JPH0460976B2 - - Google Patents
Info
- Publication number
- JPH0460976B2 JPH0460976B2 JP58119983A JP11998383A JPH0460976B2 JP H0460976 B2 JPH0460976 B2 JP H0460976B2 JP 58119983 A JP58119983 A JP 58119983A JP 11998383 A JP11998383 A JP 11998383A JP H0460976 B2 JPH0460976 B2 JP H0460976B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- chlorine
- cyano group
- compound
- fluorine
- Prior art date
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 27
- 239000004973 liquid crystal related substance Substances 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- -1 phenyl ether compound Chemical class 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 239000000463 material Substances 0.000 description 10
- 239000004988 Nematic liquid crystal Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 230000005669 field effect Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BDDVAWDNVWLHDQ-UHFFFAOYSA-N 2-chloro-4-hydroxybenzonitrile Chemical compound OC1=CC=C(C#N)C(Cl)=C1 BDDVAWDNVWLHDQ-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 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
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- UUWSLBWDFJMSFP-UHFFFAOYSA-N bromomethylcyclohexane Chemical compound BrCC1CCCCC1 UUWSLBWDFJMSFP-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
- OPYYWWIJPHKUDZ-UHFFFAOYSA-N phenyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC1=CC=CC=C1 OPYYWWIJPHKUDZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Description
本発明は置換フエニルエーテル化合物および該
化合物を含有する組成物に関し、液晶混合物の成
分として有用な化合物およびそれを含有する液晶
組成物に関する。
液晶表示素子は液晶材料が持つ光学異方性及び
誘電異方性を利用したものであり、その表示様式
によつてTN型（ねじれネマチツク型）、DS型
（動的散乱型）、ゲスト・ホスト型、DAP型など
各種の方式に分けられ、夫々の使用に適する液晶
材料の性質は異る。いずれの液晶材料も水分、空
気、熱、光等に安定であることが必要である事は
共通しており、室温を中心として出来るだけ広い
温度範囲で液晶相を示すものが求められている。
現在の所、単一化合物ではこの様な条件を満たす
物質はなく、数種の液晶化合物や非液晶化合物を
混合して得られる液晶組成物を使用している。
本発明の化合物は、
（式中、Ｒは炭素原子１〜８個のアルキル基を表
わし、ｌ、ｍはそれぞれ０、１または２の整数を
表わし、Ｘはフツ素またはシアノ基、Ｙは塩素ま
たは水素を表わす。ただし、ｌ＝０の場合はｍ＝
１で、Ｘはシアノ基、Ｙは塩素、ｌ＝１の場合は
ｍ＝０で、Ｘはフツ素、Ｙは水素、ｌ＝２の場合
はｍ＝０で、Ｘはシアノ基、Ｙは塩素である。）
で示される置換フエニルエーテル化合物である。
また、本発明の組成物は、前記式（）で示され
る置換フエニルエーテル化合物の少くとも一種を
含有することを特徴とする。
式（）においてＸがシアノ基を、Ｙが塩素を
表わす化合物は強い正の誘電異方性を有する液晶
材料化合物である。従つて、各種ネマチツク液晶
物質は、この化合物を少量含有することにより電
界効果型セルに適用が可能となる。電界効果型セ
ルを低電圧で駆動させることは当該技術分野にお
ける重要課題の一つとされているがその為には使
用するネマチツク液晶材料のしきい値電圧を出来
るだけ下げる必要がある。本化合物はこの目的を
合致する極めて有効な液晶材料である。
式（）においてｌ＝１、ｍ＝０でＸがフツ素
原子、およびＹが水素原子である化合物は非液晶
物質で例えばアルキル基がプロピル基のものは粘
度は20℃で7cpときわめて低い為に本発明の化合
物を加えた液晶組成物の粘度を低下させる効果は
著しい。
本発明の化合物は安定なもので液晶材料に於て
使用するのに非常に有利である本発明の化合物は
相溶性にすぐれており、他の液晶化合物例えば、
シクロヘキサンカルボン酸フエニルエステル系、
安息香酸フエニルエステル系、フエニルメタジオ
キサン系、シクロヘキサンカルボン酸シクロエキ
シルエステル系、シツフ塩基系、アゾキシ系等の
他のネマチツク液晶及び液晶組合物と混合させる
事により、その液晶組成物の特性を改善する事が
できる。
この様に秀れた特徴を有する本発明の化合物は
次に示す反応によつて製造することができる。
（式中Ｒ、ｌ、ｍ、Ｘ、Ｙは前述と同じである。）
即ち上記ハロゲン化物(A)とフエノール誘導体(B)
をアルコール溶媒中にて水酸化ナトリウム等のア
ルカリ金属の水酸化物存在下にて反応させる。反
応は常圧及び室温から反応混合物の還流温度範囲
の温度で行なうことができる。反応生成物に溶剤
抽出、水洗、乾燥、再結晶等の一連の精製処理を
施すことによつて目的とする式（）の化合物を
単離することができる。
以下実施例により本発明の化合物（）の製造
方法及び応用例を詳細に説明する。
実施例 １
４−トランス（トランス−4′−ペンチルシクロ
ヘキシル）シクロヘキシルメチル−３−クロロ
−４−シアノフエニルエーテルの製造
（（）式においてＲ＝C5H11、ｌ＝２、ｍ＝
０、Ｘ＝CN、Ｙ＝Cl、である化合物）
３−クロロ−４−シアノフエノール1.54ｇ
（0.01モル）を10c.c.のエチルアルコールに溶解し、
これに更に0.84ｇ（0.015モル）の水酸化カリウ
ムを２c.c.の水に溶解したものを加え、これを加熱
還流しておき、そこへ４−トランス（トランス−
4′−ペンチルシクロヘキシル）シクロヘキシルメ
チルブロミド3.3ｇ（0.01モル）を10c.c.のエチル
アルコールに溶解した溶液を加えた。この後還流
させつつ４時間反応させた。反応終了後、室温に
まで放冷し析出した結晶をトルエン10c.c.を加え抽
出した。トルエン抽出液を10％水酸化ナトリウム
溶液で、次いで水で洗浄後無水硫酸ナトリウムを
用いて乾燥後、トルエンを留去した。残つた固型
物を10c.c.の酢酸エチルを用いて再結晶して目的物
2.73ｇを得た。
この物はネマチツク液晶物質で、融点（以下Ｃ
−Ｎ点と略記する。）は97.5℃、透明点（以下Ｎ
−Ｉ点と略記する。）は111.7℃であつた。又この
ものの元素分析値は次の通りで理論値とよく一致
した。
（C25H36OH・CIとして）
分析値（重量％） 理論値（重量％）
Ｃ 75.1 74.7
Ｈ 8.7 9.0
実施例１に準じた方法にて製造した化合物の物
性を第１表に示す。
表中で結晶−透明点をＣ−Ｉ点、誘電異方性を
Δεと略記する。表中でＮ−Ｉ点の〔 〕はモノ
トロピツクを表わす。
Δε＝ε−ε⊥、但しεは分子の長軸方向
の誘電率でε⊥は分子の長軸と垂直方向の誘電率
を表わす。Δεは次の組成のネマチツク液晶組成
物(C)に混合して外挿より求めた値である。
The present invention relates to substituted phenyl ether compounds and compositions containing the compounds, and in particular to compounds useful as components of liquid crystal mixtures and liquid crystal compositions containing the same. Liquid crystal display elements utilize the optical anisotropy and dielectric anisotropy of liquid crystal materials, and are divided into TN type (twisted nematic type), DS type (dynamic scattering type), and guest/host type depending on the display format. There are various types of liquid crystals, such as type and DAP type, and the properties of the liquid crystal materials suitable for each use are different. All liquid crystal materials have in common that they must be stable against moisture, air, heat, light, etc., and there is a need for materials that exhibit a liquid crystal phase over as wide a temperature range as possible, centered around room temperature.
At present, there is no single compound substance that satisfies these conditions, and liquid crystal compositions obtained by mixing several types of liquid crystal compounds and non-liquid crystal compounds are used. The compound of the present invention is (In the formula, R represents an alkyl group having 1 to 8 carbon atoms, l and m each represent an integer of 0, 1 or 2, X represents fluorine or a cyano group, and Y represents chlorine or hydrogen. , if l=0 then m=
1, X is a cyano group, Y is chlorine, when l=1, m=0, X is fluorine, Y is hydrogen, when l=2, m=0, X is a cyano group, Y is It is chlorine. )
This is a substituted phenyl ether compound represented by
Furthermore, the composition of the present invention is characterized by containing at least one substituted phenyl ether compound represented by the above formula (). A compound in which X represents a cyano group and Y represents chlorine in formula () is a liquid crystal material compound having strong positive dielectric anisotropy. Therefore, various nematic liquid crystal materials can be applied to field effect cells by containing a small amount of this compound. Driving a field effect cell at a low voltage is considered to be one of the important issues in this technical field, and for this purpose it is necessary to lower the threshold voltage of the nematic liquid crystal material used as much as possible. The present compound is a highly effective liquid crystal material that meets this purpose. In the formula (), compounds where l = 1, m = 0, X is a fluorine atom, and Y is a hydrogen atom are non-liquid crystal substances. For example, if the alkyl group is a propyl group, the viscosity is extremely low at 7 cp at 20 ° C. The effect of reducing the viscosity of a liquid crystal composition to which the compound of the present invention is added is remarkable. The compounds of the present invention are stable and are very advantageous for use in liquid crystal materials.The compounds of the present invention have excellent compatibility with other liquid crystal compounds, such as
Cyclohexanecarboxylic acid phenyl ester,
By mixing with other nematic liquid crystals and liquid crystal combinations such as benzoic acid phenyl ester type, phenyl metadioxane type, cyclohexane carboxylic acid cycloexyl ester type, Schiff base type, azoxy type, etc., the characteristics of the liquid crystal composition can be improved. It can be improved. The compound of the present invention having such excellent characteristics can be produced by the following reaction. (In the formula, R, l, m, X, and Y are the same as above.) That is, the above halide (A) and the phenol derivative (B)
are reacted in an alcoholic solvent in the presence of an alkali metal hydroxide such as sodium hydroxide. The reaction can be carried out at normal pressure and at a temperature ranging from room temperature to the reflux temperature of the reaction mixture. The desired compound of formula () can be isolated by subjecting the reaction product to a series of purification treatments such as solvent extraction, water washing, drying, and recrystallization. The manufacturing method and application examples of the compound () of the present invention will be explained in detail using Examples below. Example 1 Production of 4-trans(trans-4'-pentylcyclohexyl)cyclohexylmethyl-3-chloro-4-cyanophenyl ether (in formula (), R= C5H11 , l= 2 , m=
0, X=CN, Y=Cl, compound) 3-chloro-4-cyanophenol 1.54g
(0.01 mol) in 10 c.c. of ethyl alcohol,
To this was added 0.84 g (0.015 mol) of potassium hydroxide dissolved in 2 c.c. of water, heated to reflux, and added 4-trans (trans-
A solution of 3.3 g (0.01 mol) of 4'-pentylcyclohexyl cyclohexyl methyl bromide in 10 c.c. of ethyl alcohol was added. Thereafter, the mixture was reacted for 4 hours under reflux. After the reaction was completed, the mixture was allowed to cool to room temperature, and the precipitated crystals were extracted by adding 10 c.c. of toluene. The toluene extract was washed with a 10% sodium hydroxide solution and then with water, dried over anhydrous sodium sulfate, and then the toluene was distilled off. The remaining solid substance was recrystallized using 10 c.c. of ethyl acetate to obtain the desired product.
2.73g was obtained. This substance is a nematic liquid crystal material, with a melting point (hereinafter C
-Abbreviated as point N. ) is 97.5℃, clearing point (hereinafter N
-Abbreviated as point I. ) was 111.7℃. The elemental analysis values of this product were as follows, which agreed well with the theoretical values. (As C 25 H 36 OH・CI) Analytical value (weight %) Theoretical value (weight %) C 75.1 74.7 H 8.7 9.0 Table 1 shows the physical properties of the compound produced by the method according to Example 1. In the table, the crystal-clearing point is abbreviated as C-I point, and the dielectric anisotropy is abbreviated as Δε. In the table, the mark in brackets between the points NI represents monotropism. Δε=ε−ε⊥, where ε represents the dielectric constant in the direction of the long axis of the molecule, and ε⊥ represents the dielectric constant in the direction perpendicular to the long axis of the molecule. Δε is a value obtained by extrapolation after mixing with a nematic liquid crystal composition (C) having the following composition.
【表】
応用例 １（使用例１）
前述の液晶組成物(C)のネマチツク液晶温度範囲
は−５〜71.9℃である。この液晶組成物をセル厚
10μｍのTNセルに封入したものの動作しきい電
圧は1.84V、飽和電圧は2.43Vであつた。又粘度
は20℃で28cpであつた。上記の液晶組成物90重
量部に本発明の化合物の１つである実施例１に示
す４−トランス（トランス−4′−ペンチルシクロ
ヘキシル）シクロヘキシルメトキシ−３−クロロ
−４−シアノフエニルエステル10重量部を加えた
ネマチツク液晶温度範囲は−８〜78℃に広がり、
これを10μｍのセル厚のTNセルに封入したもの
の動作しきい電圧は1.56V、飽和電圧は2.10Vと
低下し、粘度は20℃で38.5cpで粘度をそれほど増
加させることなく本化合物を使用した液晶組成物
の駆動電圧を低下させ、液晶温度範囲を広げる効
果は著しい。
応用例 ２（使用例２）
応用例１と同じ液晶組成物90重量部に本発明の
化合物の１つである実施例３に示す４−〔トラン
ス−4′−エチルシクロヘキシルメトキシ〕フルオ
ロベンゼン10重量部を加えたネマチツク液晶温度
範囲は−10〜57℃になり低温側の温度領域は改善
されこれを前述の如く10μｍのセル厚のTNセル
に封入したものの動作しきい電圧は1.45V、飽和
電圧は2.08Vと低下し又粘度は20℃で22.5cpと大
幅に改善された。[Table] Application Example 1 (Use Example 1) The nematic liquid crystal temperature range of the liquid crystal composition (C) described above is -5 to 71.9°C. This liquid crystal composition has a cell thickness of
When sealed in a 10 μm TN cell, the operating threshold voltage was 1.84V and the saturation voltage was 2.43V. The viscosity was 28 cp at 20°C. To 90 parts by weight of the above liquid crystal composition, 10 parts by weight of 4-trans(trans-4'-pentylcyclohexyl)cyclohexylmethoxy-3-chloro-4-cyanophenyl ester shown in Example 1, which is one of the compounds of the present invention. The nematic liquid crystal temperature range with the addition of
When this compound was sealed in a TN cell with a cell thickness of 10 μm, the operating threshold voltage was 1.56 V, the saturation voltage was 2.10 V, and the viscosity was 38.5 cp at 20°C, making it possible to use this compound without significantly increasing the viscosity. The effect of lowering the driving voltage of the liquid crystal composition and widening the liquid crystal temperature range is remarkable. Application Example 2 (Use Example 2) Add 10 parts by weight of 4-[trans-4'-ethylcyclohexylmethoxy]fluorobenzene shown in Example 3, which is one of the compounds of the present invention, to 90 parts by weight of the same liquid crystal composition as in Application Example 1. The temperature range of the nematic liquid crystal is -10 to 57℃, and the temperature range on the low temperature side is improved.As mentioned above, when this is sealed in a TN cell with a cell thickness of 10 μm, the operating threshold voltage is 1.45V, and the saturation voltage is 1.45V. decreased to 2.08V, and the viscosity was significantly improved to 22.5cp at 20℃.
Claims (1)
わしｌ、ｍはそれぞれ０、１または２の整数を表
わし、Ｘはフツ素またはシアノ基、Ｙは塩素また
は水素を表わす。ただし、ｌ＝０の場合はｍ＝１
で、Ｘはシアノ基、Ｙは塩素、ｌ＝１の場合はｍ
＝０で、Ｘはフツ素、Ｙは水素、ｌ＝２の場合は
ｍ＝０で、Ｘはシアノ基、Ｙは塩素である。）で
示される置換フエニルエーテル化合物。 ２ 一般式 で表わされる特許請求の範囲第１項記載の化合
物。 ３ 一般式 で表わされる特許請求の範囲第１項記載の化合
物。 ４ 一般式 で表わされる特許請求の範囲第１項記載の化合
物。 ５ 一般式 （式中、Ｒは炭素原子１〜８個のアルキル基を表
わし、ｌ、ｍはそれぞれ０、１または２の整数を
表わし、Ｘはフツ素またはシアノ基、Ｙは塩素ま
たは水素を表わす。ただし、ｌ＝０の場合はｍ＝
１で、Ｘはシアノ基、Ｙは塩素、ｌ＝１の場合は
ｍ＝０で、Ｘはフツ素、Ｙは水素、ｌ＝２の場合
はｍ＝０で、Ｘはシアノ基、Ｙは塩素である。）
で示される置換フエニルエーテル化合物の少くと
も一種を含有する液晶組成物。[Claims] 1. General formula (In the formula, R represents an alkyl group having 1 to 8 carbon atoms, l and m each represent an integer of 0, 1 or 2, X represents a fluorine or cyano group, and Y represents chlorine or hydrogen. However, If l=0 then m=1
, X is a cyano group, Y is chlorine, and when l=1, m
=0, X is fluorine, Y is hydrogen, and when l=2, m=0, X is a cyano group, and Y is chlorine. ) Substituted phenyl ether compound represented by 2 General formula The compound according to claim 1, which is represented by: 3 General formula The compound according to claim 1, which is represented by: 4 General formula The compound according to claim 1, which is represented by: 5 General formula (In the formula, R represents an alkyl group having 1 to 8 carbon atoms, l and m each represent an integer of 0, 1 or 2, X represents fluorine or a cyano group, and Y represents chlorine or hydrogen. , if l=0 then m=
1, X is a cyano group, Y is chlorine, when l=1, m=0, X is fluorine, Y is hydrogen, when l=2, m=0, X is a cyano group, Y is It is chlorine. )
A liquid crystal composition containing at least one substituted phenyl ether compound represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11998383A JPS6013731A (en) | 1983-07-01 | 1983-07-01 | Substituted phenyl ether compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11998383A JPS6013731A (en) | 1983-07-01 | 1983-07-01 | Substituted phenyl ether compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6013731A JPS6013731A (en) | 1985-01-24 |
| JPH0460976B2 true JPH0460976B2 (en) | 1992-09-29 |
Family
ID=14774999
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11998383A Granted JPS6013731A (en) | 1983-07-01 | 1983-07-01 | Substituted phenyl ether compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6013731A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH660003A5 (en) * | 1984-04-16 | 1987-03-13 | Merck Patent Gmbh | ANISOTROPE COMPOUNDS AND FK MIXTURES WITH THESE. |
| JPH0662476B2 (en) * | 1984-09-04 | 1994-08-17 | チッソ株式会社 | Liquid crystalline compound having methyleneoxy group and composition thereof |
| JPS61282328A (en) * | 1985-06-10 | 1986-12-12 | Chisso Corp | Cyclohexane derivative |
| DE3887084D1 (en) * | 1987-11-06 | 1994-02-24 | Hoffmann La Roche | Halogenated benzene derivatives. |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5780485A (en) * | 1980-11-07 | 1982-05-20 | Daido Steel Co Ltd | Controlling method in treatment for melting industrial waste or the like |
-
1983
- 1983-07-01 JP JP11998383A patent/JPS6013731A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5780485A (en) * | 1980-11-07 | 1982-05-20 | Daido Steel Co Ltd | Controlling method in treatment for melting industrial waste or the like |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6013731A (en) | 1985-01-24 |
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