JPH02304041A - Ether derivative of halogenoallylphenol - Google Patents
Ether derivative of halogenoallylphenolInfo
- Publication number
- JPH02304041A JPH02304041A JP12195189A JP12195189A JPH02304041A JP H02304041 A JPH02304041 A JP H02304041A JP 12195189 A JP12195189 A JP 12195189A JP 12195189 A JP12195189 A JP 12195189A JP H02304041 A JPH02304041 A JP H02304041A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- formula
- trans
- compound
- halogenoallylphenol
- 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 abstract description 5
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 28
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 18
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002262 Schiff base Substances 0.000 abstract description 3
- 150000004753 Schiff bases Chemical class 0.000 abstract description 3
- 235000010290 biphenyl Nutrition 0.000 abstract description 3
- 239000004305 biphenyl Substances 0.000 abstract description 3
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 abstract description 3
- 150000002148 esters Chemical class 0.000 abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract 1
- 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 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- -1 ester-based Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 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
- 230000000694 effects Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- HXOWMHXGHNZDFT-UHFFFAOYSA-N 1-(bromomethyl)-4-pentylcyclohexane Chemical compound CCCCCC1CCC(CBr)CC1 HXOWMHXGHNZDFT-UHFFFAOYSA-N 0.000 description 1
- NQZKLVHWFYHXGH-UHFFFAOYSA-N 4-chloro-2-prop-2-enylphenol Chemical compound OC1=CC=C(Cl)C=C1CC=C NQZKLVHWFYHXGH-UHFFFAOYSA-N 0.000 description 1
- HLYCSAINLGEGSJ-UHFFFAOYSA-N 4-fluoro-2-prop-2-enylphenol Chemical compound OC1=CC=C(F)C=C1CC=C HLYCSAINLGEGSJ-UHFFFAOYSA-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
- 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
- 238000009835 boiling Methods 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- UUWSLBWDFJMSFP-UHFFFAOYSA-N bromomethylcyclohexane Chemical compound BrCC1CCCCC1 UUWSLBWDFJMSFP-UHFFFAOYSA-N 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- GHDIHPNJQVDFBL-UHFFFAOYSA-N methoxycyclohexane Chemical compound COC1CCCCC1 GHDIHPNJQVDFBL-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 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】
「産業上の利用分野］
本発明は、新規なハロゲノアリルフェノールのエーテル
誘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 Application Field" The present invention relates to a novel halogenoallylphenol ether derivative 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、そのうちネマヂ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, and among these, 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、ケスト・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へく広
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, Kest-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 a wide temperature range in nature.
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５ＴＮ（スーパー
ツイスト）型表示方式がＭ、シャット、Ｆ、リーンフー
ーン （八ｐｐ１．Ｐｈｙｓ ｈｅｔｔ、５０，２３
６（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。この方式に望まれる液
晶の性質はＨ３／に＋が大きく、Ｋ２／Ｋｌは小さく、
△Ｃ／ε上は小さい値が望まれている（ＭＳｃｈａｄｔ
、Ｆ、Ｌｅｅｎｈｏｕｔｓ ５ｏｃｉｅｔｙ ｆｏｒ
ＩｎｆｏｒｍａｔｉｏｎＤｉｓｐｌａｙ Ｉｎｔｅｒｎ
ａｔｉｏｎａｌ Ｓｙｍｐｏｓｉｕｍ ＤｉｇｅＳｔ
ｏｆＴｅｃｈｎｉｃａｌ Ｐａｐａｒｓ Ｖｏ＋、 Ｘ
ＶＨＩ Ｎｅｗ ０ｒｌｅａｎｓ。In addition, in recent years, there has been a desire for larger display elements, and since the display quality of the conventional TN type system is inferior, a series of 5TN (super twist) type display systems has been newly developed. 50,23
6 (1987)), and the display quality does not deteriorate even when the display size is increased. The properties of the liquid crystal desired for this method are that H3/ has a large + value, K2/Kl is small, and
A small value is desired for △C/ε (MSchadt
, F, Leenhouts 5ociety for
Information Display Intern
ational Symposium DigeSt
ofTechnical Papers Vo+, X
VHI New 0rleans.
Ｌｏｕｉｓｊａｎａ Ｍａｙ １２−１４．（１９８７
） ３７２−３７５）。Louisjana May 12-14. (1987
) 372-375).
本発明の目的はバ。／に、が大きく、又△ｎが小さく相
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供することである。The object of the present invention is to An object of the present invention is to provide a novel compound which has a large / and a small Δn and has excellent compatibility, which can be used in the above-mentioned STN type display element and which is useful as a liquid crystal composition. Another object is to provide a liquid crystal composition containing the compound as an active ingredient.
［問題点を解決するための手段］
本発明（二発明）は一般式
（上式中Ｒば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、ＸはＦ又は６℃てあ
り、βは０または１を示し、ｍは１又は２を示す）て表
されるハロゲノアリルフェノールのエーテル誘導体およ
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 general formula (in the above formula, R is a straight or branched alkyl group or alkoxy group having 1 to 15 carbon atoms, and X is F or 6° C., β represents 0 or 1, and m represents 1 or 2), 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て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 components 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］
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。[Method for producing compound] The method for producing the compound of the present invention is shown, for example, by the following reaction formula.
（上式中λ、ｍ、Ｘは前記に同じである）すなわち、特
開昭６４−４５．３４０に記載の方法で製造した２−ア
リル−４−ハロゲノフェノール（λ−〇）又は３−アリ
ル−４−ヒドロキシ−４゛−ハロゲノフェニルを無水炭
酸カリウムとＮ、Ｎ〜ジメチルホルムアミド溶媒中臭化
−トランス−４−アルキルシクロへキシルメチ′ル（ｍ
’＝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（ｍ＝２
）と反応を行い、目的とするハロゲノアリルフェノール
のエーテル誘導体を製造した。(In the above formula, λ, m, and -4-Hydroxy-4'-halogenophenyl was dissolved in anhydrous potassium carbonate and -trans-4-alkylcyclohexylmethyl bromide (m
'=1) or trans-4-(trans-4-alkylcyclohexyl)cyclohexylmethyl bromide (m=2
) to produce the desired ether derivative of halogenoallylphenol.
［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が小さく、
又しきい値電圧を低くすることができる。又、Ｋ３／に
＋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 small,
Further, the threshold voltage can be lowered. Furthermore, since the + value of K3/ 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さらに
詳細に説明する。[Example] 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−フルオロフェニル−トランス−４−ペ
ンチルシクロヘキシルメチルエーテル（１式でＲ＝Ｃ，
Ｈ，、−、Ｉｌ＝ Ｏ、ｍ ＝ １の場合）の製造２−
アリル−４−フルオロフェノール１．６ｇ （ｏ、０１
モル）をＤ Ｍ Ｆ １００ｍｊ２に溶かし、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８０ｔ１１
０時間反応を行なった。反応終了後ｔＪｔの水に加える
と油状物がでてきた。Example 1 2-allyl-4-fluorophenyl-trans-4-pentylcyclohexyl methyl ether (R=C,
H,,-, Il=O, m=1) Production 2-
Allyl-4-fluorophenol 1.6 g (o, 01
mol) was dissolved in 100 mj2 of DMF, and 20 g of anhydrous potassium carbonate was added thereto. 4. Trans-4-pentylcyclohexylmethyl bromide while stirring well.
Added 9g (0.02 mol) in 5 minutes and further added 80t11
The reaction was carried out for 0 hours. After the reaction was completed, an oily substance appeared when it was added to tJt of water.
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。残った油状物を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。ｎ−ヘキサンを留去後残った油
状物をエタノールで強く冷却して再結晶を行った。室温
で油状となるので結晶を集めて真空蒸留を行った。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. The remaining oily substance is n-
It was dissolved in hexane and column chromatography was performed using activated alumina. After distilling off n-hexane, the remaining oil was strongly cooled with ethanol and recrystallized. Since it becomes oily at room temperature, the crystals were collected and vacuum distilled.
沸点１８０〜２００℃／ ３ ｍｍＨｇｘ収量２．’２
ｇ（収率６９％）。Boiling point 180-200℃/3 mmHgx Yield 2. '2
g (yield 69%).
実施例２．３
実施例１における２−アルジル−４−フルオロフェノー
ルの代りに２−アリル−４−クロロフェノール、３−ア
リル−４−ヒドロキシ−４°−フルオロビフェニルと臭
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 2-allyl-4-chlorophenol, 3-allyl-4-hydroxy-4°-fluorobiphenyl and trans-4-bromide instead of 2-aldyl-4-fluorophenol in Example 1 The desired compounds were prepared by reacting with various trans-4-alkylcyclohexylmethyl bromides or trans-4-(trans-4-alkylcyclohexyl)cyclohexylmethyl bromides in place of pentylcyclohexylmethyl. These results are shown in Table 1 together with the results of Example 1.
表１
使用例１
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 ３６
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 ２５重量％トランス−４−ペ
ンチル−（４゛−シアノビフェニル）シクロヘキサン
１５重量％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２８ｃ
ｐ、△ｎは０．１４０、Ｋ３／に＋は１．８２である。Table 1 Usage example 1 Trans-4-propyl-(4°-cyanophenyl)cyclohexane 24% by weight trans-4-pentyl-(4°-cyanophenyl)cyclohexane 36
% by weight trans-4-heptyl-(4′-cyanophenyl)cyclohexane 25% by weight trans-4-pentyl-(4′-cyanobiphenyl)cyclohexane
The N-1 point of the liquid crystal composition (A) of 15% by weight is 72.
At 0℃, △ε is +11.0.The viscosity at 20℃ is 28c
p and Δn are 0.140, and K3/+ is 1.82.
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 °C, the threshold voltage (hereinafter abbreviated as vth) was 1
．． It was 82V.
この液晶組成物（Ａ）９０重量％に本発明の実施例３で
製造した４−フルオロ−３°−アリル−４゛−ビフエニ
ル−トランス−４−（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エーテル１０重量％を溶
解した組成物のＮ−Ｉ点は６６５℃、△εは１０．１、
△ｎは０．１３０、粘度は２８０Ｐであった。Ｋ３／に
＋は１．９８で、ＳＴＮ用として好適である。4-fluoro-3°-allyl-4′-biphenyl-trans-4-(trans-4-pentylcyclohexyl)cyclohexyl methyl ether 10 prepared in Example 3 of the present invention was added to 90% by weight of this liquid crystal composition (A). The N-I point of the composition in which % by weight was dissolved is 665°C, Δε is 10.1,
Δn was 0.130 and viscosity was 280P. K3/+ is 1.98, which is suitable for STN.
以上that's all
Claims (2)
キル基またはアルコキシ基であり、ＸはＦ又はＣｌであ
り、ｌは０または１を示し、ｍは１又は２を示す）で表
されるハロゲ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. ▼ (I) (In the above formula, R is a linear or branched alkyl group or alkoxy group having 1 to 15 carbon atoms, and X is F or Cl , l represents 0 or 1, m represents 1 or 2).
キル基またはアルコキシ基であり、ＸはＦ又はＣｌであ
り、ｌは０または１を示し、ｍは１又は２を示す）で表
されるハロゲ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. ▼ (I) (In the above formula, R is a linear or branched alkyl group or alkoxy group having 1 to 15 carbon atoms, and X is F or Cl A liquid crystal composition containing as an active ingredient an ether derivative of halogenoallylphenol represented by the following formula (wherein l represents 0 or 1 and m represents 1 or 2).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12195189A JPH02304041A (en) | 1989-05-16 | 1989-05-16 | Ether derivative of halogenoallylphenol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12195189A JPH02304041A (en) | 1989-05-16 | 1989-05-16 | Ether derivative of halogenoallylphenol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02304041A true JPH02304041A (en) | 1990-12-17 |
Family
ID=14823956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12195189A Pending JPH02304041A (en) | 1989-05-16 | 1989-05-16 | Ether derivative of halogenoallylphenol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02304041A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102898284A (en) * | 2011-07-25 | 2013-01-30 | 四川大学 | 3-allyl-[1,1'-biphenyl]-4-phenol, derivatives, preparation methods and uses thereof |
-
1989
- 1989-05-16 JP JP12195189A patent/JPH02304041A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102898284A (en) * | 2011-07-25 | 2013-01-30 | 四川大学 | 3-allyl-[1,1'-biphenyl]-4-phenol, derivatives, preparation methods and uses thereof |
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