JP3009245B2 - N-substituted maleimide and method for producing the same - Google Patents
N-substituted maleimide and method for producing the sameInfo
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- JP3009245B2 JP3009245B2 JP3139951A JP13995191A JP3009245B2 JP 3009245 B2 JP3009245 B2 JP 3009245B2 JP 3139951 A JP3139951 A JP 3139951A JP 13995191 A JP13995191 A JP 13995191A JP 3009245 B2 JP3009245 B2 JP 3009245B2
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Description
【０００１】[0001]
【産業上の利用分野】本発明は新規なＮ−置換マレイミ
ドおよびその製造方法に関する。The present invention relates to a novel N-substituted maleimide and a method for producing the same.
【０００２】[0002]
【従来の技術】従来よりＮ−置換マレイミドは、ポリ塩
化ビニル、ポリスチレン、ＡＢＳ等の熱可塑性樹脂の耐
熱性改質剤や医薬、農薬の原料として使用され、特に熱
可塑性樹脂分野での使用が大半を占めている。2. Description of the Related Art N-substituted maleimides have hitherto been used as a heat-resistant modifier for thermoplastic resins such as polyvinyl chloride, polystyrene and ABS, and as raw materials for pharmaceuticals and agricultural chemicals, and are particularly used in the field of thermoplastic resins. Make up the majority.
【０００３】熱可塑性樹脂分野で使用されているＮ−置
換マレイミドとしてＮ−フェニルマレイミドが知られて
いるが、Ｎ−フェニルマレイミドはそれ自身が黄色であ
るため、これを樹脂に混ぜると、添加された樹脂が黄色
に着色してしまうという欠点を有しており、透明性の要
求される用途には使用が制限されていた。また、その欠
点を解決するために、Ｎ−シクロヘキシルマレイミドが
一部使用されているが、樹脂が黄色に着色しにくいもの
の、耐熱性改質剤としては耐熱性の向上が十分でなく満
足するに至っていない。[0003] N-phenylmaleimide is known as an N-substituted maleimide used in the field of thermoplastic resins. However, N-phenylmaleimide itself is yellow, so when N-phenylmaleimide is mixed with a resin, it is added. However, the resin has a disadvantage that it is colored yellow, and its use is restricted to applications requiring transparency. Further, in order to solve the drawback, N-cyclohexylmaleimide is partially used. However, although the resin is hardly colored yellow, the improvement in heat resistance as a heat resistance modifier is not sufficient and is satisfactory. Not reached.
【０００４】[0004]
【発明が解決しようとする課題】本発明の目的は黄色を
帯びずにそれ自体白色の耐熱性に優れた新規なＮ−置換
マレイミドを提供することである。SUMMARY OF THE INVENTION An object of the present invention is to provide a novel N-substituted maleimide which is not yellowish in itself and has excellent white heat resistance.
【０００５】[0005]
【課題を解決するための手段】本発明者らは前記したよ
うな課題を達成するため、鋭意検討した結果、本発明を
完成するに至った。すなわち、本発明は一般式（Ｉ）
（化６）Means for Solving the Problems The inventors of the present invention have conducted intensive studies to achieve the above-mentioned objects, and as a result, have completed the present invention. That is, the present invention provides a compound represented by the general formula (I)
(Formula 6)
【０００６】[0006]
【化６】 （式中、Ｘ1 、Ｘ2 はそれぞれ独立に水素原子、ハロゲ
ン原子、または炭素数１〜１０のアルキル基を表わし、
Ｒ1 は、ハロゲン原子または炭素数１〜１０のアルキル
基を表わす。但し、Ｒ1 が複数ある場合（即ち、ｍが２
以上の場合）、複数個のＲ1 は互いに同じでも又は異な
っていても良い。ｍは０から１７までの整数とする。）
で表わされる新規なＮ−置換マレイミドおよび一般式
（ＩＩ）（化７）Embedded image (Wherein X 1 and X 2 each independently represent a hydrogen atom, a halogen atom, or an alkyl group having 1 to 10 carbon atoms;
R 1 represents a halogen atom or an alkyl group having 1 to 10 carbon atoms. However, when there are a plurality of R 1 (that is, m is 2
In the above case), a plurality of R 1 may be the same or different. m is an integer from 0 to 17. )
A novel N-substituted maleimide represented by the general formula (II):
【０００７】[0007]
【化７】 （式中、Ｘ1 、Ｘ2 、Ｒ1 およびｍは一般式（Ｉ）と同
じ内容を示す）で表わされる新規なマレアミド酸を脱水
閉環反応させることを特徴とするＮ−置換マレイミドの
製造方法に関する。Embedded image (Wherein X 1 , X 2 , R 1 and m have the same contents as in the general formula (I)). A method for producing an N-substituted maleimide, comprising subjecting a novel maleamic acid represented by the following formula to a dehydration ring closure reaction. About.
【０００８】本発明で用いられる一般式（ＩＩ）で表わ
されるマレアミド酸は、新規な化合物であり、本発明で
は、一般式（III)（化８）The maleamic acid represented by the general formula (II) used in the present invention is a novel compound. In the present invention, the maleamic acid represented by the general formula (III)
【０００９】[0009]
【化８】 （式中、Ｒ1 およびｍは一般式（Ｉ）と同じ内容を示
す）で表わされる脂環式アミン化合物と一般式（ＩＶ）
（化９）Embedded image (Wherein R 1 and m are the same as those of the general formula (I)) and an alicyclic amine compound represented by the general formula (IV)
(Formula 9)
【００１０】[0010]
【化９】 （式中、Ｘ1 、Ｘ2 は一般式（Ｉ）と同じ内容を示す）
で表わされる無水マレイン酸又はその誘導体とを付加反
応させて製造される。Embedded image (Wherein, X 1 and X 2 have the same contents as in the general formula (I))
And maleic anhydride or a derivative thereof is subjected to an addition reaction.
【００１１】本発明で使用される脂環式アミン化合物
は、一般式（III)で表わされ、PATENTSCH-RIFT DD 221
172.に記載の方法に準じて製造することができる。例え
ば、９(10)−シアンテトラシクロ−［6.2.1.13,6.
02,7 ］−ドデセン−(4) をラネーコバルト又はラネー
ニッケル等の触媒により還元アミノ化して9(10)-アミノ
メチル−［6.2.1.13,6.02,7 ］−ドデカンを製造するこ
とができる。尚、一般式（III)において、ｍは０から１
７の整数である。ｍが０の場合は、置換基Ｒ1 が全く入
らない場合を示し、ｍが１７の場合は、置換可能な１〜
１２の位置に全てＲ1 で置換されている場合を示す。The alicyclic amine compound used in the present invention is represented by the general formula (III), and comprises PATENTSCH-RIFT DD 221
It can be produced according to the method described in 172. For example, 9 (10) -cyantetracyclo- [6.2.1.1 3,6 .
0 2,7] - dodecene - (4) is reduced amination by catalyst such as Raney cobalt or Raney nickel. 9 (10) - aminomethyl - [6.2.1.1 3, 6 .0 2,7] - producing dodecane be able to. In the general formula (III), m is 0 to 1
It is an integer of 7. When m is 0, it indicates the case where the substituent R 1 does not enter at all. When m is 17, it is possible to substitute 1 to 1.
The case where all of the 12 positions are substituted with R 1 is shown.
【００１２】一方、脂環式アミン化合物との反応に使用
される無水マレイン酸又はその誘導体は、一般式（Ｉ
Ｖ）で表わされ、具体的には、無水マレイン酸、３−メ
チル無水マレイン酸、３−エチル無水マレイン酸、３，
４−ジメチル無水マレイン酸、３，４−ジエチル無水マ
レイン酸、３−クロル無水マレイン酸、３，４−ジクロ
ル無水マレイン酸などが挙げられる。On the other hand, maleic anhydride or a derivative thereof used in the reaction with an alicyclic amine compound has the general formula (I)
V), specifically, maleic anhydride, 3-methylmaleic anhydride, 3-ethylmaleic anhydride,
4-dimethyl maleic anhydride, 3,4-diethyl maleic anhydride, 3-chloromaleic anhydride, 3,4-dichloromaleic anhydride and the like.
【００１３】上記した脂環式アミン化合物と無水マレイ
ン酸又はその誘導体を付加反応させてマレアミド酸が得
られるが、本発明の方法では、脂環式アミン化合物１モ
ルに対して、無水マレイン酸又はその誘導体を０．６〜
１．５倍モルの範囲で用いて反応を行う。より好ましく
は０．８〜１．２倍モルである。The above-mentioned alicyclic amine compound is subjected to an addition reaction with maleic anhydride or a derivative thereof to obtain maleamic acid. In the method of the present invention, maleic anhydride or maleic anhydride is added to 1 mol of the alicyclic amine compound. 0.6-
The reaction is carried out using a 1.5-fold molar range. More preferably, it is 0.8 to 1.2 times mol.
【００１４】反応に際しては、溶媒を使用することが好
ましく、例えば、ヘキサン、ヘプタン、シクロヘキサン
などの脂肪族炭化水素、ベンゼン、トルエン、キシレン
などの芳香族炭化水素、クロルベンゼン、ジクロルベン
ゼンなどのハロゲン系芳香族炭化水素やジメチルホルム
アミド、Ｎ−メチルピロリドン、ジメチルスルホキシド
などの非プロトン性極性溶媒およびこれらの混合溶媒を
使用することができる。より好ましくはジメチルホルム
アミドなどの非プロトン性極性溶媒である。また溶媒の
使用量は原料アミン化合物に対して１〜２０倍量（重
量）が好ましく、より好ましくは２〜１０倍量（重量）
である。In the reaction, it is preferable to use a solvent, for example, an aliphatic hydrocarbon such as hexane, heptane and cyclohexane, an aromatic hydrocarbon such as benzene, toluene and xylene, and a halogen such as chlorobenzene and dichlorobenzene. An aprotic polar solvent such as a system aromatic hydrocarbon, dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and the like, and a mixed solvent thereof can be used. More preferred are aprotic polar solvents such as dimethylformamide. The amount of the solvent used is preferably 1 to 20 times (by weight), more preferably 2 to 10 times (by weight) the raw material amine compound.
It is.
【００１５】反応においては、無水マレイン酸と原料ア
ミン化合物を最初から全量仕込んでも良いが、発熱をと
もなうためどちらかを少量づつ添加するのが好ましい。
より好ましくは無水マレイン酸を溶媒に完全に溶解さ
せ、反応釜内温が１２０℃以下、好ましくは３０〜１０
０℃の範囲に保たれるように、原料アミン化合物を攪拌
しながら滴下させるのが良い。この時、滴下する原料ア
ミンは反応溶媒と同じ溶媒で溶解しておいてもよい。[0015] In the reaction, it may be charged the total amount of maleic anhydride and starting material amine compound from the start, but is preferably gradually added either order with a fever.
More preferably, maleic anhydride is completely dissolved in the solvent, and the temperature in the reaction vessel is 120 ° C or lower, preferably 30 to 10 ° C.
It is preferable to drop the raw material amine compound while stirring so that the temperature is kept in the range of 0 ° C. At this time, the raw material amine to be dropped may be dissolved in the same solvent as the reaction solvent.
【００１６】原料アミンの滴下時間は、５〜１８０分が
好ましいが、より好ましくは３０〜１２０分の範囲で全
量を滴下するのが良い。また滴下終了後、ただちに脱水
閉環反応を行うこともできるが、好ましくはマレアミド
酸を３０〜１２０℃で０．５〜３．０時間程度熟成させ
るのが良く、より好ましくは５０〜１００℃で１．０〜
２．０時間程度熟成を行うのが良い。The time for dropping the starting amine is preferably from 5 to 180 minutes, and more preferably, the entire amount is dropped within the range from 30 to 120 minutes. After completion of the dropwise addition, the dehydration ring-closing reaction can be carried out immediately, but it is preferable that the maleamic acid is aged at 30 to 120 ° C for about 0.5 to 3.0 hours, more preferably at 50 to 100 ° C for 1 hour. .0
Aging is preferably performed for about 2.0 hours.
【００１７】前記反応によって得られる一般式（ＩＩ）
で表わされるマレアミド酸から一般式（Ｉ）で表わされ
るＮ−置換マレイミドを得る脱水閉環反応については、
特に限定されるものではなく、それ自体公知の方法が採
用できる。The general formula (II) obtained by the above reaction
For the dehydration ring closure reaction for obtaining the N-substituted maleimide represented by the general formula (I) from the maleamic acid represented by
The method is not particularly limited, and a method known per se can be adopted.
【００１８】本発明の方法では、必要に応じて触媒を使
用することができる。使用する触媒としては、例えばｐ
−トルエンスルホン酸、ベンゼンスルホン酸、メタスル
ホン酸などの有機酸やオルソリン酸、ポリリン酸、メタ
ソン酸、硫酸などの無機酸または亜鉛などの金属含有化
合物、好ましくはＺｎＯ2 、ＳｎＯ2 などの金属酸化物
を使用することができる。より好ましくはオルソリン
酸、ポリリン酸などの有機酸である。In the method of the present invention, a catalyst can be used if necessary. As the catalyst to be used, for example, p
- toluenesulfonic acid, benzenesulfonic acid, an organic acid or orthophosphoric acid such as methanesulfonic acid, polyphosphoric acid, Metason acids, metal-containing compound such as an inorganic acid or zinc, such as sulfuric acid, preferably a metal oxide such as ZnO 2, SnO 2 Can be used. More preferred are organic acids such as orthophosphoric acid and polyphosphoric acid.
【００１９】触媒の使用量はマレアミド酸１００部に対
して０．１〜２００重量部であることが好ましく、より
好ましくは２〜１００重量部使用することが適当であ
る。触媒は、全量を一度に仕込んでも良いが、発熱を伴
う反応のために触媒の使用量によっては、数回に分けて
装入する方法を採用しても良い。The amount of the catalyst used is preferably 0.1 to 200 parts by weight, more preferably 2 to 100 parts by weight, per 100 parts of maleamic acid. The catalyst may be charged in its entirety at once, or may be charged several times depending on the amount of catalyst used for the reaction involving heat generation.
【００２０】脱水閉環反応における反応温度は、５０〜
１８０℃の範囲が好ましく、より好ましくは６０〜１６
０℃程度で反応を行うのが良い。The reaction temperature in the dehydration ring closure reaction is 50 to
The temperature is preferably in the range of 180 ° C, more preferably 60 to 16 ° C.
The reaction is preferably performed at about 0 ° C.
【００２１】反応時間については、１〜１００時間程度
反応させるが、より好ましくは１〜５０時間反応を続け
るのが適当である。The reaction is carried out for about 1 to 100 hours, more preferably 1 to 50 hours.
【００２２】脱水閉環反応終了後、反応液は、濾過によ
り副反応物または酸触媒を除去した後、蒸留または昇華
精製により精製を行うことができる。好ましくは、副反
応物または酸触媒を除去した後、水洗またはアルカリ洗
浄後、再結晶により一般式（Ｉ）で表わされるＮ−置換
マレイミドを高純度で得ることができる。After the completion of the dehydration ring closure reaction, the reaction solution can be purified by distillation or sublimation purification after removing a by-product or an acid catalyst by filtration. Preferably, the N-substituted maleimide represented by the general formula (I) can be obtained with high purity by removing the by-products or the acid catalyst, washing with water or alkali, and recrystallization.
【００２３】以上のようにして得られる本発明の一般式
（Ｉ）で表わされるＮ−置換マレイミドは、従来の芳香
族Ｎ−置換マレイミドのように黄色に着色せず、白色の
結晶であり、非常に熱安定性に優れている。The N-substituted maleimide represented by the general formula (I) of the present invention obtained as described above is a white crystal without coloring yellow, unlike a conventional aromatic N-substituted maleimide, Very good thermal stability.
【００２４】[0024]
【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 攪拌機、冷却コンデンサー、温度計、窒素ガス導入管、
滴下ロートを備えた、１００ｍｌのガラス製四っ口フラ
スコ中に無水マレイン酸５．６ｇ（０．０５７モル）及
びジメチルホルムアミド２０ｇを装入し、６０℃に昇温
しながら完全に溶解させ、この中に９(10)−アミノメチ
ルテトラシクロ［6.2.1.13,6.02,7 ］ドデカン１０ｇ
（０．０５２モル）を反応温度に注意しながら１時間か
けて滴下し、さらに６０℃で２時間熟成を行ないマレア
ミド酸を合成した。次に、上記反応液にポリリン酸２０
ｇを装入した後反応温度に注意しながら昇温し、９０〜
９５℃で１２時間脱水閉環反応させた。反応終了後、室
温まで冷却しメタノール２０ｇを装入し、１時間攪拌後
結晶を濾別した。さらにこの結晶をトルエン４０ｇに溶
解しアルカリ洗浄した後、濃縮し析出した結晶を濾別
し、さらにメタノール１０ｇで洗浄し白色結晶を得た。
乾燥後の重量は６．５ｇであった。純度９９．９％この
結晶は元素分析、 1Ｈ−ＮＭＲ、ＩＲの分析結果より、
９(10)−アミノメチル−［6.2.1.13,6.02,7 ］−ドデカ
ンマレイミドと同定した。測定結果を下記に示す。 元素分析値（％） （Ｃ17Ｈ21ＮＯ2 として計算） Ｃ Ｈ Ｎ 理論値 ７５．２５ ７．８０ ５．１６ 測定値 ７５．５３ ７．６７ ５．１４ 1 Ｈ−ＮＭＲスペクトル（９０ＭＨｚ，ＣＤＣｌ3 溶媒） プロトン積分強度比 テトラシクロ環に基づくシグナル １．０〜２．３ｐｐｍ 17 −ＣＨ2 に基づくシグナル ３．３〜３．５ｐｐｍ ２ オレフィン性二重結合に基づくシグナル ６．７ｐｐｍ ２ ＩＲスペクトル（ＫＢｒ法）を第１図に示す。熱物性試
験結果を表−１に示す。 比較例１ 攪拌機、冷却コンデンサー、温度計、窒素ガス導入管、
滴下ロートを備えた、１００ｍｌのガラス製四っ口フラ
スコ中に無水マレイン酸５．４ｇ（０．０５５モル）及
びジメチルホルムアミド１０ｇを装入し、６０℃に昇温
しながら完全に溶解させ、この中にシクロヘキシルアミ
ン５ｇ（０．０５０モル）を反応温度に注意しながら１
時間かけて滴下し、さらに６０℃で２時間熟成を行ない
マレアミド酸を合成した。次に上記反応液にポリリン酸
１０ｇを装入した後、反応温度に注意しながら昇温し、
９０〜９５℃で２４時間脱水閉環反応させた。反応終了
後冷却し酢酸エチル１４ｇを加え抽出した後、分液し酢
酸エチル層を３回湯洗しエバポレーターで濃縮後１０５
〜１３０℃／２〜３ｍｍＨｇで蒸留し白色結晶６．０ｇ
を得た。熱物性試験結果を表−１に示す。The present invention will be described in more detail with reference to the following examples. Example 1 Stirrer, cooling condenser, thermometer, nitrogen gas inlet tube,
5.6 g (0.057 mol) of maleic anhydride and 20 g of dimethylformamide were charged into a 100 ml glass four-necked flask equipped with a dropping funnel, and completely dissolved while heating to 60 ° C. 9 (10) in - aminomethyl tetracyclo [6.2.1.1 3,6 .0 2,7] dodecane 10g
(0.052 mol) was added dropwise over 1 hour while paying attention to the reaction temperature, followed by aging at 60 ° C. for 2 hours to synthesize maleamic acid. Next, polyphosphoric acid 20 was added to the reaction solution.
g, and the temperature was raised while paying attention to the reaction temperature.
A dehydration ring closure reaction was performed at 95 ° C. for 12 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature, charged with 20 g of methanol, stirred for 1 hour, and filtered to remove crystals. Further, the crystals were dissolved in 40 g of toluene, washed with alkali, concentrated, and the precipitated crystals were separated by filtration and further washed with 10 g of methanol to obtain white crystals.
The weight after drying was 6.5 g. Purity 99.9% This crystal was analyzed from the results of elemental analysis, 1 H-NMR, and IR analysis.
9 (10) - aminomethyl - [6.2.1.1 3,6 .0 2,7] - was identified as dodecane maleimide. The measurement results are shown below. Elemental analysis (%) (calculated as C 17 H 21 NO 2 ) C N N theoretical 75.25 7.80 5.16 measured 75.53 7.67 5.14 1 H-NMR spectrum (90 MHz, CDCl 2) 3 solvent) Proton integral intensity ratio Signal based on tetracyclo ring 1.0-2.3 ppm Signal based on 17-CH 2 3.3-3.5 ppm 2 Signal based on olefinic double bond 6.7 ppm 2 IR spectrum (KBr) 1) is shown in FIG. Table 1 shows the thermophysical property test results. Comparative Example 1 Stirrer, cooling condenser, thermometer, nitrogen gas inlet tube,
5.4 g (0.055 mol) of maleic anhydride and 10 g of dimethylformamide were charged into a 100 ml glass four-necked flask equipped with a dropping funnel, and completely dissolved while heating to 60 ° C. 5 g (0.050 mol) of cyclohexylamine in 1 while paying attention to the reaction temperature.
The solution was dropped over a period of time, and aged at 60 ° C. for 2 hours to synthesize maleamic acid. Next, after charging 10 g of polyphosphoric acid to the reaction solution, the temperature was raised while paying attention to the reaction temperature.
A dehydration ring closure reaction was performed at 90 to 95 ° C. for 24 hours. After completion of the reaction, the mixture was cooled and extracted with 14 g of ethyl acetate. The layers were separated.
~ 130 ° C / distilled at 2-3mmHg, 6.0g of white crystals
I got Table 1 shows the thermophysical property test results.
【００２５】[0025]
【表１】 熱物性試験結果が示す通り、参考例のＮ−フェニルマレ
イミドは熱安定性は優れているが、黄色を帯びていると
いう欠点がある。また、比較例１のＮ−シクロヘキシル
マレイミドは白色で透明性には問題はないが、熱安定性
が悪いという欠点がある。従って、本発明のＮ−置換マ
レイミドは、両者の欠点を解決できる優れた特徴を有し
ている。[Table 1] As shown by the thermophysical property test results, the N-phenylmaleimide of Reference Example has excellent thermal stability, but has a drawback of being yellowish. Further, the N-cyclohexylmaleimide of Comparative Example 1 is white and has no problem in transparency, but has a disadvantage of poor thermal stability. Therefore, the N-substituted maleimide of the present invention has an excellent feature that can solve both disadvantages.
【００２６】[0026]
【発明の効果】本発明によって得られる、特定な脂環式
アミン化合物を用いた一般式（Ｉ）で表わされるＮ−置
換マレイミドは、新規な化合物であり、従来の芳香族Ｎ
−置換マレイミドに比べ、脂環式化合物特有の黄色を帯
びない性質を有し、また熱分解温度が非常に高いことか
ら、高耐熱性が要求されている熱可塑性樹脂等の分野で
の使用に最適である。The N-substituted maleimide represented by the general formula (I) obtained by using the specific alicyclic amine compound obtained by the present invention is a novel compound and has a conventional aromatic N
-Compared to substituted maleimides, it has the characteristic of not having a yellow color peculiar to alicyclic compounds, and also has a very high thermal decomposition temperature, so it is suitable for use in fields such as thermoplastic resins that require high heat resistance. Optimal.
【図１】実施例１で得た９(10)−アミノメチル−［6.2.
1.13,6.02,7 ］−ドデカンマレイミドのＩＲスペクトル
である。FIG. 1 shows 9 (10) -aminomethyl- [6.2.
1.1 3,6 .0 2,7] - is an IR spectrum of dodecane maleimide.
───────────────────────────────────────────────────── フロントページの続き (58)調査した分野(Int.Cl.7，ＤＢ名) ＣＡ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)──────────────────────────────────────────────────続 き Continued on the front page (58) Field surveyed (Int. Cl. 7 , DB name) CA (STN) REGISTRY (STN)
Claims (4)
ン原子、または炭素数１〜１０のアルキル基を表わし、
Ｒ1 は、ハロゲン原子または炭素数１〜１０のアルキル
基を表わす。但し、Ｒ1 が複数ある場合（即ち、ｍが２
以上の場合）、複数個のＲ1 は互いに同じでも又は異な
っていても良い。ｍは０から１７までの整数とする。）
で表わされるＮ−置換マレイミド。1. A compound of the general formula (I) (Wherein X 1 and X 2 each independently represent a hydrogen atom, a halogen atom, or an alkyl group having 1 to 10 carbon atoms;
R 1 represents a halogen atom or an alkyl group having 1 to 10 carbon atoms. However, when there are a plurality of R 1 (that is, m is 2
In the above case), a plurality of R 1 may be the same or different. m is an integer from 0 to 17. )
An N-substituted maleimide represented by the formula:
じ内容を示す）で表わされるマレアミド酸を脱水閉環反
応させる請求項１記載のＮ−置換マレイミドの製造方
法。2. A compound of the general formula (II) The method for producing an N-substituted maleimide according to claim 1, wherein the maleamic acid represented by the formula (wherein X 1 , X 2 , R 1 and m have the same contents as in the general formula (I)) is subjected to a dehydration ring closure reaction.
す）で表わされる脂環式アミン化合物と一般式（ＩＶ）
（化４） 【化４】 （式中、Ｘ1 、Ｘ2 は一般式（Ｉ）と同じ内容を示す）
で表わされる無水マレイン酸又はその誘導体とを付加反
応させる請求項２記載のマレアミド酸の製造方法。3. A compound of the formula (III) (Wherein R 1 and m are the same as those of the general formula (I)) and an alicyclic amine compound represented by the general formula (IV)
(Formula 4) (Wherein, X 1 and X 2 have the same contents as in the general formula (I))
The method for producing maleamic acid according to claim 2, wherein an addition reaction is performed with maleic anhydride or a derivative thereof represented by the following formula:
じ内容を示す）で表わされるマレアミド酸。4. A compound represented by the general formula (II): (Wherein X 1 , X 2 , R 1 and m have the same meaning as in the general formula (I)).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3139951A JP3009245B2 (en) | 1991-06-12 | 1991-06-12 | N-substituted maleimide and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3139951A JP3009245B2 (en) | 1991-06-12 | 1991-06-12 | N-substituted maleimide and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04368358A JPH04368358A (en) | 1992-12-21 |
| JP3009245B2 true JP3009245B2 (en) | 2000-02-14 |
Family
ID=15257478
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3139951A Expired - Fee Related JP3009245B2 (en) | 1991-06-12 | 1991-06-12 | N-substituted maleimide and method for producing the same |
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| Country | Link |
|---|---|
| JP (1) | JP3009245B2 (en) |
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|---|---|---|---|---|
| KR20010047160A (en) * | 1999-11-18 | 2001-06-15 | 구명수 | New Maleic Acid Derivatives and Their Manufacturing Processes |
| US6946523B2 (en) * | 2001-02-07 | 2005-09-20 | Henkel Corporation | Heterobifunctional monomers and uses therefor |
| US6423780B1 (en) * | 2001-02-07 | 2002-07-23 | Loctite | Heterobifunctional monomers and uses therefor |
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1991
- 1991-06-12 JP JP3139951A patent/JP3009245B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH04368358A (en) | 1992-12-21 |
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