Roche Inc.|Liquid crystals| DD215563A1|1983-04-29|1984-11-14|Univ Halle Wittenberg|CRYSTALLINE - FLUID MIXTURES FOR THE GUEST HOST EFFECT| DE3322982A1|1983-06-25|1985-01-03|Merck Patent Gmbh, 6100 Darmstadt|1,4-DIOXANES| DD245894A1|1983-09-30|1987-05-20|Dietrich Demus|CRYSTALLINE-LIQUID NEMATIVE MIXTURES| DE3405914A1|1984-02-18|1985-08-22|Merck Patent Gmbh, 6100 Darmstadt|LIQUID CRYSTAL LINKS| DE3522510A1|1984-07-11|1986-01-16|VEB Werk für Fernsehelektronik im VEB Kombinat Mikroelektronik, DDR 1160 Berlin|CRYSTALLINE-LIQUID 2-SUBSTITUTED-5-1,3-DIOXANES| DE3534106A1|1984-10-16|1986-04-17|VEB Werk für Fernsehelektronik im VEB Kombinat Mikroelektronik, DDR 1160 Berlin|CRYSTALLINE-LIQUID, 2,5-DISUBSTITUTED-TRANS-1,3-DIOXADECALINE| JPS61233689A|1985-03-22|1986-10-17|Merck Patent Gmbh|Heterocyclic boron compound| JPS6210083A|1985-07-04|1987-01-19|Chisso Corp|Pyrimidinyldioxane derivative| JPH03200782A|1989-05-31|1991-09-02|Seiko Epson Corp|1,3-dioxane derivative and liquid crystal composition using 1,3-dioxane derivative| EP0400861A1|1989-05-31|1990-12-05|Seiko Epson Corporation|1,3-dioxane derivative and liquid crystal composition incorporating the same| US5354502A|1989-10-12|1994-10-11|Seiko Epson Corporation|1,3-dioxane derivative and liquid crystal compositions containing it| DE59010243D1|1989-12-19|1996-05-02|Hoffmann La Roche|Halophenyl substituted dioxanes| GB9220189D0|1992-09-24|1992-11-04|Central Research Lab Ltd|Dioxane derivatives| US5667721A|1995-03-16|1997-09-16|Rolic Ag|Liquid crystalline di-1,3-dioxane derivatives| DE102010005038A1|2009-02-14|2010-08-19|Lofo High Tech Film Gmbh|Optical compensation films|
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申请号 | 申请日 | 专利标题 DD81232636A|DD207308A3|1981-08-18|1981-08-18|APPLICATION OF NEW CRYSTALLINE FLUID NEMATIVE SUBSTANCES| 相关专利
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