JPH02188552A - Aromatic diol and production thereof - Google Patents
Aromatic diol and production thereofInfo
- Publication number
- JPH02188552A JPH02188552A JP606689A JP606689A JPH02188552A JP H02188552 A JPH02188552 A JP H02188552A JP 606689 A JP606689 A JP 606689A JP 606689 A JP606689 A JP 606689A JP H02188552 A JPH02188552 A JP H02188552A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- tables
- formulas
- tetramethyl
- aromatic diol
- 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
- -1 Aromatic diol Chemical class 0.000 title claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 9
- 239000002798 polar solvent Substances 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract description 12
- 239000002994 raw material Substances 0.000 abstract description 7
- 229920005989 resin Polymers 0.000 abstract description 6
- 239000011347 resin Substances 0.000 abstract description 6
- 239000004695 Polyether sulfone Substances 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 239000003822 epoxy resin Substances 0.000 abstract description 3
- 150000003949 imides Chemical class 0.000 abstract description 3
- 229920001643 poly(ether ketone) Polymers 0.000 abstract description 3
- 229920000647 polyepoxide Polymers 0.000 abstract description 3
- 229920000728 polyester Polymers 0.000 abstract description 3
- 229920006393 polyether sulfone Polymers 0.000 abstract description 3
- 229920002803 thermoplastic polyurethane Polymers 0.000 abstract description 3
- 239000002861 polymer material Substances 0.000 abstract description 2
- XSTITJMSUGCZDH-UHFFFAOYSA-N 4-(4-hydroxy-2,6-dimethylphenyl)-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1C1=C(C)C=C(O)C=C1C XSTITJMSUGCZDH-UHFFFAOYSA-N 0.000 abstract 2
- 150000004984 aromatic diamines Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229920005603 alternating copolymer Polymers 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229940047583 cetamide Drugs 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002576 ketones Chemical group 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
Landscapes
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
イ 発明の目的
〈産業上の利用分野〉
本発明は、ポリオキシアリーレンスルホン及びポリオキ
シアリーレンケトン構造を持つ芳香族ジオール及びその
製造方法に間するものである。DETAILED DESCRIPTION OF THE INVENTION A. Object of the Invention <Industrial Application Field> The present invention relates to an aromatic diol having a polyoxyarylene sulfone and polyoxyarylene ketone structure, and a method for producing the same.
芳香族ジオールは耐熱性高分子材料、例えばポリエステ
ル、ポリエーテルスルホン、ポリエーテルケトン樹脂等
の原料として、或いはウレタン樹脂、エポキシ樹脂、イ
ミド樹脂等の硬化剤である芳香族ジアミン化合物の原料
として有用な化合物である。Aromatic diols are useful as raw materials for heat-resistant polymer materials such as polyester, polyether sulfone, and polyether ketone resins, or as raw materials for aromatic diamine compounds that are curing agents for urethane resins, epoxy resins, imide resins, etc. It is a compound.
〈従来の技術〉
芳香族ジオール化合物は従来多くの試みがなされて独自
のものが提供されている０例えばビスフェノールＡと苛
性ソーダを反応させナトリウムフェノラートとした後ジ
クロロジフェニルスルホンと反応させる方法（特開昭６
３−２５０３５０号〈発明が解決しようとする問題点〉
本発明の目的は、一般式（１）
％式％（１）
（ただし上記式（１）中Ｙは
あるいは
Ｃ−
を表し、ｎは１−３０の整数を表す）
で示される新規な芳香族ジオール及びその製造法を提供
するものである。<Prior art> Many attempts have been made to create aromatic diol compounds, and unique ones have been provided. Showa 6
No. 3-250350 (Problems to be Solved by the Invention) The purpose of the present invention is to solve the following problems: General formula (1) % formula % (1) (However, in the above formula (1), Y represents or C-, and n is 1 (representing an integer of −30) and a method for producing the same.
従来知られている芳香族ジオール化合物の骨格構造はビ
スフェノールＡとジハロジフェニルスルホン又はジハロ
ベンゾフェノンとの交互共重合体から構成されるもので
あり、本発明の３．３′５．５′−テトラメチル−４，
４′−ビフェノールとジハロジフェニルスルホン又はジ
ハロベンゾフェノンとの交互共重合体から構成されるも
のとは構造を異にする。The skeleton structure of conventionally known aromatic diol compounds is composed of alternating copolymers of bisphenol A and dihalodiphenylsulfone or dihalobenzophenone, and the 3.3′5.5′- of the present invention Tetramethyl-4,
Its structure is different from that composed of alternating copolymers of 4'-biphenol and dihalodiphenylsulfone or dihalobenzophenone.
口 発明の構成
く問題を解決するための手段〉
本発明者らは、上記目的を達成するため鋭意検討を行っ
た結果、本発明を完成するに至った。Structure of the Invention: Means for Solving Problems> The present inventors have conducted intensive studies to achieve the above object, and as a result, have completed the present invention.
即ち、本発明は、
ｌ 下記一般式（１）で示される新規芳香族ジオール
・ ・ ・ ・ ・ （１）
（ただし上記式（１）中Ｙは
あるいは
Ｃ−
を表し、ｎは１−３０の整数を表す。）２ 下記一般式
（２）で示される化合物と、３．３′５．５゛−テトラ
メチル−４，４′−ビフェノールのアルカリ金属塩とを
、有機極性溶媒中で反応させることを特徴とする下記一
般式（１）で示される芳香族ジオールの製造方法。That is, the present invention provides a novel aromatic diol represented by the following general formula (1) (1) (However, in the above formula (1), Y represents or C-, and n is an integer of 1-30. Represents an integer.)2 A compound represented by the following general formula (2) and an alkali metal salt of 3.3'5.5'-tetramethyl-4,4'-biphenol are reacted in an organic polar solvent. A method for producing an aromatic diol represented by the following general formula (1), characterized by:
・ ｌ ・ ・ ・ （１）
（ただし上記式（１）中Ｙは
あるいは
Ｃ−
を表し、ｎは１−３０の整数を表す。）・ ・ ・
・ （２）
（ただし上記式（２）中ＸはＦ、ＣＩ、Ｂｒを表しＹは
上記式（１）のそれと同じである。）本発明による新規
芳香族ジオールは耐熱性高分子を才科例えばポリエステ
ル、ポリエーテルスルホン、ポリエーテルケトン樹脂等
の原料として、或いはウレタン樹脂、エポキシ樹脂、イ
ミド樹脂等の硬化剤である芳香族ジアミン化合物の原料
として有用な化合物である。・ l ・ ・ ・ (1) (However, in the above formula (1), Y represents or C-, and n represents an integer from 1 to 30.) ・ ・ ・
・ (2) (However, in the above formula (2), X represents F, CI, Br, and Y is the same as that in the above formula (1).) The novel aromatic diol according to the present invention can be used as a heat-resistant polymer. For example, it is a compound useful as a raw material for polyester, polyether sulfone, polyether ketone resins, etc., or as a raw material for aromatic diamine compounds that are curing agents for urethane resins, epoxy resins, imide resins, etc.
本発明の新規芳香族ジオールの製造のためには、前記式
（２）で示される化合物と、３．３′５．５−テトラメ
チル−４，４′−ビフェノールのアルカリ金属塩を有機
極性溶媒中で反応させることにより達成できろ。In order to produce the novel aromatic diol of the present invention, the compound represented by formula (2) and the alkali metal salt of 3,3'5,5-tetramethyl-4,4'-biphenol are mixed in an organic polar solvent. This can be achieved by reacting inside.
ここで用いろ有機極性溶媒としては、ジメチルスルホン
、ジエチルスルホン、ジメチルスルホキシド、ジエチル
スルホキシド、ジメチルホルムアミド、ジメチル７セト
アミドなどが例示される。Examples of the organic polar solvent used here include dimethyl sulfone, diethyl sulfone, dimethyl sulfoxide, diethyl sulfoxide, dimethylformamide, and dimethyl 7-cetamide.
反応温度は通常５０℃−２５０℃の範囲が好ましく、更
に好ましくは８０℃−２３０℃の範囲である。温度が低
すぎる場合は反応速度が遅く、極端な場合全く反応しな
い。−刃高すぎる場合は温度を上昇させる事による利点
は特に認められない。The reaction temperature is generally preferably in the range of 50°C to 250°C, more preferably in the range of 80°C to 230°C. If the temperature is too low, the reaction rate will be slow, and in extreme cases there will be no reaction at all. -If the blade is too high, there is no particular benefit from increasing the temperature.
３．３” ５．５′−テトラメチル−４，４′−ビフエ
ノールのアルカリ金属塩と化合物（２）とのｎ＋ｏｌ比
は特に限定されないが、通常１． ０以上５゜０以下で
ある。１．０以下では末端ハロゲン基のものが多くなり
芳香族ジオールの収量が低下し、５．０以上では残存す
る３、３′５．５′−テトラメチル−４，４′−ビフェ
ノールの量が多くなり共に不利益をまぬかれない。3.3" The n+ol ratio between the alkali metal salt of 5.5'-tetramethyl-4,4'-biphenol and compound (2) is not particularly limited, but is usually 1.0 or more and 5°0 or less.1 If it is less than .0, the number of terminal halogen groups increases and the yield of aromatic diol decreases, and if it is more than 5.0, the amount of remaining 3,3'5,5'-tetramethyl-4,4'-biphenol increases. Both of us are at a disadvantage.
原料の仕込方法は、−括仕込みでも良く、３．３′５．
５′−テトラメチル−４，４′−ビフェノールのアルカ
リ金属塩を分割して仕込んでも良いが、このましくは前
記アルカリ金属塩を分割して仕込む方法である。The method of charging the raw materials may be -batch charging, and the method is 3.3'5.
Although the alkali metal salt of 5'-tetramethyl-4,4'-biphenol may be charged in portions, it is preferable to charge the alkali metal salt in portions.
生成した芳香族ジオールの分離は、反応混合物を冷却し
た後析出したアルカリ金属塩ハロゲン化物を濾過等の方
法により分離した後、得られた濾液を酸処理した後、必
要に応じ濃縮、或はメタノール等を添加することにより
析出する固体を得る二とにより達成できる。得られた芳
香族ジオールは再度極性溶媒に溶解し、次いで再沈させ
ることにより純度を向上させることができる。The produced aromatic diol is separated by cooling the reaction mixture, separating the precipitated alkali metal salt halide by a method such as filtration, treating the obtained filtrate with an acid, and then concentrating or adding methanol as necessary. This can be achieved by adding a solid to precipitate. The purity of the obtained aromatic diol can be improved by dissolving it in a polar solvent again and then reprecipitating it.
〈実施例〉 以下実施例により本発明を具体的に説明する。<Example> The present invention will be specifically explained below using Examples.
実施例１
温度計、ジムロート冷却管付の水分離器、窒素導入管、
テフロン羽根付攪拌機の付いた５００１の４つロフラス
コに、３．３′５．５′−テトラメチル−４，４′−ビ
フェノール２４． ２ ｇ （０゜１ｍｏｌ）、水酸化
ナトリウム８．４２ｇ（純度９５％として０． ２ｍｏ
ｌ）、ジメチルスルホキシド１００＋ｌ、トルエン５０
ｍ１を仕込み生成する水をトルエンとの共沸混合物とし
て留去しながら１２６℃で７時間撹拌し、ナトリウムフ
ェノラートを合成した。Example 1 Thermometer, water separator with Dimroth cooling tube, nitrogen introduction tube,
3.3'5.5'-tetramethyl-4,4'-biphenol24. 2 g (0°1 mol), 8.42 g of sodium hydroxide (0.2 mol as purity 95%)
l), dimethyl sulfoxide 100+l, toluene 50
The mixture was stirred at 126° C. for 7 hours while distilling off the water produced as an azeotrope with toluene to synthesize sodium phenolate.
冷却後４．４′−ジクロロジフェニルスルホン１４、
４ｇ（０，０５ｍｏｌ）をジメチルスルホキシド５０１
に溶解したものを加え、１３２℃で５時間反応した。After cooling 4.4'-dichlorodiphenylsulfone 14,
4g (0.05mol) of dimethyl sulfoxide 501
The solution was added to the mixture and reacted at 132°C for 5 hours.
反応混合物を室温まで冷却した後析出した塩化ナトリウ
ムを濾別し、得られた濾液に蓚酸を加え酸性化した後メ
タノール４５０１を加えることにより固形物を析出させ
た。生成したスラリーを濾過し、得られた固形物を洗浄
液のｐＨが６−７になるまで水洗を繰り返した後、真空
下６０−７０℃で乾燥させた。収量２１．３ｇ、 こ
のものについて測定したＩＲ，’Ｈ−ＮＭＲスペクトル
を第１図及び第２図に示す。After the reaction mixture was cooled to room temperature, the precipitated sodium chloride was filtered off, and the resulting filtrate was acidified by adding oxalic acid, and then methanol 4501 was added to precipitate a solid substance. The resulting slurry was filtered, and the resulting solid was washed repeatedly with water until the pH of the washing solution became 6-7, and then dried under vacuum at 60-70°C. The yield was 21.3 g. The IR and 'H-NMR spectra measured for this product are shown in FIGS. 1 and 2.
ＮＭＲの測定には、日本電子のＦＸ−２００の装置を使
用した。測定温度は室温、サンプルは溶媒にＣＤ ＨＣ
ｌ ３、リファレンスにＭｅａＳｉを用い、濃度は約１
０％とした。’Ｈ−ＮＭＲのメチル基、水酸基、芳香族
基それぞれのプロトン数の比より下記構造式と決定され
た。For NMR measurement, a JEOL FX-200 device was used. The measurement temperature is room temperature, and the sample is CD HC in the solvent.
l 3, using MeaSi as a reference, the concentration is about 1
It was set to 0%. The following structural formula was determined from the ratio of the proton numbers of the methyl group, hydroxyl group, and aromatic group in 'H-NMR.
実施例２
温度計、ジムロート冷却管付の水分°離器、窒素導入管
、テフロン羽根付攪拌機の付いた５００１の４つロフラ
スコに、３．３′５．５′−テトラメチル−４，４′−
ビフェノール２４． ２ ｇ （０゜１ｍｏｌ）、水酸
化ナトリウム８．４２ｇ（純度９５％として０． ２ｍ
ｏｌ）、ジメチルスルホキシド１００ＩＩ１１、 トル
エン５０１を仕込み、生成する水をトルエンとの共沸混
合物として留去しながら１２２℃で７時間攪拌し、ナト
リウムフェノラートを合成した。Example 2 3.3'5.5'-tetramethyl-4,4' was placed in a 5001 four-bottle flask equipped with a thermometer, a water separator with a Dimroth condenser, a nitrogen inlet tube, and a stirrer with Teflon blades. −
Biphenol 24. 2 g (0°1 mol), 8.42 g of sodium hydroxide (0.2 m as purity 95%)
ol), dimethyl sulfoxide 100II11, and toluene 501 were charged and stirred at 122° C. for 7 hours while distilling off the produced water as an azeotropic mixture with toluene to synthesize sodium phenolate.
冷却後４．４゛−ジクロロベンゾフェノン１２゜６ｇ（
０，０５＋ｗｏｌ）をジメチルスルホキシド５゜１に溶
解したものを加え、１２７℃で５時間反応した。After cooling, 4.4゛-dichlorobenzophenone 12゜6g (
A solution of 0.05+wol) in 5.1 dimethyl sulfoxide was added, and the mixture was reacted at 127°C for 5 hours.
反応混合物を室温まで冷却した後析出した塩化ナトリウ
ムを濾別し、得られた濾液に蓚酸を加え酸性化した後メ
タノール４００１を加えることにより固形物を析出させ
た。生成したスラリーを濾過し、得られた固形物を洗浄
液のｉ）Ｈが６−７になるまで水洗を繰り返した後、真
空下６０−７０℃で乾燥させた。収量１７−７８ｅ
このものについて測定したＩＲ，ＩＨ−ＮＭＲスペクト
ルを第３図及び第４図に示す。After the reaction mixture was cooled to room temperature, the precipitated sodium chloride was filtered off, and the resulting filtrate was acidified by adding oxalic acid, and then methanol 4001 was added to precipitate a solid substance. The resulting slurry was filtered, and the resulting solid was washed with water repeatedly until the i)H of the washing solution reached 6-7, and then dried under vacuum at 60-70°C. Yield 17-78e
The IR and IH-NMR spectra measured for this product are shown in FIGS. 3 and 4.
Ｎ Ｍ Ｒの測定条件は実施例１の場合と同様である。The measurement conditions for NMR are the same as in Example 1.
’Ｈ−ＮＭＲのメチル基、水酸基、芳香族基それぞれの
プロトン数の比より下記構造式と決定された。The following structural formula was determined from the ratio of the proton numbers of the methyl group, hydroxyl group, and aromatic group in 'H-NMR.
第１図及び第３図は本発明にかかる化合物の■Ｒスペク
トａグラムであり、第２図、第４図は本発明にかかる化
合物のＩＨ−ＮＭＲスペクトログラムである。FIGS. 1 and 3 are R spectrograms of the compound according to the present invention, and FIGS. 2 and 4 are IH-NMR spectrograms of the compound according to the present invention.
Claims (1)
５、５′−テトラメチル−４、４′−ビフェノールのア
ルカリ金属塩とを有機極性溶剤中で反応させることを特
徴とする下記一般式（１）で示される芳香族ジオールの
製造方法。 ▲数式、化学式、表等があります▼・・・・・・（１） （ただし上記式（１）中Ｙは ▲数式、化学式、表等があります▼ あるいは ▲数式、化学式、表等があります▼ を表し、ｎは１−３０の整数を表す） ▲数式、化学式、表等があります▼・・・・・・（２） （ただし上記式（２）中ＸはＦ、Ｃｌ、Ｂｒを表しＹは
上記式（１）のそれと同じである。）[Claims] 1. A novel aromatic diol represented by the following general formula (1). ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・(1) (However, Y in the above formula (1) is ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (n represents an integer of 1-30) 2 A compound represented by the following general formula (2), and 3, 3',
A method for producing an aromatic diol represented by the following general formula (1), which comprises reacting 5,5'-tetramethyl-4,4'-biphenol with an alkali metal salt in an organic polar solvent. ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・(1) (However, Y in the above formula (1) is ▲There are mathematical formulas, chemical formulas, tables, etc.▼ Or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (where n represents an integer from 1 to 30) ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・(2) (However, in the above formula (2), X represents F, Cl, Br, and Y is the same as that in equation (1) above.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP606689A JPH02188552A (en) | 1989-01-17 | 1989-01-17 | Aromatic diol and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP606689A JPH02188552A (en) | 1989-01-17 | 1989-01-17 | Aromatic diol and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02188552A true JPH02188552A (en) | 1990-07-24 |
Family
ID=11628209
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP606689A Pending JPH02188552A (en) | 1989-01-17 | 1989-01-17 | Aromatic diol and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02188552A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5288834A (en) * | 1993-03-25 | 1994-02-22 | National Research Council Of Canada | Functionalized polyaryletherketones |
-
1989
- 1989-01-17 JP JP606689A patent/JPH02188552A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5288834A (en) * | 1993-03-25 | 1994-02-22 | National Research Council Of Canada | Functionalized polyaryletherketones |
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