JPS61122250A - Liquid crystal ester compound - Google Patents
Liquid crystal ester compoundInfo
- Publication number
- JPS61122250A JPS61122250A JP59245532A JP24553284A JPS61122250A JP S61122250 A JPS61122250 A JP S61122250A JP 59245532 A JP59245532 A JP 59245532A JP 24553284 A JP24553284 A JP 24553284A JP S61122250 A JPS61122250 A JP S61122250A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- benzoic acid
- formula
- acid
- chloride
- 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.)
- Granted
Links
- -1 ester compound Chemical class 0.000 title claims abstract description 20
- 239000004973 liquid crystal related substance Substances 0.000 title description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000005711 Benzoic acid Substances 0.000 claims abstract description 14
- 235000010233 benzoic acid Nutrition 0.000 claims abstract description 14
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 239000007788 liquid Substances 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 39
- 150000001875 compounds Chemical class 0.000 abstract description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 8
- 239000000463 material Substances 0.000 abstract description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 6
- 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 abstract description 5
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 abstract description 5
- 150000001299 aldehydes Chemical class 0.000 abstract description 4
- 230000001747 exhibiting effect Effects 0.000 abstract description 4
- 239000004990 Smectic liquid crystal Substances 0.000 abstract description 3
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 239000012286 potassium permanganate Substances 0.000 abstract description 2
- 229960004365 benzoic acid Drugs 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 229910000108 silver(I,III) oxide Inorganic materials 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 238000001308 synthesis method Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 6
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methyl-1-butanol Substances CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- QPRQEDXDYOZYLA-YFKPBYRVSA-N (S)-2-methylbutan-1-ol Chemical compound CC[C@H](C)CO QPRQEDXDYOZYLA-YFKPBYRVSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005621 ferroelectricity Effects 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009466 transformation Effects 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】
〔産業上の利用分野〕
本発明は電気光学的素子に利用するカイラルスメクテイ
ックＣ（以下ＳｍＣ−表記する）相を示す液晶性エステ
ル化合物に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a liquid crystalline ester compound exhibiting a chiral smectic C (hereinafter referred to as SmC) phase and used in electro-optical elements.
電気光学素子に広く利用されて℃・る液晶材料の多（は
ネマティック液晶であるが、最近Ｓ ｍ Ｃ’相の強誘
電性を利用した素子が注目されている（福田敦夫、竹添
秀男、自然 ７号（１９８３）、３６）。Most of the liquid crystal materials widely used in electro-optical devices are nematic liquid crystals, but recently devices that utilize the ferroelectricity of the S m C' phase have attracted attention (Atsuo Fukuda, Hideo Takezoe, Nature No. 7 (1983), 36).
この素子は応答速度の速いことを特徴とするものであり
、液晶プリンターなどへの応用が考えられているが、こ
れに用いる液晶材料としては小数の物質しか知られてお
らず、より実用性のある液晶物質の開発が望まれている
。This element is characterized by a fast response speed, and is being considered for application in liquid crystal printers, etc. However, only a small number of substances are known as liquid crystal materials for use in this device, and it is difficult to find practical applications. It is desired to develop a certain liquid crystal material.
これまでに比較的多く研究されているのは、化合物の構
造中にシッフ基（−Ｎ＝ＣＨ−）を有するものである（
Ａ、ＨａｌＩｔｓｂｙ ｅｔ、ａｔ、、ＭａｉｌＣｒｙ
ｓｔ Ｌｉｑ Ｃｒｙｓｔ、８２（１９８２）、６１）
。Compounds that have been studied relatively extensively so far have a Schiff group (-N=CH-) in their structure (
A,HalItsby et,at,,MailCry
st Liq Cryst, 82 (1982), 61)
.
しかしながらこの系の化合物は化学的安定性に劣り、有
色であるという難点があり、ネマティック液晶材料の場
合と同様にいずれはエステル系の材料が主流になるもの
と思われる。However, this type of compound has disadvantages in that it is inferior in chemical stability and is colored, and it is thought that ester-based materials will eventually become mainstream, as in the case of nematic liquid crystal materials.
現在までに報告されている’Ｓ ｍ Ｃ’Ｎを示すエス
テル化合物としては下記のようなものがある。Ester compounds exhibiting 'S m C'N that have been reported to date include the following.
Ｒ−（Ｊ→＋−Ｃ（Ｊ −（Ｊイ＝トｃ’ｓ［＋＋ｔ
（ＩＩＫ −（Ｊ （＝トζＤ−ｃ （Ｊ−Ｕ−
Ｃ”Ｓ Ｈ，、（社）（Ｒは炭素数８〜１２の直鎖アル
キル基を示し。R-(J→+-C(J-(Ji=toc's[++t
(IIK −(J (=tζD−c (J−U−
C"S H, (Company) (R represents a straight chain alkyl group having 8 to 12 carbon atoms.
Ｃ”、Ｈ，、は光学活性なアルミ基を示す）Ｘ
Ｃｏ−（Ｊ−ｃ＞−Ｙ （ｍ）（ＸおよびＹ
は少なくとも一方は光学活性を有するアルキルを含む炭
素数５〜１２のアルキルまたはアルコキシル基を示す）
前記化合物（ＩｌおよびＩは、５０℃以下の温度でＳ
ｍ Ｃ”、ｉｆｉを示すがその温度範囲は極めて狭い。C”, H, represents an optically active aluminum group)X
Co-(J-c>-Y (m)(X and Y
represents an alkyl group having 5 to 12 carbon atoms or an alkoxyl group, at least one of which contains an alkyl group having optical activity.
m C'', ifi, but its temperature range is extremely narrow.
（Ｂ、１．（Ｊｓｔｒｏｖｓｋｉｉ ｅｔ、ａｌ、、Ｆ
ｅｒｒｏｅｌｅｃｔｒｉｃｓ。(B, 1. (Jstrovskii et al., F
erroelectrics.
２４（１９８０）、３０９）
また、前記化合物（ｍ）は広い温度範囲を有するがその
保持温度が５０℃以上であり実用上問題がある。（Ｇ、
Ｗ、Ｇｒａｙ ｅｔ、ａｌ、、Ｍｕｌ Ｃｒｙｓｔ
ＬｉｑＣｒｙｓｔ ４８（１９７’８ ）、３７）〔
発明の目的〕
そこで本発明の目的は室温近傍においてＳ ｍ Ｃ′″
相を示し、比較的広い液晶温度範囲を有するエステル化
合物を提供することである。24 (1980), 309) Furthermore, although the compound (m) has a wide temperature range, its holding temperature is 50° C. or higher, which poses a practical problem. (G,
W, Gray et al, Mul Crystal
LiqCryst 48 (197'8), 37) [
Purpose of the Invention] Therefore, the purpose of the present invention is to reduce S m C′″ near room temperature.
The object of the present invention is to provide an ester compound that exhibits a phase and has a relatively wide liquid crystal temperature range.
本発明は下記化合物（Ｘ）を新規に合成し、これがＳ
ｍ Ｃ”＠を示す化合物として優れた特性を有すること
を見出したものであり以下実施例に基づき説明する。The present invention newly synthesizes the following compound (X), which is S
It has been found that it has excellent properties as a compound exhibiting m C''@, and will be explained below based on Examples.
（合成方法１）
本発明の化合物（Ｘ）を合成する一つの方法は上記合成
方法ｌである。(Synthesis method 1) One method for synthesizing the compound (X) of the present invention is the above-mentioned synthesis method 1.
エニル）安息香酸（■）を塩化チオニル、五酸化リンな
どのハロゲン化剤で酸塩化物（ＶＩ）とし、これと４−
ヒドロキシベンツアルデヒドとをピリジン添加トルエン
中で反応させ化合物（ＶＩＩ）のアルデヒドを得る。Enyl) benzoic acid (■) is converted to acid chloride (VI) using a halogenating agent such as thionyl chloride or phosphorus pentoxide, and this and 4-
The aldehyde of compound (VII) is obtained by reacting with hydroxybenzaldehyde in toluene containing pyridine.
このアルデヒドをＡｇ、０．ＫＭｎＵ、などでアセトン
中で酸化し、安息香酸誘導体（ｖｌｌ）を得る。This aldehyde was mixed with Ag, 0. KMnU, etc. in acetone to obtain the benzoic acid derivative (vll).
この安息香酸誘導体（Ｖｌｌｌ）と光学活性なアルコー
ルとを既知の方法でエステル化すれば、目゛的物（Ｘ）
を得ることができる。この出発物質■）と中間物質（Ｖ
ｌｌ）、（■）、（Ｉｘ）はいずれも液晶性物質である
。If this benzoic acid derivative (Vlll) and an optically active alcohol are esterified by a known method, the target product (X) can be obtained.
can be obtained. This starting material ■) and intermediate material (V
ll), (■), and (Ix) are all liquid crystal substances.
本発明の化合物■）を合成する別の方法は下記のとおり
である。Another method for synthesizing the compound ① of the present invention is as follows.
（合成方法２）
すなわち（合成方法１）と同様にして得られた化合物（
Ｖｌ）に既知の方法であらかじめ合成された４−ヒドロ
キシ安息香酸の光学活性なアルコールとのエステル化合
物をピリジンなどの存在下でエステル化させることによ
り目的の化合物（Ｘ）を得ることができる。(Synthesis method 2) That is, a compound obtained in the same manner as (synthesis method 1) (
The desired compound (X) can be obtained by esterifying an ester compound of 4-hydroxybenzoic acid with an optically active alcohol, which has been synthesized in advance by a method known in Vl), in the presence of pyridine or the like.
光学活性なアルコールが多量に存在する場合には（合成
方法２）が有利であり、少量しか存在しない場合には（
合成方法１）が有利である。(Synthesis method 2) is advantageous when a large amount of optically active alcohol is present, and (synthesis method 2) is advantageous when only a small amount is present.
Synthesis method 1) is preferred.
以下具体的な実施例により説明する。This will be explained below using specific examples.
（実施例１）
キシフェニル）ベンゾイルオキシ〕安息香酸＜アクチブ
）アミルエステルの製造。(Example 1) Production of xyphenyl)benzoyloxy]benzoic acid <active)amyl ester.
既知の方法（Ｇ、Ｗ、Ｇｒａｙ ｅｔ、ａｌ、、Ｊ、Ｃ
ｈｅｍ ５Ｏｃ（１９５５）、１４１’３ ）で合成さ
れた４−（３−クロロ４−ノルマルデシルオキシフェニ
ル）安息香酸０．１モルと、３０ｇの塩化チオニルとを
５ Ｑ ＣＣのトルエンとともに還流下で加熱反応させ
た。Known methods (G.W., Gray et al., J.C.
0.1 mol of 4-(3-chloro4-n-n-decyloxyphenyl)benzoic acid synthesized by Hem 5Oc (1955), 141'3) and 30 g of thionyl chloride were combined with 5 Q CC of toluene under reflux. The reaction was carried out by heating.
約３時間の反応終了後、減圧下で過剰のチオニルとトル
エンとを留去する。残留物が前記化合物（■）に相当す
る酸の酸塩化物である。After about 3 hours of reaction, excess thionyl and toluene are distilled off under reduced pressure. The residue is an acid chloride of the acid corresponding to the compound (■).
これに０１モルの４−ヒドロキシベンツアルデヒドとピ
リジン３０ＣＣとトルエン２００ ＣＣとを加えて還流
下で加熱攪拌を約１２時間続け、水中に投入して有機層
を分離する。この有機層を６Ｎ塩酸と２Ｎ水酸化ナトリ
ウム水溶液で洗浄し、水洗乾燥ののちトルエンを留去す
る。残った残留物をエタノール３００ ＣＯから結晶化
させ前記化合物マルデシルオキシフェニル）ベンゾイル
オキシベンツアルデヒドを得る。01 mol of 4-hydroxybenzaldehyde, 30 cc of pyridine, and 200 cc of toluene are added thereto, heated and stirred under reflux for about 12 hours, and then poured into water to separate the organic layer. This organic layer is washed with 6N hydrochloric acid and 2N aqueous sodium hydroxide solution, washed with water and dried, and then toluene is distilled off. The remaining residue is crystallized from ethanol 300 CO to obtain the compound mardecyloxyphenyl)benzoyloxybenzaldehyde.
得られたアルデヒドを１リツトルのアセトンに溶解し、
２０．９の過マンガン酸カリウムを少量づつ攪拌しなが
ら添加し、４時間攪拌を続けて一夜放置する。沈澱した
二酸化マンガンを濾過し、アセトンが沈澱に残った状態
で別の容器に移し、・ ６Ｎ塩酸ｔｏｏｃｃを加えて
二酸化マンガンを分解訃
する。The obtained aldehyde was dissolved in 1 liter of acetone,
20.9 of potassium permanganate is added little by little with stirring, stirring is continued for 4 hours and left overnight. Filter the precipitated manganese dioxide, transfer it to another container with acetone remaining in the precipitate, and add 6N hydrochloric acid toocc to decompose the manganese dioxide.
・水１リットルを加えて二酸化マンガンの分解が完全に
終るのを待って吸引濾過し、エタノールとトルエンの４
対ｌの混合液から再結晶すると前記ノルマルデシルオキ
シフェニル）ヘンジイルオキシ〕安息香酸が得られる。・Add 1 liter of water, wait until the decomposition of manganese dioxide is completely completed, filter with suction, and dissolve ethanol and toluene.
Recrystallization from a mixed solution of 1 to 1 yields the above-mentioned n-decyloxyphenyl)hendiyloxy]benzoic acid.
得られた酸の０．０２モルにトルエン２０ＣＣ存在下で
塩化チオニル５ｇを反応させ、過剰な塩化チオニルとト
ルエンを留去した残留物にトルエン１００Ｃｅと光学活
性アミルアルコール（２−メチル−１−ブタノール）３
ｇを加え、ピリジン１０ＣＣを添加して攪拌し、４０℃
の温度で一夜放置する。これを水中に投入して有機層を
分離し、６Ｎ塩酸と２Ｎ水酸化す） ＩＪウム水溶液で
洗浄し、水洗乾燥ののちトルエンを留去し、残留分をエ
タノールから再結晶すると最終の目的物である４−１：
４’−（３−クロロ４−ノルマルデシルオキシフェニル
）ベンゾイルオキシ〕安息香酸（アクチブ）アミルエス
テルが得られる。0.02 mol of the obtained acid was reacted with 5 g of thionyl chloride in the presence of 20 CC of toluene, and the excess thionyl chloride and toluene were distilled off. To the residue, 100 Ce of toluene and optically active amyl alcohol (2-methyl-1-butanol) were added. )3
g, add 10 CC of pyridine, stir, and heat to 40°C.
Leave overnight at a temperature of This was poured into water to separate the organic layer, which was then washed with 6N hydrochloric acid and 2N hydroxide). After washing with water and drying, toluene was distilled off, and the residue was recrystallized from ethanol to obtain the final target product. 4-1:
4'-(3-chloro4-n-n-decyloxyphenyl)benzoyloxy]benzoic acid (active) amyl ester is obtained.
この化合物の相転位温度は下記の通りであった。The phase transition temperature of this compound was as follows.
温度上昇時、Ｃ３ｃ点５３℃、５ｃＳａ点９５℃、Ｓａ
Ｉ点１４０’Ｃ。When temperature rises, C3c point 53℃, 5cSa point 95℃, Sa
Point I 140'C.
温度下降時、ＩＳａ点１４０℃、５ａＳｃ点９５℃、２
．５℃／分の下降速度で一２０°Ｃまで相変北見られず
、１５℃に一日放置すれば２５℃からＳ ｍ Ｃ′″相
に相変化する別のスメクティノク相に変化する。When temperature falls, ISa point 140℃, 5aSc point 95℃, 2
．． At a rate of decline of 5°C/min, no phase change is observed up to 20°C, and if it is left at 15°C for a day, it changes to another smectinok phase that changes from 25°C to the S m C'' phase.
この化合物から得られた赤外線吸収スペクトル図を第１
図に示す。The first infrared absorption spectrum obtained from this compound is
As shown in the figure.
（実施例２）
エニル）ベンゾイルオキシ〕安息香酸（アクチブ）アミ
ルエステルの製造。(Example 2) Production of enyl)benzoyloxy]benzoic acid (active) amyl ester.
オキシフェニル）安息香酸を用い、（実施例１）の方法
に順じて合成を行℃・、目的とする上記エステルを得た
。この化合物の相転位温度は下記の通りであった。Synthesis was carried out according to the method of Example 1 using (oxyphenyl)benzoic acid at °C to obtain the desired ester. The phase transition temperature of this compound was as follows.
温度上昇時、Ｃ５ｃ点４３℃、５ｃＳａ点８３℃、Ｓａ
Ｉ点１３６°ｃ。When temperature rises, C5c point 43℃, 5cSa point 83℃, Sa
Point I 136°c.
温度下降時、ＩＳａ点１３６℃、５ａＳｃ点８３°Ｃ１
２，５℃／分の下降速度で一２０℃まで相変北見られず
、１０℃に三日放置した試料は２７°Ｃで相変化するス
メクティック相になっていた。この化合物から得られた
赤外線吸収スペクトル図を第２図に示す。When temperature falls, ISa point is 136°C, 5aSc point is 83°C1
No phase change was observed up to -20°C at a rate of decline of 2.5°C/min, and the sample left at 10°C for three days had a smectic phase that changed at 27°C. FIG. 2 shows an infrared absorption spectrum obtained from this compound.
（実施例３）
（実施例１）の方法に順じて、
キシフェニル）ベンゾイルオキシ〕安息香酸（アクチブ
）アミルエステル、
ジフェニル）ベンゾイルオキシ〕安息香酸（アクチブ）
アミルエステル、
ノイルオキシフェニル）ベンゾイルオキシ〕安息香酸（
アクチブ）アミルエステルを合成した。(Example 3) According to the method of (Example 1), xyphenyl)benzoyloxy]benzoic acid (active) amyl ester, diphenyl)benzoyloxy]benzoic acid (active)
Amyl ester, noyloxyphenyl)benzoyloxy]benzoic acid (
Active) amyl ester was synthesized.
これらのエステルは（・ずれもＳ ｍ Ｃ”４［を示し
た。These esters exhibited S m C''4[.
（実施例４）
４−（３−１０口４−ラウリルオキシフェニル）安息香
酸０．１モルを（実施例１）に記載したと同様に塩化チ
オニルで処理して得られた酸塩化物と、既知の方法で合
成されたバラヒドロキシ安息香酸アクチブアミルエステ
ル０，１１モルとに、トルエン１００ ｃｃとピリジン
２０ＣＣとを加えて５０’Ｃで１２時間攪拌処理し、水
に投入して有機層を分離し、６Ｎ塩酸と２Ｎ水酸化す）
ＩＪウム水溶液で洗浄し、水洗乾燥ののちトルエンを
留去し、残留物をエタノールから再結晶させて化合物を
得た。得られた化合物は（実施例２）で得られた化合物
と同一であり、その相変態挙動も同一であった。(Example 4) An acid chloride obtained by treating 0.1 mol of 4-(3-10-4-lauryloxyphenyl)benzoic acid with thionyl chloride in the same manner as described in (Example 1); 100 cc of toluene and 20 cc of pyridine were added to 0.11 mol of rose hydroxybenzoic acid active amyl ester synthesized by a known method, stirred at 50'C for 12 hours, and poured into water to separate the organic layer. (6N hydrochloric acid and 2N hydroxide)
After washing with IJum aqueous solution, washing with water and drying, toluene was distilled off, and the residue was recrystallized from ethanol to obtain a compound. The obtained compound was the same as the compound obtained in (Example 2), and its phase transformation behavior was also the same.
（実施例５）
（実施例１）で得られたエステル化合物と、（実施例２
）で得られたエステル化合物とのモル比１対ｌの混合物
はＳ ｍ Ｃ′″相を示し、ＩＳａ点は１３６°Ｃ，５
ａＳｃ点は８３℃であり、１０℃の温度に一週間放置し
てもスメクティノク状態を保持しても・た。(Example 5) The ester compound obtained in (Example 1) and (Example 2)
) with the ester compound obtained in the molar ratio of 1:1 shows an S m C'' phase, and the ISa point is 136 °C, 5
The aSc point was 83°C, and the smectinok state remained even after being left at a temperature of 10°C for one week.
本発明の液晶性エステル化合物は、室温近傍の）
比較的広い温度範囲においてＳｍＣ’相を示す新規化合
物として有用である。The liquid crystalline ester compound of the present invention can be used at temperatures near room temperature).
It is useful as a new compound that exhibits an SmC' phase over a relatively wide temperature range.
第１図及び第２図はいずれも本発明のエステル化合物か
ら得られた赤外線吸収スペクトル図である。FIG. 1 and FIG. 2 are both infrared absorption spectra obtained from the ester compound of the present invention.
Claims (1)
なアルキル基を示す）で表わされる。 ４−〔４−（３−クロロ４−アルコキシフェニル）ベン
ゾイルオキシ〕安息香酸アルキルエステルからなる液晶
性エステル化合物。[Claims] It is represented by the general formula ▲There are numerical formulas, chemical formulas, tables, etc.▼ (R represents an alkyl group having 8 to 12 carbon atoms, and R' represents an optically active alkyl group). A liquid crystalline ester compound consisting of an alkyl 4-[4-(3-chloro4-alkoxyphenyl)benzoyloxy]benzoic acid ester.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59245532A JPS61122250A (en) | 1984-11-20 | 1984-11-20 | Liquid crystal ester compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59245532A JPS61122250A (en) | 1984-11-20 | 1984-11-20 | Liquid crystal ester compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61122250A true JPS61122250A (en) | 1986-06-10 |
| JPH0522695B2 JPH0522695B2 (en) | 1993-03-30 |
Family
ID=17135091
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59245532A Granted JPS61122250A (en) | 1984-11-20 | 1984-11-20 | Liquid crystal ester compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61122250A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61210056A (en) * | 1985-03-14 | 1986-09-18 | Chisso Corp | Halogen-containing optically active liquid crystal compound and liquid crystal composition |
| JPS61249953A (en) * | 1985-04-26 | 1986-11-07 | Dainippon Ink & Chem Inc | Ferroelectric compound and liquid crystal composition |
| US4828754A (en) * | 1985-01-09 | 1989-05-09 | Dainippon Ink & Chemicals, Inc. | Novel liquid crystalline compounds having substituents |
| US4886622A (en) * | 1986-08-18 | 1989-12-12 | Chisso Corporation | Optically active liquid crystal compound having cyano group |
-
1984
- 1984-11-20 JP JP59245532A patent/JPS61122250A/en active Granted
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4828754A (en) * | 1985-01-09 | 1989-05-09 | Dainippon Ink & Chemicals, Inc. | Novel liquid crystalline compounds having substituents |
| JPS61210056A (en) * | 1985-03-14 | 1986-09-18 | Chisso Corp | Halogen-containing optically active liquid crystal compound and liquid crystal composition |
| US4780242A (en) * | 1985-03-14 | 1988-10-25 | Chisso Corporation | Halogen-containing, optically active liquid crystal compound and liquid crystal composition containing same |
| JPH0578542B2 (en) * | 1985-03-14 | 1993-10-29 | Chisso Corp | |
| US5312564A (en) * | 1985-03-14 | 1994-05-17 | Chisso Corporation | Halogen-containing, optically active liquid crystal compound and liquid crystal composition containing same |
| JPS61249953A (en) * | 1985-04-26 | 1986-11-07 | Dainippon Ink & Chem Inc | Ferroelectric compound and liquid crystal composition |
| US4886622A (en) * | 1986-08-18 | 1989-12-12 | Chisso Corporation | Optically active liquid crystal compound having cyano group |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0522695B2 (en) | 1993-03-30 |
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