JPS5829942B2 - Isopropenyl phenyl maleamic acid - Google Patents
Isopropenyl phenyl maleamic acidInfo
- Publication number
- JPS5829942B2 JPS5829942B2 JP3565279A JP3565279A JPS5829942B2 JP S5829942 B2 JPS5829942 B2 JP S5829942B2 JP 3565279 A JP3565279 A JP 3565279A JP 3565279 A JP3565279 A JP 3565279A JP S5829942 B2 JPS5829942 B2 JP S5829942B2
- Authority
- JP
- Japan
- Prior art keywords
- maleamic acid
- acid
- isopropenyl phenyl
- phenyl maleamic
- reaction
- 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.)
- Expired
Links
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】 本発明は、式（Ｉ） ド酸。[Detailed description of the invention] The present invention provides formula (I) acid.
のイソプロペニルフェニルマレアミド酸に関するもので
ある。isopropenyl phenyl maleamic acid.
本発明の化合物は新規物質であって農薬、加硫促進剤、
熱硬化性樹脂の硬化剤、塗料、接着剤として有用であり
、また分子内にカルボキシル基、２ヶ以上の二重結合を
有するので、特異な機能を要求される樹脂原料として利
用価値が極めて高いものである。The compound of the present invention is a new substance that can be used as a pesticide, a vulcanization accelerator, or
It is useful as a curing agent for thermosetting resins, paints, and adhesives, and since it has a carboxyl group and two or more double bonds in its molecule, it has extremely high utility value as a resin raw material that requires specific functions. It is something.
これらの化合物は融点が高く、耐熱性に優れた樹脂を提
供するが、これらマレアミド酸化合物を脱水して得られ
るマレイミド化合物は尚一層機能性に富んだ素材原料で
ある。These compounds have a high melting point and provide resins with excellent heat resistance, but maleimide compounds obtained by dehydrating these maleamic acid compounds are raw materials with even higher functionality.
すなわち、マレイミド化合物を成分とする樹脂は電気絶
縁性、耐衝撃性、耐熱性、成型品の寸法安定性に際立っ
た性能を発揮し、電気絶縁材料、耐熱接着剤、成型材料
など産業上極めて広く利用されるものである。In other words, resins containing maleimide compounds exhibit outstanding performance in electrical insulation, impact resistance, heat resistance, and dimensional stability of molded products, and are extremely widely used in industries such as electrical insulation materials, heat-resistant adhesives, and molding materials. It is something that is used.
例えば、本発明化合物の耐熱性の一例として、熱分解温
度（熱天秤にて測定）を示すと次のよう１１七−プ、
本発明の化合物は公知の各種マレアミド酸化合物の製造
法を用いて製造されるが、具体的には次の方法で製造す
ることができる。For example, as an example of the heat resistance of the compound of the present invention, the thermal decomposition temperature (measured with a thermobalance) is as follows: Specifically, it can be manufactured by the following method.
例えば、ｐ−イ＊＊ソソロペニルフェニルマレアミ ド酸は、 次式で示 される反応により生成する。For example, p-i** sosolopenyl phenyl maleami The acid is It is shown by the following formula It is produced by a reaction.
すなわち、ｐ−インプロペニルフェニルマレアミド酸を
製造するには、ｐ−インプロペニルアニリンをアセトン
の存在下、１０〜４０℃の温度条件下無水マレイン酸と
反応させる。That is, to produce p-impropenyl phenyl maleamic acid, p-impropenyl aniline is reacted with maleic anhydride at a temperature of 10 to 40° C. in the presence of acetone.
この反応は０〜１２０℃の温度範囲で進行するが、温和
な条件下１０〜４０℃の温度範囲で行なうことが望まし
い。This reaction proceeds in a temperature range of 0 to 120°C, but is preferably carried out under mild conditions in a temperature range of 10 to 40°C.
また反応時間は反応温度に依存するが、通常、１０〜４
０℃の温度範囲では１〜５時間の範囲で十分である。Although the reaction time depends on the reaction temperature, it is usually 10 to 4
In a temperature range of 0°C, a time period of 1 to 5 hours is sufficient.
反応の際に用いられる溶剤はアセトンが多用されるが、
この外にクロロホルム、四塩化炭素、メチルエチルケト
ン、テトラヒドロフラン、ギ酸、酢酸、酪酸、酢酸メチ
ル、酢酸エチル、メチルセロソルブ、セロソルブ、エー
テル、シクロヘキサン、シクロヘキサノン、ジオキサン
、ベンゼン、トルエン、キシレンクロルベンゼン、ピリ
ジン、ジメチルホルムアミド、ジメチルアセトアミド、
ジメチルスルホキシド、Ｎ−メチルピロリドン、ヘキサ
メチルホスホルアミド、Ｎ−メチルカプロラクタム、メ
タノール、エタノール、プロピルアルコールなどを用い
ることができる。Acetone is often used as a solvent during the reaction, but
In addition to this, chloroform, carbon tetrachloride, methyl ethyl ketone, tetrahydrofuran, formic acid, acetic acid, butyric acid, methyl acetate, ethyl acetate, methyl cellosolve, cellosolve, ether, cyclohexane, cyclohexanone, dioxane, benzene, toluene, xylene chlorobenzene, pyridine, dimethylformamide , dimethylacetamide,
Dimethyl sulfoxide, N-methylpyrrolidone, hexamethylphosphoramide, N-methylcaprolactam, methanol, ethanol, propyl alcohol, etc. can be used.
溶剤の使用量は、用いる第一級アミン重量の１．５〜７
０倍重量が望ましい。The amount of solvent used is 1.5 to 7 of the weight of the primary amine used.
Zero times the weight is desirable.
また、反応の際に用いられる無水マレイン酸の量はｐ−
インプロペニルアニリン１モルに対し、１．０〜２．０
モル用いるが、望ましくは、１．０５〜１．２モルであ
り、生成したｐ−イソプロペニルフェニルマレアミド酸
は沈澱として析出し、反応液はスラリーとなる。Furthermore, the amount of maleic anhydride used during the reaction is p-
1.0 to 2.0 per mole of impropenylaniline
The amount is desirably 1.05 to 1.2 moles, and the generated p-isopropenylphenylmaleamic acid precipitates out as a precipitate, and the reaction solution becomes a slurry.
この沈澱を１過し、溶剤または水で十分洗浄した後、乾
燥する。This precipitate is filtered once, thoroughly washed with a solvent or water, and then dried.
本発明の化合物は上記反応条件下で、高収率かつ十分に
精製された状態で得ることができる。The compound of the present invention can be obtained in high yield and in a sufficiently purified state under the above reaction conditions.
その他のイソプロペニルフェニルマレアミド酸誘導体も
同様の方法で製造することができる。Other isopropenyl phenyl maleamic acid derivatives can also be produced in a similar manner.
本発明の化合物はこれを脱水環化することによって耐熱
性樹脂素材原料として極めて利用価値の高いマレイミド
化合物の中間材料としても使用できる。By dehydrating and cyclizing the compound of the present invention, it can also be used as an intermediate material for maleimide compounds, which have extremely high utility value as raw materials for heat-resistant resin materials.
このマレイミド化合物は、本発明の化合物を酢酸ナトリ
ウム、ニッケル塩またはコバルト塩などの触媒、および
トリエチルアミン、Ｎ−Ｎ−ジメチルベンジルアミンな
どの第三級アミンの存在下、有機溶剤中で無水酢酸、無
水酪酸などの脱水剤を作用させて製造することができる
。The maleimide compound is prepared by treating the compound of the present invention with acetic anhydride, anhydrous It can be produced by applying a dehydrating agent such as butyric acid.
以下、実施例により本発明を説明する。The present invention will be explained below with reference to Examples.
実施例 １
無水マレイン酸８．６１をアセトン１００ｍ１に溶解し
、２０℃の温度下、ｐ−イソプロペニルアニリン１０．
１’を徐々に滴下した。Example 1 8.61 of maleic anhydride was dissolved in 100 ml of acetone, and 10.61 of p-isopropenylaniline was dissolved at a temperature of 20°C.
1' was gradually added dropwise.
滴下終了後、２０℃の温度にて２時間攪拌した。After the dropwise addition was completed, the mixture was stirred at a temperature of 20° C. for 2 hours.
反応液は黄色の沈澱を有するスラリーであった。The reaction solution was a slurry with yellow precipitate.
この沈澱を１過し、ついでアセトンで洗浄した後乾燥し
た。This precipitate was filtered once, then washed with acetone and dried.
黄色の粉末状のｐ−インプロペニルフェニルマレアミド
酸が得られた。A yellow powder of p-impropenylphenylmaleamic acid was obtained.
収量１７．４Ｐ（収率９４％）。赤外線吸収スペクトル
、核磁気共鳴吸収スペクトルおよび元素分析値より次式
の構造を有することを確認した。Yield 17.4P (yield 94%). It was confirmed from the infrared absorption spectrum, nuclear magnetic resonance absorption spectrum, and elemental analysis that it had the following structure.
赤外線吸収スペクトル
グループ 吸収位置
＞Ｃ＝Ｏ］、６８５ｃｒＩＬ’
Ａｒ −ＮＨ−１４９０〜］、 ’５７０ｃｍ −１核
磁気共鳴吸収スペクトル（Ｄ６−ＤＭＳＯ溶媒）グルー
プ 帰属（δ値ｐｐｍ）
−ＣＨ，２，１１
＝ＣＨ２５，０３，５，３８
Ｃ−
６，２６，６，５３（二重線、Ｊ−１２
ＣＯＯＨ１０，４７
元素分析値（ｗｔ％）
Ｈ
計算値 ６７．５２ ５．６７
分析値 ６７．４８ ５．７Ｏ
６，０６
６，０９Infrared absorption spectrum group Absorption position>C=O], 685crIL' Ar -NH-1490~], '570cm -1 Nuclear magnetic resonance absorption spectrum (D6-DMSO solvent) Group Attribution (δ value ppm) -CH,2,11 =CH25,03,5,38 C- 6,26,6,53 (double line, J-12 COOH10,47 Elemental analysis value (wt%) H Calculated value 67.52 5.67 Analysis value 67.48 5 .7O 6,06 6,09
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3565279A JPS5829942B2 (en) | 1979-03-28 | 1979-03-28 | Isopropenyl phenyl maleamic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3565279A JPS5829942B2 (en) | 1979-03-28 | 1979-03-28 | Isopropenyl phenyl maleamic acid |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3085883A Division JPS594418B2 (en) | 1983-02-28 | 1983-02-28 | Dimer of isopropenyl phenyl maleamic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55129254A JPS55129254A (en) | 1980-10-06 |
| JPS5829942B2 true JPS5829942B2 (en) | 1983-06-25 |
Family
ID=12447799
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3565279A Expired JPS5829942B2 (en) | 1979-03-28 | 1979-03-28 | Isopropenyl phenyl maleamic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5829942B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8707799D0 (en) * | 1987-04-01 | 1987-05-07 | Ici Plc | Metal treatment |
| US5278242A (en) * | 1991-10-10 | 1994-01-11 | Joel Muse | Sulfur vulcanized rubber compounds containing oligomeric maleimide |
-
1979
- 1979-03-28 JP JP3565279A patent/JPS5829942B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55129254A (en) | 1980-10-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2626767A1 (en) | IMIDYL BENZOLE DI AND TRICARBONIC ACID DERIVATIVES | |
| US4376206A (en) | N-Alkenylphenylmaleimides and N,N'-[alkenylene phenylene]bismaleimides for the same | |
| JPS5829942B2 (en) | Isopropenyl phenyl maleamic acid | |
| JPS594418B2 (en) | Dimer of isopropenyl phenyl maleamic acid | |
| EP0051687B1 (en) | Maleimides and process for the preparation of same | |
| US4400521A (en) | N-Substituted phenyl maleimides | |
| US4924005A (en) | Bismaleimide resins | |
| CA1051926A (en) | Diaminomaleonitrile derivatives and processes for preparing the same | |
| JPH0623196B2 (en) | Diacetylene group-containing imide compound having terminal double bond | |
| JPS6135173B2 (en) | ||
| JPH04368358A (en) | N-substituted maleimide and its production | |
| US3502707A (en) | Beta-(cyclohexyl and substituted phenyl)-alpha-(4,5-dimethoxy-2-nitro- or aminophenyl) acrylonitriles | |
| US4163014A (en) | 3,4,5,6-Tetrahydropyromellitdiimides | |
| US4056542A (en) | Pyrolysis of N-substituted-1-cyclohexene-1,2-dicarboximides | |
| JPS63107976A (en) | Novel polymaleimide compound and production thereof | |
| JPH04235147A (en) | New phenoxybismaleimide | |
| JPS5822113B2 (en) | Method for producing bismaleimide | |
| JPH02306960A (en) | Bismaleimide compound and production thereof | |
| US4188337A (en) | Nitrile substituted polyimide precursors | |
| Wu et al. | Synthesis and characterization of addition-type polyimides functionalized with diamine chromophore | |
| JPS6019903B2 (en) | Maleimide and its manufacturing method | |
| JPS6341456A (en) | Novel bismaleimide compound and production thereof | |
| JPH01211562A (en) | Novel bismaleimide and production thereof | |
| JPH04261145A (en) | N-substituted maleimide and its production | |
| US4193924A (en) | Pyrolysis of N-substituted-1-cyclohexene-1,2-dicarboximides |