JPH0563466B2 - - Google Patents
Info
- Publication number
- JPH0563466B2 JPH0563466B2 JP32955687A JP32955687A JPH0563466B2 JP H0563466 B2 JPH0563466 B2 JP H0563466B2 JP 32955687 A JP32955687 A JP 32955687A JP 32955687 A JP32955687 A JP 32955687A JP H0563466 B2 JPH0563466 B2 JP H0563466B2
- Authority
- JP
- Japan
- Prior art keywords
- bismaleimide
- maleic anhydride
- reaction
- mmhg
- substituent
- 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 - Lifetime
Links
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 claims description 20
- 229920003192 poly(bis maleimide) Polymers 0.000 claims description 20
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 150000004984 aromatic diamines Chemical class 0.000 claims description 7
- 150000008065 acid anhydrides Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000003949 imides Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- FSQQTNAZHBEJLS-UPHRSURJSA-N maleamic acid Chemical compound NC(=O)\C=C/C(O)=O FSQQTNAZHBEJLS-UPHRSURJSA-N 0.000 description 2
- 238000012805 post-processing Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ZVDSMYGTJDFNHN-UHFFFAOYSA-N 2,4,6-trimethylbenzene-1,3-diamine Chemical group CC1=CC(C)=C(N)C(C)=C1N ZVDSMYGTJDFNHN-UHFFFAOYSA-N 0.000 description 1
- QAYVHDDEMLNVMO-UHFFFAOYSA-N 2,5-dichlorobenzene-1,4-diamine Chemical compound NC1=CC(Cl)=C(N)C=C1Cl QAYVHDDEMLNVMO-UHFFFAOYSA-N 0.000 description 1
- BWAPJIHJXDYDPW-UHFFFAOYSA-N 2,5-dimethyl-p-phenylenediamine Chemical compound CC1=CC(N)=C(C)C=C1N BWAPJIHJXDYDPW-UHFFFAOYSA-N 0.000 description 1
- CPCPKQUNFFHAIZ-UHFFFAOYSA-N 2-chloro-5-methylbenzene-1,4-diamine Chemical compound CC1=CC(N)=C(Cl)C=C1N CPCPKQUNFFHAIZ-UHFFFAOYSA-N 0.000 description 1
- WECDUOXQLAIPQW-UHFFFAOYSA-N 4,4'-Methylene bis(2-methylaniline) Chemical compound C1=C(N)C(C)=CC(CC=2C=C(C)C(N)=CC=2)=C1 WECDUOXQLAIPQW-UHFFFAOYSA-N 0.000 description 1
- OMHOXRVODFQGCA-UHFFFAOYSA-N 4-[(4-amino-3,5-dimethylphenyl)methyl]-2,6-dimethylaniline Chemical group CC1=C(N)C(C)=CC(CC=2C=C(C)C(N)=C(C)C=2)=C1 OMHOXRVODFQGCA-UHFFFAOYSA-N 0.000 description 1
- IGSBHTZEJMPDSZ-UHFFFAOYSA-N 4-[(4-amino-3-methylcyclohexyl)methyl]-2-methylcyclohexan-1-amine Chemical compound C1CC(N)C(C)CC1CC1CC(C)C(N)CC1 IGSBHTZEJMPDSZ-UHFFFAOYSA-N 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000004807 desolvation Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 239000002648 laminated material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Pyrrole Compounds (AREA)
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、硬化性，作業性が良好で、耐熱性、
および経済性に優れた高純度のビスマレイミドの
製造方法に関するものである。
〔従来技術〕
従来、ビスマレイミドは、一般に有機溶媒中
で、無水マレイン酸と芳香族ポリアミンとを低温
で反応させ、マレアミツク酸とし、これに無水酢
酸などの脱水剤と、酢酸ナトリウムなどの脱水触
媒とを加え、比較的低温で、マレイミド化する二
段法で作れる、脱溶媒、再結晶、再沈殿または水
洗などの非常に工数のかかる後処理工程を経てつ
くられている。更に、使用した溶剤、脱水剤、水
洗液などの後処理にも多大の経費を要するため、
非常に高価なものとなつている。
これに対し、無水マレイン酸とアミン類とを無
溶媒、無触媒で、高温下、付加反応と縮合反応と
を同時におこなわせて、ビスマレイミドを得よう
とする１段法の試みも、古くからおこなわれてい
たが、ビスマレイミドの収率が悪く、分子間の縮
合反応が起つて、ゲル化し易いため、実用には至
らなかつた。
〔発明の目的〕
本発明は、従来、１段法ではできなかつた高純
度・高収率のビスマレイミドを得んとして、研究
した結果、オルソ位に置換基を有する芳香族ジア
ミンを使用することにより、作業性の良い、高純
度・高収率のビスマレイミドが得られるとの知見
を得、更に、この知見に基づき種々研究を進め
て、本発明を完成するに至つたものである。その
目的とするところは、作業性、硬化性が良好で、
ガラス転移温度が高く、低熱膨脹で、耐熱性およ
び経済性に優れた高純度のビスマレイミドの製造
方法を提供するにある。
〔発明の構成〕
本発明は、無水マレイン酸の融解液に酸無水物
環に対するNH2基の当量比0.81.0の範囲でオルソ
位に置換基を有する芳香族ジアミンを徐々に添加
し、130〜200℃で、760〜200mmHgの常圧または
減圧下で反応させ、反応後、速やかに100mmHg以
下に減圧し、未反応の無水マレイン酸を除去する
ことを特徴とするビスマレイミドの製造方法であ
る。
本発明において用いられるオルソ位に置換基を
有する芳香族ジアミンとしては、例えば、３，
3′−ジメチル−４，4′−ジアミノジフエニルメタ
ン、３，3′−ジエチル−４，4′−ジアミノジフエ
ニルメタン、４，６−ジメチル−ｎ−フエニレン
ジアミン、２，５−ジメチル−ｐ−フエニレンジ
アミン、２，４−ジアミノメシチレン、２，５−
ジクロロ−ｐ−フエニレンジアミン、５−クロロ
−２−メチル−ｐ−フエニレンジアミン、４，
4′−メチレンジ−２，６−キシリジン、４，4′−
メチレンジ−２，６−ジブロムアニリン、４，
4′−メチレンジ−２−ブロム−６−クロロアニリ
ン、４，4′−メチレンジ−６−ブロム−２−トル
イジン、４，4′−メチレンジ−２，６−ジエチル
アニリン、４，4′−ジアミノ−３，3′−ジメチル
ジシクロヘキシルメタン、４，4′−ジアミノ−
３，3′−ジメチルシクロヘキシルなどをあげるこ
とができる。
これらのオルソ位に置換基をもつ芳香族シアミ
ンは、NH2基／酸無水物環の当量比が、0.8〜1.0
の範囲で用いるのがよい。オルソ位に置換基を有
するジアミンは分子間縮合反応を抑制する作用を
有する。即ち、ゲル化防止剤としても作用する。
そのため、ビスマレイミドの高純度・高収率に有
効に作用する。
NH2基／酸無水物環の当量比が1.0より大きい
と、分子間の縮合反応が増えて、ビスマレイミド
の収率が減るとともに、反応中、非常にゲル化し
易くなる。NH2基／酸無水物環の当量比が0.8よ
り小さいと、少量ではあるが、一部、NH2基に、
２個の無水マレイン酸が付加してビスマレイミド
の純度・収率を低減し、耐熱性を低下させるとと
もに、酸無水物の除去に、余計な工数をかけるこ
とになつて、得策でない。
反応は、無水マレイン酸を、130〜200℃、好ま
しくは、140〜180に加熱して、融解し、これにオ
ルソ位に置換基を有する芳香族ジアミンを、急激
な温度上昇をさけながら、徐々に添加しておこな
われる。添加後、その温度で760〜200mmHgの常
圧または減圧下で、好ましくは、750〜300mmHg
の減圧下で、約２〜120分反応する。
反応温度が130℃より低いと、付加物であるア
ミツク酸がいつまでも、不溶物のまゝ残り、分子
内縮合によりイミド環の生成を阻害する。反応温
度が200℃より高いと、分子環縮合およびイミド
環の不飽和基へのアミンの付加も起つて、反応中
にゲル化し易くなる。
圧力は、減圧によりイミド環生成の際に副生す
る水を脱水除去させ、反応を促進させるため、
760mmHg〜200mmHgがよい。圧力を200mmHgより
低くすると、原料の無水マレイン酸まで除去され
てしまうので不利である。圧力を760mmHgより高
くすると沸点が上昇し副生する水を脱水除去しに
くくなる。
また反応後は未反応の無水マレイン酸をすみや
かに除去するため、圧力を100mmHg以下とする。
100mmHg以上だと無水マレイン酸をすみやかに除
去できない。
〔発明の効果〕
本発明方法に従うと、無水マレイン酸とオルソ
位に置換基を有する芳香族ジアミンとから無溶
媒、無触媒で、高純度・高収率のビスマレイミド
を得ることができ、経済性に優れている。得られ
たビスマレイミドは、純度が高く、置換基を有し
ているため溶媒に対する溶解性も良く、硬化性は
非常に良好で、耐熱性にも優れているので、成形
材料、粉体塗料、積層材料、接着剤などの用途に
好適である。
〔実施例〕
実施例 １〜４
無水マレイン酸を融解し、これに第１表に示し
たオルソ位に置換基を有する芳香族ジアミンを
徐々に添加し、添加後、400〜500mmHgの減圧下
で第１表に示す条件で反応し、脱水した。反応
後、で30分、減圧して未反応の無水マレイン酸を
留去し、ビスマレイミドを得た。
比較例 １
オルソ位に置換基を持たない４，4′−ジアミノ
ジフエニルタメタンを用いて実施例と同様の反応
をおこなつた。しかし、４，4′−ジアミノジフエ
ニルメタンの添加終了と同時にゲル化してしまつ
た。
各例の特性値を第１表に示す。
実施例１〜４は、無触媒、無溶媒といつた経済
性に優れており、比較例１と較べてもゲル化せ
ず、純度の高いものが得られている。
参考例として従来法（二段法）であるアセトン
中で、無水マレイン酸と４，4′−ジアミノジフエ
ニルメタンとを低温で反応させ、マレアミツク酸
とし、これに脱水剤として無水酢酸と酢酸ナトリ
ウムとを加え、マレイミド化した４，4′−ジアミ
ノジフエニルメタンビスマレイミドを合成した。
これを対象として、実施例の純度を赤外線吸収
スペクトルで比較した。
実施例２のビスマレイミドの赤外線吸収スペク
トルを第１図に示したが、参考例の赤外線吸収ス
ペクトル第２図とほとんど一致し、高純度であ
る。
ゲルタイムは、参考例とほぼ同じであり、ガラ
ス転移温度（Tg）はほぼ同じであつた。
【表】[Detailed description of the invention] [Industrial application field] The present invention has good curability and workability, heat resistance,
The present invention also relates to a highly economical method for producing bismaleimide of high purity. [Prior art] Bismaleimide has conventionally been produced by reacting maleic anhydride and an aromatic polyamine at low temperatures in an organic solvent to obtain maleamic acid, which is then treated with a dehydrating agent such as acetic anhydride and a dehydrating catalyst such as sodium acetate. It can be made by a two-step process of adding and converting into maleimide at a relatively low temperature, and it is made through a very time-consuming post-processing process such as desolvation, recrystallization, reprecipitation, or washing with water. Furthermore, post-processing of the used solvents, dehydrating agents, washing liquids, etc. requires a great deal of expense.
It has become extremely expensive. On the other hand, attempts have been made for a long time to use a one-step method to obtain bismaleimide by simultaneously carrying out an addition reaction and a condensation reaction between maleic anhydride and amines without a solvent or catalyst at high temperatures. However, it was not put to practical use because the yield of bismaleimide was poor and intermolecular condensation reactions were likely to occur, resulting in gelation. [Purpose of the Invention] The present invention aims to obtain bismaleimide of high purity and high yield, which could not be obtained by conventional one-stage methods, and as a result of research, the present invention has been made to use an aromatic diamine having a substituent at the ortho position. The inventors have found that bismaleimide with good workability, high purity, and high yield can be obtained by the above method, and based on this knowledge, they have carried out various studies and have completed the present invention. The purpose is to have good workability and hardenability,
It is an object of the present invention to provide a method for producing highly pure bismaleimide which has a high glass transition temperature, low thermal expansion, excellent heat resistance and economical efficiency. [Structure of the Invention] The present invention involves gradually adding an aromatic diamine having a substituent at the ortho position to a melt of maleic anhydride at an equivalent ratio of NH 2 to the acid anhydride ring of 0.81.0. A method for producing bismaleimide, which is characterized by reacting at ~200°C and under normal pressure or reduced pressure of 760 to 200 mmHg, and after the reaction, immediately reducing the pressure to 100 mmHg or less to remove unreacted maleic anhydride. . Examples of the aromatic diamine having a substituent at the ortho position used in the present invention include 3,
3'-dimethyl-4,4'-diaminodiphenylmethane, 3,3'-diethyl-4,4'-diaminodiphenylmethane, 4,6-dimethyl-n-phenylenediamine, 2,5-dimethyl- p-phenylenediamine, 2,4-diaminomesitylene, 2,5-
Dichloro-p-phenylenediamine, 5-chloro-2-methyl-p-phenylenediamine, 4,
4'-methylenedi-2,6-xylidine, 4,4'-
Methylenedi-2,6-dibromoaniline, 4,
4'-Methylenedi-2-bromo-6-chloroaniline, 4,4'-methylenedi-6-bromo-2-toluidine, 4,4'-methylenedi-2,6-diethylaniline, 4,4'-diamino- 3,3'-dimethyldicyclohexylmethane, 4,4'-diamino-
Examples include 3,3'-dimethylcyclohexyl. These aromatic cyamines having a substituent at the ortho position have an equivalent ratio of NH 2 group/acid anhydride ring of 0.8 to 1.0.
It is recommended to use within the range of . A diamine having a substituent at the ortho position has the effect of suppressing an intermolecular condensation reaction. That is, it also acts as an anti-gelling agent.
Therefore, it effectively acts on high purity and high yield of bismaleimide. If the equivalent ratio of NH 2 group/acid anhydride ring is greater than 1.0, the condensation reaction between molecules will increase, the yield of bismaleimide will decrease, and gelation will occur very easily during the reaction. If the equivalent ratio of NH 2 groups/acid anhydride ring is less than 0.8, some NH 2 groups, albeit a small amount,
The addition of two maleic anhydrides reduces the purity and yield of bismaleimide, lowers the heat resistance, and requires extra man-hours to remove the acid anhydride, which is not a good idea. In the reaction, maleic anhydride is heated to 130 to 200°C, preferably 140 to 180°C to melt it, and an aromatic diamine having a substituent at the ortho position is gradually added thereto while avoiding a sudden temperature rise. It is done by adding it to. After addition, under normal pressure or reduced pressure of 760-200 mmHg at that temperature, preferably 750-300 mmHg
React for about 2 to 120 minutes under reduced pressure. If the reaction temperature is lower than 130°C, the adduct, amic acid, remains as an insoluble substance and inhibits the formation of imide rings due to intramolecular condensation. If the reaction temperature is higher than 200° C., molecular ring condensation and addition of amine to the unsaturated group of the imide ring also occur, making it easy to gel during the reaction. The pressure is determined by reducing the pressure to dehydrate and remove the water that is produced as a by-product during imide ring formation, thereby promoting the reaction.
760mmHg to 200mmHg is good. If the pressure is lower than 200 mmHg, it is disadvantageous because even the raw material maleic anhydride is removed. If the pressure is higher than 760 mmHg, the boiling point will rise, making it difficult to dehydrate and remove by-product water. After the reaction, the pressure is kept at 100 mmHg or less in order to promptly remove unreacted maleic anhydride.
If the temperature is 100 mmHg or higher, maleic anhydride cannot be removed quickly. [Effects of the Invention] According to the method of the present invention, bismaleimide of high purity and high yield can be obtained from maleic anhydride and an aromatic diamine having a substituent at the ortho position without a solvent or a catalyst, and is economical. Excellent in sex. The obtained bismaleimide has high purity, has a substituent group, has good solubility in solvents, has very good curability, and has excellent heat resistance, so it can be used as a molding material, powder coating, Suitable for applications such as laminated materials and adhesives. [Example] Examples 1 to 4 Maleic anhydride was melted, and an aromatic diamine having a substituent at the ortho position shown in Table 1 was gradually added thereto, and after the addition, the mixture was heated under reduced pressure of 400 to 500 mmHg. The reaction was carried out under the conditions shown in Table 1, followed by dehydration. After the reaction, unreacted maleic anhydride was distilled off under reduced pressure for 30 minutes to obtain bismaleimide. Comparative Example 1 A reaction similar to that in Example was carried out using 4,4'-diaminodiphenyltamethane having no substituent at the ortho position. However, as soon as the addition of 4,4'-diaminodiphenylmethane was completed, the mixture turned into a gel. Table 1 shows the characteristic values of each example. Examples 1 to 4 are excellent in economy as they are catalyst-free and solvent-free, and even when compared with Comparative Example 1, they do not gel and have high purity. As a reference example, in the conventional method (two-step method), maleic anhydride and 4,4'-diaminodiphenylmethane are reacted in acetone at low temperature to form maleamic acid, and then acetic anhydride and sodium acetate are added as dehydrating agents. was added to synthesize maleimidated 4,4'-diaminodiphenylmethane bismaleimide. Using this as a subject, the purity of Examples was compared using infrared absorption spectra. The infrared absorption spectrum of the bismaleimide of Example 2 is shown in FIG. 1, which almost matches the infrared absorption spectrum of the reference example in FIG. 2, indicating high purity. The gel time was almost the same as that of the reference example, and the glass transition temperature (Tg) was almost the same. 【table】
第１図は実施例２で得たビスマレイミドの赤外
線吸収スペクトルである。第２図は参考例による
従来のビスマレイミドのものである。第１図と第
２図はほとんど一致しており、高純度のビスマレ
イミドが得られたことがわかる。
FIG. 1 is an infrared absorption spectrum of bismaleimide obtained in Example 2. FIG. 2 shows a conventional bismaleimide according to a reference example. FIG. 1 and FIG. 2 almost match, indicating that highly pure bismaleimide was obtained.
Claims (1)
するNH2基の当量比0.8〜1.0の範囲で、オルソ位
に置換基を有する芳香族ジアミンを徐々に添加
し、130〜200℃で、760〜200mmHgの圧力下で反
応させ、反応後速やかに100mmHg以下に減圧し、
未反応の無水マレイン酸を除去することを特徴と
するビスマレイミドの製造方法。1. To a molten solution of maleic anhydride, an aromatic diamine having a substituent at the ortho position was gradually added at an equivalent ratio of NH 2 groups to the acid anhydride ring in the range of 0.8 to 1.0, and the mixture was heated at 130 to 200 °C to 760 °C. React under a pressure of ~200 mmHg, and immediately reduce the pressure to 100 mmHg or less after the reaction.
A method for producing bismaleimide, which comprises removing unreacted maleic anhydride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32955687A JPH01172372A (en) | 1987-12-28 | 1987-12-28 | Production of bismaleimide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32955687A JPH01172372A (en) | 1987-12-28 | 1987-12-28 | Production of bismaleimide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01172372A JPH01172372A (en) | 1989-07-07 |
| JPH0563466B2 true JPH0563466B2 (en) | 1993-09-10 |
Family
ID=18222676
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP32955687A Granted JPH01172372A (en) | 1987-12-28 | 1987-12-28 | Production of bismaleimide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01172372A (en) |
-
1987
- 1987-12-28 JP JP32955687A patent/JPH01172372A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01172372A (en) | 1989-07-07 |
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