JPH0331248A - Ether derivative of cyanoallylphenol - Google Patents
Ether derivative of cyanoallylphenolInfo
- Publication number
- JPH0331248A JPH0331248A JP1166309A JP16630989A JPH0331248A JP H0331248 A JPH0331248 A JP H0331248A JP 1166309 A JP1166309 A JP 1166309A JP 16630989 A JP16630989 A JP 16630989A JP H0331248 A JPH0331248 A JP H0331248A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- trans
- formula
- allyl
- compound
- 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
- 150000002170 ethers Chemical class 0.000 title claims 2
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 28
- 239000000203 mixture Substances 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 3
- 239000000126 substance Substances 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract description 6
- ORYLHBCOOJPTRE-UHFFFAOYSA-N 4-hydroxy-3-prop-2-enylbenzonitrile Chemical compound OC1=CC=C(C#N)C=C1CC=C ORYLHBCOOJPTRE-UHFFFAOYSA-N 0.000 abstract description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract description 3
- UUWSLBWDFJMSFP-UHFFFAOYSA-N bromomethylcyclohexane Chemical compound BrCC1CCCCC1 UUWSLBWDFJMSFP-UHFFFAOYSA-N 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- HXOWMHXGHNZDFT-UHFFFAOYSA-N 1-(bromomethyl)-4-pentylcyclohexane Chemical compound CCCCCC1CCC(CBr)CC1 HXOWMHXGHNZDFT-UHFFFAOYSA-N 0.000 description 1
- NOPVDHPLKSDADZ-UHFFFAOYSA-N 1-bromo-4-pentylcyclohexane Chemical compound CCCCCC1CCC(Br)CC1 NOPVDHPLKSDADZ-UHFFFAOYSA-N 0.000 description 1
- XXUSEPRYHRDKFV-CTYIDZIISA-N C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(C#N)C=C1 XXUSEPRYHRDKFV-CTYIDZIISA-N 0.000 description 1
- FURZYCFZFBYJBT-JCNLHEQBSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 FURZYCFZFBYJBT-JCNLHEQBSA-N 0.000 description 1
- NSGMZTNTQKRAFA-UAPYVXQJSA-N C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 NSGMZTNTQKRAFA-UAPYVXQJSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- -1 ester-based Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 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】
［産業上の利用分！ｉ’Ｆ］
本発明は、新規なシアノアリルフェノールのエーテル話
導体および該化合物を有効成分とする液晶組成物に関す
る。[Detailed description of the invention] [Industrial use! i'F] The present invention relates to a novel cyanoallylphenol ether conductor and a liquid crystal composition containing the compound as an active ingredient.
［従来の技術とその問題点］
液晶を利用した表示素子は時計、電卓等に広く使用され
ている。これらの液晶表示素子は液晶物質の光学異方性
および誘電異方性を利用したものである。液晶相にはネ
マチック液晶相、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。[Prior art and its problems] Display elements using liquid crystals are widely used in watches, calculators, etc. These liquid crystal display elements utilize optical anisotropy and dielectric anisotropy of liquid crystal materials. Liquid crystal phases include a nematic liquid crystal phase, a smectic liquid crystal phase, and a cholesteric liquid crystal phase, among which those using nematic liquid crystal are most widely put into practical use.
それらには液晶表示に応用されている電気光学効果に対
応して、ＴＮ（ねじれネマチック）型、ＤＳ（動的散乱
）型、ゲスト・ホスト型、ＤＡＰ型等の表示素子があり
、それぞれに使用される液晶物質は自然界のなるべく広
い温度範囲で液晶相を示すものが望ましい。There are display elements such as TN (twisted nematic) type, DS (dynamic scattering) type, guest-host type, and DAP type, which correspond to the electro-optic effect applied to liquid crystal displays, and each type is used. It is desirable that the liquid crystal material used exhibits a liquid crystal phase over as wide a natural temperature range as possible.
現在のところ単一の液晶物質でそのような条件をみたす
物質はなく、数種の液晶物質またはさらに非液晶物質を
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ている
。At present, there is no single liquid crystal substance that satisfies these conditions, and several types of liquid crystal substances or even non-liquid crystal substances are mixed and put into practical use. These substances include water, light,
It is also required to be stable against heat, air, etc.
又近年表示素子の大型化が望まれ、従来のＴＮ型方式で
は表示品位が劣るため、新たに一連のＳＴＮ （スーパ
ーツィステッド・ネマチック）型表示方式がＭ、シャッ
ト、Ｆ、リーンフーツ（＾ｐｐｌＰｈｙｓ ｈｅｔｔ、
５０，２３６ （１９８７））により開発され、大型化
しても表示品位が劣らないですむものである。In addition, in recent years, there has been a desire for larger display elements, and since the display quality of the conventional TN type method is inferior, a series of new STN (super twisted nematic) type display systems have been developed. ,
50, 236 (1987)), and the display quality does not deteriorate even when the display size is increased.
この方式に望まれる液晶の性質はＫｎ／に１が大きく、
Ｉｈ／に１は小さく、Δε／ε上は小さい値が望まれて
いる（Ｍ、５ｃｈａｄｔ、Ｆ、Ｌｅｅｎｈｏｕｔｓ ５
ｏｃｉｅｔｙ ｆｏｒＩｎｆｏｒｍａｔｉｏｎＤｉｓｐ
ｌａｙ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｓｙｍｐｏｓｉ
ｕｍＤｉｇｅｓｔ ｏｆ Ｔｅｃｈｎｉｃａｌ Ｐａｐ
ａｒｓ Ｖｏｌ、 Ｘ ■ Ｎｅ＋ｖＯｒｌｅａｎｓ
、Ｌｏｕｊｓｌａｎａ Ｍａｙ １２−１４．（１９８
７） ３７２−３７５）。The properties of the liquid crystal desired for this method are as follows: Kn/ has a large value of 1;
1 is small for Ih/, and a small value for Δε/ε is desired (M, 5chadt, F, Leenhouts 5
society forInformationDisp
lay International Symposia
umDigest of Technical Pap
ars Vol, X ■ Ne+vOrleans
, Loujslana May 12-14. (198
7) 372-375).
本発明の目的はに、／に、が大きく、又Δｎが大きく相
溶性に優れており、上述のＳＴＮ型表示素子に使用でき
る化合物であって、液晶組成物とじて有用な新規化合物
を提供することである。他の目的は、該化合物を有効成
分とする液晶組成物を提イ共することである。An object of the present invention is to provide a novel compound which has a large value of /, a large value of Δn and excellent compatibility, which can be used in the above-mentioned STN type display element, and which is useful as a liquid crystal composition. That's true. Another object is to provide a liquid crystal composition containing the compound as an active ingredient.
本発明の化合物の製造法は、例えば次式の反応式によっ
て示される。The method for producing the compound of the present invention is shown, for example, by the following reaction formula.
［問題点を解決するための手段］
本発明（二発明）は−数式
（上式中Ｒは直鎮又は枝分れした炭素数１〜１５のアル
キル基またはアルコキシ基であり、ｎは１又は２を示し
、ｍはＯ又は１を示す）で表されるシアノアリルフェノ
ールのエーテル話導体および該化合物を有効成分とする
液晶組成物である。[Means for Solving the Problems] The present invention (second invention) is based on the formula 2 and m represents O or 1) and a liquid crystal composition containing the compound as an active ingredient.
本発明の液晶組成物の成分にできる本発明の化合物以外
の他の成分としては、例えばエステル系、シッフ塩基系
、ビフェニル系、フェニルシクロヘキサン系、複素環系
等の液晶化合物をあげることができる。Other components other than the compound of the present invention that can be used as a component of the liquid crystal composition of the present invention include, for example, ester-based, Schiff base-based, biphenyl-based, phenylcyclohexane-based, and heterocyclic-based liquid crystal compounds.
［化合物の製造法］
（上式中ｎ、ｍは前記に同じである）
すなわち、特開昭６４−７５，４５９号に記載の方法で
製造した２−アリル−４−シアノフェノール（ｍ＝Ｏ）
又は３−アリル−４−ヒドロキシ−４°−シアノビフェ
ニルを無水炭酸カリウムとＮ、Ｎ−ジメチルホルムアミ
ド（以下ＤＭＦと略す）溶媒中臭化−トランス−４−ア
ルキルシクロヘキシルメチル（ｎ＝１）又は臭化−トラ
ンス−４−（トランス−４−アルキルシクロヘキシル）
シクロヘキシルメチル（ｎ＝ｍ２）と反応を行い、目的
とするシアノアリルフェノールのエーテル話導体を製造
した。[Production method of compound] (In the above formula, n and m are the same as above.) That is, 2-allyl-4-cyanophenol (m=O )
or 3-allyl-4-hydroxy-4°-cyanobiphenyl in anhydrous potassium carbonate and N,N-dimethylformamide (hereinafter abbreviated as DMF) solvent-trans-4-alkylcyclohexylmethyl bromide (n=1) or odor. -trans-4-(trans-4-alkylcyclohexyl)
A reaction was carried out with cyclohexylmethyl (n=m2) to produce the desired ether conductor of cyanoallylphenol.
［発明の効果］
本発明の化合物は他の多くの液晶化合物、すなわちエス
テル系、シッフ塩基系、ビフェニル系、フェニルシクロ
ヘキサン系、複素環系等の液晶化合物との相溶性がよく
、本発明の化合物を液晶組成物に加え、△ｎが大きく、
又しきい値電圧を低くすることができる。又、に、／に
１の値を大きくできるため、ＳＴＮ型表示素子用の液晶
組成物に好適な化合物である。[Effects of the Invention] The compound of the present invention has good compatibility with many other liquid crystal compounds, such as ester-based, Schiff base-based, biphenyl-based, phenylcyclohexane-based, and heterocyclic-based liquid crystal compounds. is added to the liquid crystal composition, △n is large,
Further, the threshold voltage can be lowered. Furthermore, since the value of 1 and 1 can be increased, it is a compound suitable for liquid crystal compositions for STN type display elements.
［実施例］
以下に述べる実施例により本発明の化合物につきざらに
詳細に説明する。[Examples] The compounds of the present invention will be explained in more detail with reference to the following examples.
実施例１
２−アリル−４−シアノフェニル−トランス−４−ペン
チルシクロヘキシルメチルエーテル（（り式でｐ＝ Ｃ
ＨＨ＋＋−、ｎ ＝ １ 、 ｍ ＝ Ｏｆ）場合）の
製造２−アリル−４−シアノフェノール１．９ｇ （０
，０１モル）をＤ Ｍ Ｆ １００ｍｊ２ ＆：溶解し
、これに無水炭酸カリウム２０ｇを加えた。よくかきま
ぜながら臭化−トランス−４−ペンチルシクロヘキシル
メチル４．９ｇ（０，０２モル）を５分で加え、さらに
８０℃、１０時間反応を行なった０反応終了後１ｊ２の
水に加えると油状物がでてきた。Example 1 2-allyl-4-cyanophenyl-trans-4-pentylcyclohexyl methyl ether ((in the formula p=C
Preparation of HH++-, n = 1, m = Of) 2-allyl-4-cyanophenol 1.9 g (0
, 01 mol) was dissolved in 100 mj2 &: of DMF, and 20 g of anhydrous potassium carbonate was added thereto. While stirring well, 4.9 g (0.02 mol) of trans-4-pentylcyclohexyl bromide was added over 5 minutes, and the reaction was further carried out at 80°C for 10 hours. After the reaction was completed, when added to the water in 1j2, an oily substance was formed. has appeared.
この油状物をトルエンで抽出し、トルエン層を２Ｎ水酸
化ナトリウムで、ついで水で洗った。トルエン層を無水
硫酸ナトリウムで乾燥した後トルエンを減圧で留去、さ
らに真空ポンプで完全に留去した。残？た油状物をｎ−
ヘキサンに溶解し、活性アルミナを用いてカラムクロナ
トグラフィーを行った。This oil was extracted with toluene and the toluene layer was washed with 2N sodium hydroxide and then water. After drying the toluene layer over anhydrous sodium sulfate, toluene was distilled off under reduced pressure and then completely distilled off using a vacuum pump. What's left? n-
It was dissolved in hexane and column chromatography was performed using activated alumina.
ｎ〜ヘキサンを留去後残った固体をエタノールで再結晶
を行った。融点は４４．０〜４４．８℃で液晶相は示さ
なかった。収量２．５ｇ （収率８３％）。After distilling off n~hexane, the remaining solid was recrystallized from ethanol. The melting point was 44.0 to 44.8°C, and no liquid crystal phase was observed. Yield: 2.5 g (yield: 83%).
実施例２．３
実施例１における２−アリル−４−シアノフェノールの
代りに、３−アリル−４−ヒドロキシ−４゛−シアノビ
フェニルと臭化−トランス−４−ペンチルシクロヘキシ
ルメチルの代りに種々の臭化−トランス−４−アルキル
シクロヘキシルメチル又は臭化−トランス−４−（トラ
ンス−４−アルキルシクロヘキシル）シクロヘキシルメ
チルとを反応して目的の化合物を製造した。これらの結
果を実施例１の結果と共に表１に示した。Example 2.3 In place of 2-allyl-4-cyanophenol in Example 1, 3-allyl-4-hydroxy-4'-cyanobiphenyl and in place of trans-4-pentylcyclohexylmethyl bromide, various The desired compound was prepared by reacting with trans-4-alkylcyclohexylmethyl bromide or trans-4-(trans-4-alkylcyclohexyl)cyclohexylmethyl bromide. These results are shown in Table 1 together with the results of Example 1.
表１
使用例！
トランス−４−プロピル−（４゛−シアノフェニル）シ
クロヘキサン ２４重量％トランス−４−ペンチル
ー（４゛−シアノフェニル）シクロヘキサン ３５
重量％トランス−４−ヘプチル−（４゛−シアノフェニ
ル）シクロヘキサン ２５ｆｉ ｆｉ％トランス−
４−ペンチル−（４′−シアンビフェニル）シクロヘキ
サン １５１ｉ％なる液晶組成物（Ａ）のＮ−１点は
７２．０℃、△εは＋１１．０．２０℃における粘度は
２１１ｃｐ、Δｎは０．１４０．に、／に１は１．８２
である。Table 1 Usage example! trans-4-propyl-(4'-cyanophenyl)cyclohexane 24% by weight trans-4-pentyl-(4'-cyanophenyl)cyclohexane 35
Weight% trans-4-heptyl-(4'-cyanophenyl)cyclohexane 25fi fi% trans-
The N-1 point of the liquid crystal composition (A) consisting of 151i% of 4-pentyl-(4'-cyambiphenyl)cyclohexane is 72.0°C, Δε is +11.0. The viscosity at 20°C is 211 cp, and Δn is 0. 140. ni, /ni 1 is 1.82
It is.
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組
立てた、電極間距離が１０μｍのものを用意し、上記の
液晶組成物（Ａ）を封入して２０℃でその特性を測定し
たところ、しきい電圧（以下、Ｖｔｈと略記する）は１
．８２Ｖであった。A liquid crystal cell was prepared in which substrates having silicon oxide coated and rubbed tin oxide transparent electrodes were assembled to face each other, and the distance between the electrodes was 10 μm, and the above liquid crystal composition (A) was sealed in the cell for 20 minutes. When its characteristics were measured at ℃, the threshold voltage (hereinafter abbreviated as Vth) was 1
．． It was 82V.
この液晶組成物（Ａ）９５１ｉＥｋ％に本発明の実施例
２で製造した４−シアノ−３−アリル−４°−ビフェニ
ルートランス−４−ペンチルシクロヘキシルメチルエー
テル５ｆｆｉｆｆｉ％を溶解した組成物のＮ−１点は７
２．５℃、△６は＋１１．０、△ｎは０．＋４５、粘度
は２９ＣＰＫ３／に＋は１．９９”Ｃ”、Ｖｔｈは１．
８０Ｖ テあり、ＳＴＮ用として好適である。The N- 1 point is 7
2.5℃, △6 is +11.0, △n is 0. +45, viscosity is 29CPK3/+ is 1.99"C", Vth is 1.
80V, suitable for STN use.
以上 特許 出 願人 チッソ株式会社that's all patent Out applicant Chisso Corporation
Claims (2)
キル基またはアルコキシ基であり、ｎは１又は２を示し
、ｍは０または１を示す）で表されるシアノアリルフェ
ノールのエーテル誘導体。(1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (1) (In the above formula, R is a linear or branched alkyl group or alkoxy group having 1 to 15 carbon atoms, and n is 1 or 2 and m represents 0 or 1).
キル基またはアルコキシ基であり、ｎは１又２を示し、
ｍは０又は１を示す）で表されるシアノアリルフェノー
ルのエーテル誘導体を有効成分とする液晶組成物。(2) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (1) (In the above formula, R is a linear or branched alkyl group or alkoxy group having 1 to 15 carbon atoms, and n is 1 or 2 shows,
A liquid crystal composition containing as an active ingredient an ether derivative of cyanoallylphenol represented by (m represents 0 or 1).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1166309A JPH0331248A (en) | 1989-06-28 | 1989-06-28 | Ether derivative of cyanoallylphenol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1166309A JPH0331248A (en) | 1989-06-28 | 1989-06-28 | Ether derivative of cyanoallylphenol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0331248A true JPH0331248A (en) | 1991-02-12 |
Family
ID=15828954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1166309A Pending JPH0331248A (en) | 1989-06-28 | 1989-06-28 | Ether derivative of cyanoallylphenol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0331248A (en) |
-
1989
- 1989-06-28 JP JP1166309A patent/JPH0331248A/en active Pending
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