JPS62234063A - Thermal stabilization of n-cyclohexylmaleimide - Google Patents
Thermal stabilization of n-cyclohexylmaleimideInfo
- Publication number
- JPS62234063A JPS62234063A JP7429486A JP7429486A JPS62234063A JP S62234063 A JPS62234063 A JP S62234063A JP 7429486 A JP7429486 A JP 7429486A JP 7429486 A JP7429486 A JP 7429486A JP S62234063 A JPS62234063 A JP S62234063A
- Authority
- JP
- Japan
- Prior art keywords
- cyclohexylmaleimide
- acid
- amine salt
- maleic acid
- salt
- 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
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 230000006641 stabilisation Effects 0.000 title abstract description 5
- 238000011105 stabilization Methods 0.000 title abstract description 5
- -1 maleamic acid amine salt Chemical class 0.000 claims abstract description 14
- 239000000654 additive Substances 0.000 claims abstract description 13
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000011976 maleic acid Substances 0.000 claims abstract description 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 230000000996 additive effect Effects 0.000 claims abstract description 8
- FSQQTNAZHBEJLS-UPHRSURJSA-N maleamic acid Chemical compound NC(=O)\C=C/C(O)=O FSQQTNAZHBEJLS-UPHRSURJSA-N 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 6
- 230000000087 stabilizing effect Effects 0.000 claims description 5
- 230000000694 effects Effects 0.000 abstract description 10
- 229920001519 homopolymer Polymers 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000004040 coloring Methods 0.000 abstract description 4
- 229920001577 copolymer Polymers 0.000 abstract description 4
- 229920006015 heat resistant resin Polymers 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- DEWAGGNAHQGYBD-SREVYHEPSA-N (z)-4-(cyclohexylamino)-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)NC1CCCCC1 DEWAGGNAHQGYBD-SREVYHEPSA-N 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000007086 side reaction Methods 0.000 abstract description 2
- RETPXDPQNQCOBY-BTJKTKAUSA-N cyclohexylazanium;(z)-4-hydroxy-4-oxobut-2-enoate Chemical compound NC1CCCCC1.OC(=O)\C=C/C(O)=O RETPXDPQNQCOBY-BTJKTKAUSA-N 0.000 abstract 1
- 238000001879 gelation Methods 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 description 10
- 238000007334 copolymerization reaction Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000012719 thermal polymerization Methods 0.000 description 2
- HBQGCOWNLUOCBU-ONEGZZNKSA-N (e)-4-(ethylamino)-4-oxobut-2-enoic acid Chemical compound CCNC(=O)\C=C\C(O)=O HBQGCOWNLUOCBU-ONEGZZNKSA-N 0.000 description 1
- ZRPAIVPIYDTPDO-ODZAUARKSA-N (z)-but-2-enedioic acid;ethanamine Chemical compound CCN.OC(=O)\C=C/C(O)=O ZRPAIVPIYDTPDO-ODZAUARKSA-N 0.000 description 1
- TTWIZPJIKOAWBJ-BTJKTKAUSA-N (z)-but-2-enedioic acid;n-ethylethanamine Chemical compound CCNCC.OC(=O)\C=C/C(O)=O TTWIZPJIKOAWBJ-BTJKTKAUSA-N 0.000 description 1
- KPQOXMCRYWDRSB-UHFFFAOYSA-N 1-(2-chlorophenyl)pyrrole-2,5-dione Chemical compound ClC1=CC=CC=C1N1C(=O)C=CC1=O KPQOXMCRYWDRSB-UHFFFAOYSA-N 0.000 description 1
- PSUVEXAYACEVGC-UHFFFAOYSA-N 1-(6,6-dichlorohexyl)pyrrole-2,5-dione Chemical compound ClC(Cl)CCCCCN1C(=O)C=CC1=O PSUVEXAYACEVGC-UHFFFAOYSA-N 0.000 description 1
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 1
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 1
- UJTRCPVECIHPBG-UHFFFAOYSA-N 3-cyclohexylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C2CCCCC2)=C1 UJTRCPVECIHPBG-UHFFFAOYSA-N 0.000 description 1
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 1
- JZBCNGVOCGQOBM-UHFFFAOYSA-N C1(=CC=CC=C1)NC1=CC=CC=C1.C(C=C/C(=O)O)(=O)O Chemical compound C1(=CC=CC=C1)NC1=CC=CC=C1.C(C=C/C(=O)O)(=O)O JZBCNGVOCGQOBM-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical class NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 1
- 150000003946 cyclohexylamines Chemical class 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- RCFKIGITIBNPQE-UHFFFAOYSA-N methyl 2,2-difluoro-3-oxopentanoate Chemical compound CCC(=O)C(F)(F)C(=O)OC RCFKIGITIBNPQE-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
Landscapes
- Pyrrole Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は耐熱性重合体を得るための出発原料として最近
非常に重要となってきたＮ−シクロヘキシルマレイミド
の熱安定化法に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a method for thermally stabilizing N-cyclohexylmaleimide, which has recently become very important as a starting material for obtaining heat-resistant polymers.
従来から、熱に対して不安定な物質の熱安定化１こ
のため１、ｐ−ｔ−ブチルカテコール、ヒドロキノン、
塩化第二銅等の１合防止剤を添加するとと得るためのフ
モノマーとして 重合反応に影響を与えずしかも、着色
しない適当な方法は知られていない。Conventionally, thermal stabilization of thermally unstable substances 1. For this purpose, 1. p-t-butylcatechol, hydroquinone,
There is no known suitable method that does not affect the polymerization reaction and does not cause coloration when a monomer is added to the polymerization inhibitor such as cupric chloride.
高純度のＮ−シクロヘキシルマレイミドは融点する。す
なわち加熱溶融するだけで、Ｎ−シクロヘキシルマレイ
ミドの２〜５量体のオリゴマーが生成し、溶融粘度の上
昇がみられ、更に加熱溶融を長時間つづけると、高分子
量の石油樹脂に似たゲル状のホモポリマーとなる。この
現象は特にＮ−シクロヘキシルマレイミドに見らし、他
のマレイミド類例えばＮ−フェニルマレイミド、Ｎ−オ
ルソクロルフェニルマレイミドには見られない。High purity N-cyclohexylmaleimide has a melting point. In other words, just by heating and melting, dimer to pentamer oligomers of N-cyclohexylmaleimide are generated, and the melt viscosity increases, and when heating and melting is continued for a long time, a gel-like substance similar to high molecular weight petroleum resin is formed. becomes a homopolymer. This phenomenon is particularly observed in N-cyclohexylmaleimide, but not in other maleimides such as N-phenylmaleimide and N-orthochlorophenylmaleimide.
このように、Ｎ−シクロヘキシルマレイミドを出発原料
とする工業製品の製造の際に、例えば塩化ビニルとの共
１合による耐熱樹脂゛の製造において、製造中にＮ−シ
クロヘキシルマレイミドのホモポリマーが共重合の初期
に生成することは、懸濁重合の分散系を乱し、共重合反
応のお（れや、共重合物の着色の原因となり、大きな障
害となりていた。In this way, in the production of industrial products using N-cyclohexylmaleimide as a starting material, for example, in the production of heat-resistant resins by copolymerization with vinyl chloride, homopolymers of N-cyclohexylmaleimide are copolymerized during production. The initial formation of nitric acid disturbs the dispersion system of suspension polymerization, causes the copolymerization reaction to deteriorate, and causes coloration of the copolymer, posing a major hindrance.
前記の重合防止剤の添加は、Ｎ−シクロヘキシルマレイ
ミドの熱安定化にある程度の効果はあるが、着色の原因
となり、また他のモノマーとの共重合反応の際に、重合
防止剤の影響を考慮して１合開始剤の使用葉なと重合反
応条件の調整を余儀なくさせられるという問題が生じる
。Addition of the polymerization inhibitor described above has some effect on thermal stabilization of N-cyclohexylmaleimide, but it causes coloration, and the influence of the polymerization inhibitor must be taken into consideration during copolymerization reactions with other monomers. However, if a single initiator is used, a problem arises in that the polymerization reaction conditions must be adjusted.
本発明は、上記の問題のない新しい添加剤を用る。The present invention uses a new additive that does not have the above problems.
本発明は、Ｎ−シクロヘキシルマレイミド１００重量部
に、マレアミン酸、マレアミン酸アミン塩およびマレイ
ン酸アミン塩から選ばれる少な（ともｌｆｉの添加剤を
Ｏ，００１〜５１量部、好ましくは０．００３〜０．Ｉ
ｉ量郡部添加ることを特徴とするＮ−シクロヘキシルマ
レイミドの熱安定化ｊ法である。In the present invention, 100 parts by weight of N-cyclohexylmaleimide is added with a small amount (both lfi) of an additive selected from maleamic acid, maleic acid amine salt, and maleic acid amine salt, to 100 parts by weight of N-cyclohexylmaleimide. 0.I
This is a method for thermally stabilizing N-cyclohexylmaleimide, which is characterized by adding different amounts of N-cyclohexylmaleimide.
本発明に用いる添加剤は、マレアミン酸として例工ばＮ
−シクロヘキシルマレアミン［、Ｎ−フェニルマレアミ
ン酸、Ｎ−ｔ−７’チルマレアミン酸、Ｎ−ブーピルマ
レアミン酸、工びＮ−エチルマレアミノ酸などがあり、
マレアミン酸アミン塩として例えｔｆＮ−シクロヘキシ
ルマレアミン酸シクロヘキシルア汁蓬、Ｈ−フェニルマ
レアミン酸アニリン［、Ｎ−エチルマレアミン酸シクロ
ヘキシルアミン塩等があり、マレイン酸アミン塩としテ
例ｔ ハ、マレイン酸モノシクロヘキシルアミン塩、マ
レイン酸七ノアニリン塩、マレイン酸モ／ｌ−ブチルア
ミン塩、マレイン酸モノエチルアミン塩、マレイン酸ジ
シクジヘキシルアミン塩、マレイン酸ジエチルアミン塩
、マレインＦＩＮ ：）ｔ −７’チルアミン塩、マレ
イン酸ジフェニルアミン塩等があり、上記の化合旬は単
独でまたは２ｆｉ以上混合して使用することができる。The additive used in the present invention is maleamic acid, for example, N
-cyclohexylmaleamin[, N-phenylmaleamic acid, N-t-7'tilmaleamic acid, N-bupylmaleamic acid, and N-ethylmaleamic acid, etc.
Examples of maleic acid amine salts include tfN-cyclohexylmaleamic acid cyclohexylamine salt, H-phenylmaleamic acid aniline [, N-ethylmaleamic acid cyclohexylamine salt, and examples of maleic acid amine salts. Acid monocyclohexylamine salt, maleic acid heptanoaniline salt, maleic acid mo/l-butylamine salt, maleic acid monoethylamine salt, maleic acid dicyclohexylamine salt, maleic acid diethylamine salt, maleic acid FIN:) t-7' tylamine salt , maleic acid diphenylamine salt, etc., and the above compounds can be used alone or in a mixture of 2fi or more.
特に、マレアミン酸は、その共１合反応性比がＮ−シク
ロへキシルマレイミドよりも小さく、従って、微量のマ
レ婆アミン酸の添加によつて、共重合反応速度に影響を
与えないので好ましい。In particular, maleamic acid is preferred because its copolymerization reactivity ratio is lower than that of N-cyclohexylmaleimide, and therefore, the addition of a trace amount of maleamic acid does not affect the copolymerization reaction rate.
屯添加ではＮ−シクロヘキシルマレイミドの純度を低下
させるばかりでなく、９０〜１４０″Ｃで溶しくな〜・
。Addition of tonne not only reduces the purity of N-cyclohexylmaleimide, but also makes it insoluble at 90 to 140"C.
.
融後かくはんにより混合してもよい。ただし、水に溶解
する目添加剤を
水の存在下で懸濁及び乳化共
重合もしくは反応原料に供する場嘘添加剤が水系に移行
するため、熱安定化の効果が乏しくなる場合がちる。こ
の場合には、水に難溶のマレアミン酸棒を各徨モノマー
及び有機溶媒に溶解して用いると所定の効果が得られる
。They may be mixed by stirring after melting. However, when water-soluble additives are subjected to suspension or emulsion copolymerization or reaction raw materials in the presence of water, the additives migrate into the water system, which often results in poor thermal stabilization effects. In this case, the desired effect can be obtained by dissolving a maleamic acid rod, which is sparingly soluble in water, in each free monomer and an organic solvent.
本発明の方法によれば、前記の新規な添加剤の効果によ
りＮ−シクロヘキシルマレイミドの熱安定性が著しく向
上する。したがって、これを用いた耐熱性樹脂の製造の
際に、副反応であるＮ−ジクロヘキシルマレイミドのホ
モポリマーが生成してゲル化することを防止し、共重倉
体の着色を防ぎ、さらに共重合反応に悪影響を与えない
ので工業上の価値が大きい。According to the method of the present invention, the thermal stability of N-cyclohexylmaleimide is significantly improved due to the effect of the above-mentioned novel additive. Therefore, when producing a heat-resistant resin using this product, it is possible to prevent the formation of a homopolymer of N-dichlorohexylmaleimide, which is a side reaction, from forming a gel, to prevent coloring of the copolymer body, and to further prevent copolymerization. It has great industrial value because it does not adversely affect the reaction.
次に実施例および比較例により本発明を具体的に説明す
る。Next, the present invention will be specifically explained using Examples and Comparative Examples.
実施例−１
蒸留精類したＮ−シクロヘキシルマレイミド（融点８８
〜９０°Ｃ：窒素含量７．７８係）Ｚｏｏ／を２００
ｅｒｒのガラスビンに入れ、Ｎ−シクロヘキシルマレア
ミン酸を表−１に示す量を添加し、密栓したのち１２０
±２°Ｃの恒温乾燥器内でＯ〜４８時間加熱靜置し装も
のについて動粘度を測定して、熱安定性を評価した。そ
の結果を表−１に示表−１
なお、動粘度はキャノンフェンスケ粘度計を用いて測定
した。Example-1 Distilled purified N-cyclohexylmaleimide (melting point 88
~90°C: Nitrogen content 7.78) Zoo/200
err glass bottle, add N-cyclohexylmaleamic acid in the amount shown in Table 1, seal it tightly, and then
The thermal stability was evaluated by measuring the kinematic viscosity of the product after heating it in a constant temperature dryer at ±2°C for 48 hours. The results are shown in Table 1. Note that the kinematic viscosity was measured using a Cannon-Fenske viscometer.
また、動粘度とＮ−シクロヘキシルマレイミドの熱重合
の関保は表−２に示した。In addition, the kinematic viscosity and thermal polymerization coefficients of N-cyclohexylmaleimide are shown in Table 2.
表−２
表−１の結果から、添加剤を未添加のＮ−シクロヘキシ
ルマレイミドは、加熱溶融することで短時間のうちに動
粘度が上昇し、１時間後には高粘度のオリゴマーが生成
し、１２０°Ｃで５時間以上加熱すると石油樹脂に似た
硬いゲル状のホモポリマーが生成することが認められる
。Table 2 From the results in Table 1, the kinematic viscosity of N-cyclohexylmaleimide without additives increases in a short time when heated and melted, and after 1 hour, high viscosity oligomers are produced. It is observed that when heated at 120°C for 5 hours or more, a hard gel-like homopolymer similar to petroleum resin is produced.
一方、添加剤を添加したものはその量に応じて動粘度の
上昇およびゲル状のホモポリマーの生成が著しく抑制さ
れており、熱安定性が優れていることが認められる。On the other hand, it is recognized that the increase in kinematic viscosity and the formation of gel-like homopolymer are significantly suppressed depending on the amount of additives added, and the thermal stability is excellent.
実施例−２
表−３に示す添加剤を０．ＩＰ添加し、加熱温度を１０
０°Ｃとした以外は、実施例−１と同様にして熱安定性
を評価した。その結果を表−３に示す。Example-2 Additives shown in Table-3 were added to 0. Add IP and increase heating temperature to 10
Thermal stability was evaluated in the same manner as in Example-1 except that the temperature was 0°C. The results are shown in Table-3.
表−３
表−３の結果から、本発明の添加剤を用いたものはすべ
て熱安定性向上効果が認められるが、マレイン酸の異性
体であるフマル酸の誘導体は全く効果が認められない。Table 3 From the results shown in Table 3, the effect of improving thermal stability is observed in all of the samples using the additive of the present invention, but no effect is observed with the derivatives of fumaric acid, which is an isomer of maleic acid.
ヒト−キノンは熱安定効果はあるが、後述するような欠
点がある。Although human quinone has a heat stabilizing effect, it has drawbacks as described below.
実施例−３
２５１攪拌槽中ＫＯ０５憾（３０Ｐ）の部分鹸化がら、
ｓｏ”ｃで重合した。Example-3 Partial saponification of KO05 (30P) in a 251 stirring tank,
Polymerization was carried out in so”c.
監合時の反応圧力の低下するまでの時間を重合時間とし
た。The time required for the reaction pressure to decrease during polymerization was defined as the polymerization time.
反応を終了し、水を分離乾燥した後、４．８ Ｉｌｌの
生成物が得られた。After finishing the reaction and separating and drying the water, 4.8 Ill of product was obtained.
上記と同様にして、Ｎ−シクロヘキシルマレイミド１０
０７ＫＮ−シクロヘキシルマレアミン酸を０．０１７’
の割合で添加して共重合した場合と比ｌの重合時間ｍ及
び生成物の粒子、着色度、軟化点を表−４に示す。In the same manner as above, N-cyclohexylmaleimide 10
0.017' of 07KN-cyclohexylmaleamic acid
Table 4 shows the polymerization time (m), product particles, degree of coloring, and softening point in comparison with the case of copolymerization by adding at a ratio of .
表−４
−シクロヘキシルマレイミドの熱安定化および熱重合防
止に効果を有するばかりでなく、塩化ビニルとの懸濁員
合法において反応を乱さず、着色のない均一な粒子径を
もつ共重合体が得られることがわかる。ヒドロキノンは
ゲル化防止効果はあるが、重合反応系に悪影響を与えて
製品の着色の原因となる。Table 4 - A copolymer that is not only effective in thermally stabilizing cyclohexylmaleimide and preventing thermal polymerization, but also does not disturb the reaction with vinyl chloride in the suspension member method and has a uniform particle size without coloration can be obtained. I know that it will happen. Although hydroquinone has an anti-gelling effect, it has an adverse effect on the polymerization reaction system and causes coloring of the product.
特許出願人 日本油脂株式会社 手続補正！Ｆ（自発） 昭和６１年５月２１日Patent applicant: NOF Corporation Procedural correction! F (voluntary) May 21, 1986
Claims (1)
ミン酸、マレアミン酸アミン塩およびマレイン酸アミン
塩から選ばれる少くとも１種の添加剤を０．００１〜５
重量部添加することを特徴とするＮ−シクロヘキシルマ
レイミドの熱安定化法。To 100 parts by weight of N-cyclohexylmaleimide, at least one additive selected from maleamic acid, maleamic acid amine salt, and maleic acid amine salt is added at 0.001 to 5 parts by weight.
A method for thermally stabilizing N-cyclohexylmaleimide, which comprises adding parts by weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7429486A JPS62234063A (en) | 1986-04-02 | 1986-04-02 | Thermal stabilization of n-cyclohexylmaleimide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7429486A JPS62234063A (en) | 1986-04-02 | 1986-04-02 | Thermal stabilization of n-cyclohexylmaleimide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62234063A true JPS62234063A (en) | 1987-10-14 |
| JPH0314003B2 JPH0314003B2 (en) | 1991-02-25 |
Family
ID=13542973
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7429486A Granted JPS62234063A (en) | 1986-04-02 | 1986-04-02 | Thermal stabilization of n-cyclohexylmaleimide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62234063A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0794201A1 (en) * | 1995-09-27 | 1997-09-10 | Nippon Shokubai Co., Ltd. | Raw material for the production of heat-resistant resin, heat-resistant resin and process for the production of the resin |
-
1986
- 1986-04-02 JP JP7429486A patent/JPS62234063A/en active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0794201A1 (en) * | 1995-09-27 | 1997-09-10 | Nippon Shokubai Co., Ltd. | Raw material for the production of heat-resistant resin, heat-resistant resin and process for the production of the resin |
| US5998556A (en) * | 1995-09-27 | 1999-12-07 | Nippon Shokubai Co., Ltd. | Raw material used for producing heat-resistant resins, heat-resistant resins, and process for producing heat-resistant resins |
| EP0794201A4 (en) * | 1995-09-27 | 2001-01-24 | Nippon Catalytic Chem Ind | Raw material for the production of heat-resistant resin, heat-resistant resin and process for the production of the resin |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0314003B2 (en) | 1991-02-25 |
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