JPH06116191A - Production of 1,3-dihydroxy-4,6-bis(alpha-methyl-alpha-@(3754/24)4'-hydroxyphenyl)ethyl)benzene - Google Patents
Production of 1,3-dihydroxy-4,6-bis(alpha-methyl-alpha-@(3754/24)4'-hydroxyphenyl)ethyl)benzeneInfo
- Publication number
- JPH06116191A JPH06116191A JP4270158A JP27015892A JPH06116191A JP H06116191 A JPH06116191 A JP H06116191A JP 4270158 A JP4270158 A JP 4270158A JP 27015892 A JP27015892 A JP 27015892A JP H06116191 A JPH06116191 A JP H06116191A
- Authority
- JP
- Japan
- Prior art keywords
- isopropenylphenol
- hydroxyphenyl
- benzene
- compound
- bis
- 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
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Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、ポリカーボネート、ポ
リエステル等の枝分かれ剤、レジスト用感放射線性成分
の原料、エポキシ樹脂の原料およびエポキシ樹脂の硬化
剤等として有用な化合物である１，３−ジヒドロキシ−
４，６−ビス〔α−メチル−α−（４’−ヒドロキシフ
ェニル) エチル〕ベンゼンの製造方法に関する。FIELD OF THE INVENTION The present invention relates to 1,3-dihydroxy compounds which are useful as branching agents such as polycarbonate and polyester, raw materials for radiation-sensitive components for resists, raw materials for epoxy resins and curing agents for epoxy resins. −
The present invention relates to a method for producing 4,6-bis [α-methyl-α- (4′-hydroxyphenyl) ethyl] benzene.
【０００２】[0002]
【従来の技術】上記用途に用いられる多価フェノール化
合物として、例えば、特開昭５５−１６２７２８号公報
には、下記一般式（２）〔化２〕2. Description of the Related Art As a polyhydric phenol compound used for the above applications, for example, JP-A-55-162728 discloses the following general formula (2):
【０００３】[0003]
【化２】 （式中、Ａｒは置換または非置換の単環式、二環式また
は三環式芳香族Ｃ6〜Ｃ1 4炭化水素基、置換または非置
換のＣ4〜Ｃ14複素環式基であり、Ｒは水素またはＣ1〜
Ｃ6アルキル基であり、各Ｘ置換基はそれぞれ独立に
Ｈ、Ｃｌ、Ｂｒ、Ｃ1〜Ｃ6アルキル基およびフェニル基
から選択し、ｎは２、３または４であり、従ってＡｒは
二価、三価または四価である）で表される多価フェノー
ル化合物が開示されている。[Chemical 2] (In the formula, Ar monocyclic substituted or unsubstituted, di or tricyclic aromatic C 6 -C 1 4 hydrocarbon group, a substituted or unsubstituted C 4 -C 14 heterocyclic group , R is hydrogen or C 1 ~
A C 6 alkyl group, each X substituent is independently selected from H, Cl, Br, a C 1 -C 6 alkyl group and a phenyl group, n is 2, 3 or 4, and thus Ar is a divalent group. , Trivalent or tetravalent) are disclosed.
【０００４】そして、該多価フェノール化合物を製造す
る方法として、例えば、触媒として塩化水素を用い、ｐ
−ジアセチルベンゼンにフェノールを反応させる方法が
開示されている。As a method for producing the polyhydric phenol compound, for example, hydrogen chloride is used as a catalyst and p
-A method for reacting diacetylbenzene with phenol is disclosed.
【０００５】また、特開昭６２−８４０３５号公報に
は、下記一般式（３）〔化３〕Further, Japanese Patent Laid-Open No. 62-84035 discloses the following general formula (3) [Chemical formula 3]
【０００６】[0006]
【化３】 （式中、Ｒ1、Ｒ2、Ｒ3、Ｒ4、Ｒ5およびＲ6 は互いに
同一であっても異なっていてもよく、それぞれ水素、ハ
ロゲン、Ｃ1〜Ｃ5アルキル基またはＣ1〜Ｃ5アルコキシ
基である）で表されるトリフェノール系化合物が開示さ
れている。[Chemical 3] (In the formula, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 may be the same or different from each other, and each is hydrogen, halogen, a C 1 to C 5 alkyl group or C 1 to A triphenol-based compound represented by (C 5 alkoxy group) is disclosed.
【０００７】そして、トリフェノール系化合物を製造す
る方法として、例えば、塩酸等のプロトン酸を触媒とし
て用い、イソプロペニルアセトフェノンに過剰のフェノ
ール化合物を反応させる方法が開示されている。As a method for producing a triphenol compound, for example, a method of reacting isopropenylacetophenone with an excess of a phenol compound using a protonic acid such as hydrochloric acid as a catalyst is disclosed.
【０００８】しかし、これらに開示される多価フェノー
ル化合物の製造工程が長く、しかも目的である多価フェ
ノール化合物の純度が低く精製が困難であった。However, the production process of the polyhydric phenol compounds disclosed therein is long, and the polyhydric phenol compound of interest has low purity and is difficult to purify.
【０００９】そこで、本出願人は、先に特願平３−１６
９６９６号に係わる特許出願において、上記用途として
有用な多価フェノール化合物として、４−イソプロペニ
ルフェノールまたは４−イソプロペニルフェノールの線
状重合体とレゾルシンを酸性触媒下で反応させることに
より得られる高純度の１，３−ジヒドロキシ−４，６−
ビス〔α−メチル−α−（４’−ヒドロキシフェニル）
エチル〕ベンゼンおよびその製造方法を提案した。Therefore, the present applicant previously filed Japanese Patent Application No. 3-16.
In the patent application relating to 9696, as a polyhydric phenol compound useful as the above-mentioned use, high purity obtained by reacting 4-isopropenylphenol or a linear polymer of 4-isopropenylphenol with resorcin under an acidic catalyst. 1,3-dihydroxy-4,6-
Bis [α-methyl-α- (4′-hydroxyphenyl)
Ethyl] benzene and its manufacturing method were proposed.
【００１０】[0010]
【発明が解決しょうとする課題】本発明の目的は、ポリ
カーボネート、ポリエステル等の枝分かれ剤、レジスト
用感放射線性成分の原料、エポキシ樹脂の原料およびエ
ポキシ樹脂の硬化剤等として有用な化合物である１，３
−ジヒドロキシ−４，６−ビス〔α−メチル−α−
（４’−ヒドロキシフェニル) エチル〕ベンゼンの新規
な製造方法を提供することにある。The object of the present invention is a compound useful as a branching agent such as polycarbonate and polyester, a raw material of a radiation sensitive component for resist, a raw material of epoxy resin and a curing agent of epoxy resin. , 3
-Dihydroxy-4,6-bis [α-methyl-α-
(4'-Hydroxyphenyl) ethyl] benzene is to be provided in a novel manner.
【００１１】[0011]
【課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した結果、反応溶媒中、酸性触媒
の存在下で、２−（２，４−ジヒドロキシフェニル）−
２−（４−ヒドロキシフェニル）プロパンと、４−イソ
プロペニルフェノール類を反応させることにより、容易
に、しかも高純度で上記多価フェノール化合物が得られ
ることを見出し、本発明に到った。Means for Solving the Problems As a result of intensive studies for achieving the above object, the present inventors have found that 2- (2,4-dihydroxyphenyl) -in the reaction solvent in the presence of an acidic catalyst.
The present inventors have found that the polyhydric phenol compound can be easily obtained with high purity by reacting 2- (4-hydroxyphenyl) propane with 4-isopropenylphenols, and thus the present invention has been completed.
【００１２】即ち、本発明は、反応溶媒中で酸性触媒の
存在下、２−（２，４−ジヒドロキシフェニル）−２−
（４−ヒドロキシフェニル）プロパンに対し、４−イソ
プロペニルフェノールおよび４−イソプロペニルフェノ
ールの線状重合体から選ばれた少なくとも一種のフェノ
ール化合物を反応させることを特徴とする下記式（１）
〔化４〕That is, the present invention provides 2- (2,4-dihydroxyphenyl) -2- in the presence of an acidic catalyst in a reaction solvent.
At least one phenol compound selected from linear polymers of 4-isopropenylphenol and 4-isopropenylphenol is reacted with (4-hydroxyphenyl) propane, and the following formula (1) is characterized.
[Chemical 4]
【００１３】[0013]
【化４】 で表される１，３−ジヒドロキシ−４，６−ビス〔α−
メチル−α−（４’−ヒドロキシフェニル) エチル〕ベ
ンゼンの製造方法である。[Chemical 4] 1,3-dihydroxy-4,6-bis [α-
This is a method for producing methyl-α- (4′-hydroxyphenyl) ethyl] benzene.
【００１４】以下、本発明について詳細に説明する。The present invention will be described in detail below.
【００１５】本発明において用いる４−イソプロペニル
フェノールおよびその線状重合体は、公知の技術である
ジヒドロキシジフェニルプロパンを塩基性触媒の存在下
で開裂して得られるフェノール、４−イソプロペニルフ
ェノールおよび４−イソプロペニルフェノールの重合体
を含む混合物よりフェノールを除去したものである。The 4-isopropenylphenol and the linear polymer thereof used in the present invention are phenol, 4-isopropenylphenol and 4 obtained by cleaving dihydroxydiphenylpropane, which is a known technique, in the presence of a basic catalyst. -Phenol is removed from a mixture containing a polymer of isopropenylphenol.
【００１６】また、この混合物より得られる線状２量体
の４−メチル−２，４−ビス（４−ヒドロキシフェニ
ル) ペンテン−１、４−メチル−２，４−ビス（４−ヒ
ドロキシフェニル) ペンテン−２、およびそれらの混合
物も使用することができる。Further, a linear dimer of 4-methyl-2,4-bis (4-hydroxyphenyl) pentene-1,4-methyl-2,4-bis (4-hydroxyphenyl) obtained from this mixture. Pentene-2, and mixtures thereof can also be used.
【００１７】また、本発明に用いられる２−（２，４−
ジヒドロキシフェニル）−２−（４−ヒドロキシフェニ
ル）プロパンの製造方法には特に制限はなく、公知の方
法、例えば、特開平２−２６９３５１号公報に開示され
る方法、すなわち、塩化アルミニウムの存在下で、レゾ
ルシンに２−（４−ヒドロキシフェニル）プロペンを反
応させる方法により得られたもので差し支えない。Further, 2- (2,4-used in the present invention
The method for producing dihydroxyphenyl) -2- (4-hydroxyphenyl) propane is not particularly limited, and is a known method, for example, the method disclosed in JP-A-2-269351, that is, in the presence of aluminum chloride. , Which may be obtained by a method of reacting resorcin with 2- (4-hydroxyphenyl) propene.
【００１８】本発明において２−（２，４−ジヒドロキ
シフェニル）−２−（４−ヒドロキシフェニル）プロパ
ンと、４−イソプロペニルフェノール、４−イソプロペ
ニルフェノールの線状重合体またはそれらの混合物を反
応するに際し、用いる酸性触媒としては、塩酸、臭化水
素酸、硫酸、燐酸等の無機酸、メタンスルホン酸、パラ
トルエンスルホン酸等の有機酸が挙げられる。これらの
中でも塩酸が好ましい。In the present invention, 2- (2,4-dihydroxyphenyl) -2- (4-hydroxyphenyl) propane is reacted with 4-isopropenylphenol, a linear polymer of 4-isopropenylphenol or a mixture thereof. Examples of the acidic catalyst used in this case include inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid and phosphoric acid, and organic acids such as methanesulfonic acid and paratoluenesulfonic acid. Of these, hydrochloric acid is preferred.
【００１９】触媒の使用量は、反応溶媒の種類にもよる
が、反応系に対し０．０１〜１．０重量％が好ましく、
更に好ましくは０．０３〜０．７重量％の範囲である。
触媒量が０．０１％未満の場合は反応時間が長くなり、
１．０％を超えると不純物の生成が多くなる。The amount of the catalyst used depends on the kind of the reaction solvent, but is preferably 0.01 to 1.0% by weight based on the reaction system.
More preferably, it is in the range of 0.03 to 0.7% by weight.
When the amount of catalyst is less than 0.01%, the reaction time becomes long,
If it exceeds 1.0%, the generation of impurities increases.
【００２０】２−（２，４−ジヒドロキシフェニル）−
２−（４−ヒドロキシフェニル）プロパンに対する４−
イソプロペニルフェノール、４−イソプロペニルフェノ
ールの線状重合体またはそれらの混合物のモル比は、２
−（２，４−ジヒドロキシフェニル）−２−（４−ヒド
ロキシフェニル）プロパン１モルに対し０．５〜１．５
モル（４−イソプロペニルフェノールの線状重合体のモ
ル数は４−イソプロペニルフェノール単位）が好まし
い。更に好ましくは０．７〜１．３モルである。０．５
未満の場合は２−（２，４−ジヒドロキシフェニル）−
２−（４−ヒドロキシフェニル）プロパンの残留が多く
なり、１．５を越える場合は４−イソプロペニルフェノ
ールのオリゴマー化合物が多くなり、精製工程が煩雑と
なる。2- (2,4-dihydroxyphenyl)-
4-to 2- (4-hydroxyphenyl) propane
The molar ratio of isopropenylphenol, 4-isopropenylphenol linear polymer or a mixture thereof is 2
0.5-1.5 per mol of-(2,4-dihydroxyphenyl) -2- (4-hydroxyphenyl) propane
It is preferable that the molar ratio of the linear polymer of 4-isopropenylphenol is 4-isopropenylphenol unit. More preferably, it is 0.7 to 1.3 mol. 0.5
2- (2,4-dihydroxyphenyl) -if less than
The residual amount of 2- (4-hydroxyphenyl) propane increases, and when it exceeds 1.5, the oligomer compound of 4-isopropenylphenol increases and the purification process becomes complicated.
【００２１】反応は溶媒中で行うことが好ましい。反応
溶媒としては、例えば、ヘプタン、シクロキサン等の脂
肪族炭化水素、ベンゼン、トルエン等の芳香族炭化水
素、クロロホルム、四塩化炭素等のハロゲン化炭化水素
およびメタノール、エタノール等のアルコール類が挙げ
られる。これらの反応溶媒は、単独または２種以上混合
して用いることができる。The reaction is preferably carried out in a solvent. Examples of the reaction solvent include aliphatic hydrocarbons such as heptane and cycloxane, aromatic hydrocarbons such as benzene and toluene, halogenated hydrocarbons such as chloroform and carbon tetrachloride, and alcohols such as methanol and ethanol. These reaction solvents can be used alone or in combination of two or more.
【００２２】反応温度は０〜１００℃が好ましく、更に
好ましくは３０〜６０℃である。温度が０℃未満の場合
は反応時間が長くなり、１００℃を超えると不純物の生
成が多くなる。The reaction temperature is preferably 0 to 100 ° C, more preferably 30 to 60 ° C. If the temperature is lower than 0 ° C, the reaction time becomes long, and if it exceeds 100 ° C, the production of impurities increases.
【００２３】[0023]
【実施例】以下，本発明を実施例によりさらに詳細に説
明する。 実施例１ 還流器、温度計および撹拌機を備えた２００ｍｌのセパ
ラブルフラスコに、２−（２，４−ジヒドロキシフェニ
ル）−２−（４−ヒドロキシフェニル）プロパン２４．
４ｇとベンゼン７０ｇを仕込み４０℃に保ち、撹拌下に
３６％塩酸０．１５ｇを入れ、さらに４−イソプロペニ
ルフェノール１３．４ｇをベンゼン６０ｇでスラリー化
した液を４０℃に保ちながら１５分間で装入した後、４
５℃に昇温して１時間撹拌した。EXAMPLES The present invention will now be described in more detail by way of examples. Example 1 In a 200 ml separable flask equipped with a reflux condenser, thermometer and stirrer, 2- (2,4-dihydroxyphenyl) -2- (4-hydroxyphenyl) propane 24.
4 g and 70 g of benzene were charged and kept at 40 ° C., 0.15 g of 36% hydrochloric acid was added with stirring, and further, 13.4 g of 4-isopropenylphenol was slurried with 60 g of benzene, and a liquid was prepared in 15 minutes while keeping at 40 ° C. After entering, 4
It heated up at 5 degreeC and stirred for 1 hour.
【００２４】次いで、反応物である結晶性スラリーを吸
引濾過し、結晶を水で中性になるまで洗浄し、真空乾燥
機で１２０℃、３時間乾燥して融点２１７〜２１９℃の
結晶３５．５ｇを得た。この結晶は元素分析、質量分
析、プロトン核磁気共鳴スペクトルの結果から下記式
（１）〔化５〕Then, the crystalline slurry as a reaction product was suction-filtered, the crystals were washed with water until neutral, and dried in a vacuum dryer at 120 ° C. for 3 hours to give crystals 35.p. having a melting point of 217-219 ° C. 5 g was obtained. This crystal has the following formula (1) [Chemical formula 5] based on the results of elemental analysis, mass spectrometry and proton nuclear magnetic resonance spectrum.
【００２５】[0025]
【化５】 で表される１，３−ジヒドロキシ−４，６−ビス〔α−
メチル−α−（４’−ヒドロキシフェニル) エチル〕ベ
ンゼンであることが確認され、液体クロマトグラフィー
による純度は９８．０％であった。[Chemical 5] 1,3-dihydroxy-4,6-bis [α-
It was confirmed to be methyl-α- (4′-hydroxyphenyl) ethyl] benzene, and the purity by liquid chromatography was 98.0%.
【００２６】元素分析の結果は、Ｃ＝７６．０％、Ｈ＝
６．９％、Ｎ＝０．０５％以下であった（理論値、Ｃ＝
７６．２％、Ｈ＝６．９％）。質量分析（ＥＩ−ＭＳ）
の結果、Ｍ+＝３７８であった。The results of elemental analysis are C = 76.0%, H =
6.9% and N = 0.05% or less (theoretical value, C =
76.2%, H = 6.9%). Mass spectrometry (EI-MS)
As a result, M + was 378.
【００２７】溶媒としてＣＤ3ＣＯＣＤ3、化学シフト基
準物質としてテトラメチルシラン（ＴＭＳ）を用いたプ
ロトン核磁気共鳴分析の結果を〔表１〕に示す。The results of the proton nuclear magnetic resonance analysis using CD 3 COCD 3 as a solvent and tetramethylsilane (TMS) as a chemical shift reference substance are shown in Table 1.
【００２８】[0028]
【表１】 [Table 1]
【００２９】実施例２ 実施例１と同じ容器に、２−（２，４−ジヒドロキシフ
ェニル）−２−（４−ヒドロキシフェニル）プロパン２
４．４ｇとベンゼン／メタノールの混合溶媒（重量比９
／１）７０ｇを仕込み４０℃に保ち、撹拌下に３６％塩
酸０．８５ｇを入れ、さらに４−イソプロペニルフェノ
ール１３．４ｇを上記混合溶媒６０ｇに溶解した溶液を
４０℃に保ちながら１５分間で装入した後、４５℃に昇
温して１時間撹拌した。次いで反応物を実施例１と同様
に処理して結晶３２．２ｇを得た。この結晶の純度は９
９．５％であった。Example 2 2- (2,4-dihydroxyphenyl) -2- (4-hydroxyphenyl) propane 2 was placed in the same container as in Example 1.
4.4g and benzene / methanol mixed solvent (weight ratio 9
/ 1) 70 g was charged and kept at 40 ° C., 36% hydrochloric acid 0.85 g was added under stirring, and further, a solution of 4-isopropenylphenol 13.4 g dissolved in 60 g of the above mixed solvent was kept at 40 ° C. for 15 minutes. After charging, the temperature was raised to 45 ° C. and the mixture was stirred for 1 hour. Then, the reaction product was treated in the same manner as in Example 1 to obtain 32.2 g of crystals. The purity of this crystal is 9
It was 9.5%.
【００３０】実施例３ 実施例１と同じ容器に、２−（２，４−ジヒドロキシフ
ェニル）−２−（４−ヒドロキシフェニル）プロパン２
４．４ｇと４−イソプロペニルフェノールの線状２量体
１３．４ｇ（４−イソプロペニルフェノール単位で０．
１モル）とジクロルメタン１７０ｇを仕込み４５℃に保
ち、撹拌下に３６％塩酸０．２ｇを入れ１時間撹拌し
た。次いで反応物を実施例１と同様に処理して結晶３
５．０ｇを得た。結晶の純度は９８．５％であった。Example 3 2- (2,4-dihydroxyphenyl) -2- (4-hydroxyphenyl) propane 2 was placed in the same container as in Example 1.
4.4 g and a linear dimer of 4-isopropenylphenol 13.4 g (0.4-isopropenylphenol unit of 0.
(1 mol) and 170 g of dichloromethane were charged and maintained at 45 ° C., 0.2 g of 36% hydrochloric acid was added with stirring, and the mixture was stirred for 1 hour. The reaction product was then treated as in Example 1 to give crystals 3
5.0 g was obtained. The crystal purity was 98.5%.
【００３１】実施例４ 実施例１と同じ容器に、２−（２，４−ジヒドロキシフ
ェニル）−２−（４−ヒドロキシフェニル）プロパン２
４．４ｇと純度の悪い４−イソプロペニルフェノールの
線状重合体１７．２ｇ（４−イソプロペニルフェノール
単位で０．１モル）とベンゼン１３０ｇを仕込み４５℃
に保ち、撹拌下に３６％塩酸０．２ｇを入れ１時間撹拌
した。次いで反応物である結晶性スラリーを吸引濾過
し、結晶を１００ｇのベンゼンで２回洗浄し、更に８０
℃の熱水１００ｇで２回洗浄し、真空乾燥機で１２０
℃、３時間乾燥して結晶３０．２ｇを得た。結晶の純度
は９８．０％であった。Example 4 2- (2,4-dihydroxyphenyl) -2- (4-hydroxyphenyl) propane 2 was placed in the same container as in Example 1.
4.4 g and poor purity 4-isopropenylphenol 17.2 g linear polymer (0.1 mol of 4-isopropenylphenol units) and benzene 130 g were charged at 45 ° C.
While maintaining the temperature at 0.2%, 0.2 g of 36% hydrochloric acid was added with stirring and the mixture was stirred for 1 hour. The reaction crystalline slurry is then suction filtered and the crystals are washed twice with 100 g of benzene and then washed with 80
Wash 2 times with 100g of hot water at ℃ and vacuum dryer for 120
The crystals were dried at 3 ° C. for 3 hours to obtain 30.2 g of crystals. The crystal purity was 98.0%.
【００３２】[0032]
【発明の効果】本発明の製造方法によれば、実施例より
明らかなように操作が容易で、収率良く高純度の１，３
−ジヒドロキシ−４，６−ビス〔α−メチル−α−
（４’−ヒドロキシフェニル) エチル〕ベンゼンを製造
することができる。得られた該フェノール性化合物はポ
リカーボネート、ポリエステル等の枝分かれ剤、レジス
ト用感放射線性成分の原料、エポキシ樹脂の原料および
エポキシ樹脂の硬化剤等として有用な化合物である。EFFECTS OF THE INVENTION According to the production method of the present invention, as is apparent from the examples, the operation is easy, and the yield of high-purity 1,3 is high.
-Dihydroxy-4,6-bis [α-methyl-α-
(4'-Hydroxyphenyl) ethyl] benzene can be produced. The obtained phenolic compound is a compound useful as a branching agent such as polycarbonate and polyester, a raw material of a radiation-sensitive component for resist, a raw material of epoxy resin and a curing agent of epoxy resin.
Claims (2)
（２，４−ジヒドロキシフェニル）−２−（４−ヒドロ
キシフェニル）プロパンと、４−イソプロペニルフェノ
ールおよび４−イソプロペニルフェノールの線状重合体
から選ばれた少なくとも一種のフェノール化合物を反応
させることを特徴とする下記式（１）〔化１〕 【化１】 で表される１，３−ジヒドロキシ−４，６−ビス〔α−
メチル−α−（４’−ヒドロキシフェニル) エチル〕ベ
ンゼンの製造方法。1. In a reaction solvent in the presence of an acidic catalyst, 2-
Reacting (2,4-dihydroxyphenyl) -2- (4-hydroxyphenyl) propane with at least one phenol compound selected from linear polymers of 4-isopropenylphenol and 4-isopropenylphenol. Characteristic formula (1) [Chemical formula 1] [Chemical formula 1] 1,3-dihydroxy-4,6-bis [α-
A method for producing methyl-α- (4′-hydroxyphenyl) ethyl] benzene.
ェニル）−２−（４−ヒドロキシフェニル）プロパンに
対し、０．５〜１．５モルの４−イソプロペニルフェノ
ールおよび４−イソプロペニルフェノールの線状重合体
から選ばれた少なくとも一種のフェノール化合物（４−
イソプロペニルフェノールの線状重合体のモル数は４−
イソプロペニルフェノール単位）を反応させることを特
徴とする請求項１記載の１，３−ジヒドロキシ−４，６
−ビス〔α−メチル−α−（４’−ヒドロキシフェニ
ル) エチル〕ベンゼンの製造方法。2. 0.5 to 1.5 mol of 4-isopropenylphenol and 4-isopropenyl relative to 1 mol of 2- (2,4-dihydroxyphenyl) -2- (4-hydroxyphenyl) propane. At least one phenol compound selected from linear polymers of phenol (4-
The number of moles of the isopropenylphenol linear polymer is 4-
1,3-dihydroxy-4,6 according to claim 1, characterized in that it is reacted with (isopropenylphenol units).
-A method for producing bis [α-methyl-α- (4'-hydroxyphenyl) ethyl] benzene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4270158A JP2593276B2 (en) | 1992-10-08 | 1992-10-08 | Method for producing 1,3-dihydroxy-4,6-bis [α-methyl-α- (4′-hydroxyphenyl) ethyl] benzene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4270158A JP2593276B2 (en) | 1992-10-08 | 1992-10-08 | Method for producing 1,3-dihydroxy-4,6-bis [α-methyl-α- (4′-hydroxyphenyl) ethyl] benzene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06116191A true JPH06116191A (en) | 1994-04-26 |
| JP2593276B2 JP2593276B2 (en) | 1997-03-26 |
Family
ID=17482353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4270158A Expired - Lifetime JP2593276B2 (en) | 1992-10-08 | 1992-10-08 | Method for producing 1,3-dihydroxy-4,6-bis [α-methyl-α- (4′-hydroxyphenyl) ethyl] benzene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2593276B2 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0689097A1 (en) * | 1994-06-15 | 1995-12-27 | Sumitomo Chemical Company, Limited | A polyhydroxy compound and a positive photoresist containing the same |
| US5744653A (en) * | 1994-02-25 | 1998-04-28 | Mitsui Toatsu Chemicals, Inc. | Method for preparing 1,3-dihydroxy-4,6-bis(α-methyl-α(4'-hydroxyphenyl)ethyl)benzene |
| CN104276928A (en) * | 2014-10-08 | 2015-01-14 | 苏州市吴赣药业有限公司 | Preparation method of 4,6-bi[1-(4-hydroxypheny)-1-methyl ethyl]-1,3-hydroquinone |
| CN113443969A (en) * | 2021-05-19 | 2021-09-28 | 辽宁靖帆新材料有限公司 | Method for preparing 4- [1- (4-hydroxyphenyl) -1-methyl-ethyl ] pyrogallol by resin method |
| CN113620786A (en) * | 2021-05-19 | 2021-11-09 | 辽宁靖帆新材料有限公司 | Method for synthesizing polyhydroxy phenolic compound by acid method |
-
1992
- 1992-10-08 JP JP4270158A patent/JP2593276B2/en not_active Expired - Lifetime
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5744653A (en) * | 1994-02-25 | 1998-04-28 | Mitsui Toatsu Chemicals, Inc. | Method for preparing 1,3-dihydroxy-4,6-bis(α-methyl-α(4'-hydroxyphenyl)ethyl)benzene |
| EP0689097A1 (en) * | 1994-06-15 | 1995-12-27 | Sumitomo Chemical Company, Limited | A polyhydroxy compound and a positive photoresist containing the same |
| CN104276928A (en) * | 2014-10-08 | 2015-01-14 | 苏州市吴赣药业有限公司 | Preparation method of 4,6-bi[1-(4-hydroxypheny)-1-methyl ethyl]-1,3-hydroquinone |
| CN104276928B (en) * | 2014-10-08 | 2016-04-13 | 苏州市吴赣药业有限公司 | The preparation method of two [1-(4-hydroxy phenyl)-1-the methylethyl]-Resorcinol of a kind of 4,6- |
| CN113443969A (en) * | 2021-05-19 | 2021-09-28 | 辽宁靖帆新材料有限公司 | Method for preparing 4- [1- (4-hydroxyphenyl) -1-methyl-ethyl ] pyrogallol by resin method |
| CN113620786A (en) * | 2021-05-19 | 2021-11-09 | 辽宁靖帆新材料有限公司 | Method for synthesizing polyhydroxy phenolic compound by acid method |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2593276B2 (en) | 1997-03-26 |
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