JPS63223020A - Production of polyphenols - Google Patents
Production of polyphenolsInfo
- Publication number
- JPS63223020A JPS63223020A JP5665587A JP5665587A JPS63223020A JP S63223020 A JPS63223020 A JP S63223020A JP 5665587 A JP5665587 A JP 5665587A JP 5665587 A JP5665587 A JP 5665587A JP S63223020 A JPS63223020 A JP S63223020A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- polyphenols
- water
- phenols
- weight
- 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
- 150000008442 polyphenolic compounds Chemical class 0.000 title claims abstract description 21
- 235000013824 polyphenols Nutrition 0.000 title claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N alpha-ketodiacetal Natural products O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000002989 phenols Chemical class 0.000 claims abstract description 13
- 238000006482 condensation reaction Methods 0.000 claims abstract description 10
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003377 acid catalyst Substances 0.000 claims abstract description 7
- 229940015043 glyoxal Drugs 0.000 claims abstract description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 12
- 150000001875 compounds Chemical class 0.000 abstract description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract description 6
- 150000003384 small molecules Chemical class 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229920001568 phenolic resin Polymers 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000003822 epoxy resin Substances 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
- 238000010438 heat treatment Methods 0.000 description 2
- -1 methylol group Chemical group 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- UBVXRQAPDRCBOE-UHFFFAOYSA-N 2-[1,2,2-tris(2-hydroxyphenyl)ethyl]phenol Chemical compound OC1=CC=CC=C1C(C=1C(=CC=CC=1)O)C(C=1C(=CC=CC=1)O)C1=CC=CC=C1O UBVXRQAPDRCBOE-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000005007 epoxy-phenolic resin Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、耐熱性エポキシ樹脂や耐熱性フェノール樹脂
の原料、プラスチックの改質剤として優れている低分子
化合物の含有量の少ないポリフェノール類の製造法に関
するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing polyphenols with a low content of low-molecular-weight compounds, which are excellent as raw materials for heat-resistant epoxy resins and heat-resistant phenolic resins, and as modifiers for plastics.
［従来技術及び問題点］
フェノール類と、グリオキザールまたはグルタルアルデ
ヒドとを酸触媒の存在下に縮合反応させると式（Ｉ）お
よび高次縮合物からなるポリフェノール類が生成するが
、このほかに活性なメチロール基（ンＣ１（ＯＨ）を有
する式（ＩＩ ）及び式（ｍ）の低分子化合物、及びこ
れら式（■）。[Prior art and problems] When phenols are subjected to a condensation reaction with glyoxal or glutaraldehyde in the presence of an acid catalyst, polyphenols consisting of formula (I) and higher-order condensates are produced. Low molecular weight compounds of formula (II) and formula (m) having a methylol group (C1(OH)), and these formulas (■).
式（ｍ）の分子内脱水で生成した化合物（以下、式（■
）９式（ｍ）及びこれらの脱水生成物を「低分子化合物
」と言う）が生成する。A compound produced by intramolecular dehydration of formula (m) (hereinafter referred to as formula (■
) 9 formula (m) and their dehydrated products are referred to as "low molecular compounds") are produced.
ｎ＝０または３
（Ｉ）
（ＩＩＩ）
これらの低分子化合物を含むポリフェノール類をエポキ
シ樹脂およびフェノール樹脂の原料にした場合、耐熱性
及び機械的強度が著しく低下する。しかも、これらの低
分子化合物とポリフェノール類との分離は極めて難しく
、工業的な分離方法は見い出されていない。n=0 or 3 (I) (III) When polyphenols containing these low molecular weight compounds are used as raw materials for epoxy resins and phenolic resins, heat resistance and mechanical strength are significantly reduced. Furthermore, it is extremely difficult to separate these low-molecular compounds from polyphenols, and no industrial separation method has yet been found.
そこで、低分子化合物を低減させる改良法として、フェ
ノール類とアルデヒドとを反応させた後、未反応フェノ
ールと水とを留去し、その後、低分子化合物を含むポリ
フェノール類に、再びフェノール類と酸触媒を加えて縮
合反応し、引続いてフェノール類と水とを除去してポリ
フェノール類を製造する方法（特開昭５８−１４２９０
８号）が提案されている。しかし、製造工程が複雑なた
め実用的でない。Therefore, as an improved method for reducing low-molecular compounds, after reacting phenols with aldehydes, unreacted phenol and water are distilled off, and then polyphenols containing low-molecular compounds are mixed with phenols and acids again. A method for producing polyphenols by adding a catalyst and carrying out a condensation reaction, and subsequently removing phenols and water (Japanese Patent Laid-Open No. 58-14290
No. 8) has been proposed. However, it is not practical because the manufacturing process is complicated.
［問題点を解決するための手段］ 本発明は、フェノール類と、グリオキザール。[Means for solving problems] The present invention relates to phenols and glyoxal.
グルタルアルデヒドより選ばれたジアルデヒド類とを酸
触媒の存在下に縮合反応によってポリフェノール類を製
造する方法において、反応系中の水の濃度を２重量％以
下に保持することを特徴とするポリフェノール類の製造
法である。A method for producing polyphenols by a condensation reaction with a dialdehyde selected from glutaraldehyde in the presence of an acid catalyst, characterized in that the concentration of water in the reaction system is maintained at 2% by weight or less. This is the manufacturing method.
本発明に用いられるフェノール類としては、フェノール
、クレゾール、キシレノール、カテコール、レゾルシン
、ハイドロキノンなどが挙げられ、フェノール類（ａ）
とジアルデヒド類（ｂ）とのモル比（ａ／ｂ）は４〜５
０、好ましくは５〜３０である。（ａ／ｂ）が４より小
さいと高次縮合物が多く生成し、一方、（ａ／ｂ）が５
０より大きいとポリフェノール類に対する未反応フェノ
ーノに量が多く、これの回収に多量のエネルギーを費や
すので好ましくない。Examples of the phenols used in the present invention include phenol, cresol, xylenol, catechol, resorcinol, hydroquinone, etc. Phenols (a)
The molar ratio (a/b) of and dialdehyde (b) is 4 to 5
0, preferably 5-30. When (a/b) is smaller than 4, many higher-order condensates are produced; on the other hand, when (a/b) is 5
If it is larger than 0, there will be a large amount of unreacted phenol with respect to polyphenols, and a large amount of energy will be expended to recover it, which is not preferable.
酸触媒としては、硫酸、塩酸、過塩素酸、フェノールス
ルホンｓ、トルエンスルホン酸、シュウ酸などが挙げら
れ、これらの触媒濃度は原料フェノール類に対して０．
０１〜４重量％が好ましい。Examples of acid catalysts include sulfuric acid, hydrochloric acid, perchloric acid, phenolsulfone s, toluenesulfonic acid, and oxalic acid, and the concentration of these catalysts is 0.0% relative to the raw material phenols.
01 to 4% by weight is preferred.
反応温度は８０−１４０℃、好ましくは９０〜１２０℃
であり、８０℃より低いと反応速度が遅く、しかも低分
子化合物の生成量が多くなる。一方、１４０℃より高い
温度では高次縮合物の生成量が多くなるので好ましくな
い。Reaction temperature is 80-140℃, preferably 90-120℃
If the temperature is lower than 80°C, the reaction rate will be slow and the amount of low molecular weight compounds produced will increase. On the other hand, temperatures higher than 140° C. are not preferred because the amount of higher-order condensates produced increases.
グリオキザール及びグルタルアルデヒドは無水の状態で
は非常に不安定なため４０〜５０％水溶液で市販されて
いる。したがって、反応系（反応液）には通常、ジアル
デヒド水溶液として混入する水と、フェノール類とジア
ルデヒド類との縮合反応によって生成する水が存在する
０反応系の水の濃度が２重量％より高い条件でフェノー
ルとジアルデヒド類との縮合反応をすると低分子化合物
が著しく多く生成するが、２重量％以下の濃度に保持す
ると、低分子化合物の生成量が少ない。Since glyoxal and glutaraldehyde are very unstable in anhydrous state, they are commercially available as 40-50% aqueous solutions. Therefore, the concentration of water in the reaction system (reaction liquid) usually contains water mixed as an aqueous solution of dialdehyde and water generated by the condensation reaction between phenols and dialdehydes, and the concentration of water in the reaction system is less than 2% by weight. If the condensation reaction between phenol and dialdehydes is carried out under high conditions, a significantly large amount of low molecular weight compounds will be produced, but if the concentration is maintained at 2% by weight or less, the amount of low molecular weight compounds produced will be small.
水を除去する方法としては特に制約はないが、一般には
蒸留除去が望ましい、すなわち、反応系内を常圧または
減圧にして加熱留出させるか、または窒素、ヘリウムな
どの不活性ガスを通気しながら除去するか、またはトル
エン、キシレンなどの溶媒と共沸させて除去する方法が
挙げられる。There are no particular restrictions on the method of removing water, but it is generally desirable to remove it by distillation. In other words, by heating the reaction system under normal pressure or reduced pressure, or by passing an inert gas such as nitrogen or helium through the reaction system. Examples of methods include removing the compound while removing the compound, or removing the compound by azeotropic distillation with a solvent such as toluene or xylene.
なお、反応後、反応系の触媒を除去またはアルカリで中
和し、水及び未反応フェノールを留去してポリフェノー
ル類を得る。After the reaction, the catalyst in the reaction system is removed or neutralized with an alkali, and water and unreacted phenol are distilled off to obtain polyphenols.
［発明の効果］
本発明によれば、簡単な製造法で低分子化合物の含有量
が少なく、純度の高いポリフェノール類が得られ、これ
は優れた耐熱性と機械的強度を有するエポキシ樹脂用及
びフェノール樹脂用の原料として使用される。[Effects of the Invention] According to the present invention, polyphenols with a low content of low-molecular-weight compounds and high purity can be obtained by a simple production method. Used as a raw material for phenolic resins.
［本発明の実施例］
実施例１
水分離器及び滴下ロートを備えた内容積２ｆＬのフラス
コにフェノール９４０ｇと市販の４０％グリオキザール
水溶液２３０ｇ （ａ／ｂ＝６．３）を仕込み、この反
応液を１００−１０５℃、圧力７００ｍｍＨｇに加熱、
減圧にして、反応系内の水１２０ｇを系外に留出させた
０反応液の水の濃度が１．７重量％になった時点で５０
％Ｐ−トルエンスルホン酸水溶液３．８ｇを滴下ロート
から徐々に添加し、縮合反応によって生成する水を連続
的に留去しながら、反応系の水の濃度を０．９〜１．９
重量％に保持し、１１０℃、２時間反応させた０反応後
、４％苛性ソーダ水溶液１００８ｇを添加してｐ−）ル
エンスルホン酸触媒を中和した。引続き減圧下に反応系
を１８０℃まで加熱しながら、水と未反応フェノールを
留去し、低分子化合物８重量％、１，１，２．２−テト
ラキス（ヒドロキシフェニル）エタン５４重ＩＪ％、及
び高次縮合物３８重量％からなるポリフェノール類（軟
化点１５２℃）４７０ｇを得た。。[Examples of the present invention] Example 1 A flask with an internal volume of 2 fL equipped with a water separator and a dropping funnel was charged with 940 g of phenol and 230 g of a commercially available 40% glyoxal aqueous solution (a/b = 6.3), and the reaction solution was heated to 100-105℃ and pressure 700mmHg,
The pressure was reduced and 120 g of water in the reaction system was distilled out of the system. When the concentration of water in the reaction solution reached 1.7% by weight,
%P-Toluenesulfonic acid aqueous solution (3.8 g) was gradually added from the dropping funnel, and the water concentration in the reaction system was adjusted to 0.9 to 1.9 while continuously distilling off the water produced by the condensation reaction.
After the reaction was carried out at 110° C. for 2 hours while maintaining the same weight percentage, 1008 g of a 4% aqueous sodium hydroxide solution was added to neutralize the p-)luenesulfonic acid catalyst. While subsequently heating the reaction system to 180°C under reduced pressure, water and unreacted phenol were distilled off, and 8% by weight of low molecular weight compounds, 54% by weight IJ of 1,1,2.2-tetrakis(hydroxyphenyl)ethane, and 470 g of polyphenols (softening point: 152° C.) consisting of 38% by weight of higher-order condensates were obtained. .
なお、低分子化合物はテトラヒドロフラン溶液を高速液
体クロマトグラフ（東洋曹達製Ｈ’ＬＣ８０２型）で分
析した。Note that low molecular weight compounds were analyzed by analyzing a tetrahydrofuran solution using a high performance liquid chromatograph (Model H'LC802 manufactured by Toyo Soda).
実施例２
実施例１と同一反応器にフェノール９４０ｇと４９％グ
ルタルアルデヒド水溶液２００ｇ（ａ／ｂ＝１０．２）
を仕込み、この反応液を１００〜１０５℃、圧カフ００
ｍｍＨＨに加熱。Example 2 940 g of phenol and 200 g of 49% glutaraldehyde aqueous solution (a/b = 10.2) were placed in the same reactor as in Example 1.
This reaction solution was heated to 100-105°C with a pressure cuff of 00
Heat to mmHH.
減圧して反応系内の水８９ｇを系外に留出させた０反応
液の水の濃度が１ 、２ｆｉ量％になった時点で５０％
ｐ−）ルエンスルホン酸水溶液７．２ｇを滴下ロートか
ら徐々に添加し、縮合反応によって生成する水を連続的
に留去しながら、反応系の水の濃度を０．７〜１．２重
量％に保持し、１００℃、３時間反応させた０反応後、
４％苛性ソーダ水溶液２１ｇを添加して触媒を中和した
。引続き減圧下に反応系を１８０℃まで加熱しながら、
水と未反応フェノールを留去し、低分子化合物３重量％
、１，１，５．５−テトラキス（ヒドロキシフェニル）
ペンタン４５ｉ１１％、及び高次縮合物５２重量％から
なるポリフェノール類（軟化点１３８℃）３９６ｇを得
た。89g of water in the reaction system was distilled out of the system by reducing the pressure.When the concentration of water in the reaction solution reached 1.2fi%, it was 50%.
p-) Gradually add 7.2 g of an aqueous solution of luenesulfonic acid from the dropping funnel, and while continuously distilling off the water produced by the condensation reaction, the concentration of water in the reaction system is adjusted to 0.7 to 1.2% by weight. After 0 reaction, which was maintained at 100°C for 3 hours,
21 g of 4% aqueous sodium hydroxide solution was added to neutralize the catalyst. While continuing to heat the reaction system to 180°C under reduced pressure,
Water and unreacted phenol were distilled off, resulting in 3% by weight of low molecular weight compounds.
, 1,1,5.5-tetrakis(hydroxyphenyl)
396 g of polyphenols (softening point: 138° C.) consisting of 11% pentane 45i and 52% by weight of higher order condensates was obtained.
比較例１
内容積２Ｍのフラスコにフェノール９４０ｇ、４０％グ
リオキザール水溶液２３０ｇ（ａ／ｂ−６，３）、及び
ｐ−）ルエンスルホン！１．９ｇを仕込み、１１０℃で
６時間反応させた（反応系中の水の濃度を１１〜１６重
量％に保持した）。Comparative Example 1 In a flask with an internal volume of 2M, 940 g of phenol, 230 g of a 40% glyoxal aqueous solution (a/b-6,3), and p-)luenesulfone! 1.9 g was charged and reacted at 110° C. for 6 hours (the concentration of water in the reaction system was maintained at 11 to 16% by weight).
反応後、実施例１と同様に処理し、低分子化合物３６重
量％、１．１．２．２−テトラキス（ヒドロキシフェニ
ル）エタン４８重量％、及び高次縮合物１６重量％から
なるポリフェノール類（軟化点１１６℃）を得た。After the reaction, it was treated in the same manner as in Example 1 to obtain polyphenols ( A softening point of 116° C.) was obtained.
比較例２
内容１ａ２１のフラスコにフェノール９４０ｇ、４９％
グルタルアルデヒド水溶液２００ｇ（ａ／ｂ＝１０．２
）、及びｐ−トルエンスルホン酸３．６ｇを仕込み、１
００℃で６時間反応させた（反応系中の水の濃度を８６
８〜１１．５重量％に保持した）０反応後、実施例２と
同様に処理し、低分子化合物４１重量％、１．１．５．
５−テトラキス（ヒドロキシフェニル）ペンタン３７重
量％、及び高次縮合物２２重量％からなるポリフェノー
ルを得た。Comparative Example 2 940g of phenol, 49% in a flask with contents 1a21
200g of glutaraldehyde aqueous solution (a/b=10.2
), and 3.6 g of p-toluenesulfonic acid, 1
The reaction was carried out at 00°C for 6 hours (the concentration of water in the reaction system was 86°C).
After the reaction (maintained at 8 to 11.5% by weight), the same treatment as in Example 2 was carried out, and the low molecular weight compound was 41% by weight, 1.1.5.
A polyphenol consisting of 37% by weight of 5-tetrakis(hydroxyphenyl)pentane and 22% by weight of a higher order condensate was obtained.
Claims (1)
アルデヒドより選ばれたジアルデヒド類（ｂ）とを酸触
媒の存在下に縮合反応によってポリフェノール類を製造
する方法において、反応系中の水の濃度を２重量％以下
に保持することを特徴とするポリフェノール類の製造法
。 ２）フェノール類（ａ）とジアルデヒド類（ｂ）とのモ
ル比（ａ／ｂ）が４〜５０であることを特徴とする特許
請求の範囲第１項記載のポリフェノール類の製造法。 ３）反応温度が８０〜１４０℃であることを特徴とする
特許請求の範囲第１項記載のポリフェノール類の製造法
。[Claims] 1) A method for producing polyphenols by a condensation reaction of phenols (a) and dialdehydes (b) selected from glyoxal and glutaraldehyde in the presence of an acid catalyst, comprising: A method for producing polyphenols, which comprises maintaining the concentration of water at 2% by weight or less. 2) The method for producing polyphenols according to claim 1, wherein the molar ratio (a/b) of phenols (a) and dialdehydes (b) is 4 to 50. 3) The method for producing polyphenols according to claim 1, wherein the reaction temperature is 80 to 140°C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5665587A JPH0762060B2 (en) | 1987-03-13 | 1987-03-13 | Method for producing polyphenols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5665587A JPH0762060B2 (en) | 1987-03-13 | 1987-03-13 | Method for producing polyphenols |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63223020A true JPS63223020A (en) | 1988-09-16 |
| JPH0762060B2 JPH0762060B2 (en) | 1995-07-05 |
Family
ID=13033390
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5665587A Expired - Lifetime JPH0762060B2 (en) | 1987-03-13 | 1987-03-13 | Method for producing polyphenols |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0762060B2 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5157165A (en) * | 1990-11-26 | 1992-10-20 | Mitsui Toatsu Chemicals, Inc. | Method for preparing highly pure 1,1,2,2-tetrakis(4-hydroxy-3,5-dimethylphenyl)ethane |
| WO2000017243A1 (en) * | 1998-09-22 | 2000-03-30 | Borden Chemical, Inc. | Phenol-novolacs with improved optical properties |
| JP2006273774A (en) * | 2005-03-30 | 2006-10-12 | Asahi Organic Chem Ind Co Ltd | Method for producing tetrakis(hydroxyphenyl)alkane |
| CN111333796A (en) * | 2020-04-01 | 2020-06-26 | 山东莱芜润达新材料有限公司 | Preparation method of tetraphenol ethane phenolic resin |
| WO2020225884A1 (en) * | 2019-05-08 | 2020-11-12 | 昭和電工マテリアルズ株式会社 | Resin particle mixture |
-
1987
- 1987-03-13 JP JP5665587A patent/JPH0762060B2/en not_active Expired - Lifetime
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5157165A (en) * | 1990-11-26 | 1992-10-20 | Mitsui Toatsu Chemicals, Inc. | Method for preparing highly pure 1,1,2,2-tetrakis(4-hydroxy-3,5-dimethylphenyl)ethane |
| US5304624A (en) * | 1990-11-26 | 1994-04-19 | Mitsui Toatsu Chemicals, Incorporated | Epoxy resin derived from the highly pure compound and method for preparing the resin and composition |
| WO2000017243A1 (en) * | 1998-09-22 | 2000-03-30 | Borden Chemical, Inc. | Phenol-novolacs with improved optical properties |
| EP1034193A4 (en) * | 1998-09-22 | 2004-05-26 | Borden Chem Inc | Phenol-novolacs with improved optical properties |
| JP2006273774A (en) * | 2005-03-30 | 2006-10-12 | Asahi Organic Chem Ind Co Ltd | Method for producing tetrakis(hydroxyphenyl)alkane |
| WO2020225884A1 (en) * | 2019-05-08 | 2020-11-12 | 昭和電工マテリアルズ株式会社 | Resin particle mixture |
| JPWO2020225884A1 (en) * | 2019-05-08 | 2020-11-12 | ||
| CN111333796A (en) * | 2020-04-01 | 2020-06-26 | 山东莱芜润达新材料有限公司 | Preparation method of tetraphenol ethane phenolic resin |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0762060B2 (en) | 1995-07-05 |
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