JPS6028954A - 4-alkanoyloxybenzoic acid-4-substituted phenyl esters - Google Patents
4-alkanoyloxybenzoic acid-4-substituted phenyl estersInfo
- Publication number
- JPS6028954A JPS6028954A JP13635183A JP13635183A JPS6028954A JP S6028954 A JPS6028954 A JP S6028954A JP 13635183 A JP13635183 A JP 13635183A JP 13635183 A JP13635183 A JP 13635183A JP S6028954 A JPS6028954 A JP S6028954A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- acid
- compound
- liquid crystal
- branched
- 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.)
- Pending
Links
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title description 3
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- -1 4-substituted phenol Chemical class 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 241000251468 Actinopterygii Species 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract description 4
- 239000008096 xylene Substances 0.000 abstract description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 abstract description 3
- 239000004327 boric acid Substances 0.000 abstract description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 3
- 150000002148 esters Chemical class 0.000 abstract description 3
- 125000005274 4-hydroxybenzoic acid group Chemical group 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 abstract 2
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- ZNPSUQQXTRRSBM-UHFFFAOYSA-N 4-n-Pentylphenol Chemical compound CCCCCC1=CC=C(O)C=C1 ZNPSUQQXTRRSBM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 210000002858 crystal cell Anatomy 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- VNVPODULZFZFRC-UHFFFAOYSA-N (4-pentylphenyl) 4-hydroxybenzoate Chemical compound C1=CC(CCCCC)=CC=C1OC(=O)C1=CC=C(O)C=C1 VNVPODULZFZFRC-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 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
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は４−アルカノイルオキシ安息香酸−４−置換フ
ェニルエステル類及びその組成物に関し、より具体的に
は新規液晶物質もしくは液晶性＃！Ｊｆｉ及びそれを含
有する液晶組成物に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to 4-alkanoyloxybenzoic acid-4-substituted phenyl esters and compositions thereof, and more specifically to novel liquid crystal substances or liquid crystal #! The present invention relates to Jfi and a liquid crystal composition containing the same.
液晶を使用した表示素子は時計、電卓など（（広く使用
されている。この液晶表示素子は液晶物質の光学異方性
及び銹電異方性管利用したもので、液晶相にはネマチッ
ク、夜晶相、スメクチック液晶相、コレステリック液晶
相があり、そのうちネマチック液晶を利用したものが最
も広く実用化されている。即ちそれらにはＴＮ （ねじ
れネマチック）型、ＤＳ型（動的散乱型）、ゲスト・ホ
ストＷ、ＤＡＰ型などがあり、それぞれに使用される液
晶で液晶相を示すものが望ましく、現在のところ単一物
質でその様な条件をみたす様な物質はなく、数種の液晶
物置又は非液晶物質を混合して実用に供している。これ
らの物質は水分、光、熱、空気等に対しても安定である
ことを要求され、更に表示素子を駆動させる必要なしき
い電圧、飽和電圧がなるべく低いこと、又応答速度を早
くするためには粘度が出来るだけ低いことが望ましい。Display elements using liquid crystals are widely used in watches, calculators, etc. This liquid crystal display element utilizes the optical anisotropy of the liquid crystal material and the galvanic anisotropy tube, and the liquid crystal phase has nematic, night, etc. There are three types: crystal phase, smectic liquid crystal phase, and cholesteric liquid crystal phase. Among them, those using nematic liquid crystal are the most widely used. Namely, they include TN (twisted nematic) type, DS (dynamic scattering type), and guest liquid crystal.・There are host W, DAP types, etc., and it is desirable that the liquid crystal used for each exhibits a liquid crystal phase.Currently, there is no single substance that satisfies such conditions, and several types of liquid crystal storage or Non-liquid crystal substances are mixed and put into practical use.These substances are required to be stable against moisture, light, heat, air, etc., and also have a high threshold voltage and saturation voltage necessary to drive the display element. It is desirable that the viscosity be as low as possible, and that the viscosity be as low as possible in order to increase the response speed.
本発明の目的はこの様な用途に適した新規な液晶化合物
もしくは液晶性化合物を提供することにある。An object of the present invention is to provide a novel liquid crystal compound or liquid crystalline compound suitable for such uses.
即ち、本発明は一般式
％式％
（上式中Ｒは炭素数３〜ｌＯの分校アルキル基、Ｒ′は
炭素数１〜１０の直鎖または分枝のアルキル基またはア
ルコキン基を示す。）
で表わされる４−アルカノイルオキク安息香酸−４−置
換フェニルエステル類及びそれを含有することを特徴と
する液晶組成物でおる。That is, the present invention is based on the general formula % (in the above formula, R represents a branched alkyl group having 3 to 10 carbon atoms, and R' represents a linear or branched alkyl group or an alkoxy group having 1 to 10 carbon atoms). 4-alkanoyl oxicbenzoic acid-4-substituted phenyl esters represented by the formula and a liquid crystal composition containing the same.
本発明の化合物の一つである４−（３−メチル）ペンタ
ノイルオキ７安息香酸−４−ペンチルフェニルニステル
ハ融点が２９．５℃でネマチック−透明点（以下ムーエ
点と略記する）は４５．０℃と低いが低粘性であるため
この化合物を添加することによって、大幅に粘度を増加
させることなく、低電圧で駆動することができる液晶表
示素子を作ることが可能である。One of the compounds of the present invention, 4-(3-methyl)pentanoylox7benzoic acid-4-pentylphenylnister, has a melting point of 29.5°C and a nematic clearing point (hereinafter abbreviated as the Moue point) of 45.0. By adding this compound, it is possible to create a liquid crystal display element that can be driven at low voltage without significantly increasing the viscosity, since it has a low viscosity at a low temperature of .degree.
つぎに本発明の化合物の製造法を示す。Next, a method for producing the compound of the present invention will be described.
Ｗ、 Ｗ、 ＩＩＤＷｒａｎＣｆ３ＨＪｒ 、 （’ｒ
ｅｔｒａｈｅａｒｏｎ ′Ｌ８ｔｔｅｒｅ、 ３４５３
（１９’ｉ’ｌ） ’）の示す方法に従って４−ヒト日
中７安息香酸（化合物（１））とＲ′によるアルキル基
またはアルコキシ基を有する４−置換フェノール（化合
物（１）をキシレン中でホウ酸と硫酸を触媒にして反応
させ、４−ヒト日中７安息香酸−４−置換フエニルエス
テル（化合物（ｍＶ）を製造する。ついでこれをピリジ
ン存在下で対応するＲによるアルキル基を有する分校カ
ルボン酸クロリド（化合物（Ｖ））と反応させ目的の４
−アルカノイルオキシ安息香酸−＊−置！フェニルエス
テル（化合物（１））を製造することができる。以上を
化学式で示すと欠の様になる。W, W, IIDWranCf3HJr, ('r
etrahearon'L8ttere, 3453
(19'i'l) '), 4-human dibenzoic acid (compound (1)) and 4-substituted phenol having an alkyl group or alkoxy group by R' (compound (1)) were mixed in xylene. The reaction is carried out using boric acid and sulfuric acid as catalysts to produce 4-substituted phenyl ester of 4-human dibenzoic acid (compound (mV)).This is then reacted with the corresponding alkyl group by R in the presence of pyridine. react with a branched carboxylic acid chloride (compound (V)) having the desired 4
-Alkanoyloxybenzoic acid-*-place! Phenyl ester (compound (1)) can be produced. When the above is expressed as a chemical formula, it looks like a missing part.
（１）
（上式中Ｒ及びＲ′は前記Ｖこ同じである。）以下実施
例により本発明の化合物につき更に詳細に説明する。(1) (In the above formula, R and R' are the same as V above.) The compounds of the present invention will be explained in more detail with reference to Examples below.
実施例１
４−（３−メチル）ペンタノイルオキシ安息香酸−４−
ペンチルフェニルエステルの製造（化合物び・
（＋）ｌｃオイテＲｙ）Ｅ Ｃ２Ｈ６ＣＨ２ＣＥ［２−
、Ｒ’ カＣ６Ｈ１ｌ テｈるもの）
（１） ４−ヒト日中７安息香酸−４−ペンチルフェニ
ルエステル（化合物（２））の製造
４−ヒト日中７安息香酸（化合物（１））ｚｏ２ｔと４
−ペンチルフェノール（化合物（１）） ４ｖｘｔを５
１の三ツロフラスコに入れ、攪拌機及び水分定量器をつ
けた後、キシレン２１を加え、ホウ酸９，５＃、硫酸１
４．８＃を加えて攪拌しながら加熱還流した。還流は水
分定量器に水がもはや留出しなくなるまで（２０時間）
続行した。Example 1 4-(3-methyl)pentanoyloxybenzoic acid-4-
Manufacture of pentylphenyl ester (compound bi- (+)lc oieteRy)E C2H6CH2CE[2-
, R' KaC6H1l) (1) Production of 4-human 7-benzoic acid-4-pentylphenyl ester (compound (2)) 4-human 7-benzoic acid (compound (1)) zo2t and 4
-pentylphenol (compound (1)) 4vxt to 5
Put it in the Mitsuro flask from step 1, attach a stirrer and a water meter, add 21 xylene, 9.5 # of boric acid, 1 # of sulfuric acid.
4.8# was added and heated to reflux while stirring. Reflux until no more water distills into the water meter (20 hours)
Continued.
反応終了後減圧下にてキシレンを１．８１留去し、室温
まで冷却して析出した結晶をＦ別、トルエンで洗滌シ過
剰の４−ペンチルフェノールを除去した。この結晶をエ
タノール８水＝３＝２の混合溶媒１ｔで再結晶して４−
ヒドロキシ安息香酸−４−ペンチルフェニルエステル（
化合物ＱＶ））２１２ｔを得た。融点は１４４〜１４６
℃であった。After the reaction was completed, 1.81 g of xylene was distilled off under reduced pressure, and the precipitated crystals were cooled to room temperature, separated from F, and washed with toluene to remove excess 4-pentylphenol. This crystal was recrystallized with 1 t of mixed solvent of ethanol, 8 water = 3 = 2, and 4-
Hydroxybenzoic acid-4-pentylphenyl ester (
Compound QV))212t was obtained. Melting point is 144-146
It was ℃.
（２） エステル化
前述の４−ヒドロキシ安息香酸−４−ベンチルフェニル
エステル（化合物（ＩＶ）） ４，３ ｔ （０，０１
５モル）をピリ９フ１０ｍ／ＩｃＩ？？解し、３−メチ
ルヘンタノイルクロリド（化合物（Ｖ））２．３ ＃
＜ ｏ、ｏ１７モル）を振り混ぜながら力１１えた。反
応後−晩装置しだ酸トルエン５０ｍｊを加え水にあけた
。屑状に分離したトル１７層を６Ｎ塩酸、２Ｎ水酸化ナ
トリウム溶液次いで水で洗滌し、最後に無水硫酸ナトリ
ウムを用いて乾燥した。次いでトルエンを減圧下にて留
去して油状物を慴、それをエタノールで再結晶し目的物
である４−（３−メチル）ペンタノイルオキ７安息香酸
−４−ペンチルフェニルエｘｆル２，３ｆ （０，００
６０モル）を得た。収率は４−ヒドロ＋ｌｉｊ息香酸−
４−ペンチルフェニルエステルから計算して４０俤であ
った。このものの融点は２９．５℃Ｎ−工点１よ４５．
Ｏ’Ｃであった。(2) Esterification 4-hydroxybenzoic acid-4-bentylphenyl ester (compound (IV)) 4,3 t (0,01
5 mol) to pyri9f10m/IcI? ? 3-methylhentanoyl chloride (compound (V)) 2.3 #
The strength was increased to 11 while shaking and mixing. After the reaction, 50 mj of toluene was added to the apparatus overnight and poured into water. The 17 layers separated into scraps were washed with 6N hydrochloric acid, 2N sodium hydroxide solution, then water, and finally dried using anhydrous sodium sulfate. Next, toluene was distilled off under reduced pressure to obtain an oily substance, which was recrystallized with ethanol to obtain the target product, 4-(3-methyl)pentanoylox7benzoic acid-4-pentylphenylexf2,3f ( 0,00
60 mol) was obtained. The yield is 4-hydro+lijzoic acid-
It was calculated from 4-pentylphenyl ester to be 40 yen. The melting point of this product is 29.5℃N-Working point 1 to 45.
It was O'C.
実施例２〜４
実−施例１に準じた方法で、４−ヒドロギア安息香酸−
＋−アルキルフェニルニスアル（化合物（Ｉｖ））０．
０１４モルと分枝カルボン酸クロリド（化合物（Ｖ））
０．０１７モルから（１）式の化合物を製造した。これ
らの結果を実施例１の結果と共に第１表に示す。Examples 2 to 4 In a method similar to Example 1, 4-hydrogiabenzoic acid
+-alkylphenylnisal (compound (Iv)) 0.
014 mol and branched carboxylic acid chloride (compound (V))
A compound of formula (1) was produced from 0.017 mol. These results are shown in Table 1 together with the results of Example 1.
第１表
実施例５（応用例）
なる組成の液晶混合物い）のＮ−１点は７２．０℃、粘
度は２０℃で２’ｉ’、８０１）、誘電異方性値（以下
Δεと略記する）は１１，６、光学異方性値（以下Δｎ
と略記する）は０．１４０である。液晶セルとして酸化
ケイ素をコーティングしラビング処理した酸化スズ透明
電極を有する基板を対向させて組立てた電極間距離がｔ
ｏ／’ｍ のものを用意し、前記液晶組成物忰）を封入
して液晶セルとし、２０℃でその特性を６１１１定した
ところ、しきい電圧（以下ｖｔｈと略記する）ｌｄｌ、
７６Ｖ、飽和電圧（以下Ｖａａｔと略記する）は２．４
０Ｖであった。Table 1 Example 5 (Application example) The N-1 point of the liquid crystal mixture (I) with the following composition is 72.0°C, the viscosity is 2'i' at 20°C, 801), and the dielectric anisotropy value (hereinafter referred to as Δε). ) is 11,6, and the optical anisotropy value (hereinafter Δn
) is 0.140. The distance between electrodes assembled by assembling substrates having tin oxide transparent electrodes coated with silicon oxide and rubbed with silicon oxide as a liquid crystal cell is t.
o/'m was prepared, the liquid crystal composition 1) was sealed to form a liquid crystal cell, and its characteristics were determined at 20°C. As a result, the threshold voltage (hereinafter abbreviated as vth) ldl,
76V, saturation voltage (hereinafter abbreviated as Vaat) is 2.4
It was 0V.
この液晶組成物９０Ｊｋ！’Ｊに本発明の実施例１の４
−（３−メチル）ペンタノイルオキ７安息香酸−４−ペ
ンチルフェニルエステル１０ｉ量俤を加え？１組成物の
Ｎ−１点＃′ｉ６９．５℃、粘度は２０℃で２８．７Ｃ
ｐ１Δεは１０．７ 、Δｎ Ｉｄ Ｏ，１３０とな９
、Ｖ’ｔｈカ１，５７Ｖ、 Ｖｓａｔカ２，１ｇＶト駆
動駆動全圧下させることができた。This liquid crystal composition 90Jk! 'J to Example 1-4 of the present invention
Add 10i of -(3-methyl)pentanoylox7benzoic acid-4-pentylphenyl ester? N-1 point #'i of 1 composition 69.5℃, viscosity is 28.7C at 20℃
p1Δε is 10.7, Δn Id O, 130 and 9
, V'th was 1,57V, and Vsat was 2,1gV.
実施例６〜８（応用例）
実施例５と同じ組成の液晶混合物（Ａ）９０重量％に、
本発明の実施例２〜４の化合物をそれぞれについて１０
重Ｉｋ俤溶解した組成物について、同様に測定した結果
を実施例δと共に第２表に示す。Examples 6 to 8 (Application example) 90% by weight of the liquid crystal mixture (A) having the same composition as in Example 5,
10 for each of the compounds of Examples 2 to 4 of the present invention.
The results of similar measurements for compositions in which heavy Ik was dissolved are shown in Table 2 together with Example δ.
Claims (2)
炭素数１〜１０の直鎖または分枝のアルキル基またはア
ルコキシ基を示す。） で表わされる４−アルカノイルオキシ安息香酸−４−［
換フェニルエステル魚。(1) 4- represented by the general formula (in the above formula, R represents a branched alkyl group having 3 to 10 carbon atoms, and R' represents a linear or branched alkyl group or alkoxy group having 1 to 10 carbon atoms). Alkanoyloxybenzoic acid-4-[
Translated phenyl ester fish.
炭素数１〜１０の直鎖またけ分枝のアルキル基またはア
ルコキシ基を示す。 で表わされる４−アルカノイルオキシ安息香酸−４−置
換フェニルエステル類を含有することを特徴とする液晶
組成物。(2) General formula % Formula % (In the above formula, R represents a branched alkyl group having 3 to 10 carbon atoms, and R' represents a linear or branched alkyl group or alkoxy group having 1 to 10 carbon atoms. A liquid crystal composition comprising a 4-alkanoyloxybenzoic acid-4-substituted phenyl ester.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13635183A JPS6028954A (en) | 1983-07-26 | 1983-07-26 | 4-alkanoyloxybenzoic acid-4-substituted phenyl esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13635183A JPS6028954A (en) | 1983-07-26 | 1983-07-26 | 4-alkanoyloxybenzoic acid-4-substituted phenyl esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6028954A true JPS6028954A (en) | 1985-02-14 |
Family
ID=15173154
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13635183A Pending JPS6028954A (en) | 1983-07-26 | 1983-07-26 | 4-alkanoyloxybenzoic acid-4-substituted phenyl esters |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6028954A (en) |
-
1983
- 1983-07-26 JP JP13635183A patent/JPS6028954A/en active Pending
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