JP2782383B2 - Method for producing N, N-dialkyl (meth) acrylamide - Google Patents
Method for producing N, N-dialkyl (meth) acrylamideInfo
- Publication number
- JP2782383B2 JP2782383B2 JP2330595A JP33059590A JP2782383B2 JP 2782383 B2 JP2782383 B2 JP 2782383B2 JP 2330595 A JP2330595 A JP 2330595A JP 33059590 A JP33059590 A JP 33059590A JP 2782383 B2 JP2782383 B2 JP 2782383B2
- Authority
- JP
- Japan
- Prior art keywords
- aminoamide
- acrylamide
- meth
- dialkyl
- thermal decomposition
- 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 - Fee Related
Links
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【発明の詳細な説明】 （産業上の利用分野） 本発明はN,N−ジアルキルアクリルアミド及びN,N−ジ
アルキルメタクリルアミド（以下、N,N−ジアルキル
（メタ）アクリルアミドと略す）の製造方法に関するも
のである。The present invention relates to a method for producing N, N-dialkylacrylamide and N, N-dialkylmethacrylamide (hereinafter abbreviated as N, N-dialkyl (meth) acrylamide). Things.
本発明によって製造されるN,N−ジアルキル（メタ）
アクリルアミドはその性質上、繊維・プラスチック等の
高分子改質剤、接着剤、石油二次回収剤及び医薬品等の
合成原料として広い用途を有する有用な化合物である。N, N-dialkyl (meth) produced according to the invention
Acrylamide is a useful compound having a wide range of uses as a raw material for synthesizing polymers such as polymer modifiers for fibers and plastics, adhesives, secondary oil recovery agents, and pharmaceuticals.
（従来の技術） 一般式（Ｉ） （式中、R1は水素原子またはメチル基、R2〜R5はそれぞ
れ炭素数１〜４のアルキル基を示す。）で表されるアミ
ノアミド（以下、アミノアミドと略す）を液相にて加熱
分解しN,N−ジアルキル（メタ）アクリルアミドを製造
する従来技術においては、アミノアミドに重合禁止剤を
添加して熱分解する方法（ジャーナル・オブ・アメリカ
ン・ケミカル・ソサイエティ第74巻6281頁（1752
年））、USP2,683,741、特公昭47−40777号公報、特公
昭48−31086号公報、特開昭58−18346号公報、特開昭61
−145151号公報が知られている。(Prior art) General formula (I) (Wherein R 1 represents a hydrogen atom or a methyl group, and R 2 to R 5 each represent an alkyl group having 1 to 4 carbon atoms.) An aminoamide (hereinafter abbreviated as aminoamide) represented by the following formula: In the prior art for producing N, N-dialkyl (meth) acrylamide by decomposition, a method of thermal decomposition by adding a polymerization inhibitor to aminoamide (Journal of American Chemical Society, vol. 74, p. 6281 (1752)).
)), USP 2,683,741, JP-B-47-40777, JP-B-48-31086, JP-A-58-18346, JP-A-61
-145151 is known.
また、アミノアミドの液相熱分解により発生するジア
ルキルアミンを液相に補足して回収するために、補足剤
として解離定数1.0×10-2以上の強酸をアミノアミドと
同当量以上添加し、加熱分解する方法（USP2,451,436）
も知られている。In addition, in order to capture and recover the dialkylamine generated by the liquid-phase thermal decomposition of aminoamide in the liquid phase, a strong acid with a dissociation constant of 1.0 × 10 -2 or more is added as a supplementary agent in the same amount or more as the aminoamide, and is thermally decomposed. Method (USP2,451,436)
Is also known.
（発明が解決しようとする課題） アミノアミドを液相にて熱分解し、N,N−ジアルキル
（メタ）アクリルアミドを製造する従来技術において
は、熱分解の反応速度が比較的遅いため、目的の分解率
を達成するためには高温、長時間という過酷な条件が必
須であり、そのような条件下では、生成するN,N−ジア
ルキル（メタ）アクリルアミドモノマーの重合によるポ
リマーの発生、各種不純物の増加による収率低下及び製
品々質の低下という問題を引き起こす（ジャーナル・オ
ブ・アメリカン・ソサイエティ第74巻6281頁（1952
年））。(Problems to be Solved by the Invention) In the prior art for producing N, N-dialkyl (meth) acrylamide by thermally decomposing an aminoamide in a liquid phase, the reaction rate of the thermal decomposition is relatively slow. In order to achieve the rate, severe conditions such as high temperature and long time are indispensable. Under such conditions, polymerization of the N, N-dialkyl (meth) acrylamide monomer to be generated generates polymers and increases various impurities. Causes problems of reduced yield and product quality (Journal of the American Society, Vol. 74, p. 6281 (1952
Year)).
また、アミノアミドの液相熱分解時に生成するジアル
キルアミンをジアルキルアミン塩として液相に補足する
ために、補足剤として解離定数1.0×10-2以上の酸を添
加する方法（USP2,683,741）においては、アミノアミド
と当量以上の酸が必要であり、N,N−ジアルキル（メ
タ）アクリルアミドをジアルキルアミン塩から分離する
工程が必要となる。熱分解後のN,N−ジアルキル（メ
タ）アクリルアミドの粗モノマー中には大量のジアルキ
ルアミンの塩が含まれており、このような大量の塩を溶
解している液から蒸発により粗モノマーを回収しようと
すると、初期の段階からジアルキルアミンの塩が析出
し、最終的には固体中に残存する液体を蒸発させる状態
となり、固体中に数％〜10数％の未蒸発液体が必ず残
る。また、そのような状態では10数度〜20数度の沸点上
昇が起きるため、ポリマーの発生は避けられない。この
ようなことから、大量の酸を使用することは収率の面か
らも大きな損失をもたらす。また、一度補足したジアル
キルアミンを回収するには、さらに大量のアルカリ性物
質（例えば水酸化ナトリウム）が必要であり、コストの
上昇と大量の塩の発生という問題を引き起こす。In addition, in order to capture the dialkylamine generated during the thermal decomposition of aminoamide in the liquid phase as a dialkylamine salt, a method in which an acid having a dissociation constant of 1.0 × 10 -2 or more is added as a scavenger (USP 2,683,741) , An acid equivalent to the aminoamide or more is required, and a step of separating N, N-dialkyl (meth) acrylamide from the dialkylamine salt is required. The crude monomer of N, N-dialkyl (meth) acrylamide after pyrolysis contains a large amount of dialkylamine salt, and the crude monomer is recovered by evaporation from a solution in which such a large amount of salt is dissolved. If this is attempted, the salt of the dialkylamine precipitates from the initial stage, and eventually the liquid remaining in the solid is evaporated, leaving several to ten to several percent of the unevaporated liquid in the solid. Further, in such a state, a boiling point rise of several tens of degrees to several tens of degrees occurs, so that generation of a polymer is inevitable. For this reason, using a large amount of acid causes a large loss in terms of yield. Further, in order to recover the dialkylamine once captured, a larger amount of an alkaline substance (for example, sodium hydroxide) is required, which causes a problem of an increase in cost and generation of a large amount of salt.
（課題を解決するための手段） 本発明者らは前述したN,N−ジアルキル（メタ）アク
リルアミドの製造法に関する従来技術の問題点を解決す
べく鋭意検討した結果、従来予想もされなかったこと
に、ある種の酸性物質がアミノアミドの触媒として著し
い効果があり、このような触媒を使用することでアミノ
アミドの熱分解が比較的低温で短時間に進行し、また、
生成するジアルキルアミンは気相中に蒸発させ、必要な
らばジアルキルアミンを気相より回収すればN,N−ジア
ルキル（メタ）アクリルアミドをジアルキルアミン塩か
ら分離する工程を必要としないことを見い出し、本発明
を完成するに至った。(Means for Solving the Problems) The inventors of the present invention have conducted intensive studies to solve the problems of the prior art relating to the method for producing N, N-dialkyl (meth) acrylamide described above, and as a result, were not expected in the past. In addition, certain acidic substances have a remarkable effect as a catalyst for aminoamide, and the thermal decomposition of aminoamide proceeds at a relatively low temperature in a short time by using such a catalyst.
The resulting dialkylamine is evaporated in the gas phase, and if necessary, a step of separating N, N-dialkyl (meth) acrylamide from the dialkylamine salt is not required if the dialkylamine is recovered from the gas phase. The invention has been completed.
すなわち、本発明はアミノアミドの液相熱分解時にあ
る種の酸性物質を触媒量添加することを要旨とするもの
である。ある種の酸性物質を添加することにより、アミ
ノアミドの熱分解反応速度は無触媒系に比べ、数倍から
数十倍に飛躍的に上昇し、低温かつ短時間に目的の反応
率まで達成させることが可能となった。That is, the gist of the present invention is to add a catalytic amount of a certain acidic substance during the liquid phase thermal decomposition of aminoamide. By adding a certain kind of acidic substance, the thermal decomposition reaction rate of aminoamide can be dramatically increased several times to several tens times compared to a non-catalyst system, and the target reaction rate can be achieved at low temperature and in a short time. Became possible.
本発明でいうアミノアミドの液相熱分解反応に使用さ
れる触媒としてのある種の酸性物質とは、アミノアミド
の液相熱分解条件（温度、圧力）において継続して反応
液の中に存在し、かつ、その存在する状態において酸性
を示す物質のことである。このような酸性物質とは常態
として酸性を示す物質を含むことは当然であるが、常態
としては塩、その他の物質であるため酸性を示さない
が、アミノアミドが液相熱分解される条件下において
は、塩、その他の物質が分解し、結果として酸性を示す
物質に変わる物質も包含される。Certain acidic substances as a catalyst used in the liquid phase pyrolysis reaction of aminoamide referred to in the present invention are present in the reaction solution continuously under the liquid phase pyrolysis conditions (temperature, pressure) of aminoamide, In addition, it refers to a substance that is acidic in its existing state. It is natural that such an acidic substance includes a substance which shows an acidity as a normal state.However, as a normal state, it does not show an acidity because it is a salt or other substance, but under conditions where aminoamide is thermally decomposed in a liquid phase. Also includes substances in which salts and other substances are decomposed, and as a result, are converted into acidic substances.
本発明におけるアミノアミドの液相における熱分解反
応を促進させる触媒としての酸性物質の具体例を次に示
す。Specific examples of the acidic substance as a catalyst for promoting the thermal decomposition reaction of the aminoamide in the liquid phase in the present invention are shown below.
（１）常態として酸性を示す物質 無機酸（ブレンステッド酸） 硫酸、硝酸、リン酸、ピロリン酸、ポリリン酸、ジメチ
ル硫酸、パラトルエンスルホン酸、Ｈ型イオン交換樹
脂、含水酸化ジルコニア等。(1) Substances that are acidic as a normal state Inorganic acids (Bronsted acids) Sulfuric acid, nitric acid, phosphoric acid, pyrophosphoric acid, polyphosphoric acid, dimethyl sulfate, paratoluenesulfonic acid, H-type ion exchange resin, hydrous zirconia, and the like.
無機酸（ルイス酸） 塩化アルミニウム、塩化鉄（III）、塩化亜鉛、塩化す
ず等。Inorganic acid (Lewis acid) Aluminum chloride, iron (III) chloride, zinc chloride, tin chloride, etc.
有機酸 酢酸、フタル酸、安息香酸等。Organic acids Acetic acid, phthalic acid, benzoic acid, etc.
酸性有機物 フェノール等。Acidic organic matter phenol etc.
（２）常態として塩、その他の物質 前項で示した無機酸（ブレンステッド酸）及び有機酸
のアンモニウム塩。具体的には硫酸アンモニウム、硝酸
アンモニウム、リン酸アンモニウム、モノメチル硫酸ア
ンモニウム、パラトルエン硫酸アンモニウム、酸性イオ
ン交換樹脂のアンモニウム塩、酢酸アンモニウム等。(2) Normally, salts and other substances Ammonium salts of inorganic acids (Bronsted acids) and organic acids shown in the preceding section. Specific examples include ammonium sulfate, ammonium nitrate, ammonium phosphate, ammonium monomethyl sulfate, ammonium paratoluene sulfate, ammonium salts of acidic ion exchange resins, and ammonium acetate.
アミノアミドの液相における熱分解反応を促進させる
上記触媒のうち、常態として塩、その他の物質はアミノ
アミドの熱分解の条件下では、触媒として添加した物質
も分解し、酸性物質に変化することにより、酸性物質を
直接使用した場合と同様な効果が得られる。Among the above catalysts that promote the thermal decomposition reaction of aminoamide in the liquid phase, salts and other substances are normally decomposed under the conditions of thermal decomposition of aminoamide, and the substances added as catalysts also decompose and change to acidic substances. The same effect as when the acidic substance is directly used can be obtained.
本発明において、アミノアミドの液相熱分解に加える
熱分解触媒の量については特に制限はないが、通常1000
〜100000ppm、好ましくは3000〜30000ppm程度である。In the present invention, the amount of the pyrolysis catalyst to be added to the liquid-phase pyrolysis of aminoamide is not particularly limited, but is usually 1000
1100,000 ppm, preferably about 3,000 to 30,000 ppm.
また、このようなアミノアミドの液相用熱分解触媒と
しての酸性物質は２種類以上併用してもよい。さらにア
ミノアミドの液相熱分解には通常よく重合禁止剤が使用
されるが、これらの重合禁止剤と本発明でいう熱分解触
媒としての酸性物質を併用しても何ら差しさわりはな
い。In addition, two or more kinds of such acidic substances as a thermal decomposition catalyst for a liquid phase of aminoamide may be used in combination. Further, polymerization inhibitors are often used for the liquid phase thermal decomposition of aminoamides, but it does not matter if these polymerization inhibitors are used in combination with an acidic substance as a thermal decomposition catalyst in the present invention.
（実施例） 次に、実施例をもって本発明を具体的に説明するが、
これらの実施例は本発明を限定するものではない。(Examples) Next, the present invention will be described specifically with reference to Examples.
These examples do not limit the invention.
実施例１ マクマホンを10cm詰めた充填塔と温度計の付いた200m
l三ッ口フラスコに３−ジメチルアミノ−N,N−ジメチル
プロパンアミド100gを入れ、内温が195℃になるよう
に、油浴にて加熱した。充填塔の先は窒素シールとし、
その先は開放とした。Example 1 200 m with a packed tower packed with 10 cm of McMahon and a thermometer
l 100 g of 3-dimethylamino-N, N-dimethylpropanamide was placed in a three-necked flask, and heated in an oil bath so that the internal temperature became 195 ° C. The end of the packed tower is a nitrogen seal,
The end was open.
内温が195℃となったところで、濃硫酸0.7gを投入
し、経時的にフラスコ内の液をサンプリングし、内部標
準法ガスクロマトグラフィーにて３−ジメチルアミノ−
N,N−ジメチルプロパンアミドの残存量を実測し、それ
から分解率を計算した。その結果を表１に示す。When the internal temperature reached 195 ° C., 0.7 g of concentrated sulfuric acid was added, and the liquid in the flask was sampled with time, and 3-dimethylamino- was determined by internal standard method gas chromatography.
The residual amount of N, N-dimethylpropanamide was actually measured, and then the decomposition rate was calculated. Table 1 shows the results.
比較例１ 濃硫酸を使用しない以外は実施例１と同様の装置、条
件のもとで無触媒系での３−ジメチルアミノ−N,N−ジ
メチルプロパンアミドの分解速度を測定した。その結果
を表２に示す。 Comparative Example 1 The decomposition rate of 3-dimethylamino-N, N-dimethylpropanamide in a noncatalytic system was measured under the same apparatus and conditions as in Example 1 except that concentrated sulfuric acid was not used. Table 2 shows the results.
実施例２〜５ 熱分解触媒としての濃硫酸の添加量の違いによる効果
をみるために表３に示すように濃硫酸の添加量を変え、
それ以外は実施例１と同様の装置と条件にて３−ジメチ
ルアミノ−N,N−ジメチルプロパンアミドの熱分解実験
を実施した。熱分解速度として、反応開始後30分の値を
採用した。その結果を表３に示す。 Examples 2 to 5 In order to see the effect of the difference in the amount of concentrated sulfuric acid added as a pyrolysis catalyst, the amount of concentrated sulfuric acid was changed as shown in Table 3;
Other than that, the thermal decomposition experiment of 3-dimethylamino-N, N-dimethylpropanamide was carried out under the same apparatus and conditions as in Example 1. As the thermal decomposition rate, a value 30 minutes after the start of the reaction was adopted. Table 3 shows the results.
実施例６〜15 熱分解触媒として硫酸に変え、表４に示すように他の
酸及び酸性物質を使用して３−ジメチルアミノ−N,N−
ジメチルプロパンアミドの液相熱分解実験を実施した。
触媒以外の装置、条件は実施例１と同様である。その結
果を表４に示す。 Examples 6-15 Using 3-dimethylamino-N, N- as an alternative to sulfuric acid as the pyrolysis catalyst and using other acids and acidic substances as shown in Table 4.
A liquid phase pyrolysis experiment of dimethylpropanamide was performed.
The equipment and conditions other than the catalyst are the same as in Example 1. Table 4 shows the results.
実施例16〜18及び比較例２ 熱分解触媒として硫酸に変え表５に示すように各種酸
のアンモニウム塩を使用し、それ以外の装置、条件は実
施例１と同様にして３−ジメチルアミノ−N,N−ジメチ
ルプロパンアミドの液相熱分解実験を実施した。 Examples 16 to 18 and Comparative Example 2 Instead of sulfuric acid as a pyrolysis catalyst, ammonium salts of various acids were used as shown in Table 5, and the other equipment and conditions were the same as in Example 1 except for 3-dimethylamino- Liquid phase pyrolysis experiments of N, N-dimethylpropanamide were performed.
また、比較例２として硫酸の代わりに炭酸アンモニウ
ムを使用して同様な実験を行った。実験結果をまとめて
表５に示す。As Comparative Example 2, a similar experiment was performed using ammonium carbonate instead of sulfuric acid. Table 5 summarizes the experimental results.
この比較例２は、添加した炭酸アンモニウムが熱分解
条件下でアンモニアと二酸化炭素となり液相中に残在し
ないため、熱分解触媒としての効果がないことを示して
いる。Comparative Example 2 shows that the added ammonium carbonate was not effective as a thermal decomposition catalyst because the added ammonium carbonate became ammonia and carbon dioxide under thermal decomposition conditions and did not remain in the liquid phase.
（発明の効果） アミノアミドの液相熱分解によるN,N−ジメチル（メ
タ）アクリルアミドの製造において、酸性物質を触媒と
して使用することにより熱分解反応が飛躍的に促進し、
比較的温和な条件下で熱分解反応を行わせることが可能
となった。 (Effect of the Invention) In the production of N, N-dimethyl (meth) acrylamide by liquid phase thermal decomposition of aminoamide, the thermal decomposition reaction is drastically accelerated by using an acidic substance as a catalyst,
It became possible to carry out the thermal decomposition reaction under relatively mild conditions.
また、生成するジアルキルアミンを気相中に蒸発さ
せ、必要ならば気相より回収することにより、従来のよ
うにN,N−ジアルキル（メタ）アクリルアミドをジアル
キルアミン塩から分離する工程もなく、製造コストを低
減できた。In addition, the dialkylamine produced is evaporated in the gas phase and, if necessary, recovered from the gas phase, so that there is no step of separating N, N-dialkyl (meth) acrylamide from the dialkylamine salt as in the conventional method. The cost was reduced.
本発明を実施することにより、従来技術の欠点を解決
することが万能となり、その工業的意義は大きい。By practicing the present invention, it is versatile to solve the disadvantages of the prior art, and its industrial significance is great.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 ＦＩ Ｃ０７Ｃ 231/12 Ｃ０７Ｃ 231/12 // Ｂ０１Ｊ 21/06 Ｂ０１Ｊ 21/06 Ｘ 31/02 31/02 Ｚ 31/04 31/04 Ｚ Ｃ０７Ｂ 61/00 ３００ Ｃ０７Ｂ 61/00 ３００ ──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 6 Identification code FI C07C 231/12 C07C 231/12 // B01J 21/06 B01J 21/06 X 31/02 31/02 Z 31/04 31/04 Z C07B 61/00 300 C07B 61/00 300
Claims (1)
れ炭素数１〜４のアルキル基を示す。）で表されるアミ
ノアミドを液相にて熱分解する際に、熱分解反応を促進
する触媒として反応液の中に継続して存在し熱分解条件
下において酸性を示す酸性物質をアミノアミドに対し10
00〜100000ppm使用することを特徴とするN,N−ジアルキ
ル（メタ）アクリルアミドの製造法。1. The compound of the general formula (I) (Wherein, R 1 represents a hydrogen atom or a methyl group, and R 2 to R 5 each represent an alkyl group having 1 to 4 carbon atoms). An acidic substance which is continuously present in the reaction solution as a catalyst for accelerating the reaction and which shows
A process for producing N, N-dialkyl (meth) acrylamide, characterized by using from 100 to 100,000 ppm.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2330595A JP2782383B2 (en) | 1990-11-30 | 1990-11-30 | Method for producing N, N-dialkyl (meth) acrylamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2330595A JP2782383B2 (en) | 1990-11-30 | 1990-11-30 | Method for producing N, N-dialkyl (meth) acrylamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04208258A JPH04208258A (en) | 1992-07-29 |
| JP2782383B2 true JP2782383B2 (en) | 1998-07-30 |
Family
ID=18234413
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2330595A Expired - Fee Related JP2782383B2 (en) | 1990-11-30 | 1990-11-30 | Method for producing N, N-dialkyl (meth) acrylamide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2782383B2 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69308817T2 (en) * | 1992-10-21 | 1997-07-31 | Kohjin Co | METHOD FOR PRODUCING N-MONO SUBSTITUTED METHACRYLAMIDE |
| JP2000273072A (en) * | 1999-03-24 | 2000-10-03 | Kohjin Co Ltd | Production of (meth)acrylamide derivative |
| EP2664611A1 (en) | 2009-05-01 | 2013-11-20 | Idemitsu Kosan Co., Ltd | Method for producing alpha,beta-unsaturated carboxylic acid-N,N-disubstituted amide and method for producing 3-alkoxycarboxylic acid-N,N-disubstituted amide |
| JP5649333B2 (en) | 2010-06-01 | 2015-01-07 | 株式会社神戸製鋼所 | Ion bombardment apparatus and substrate surface cleaning method using the apparatus |
| JP5689051B2 (en) | 2011-11-25 | 2015-03-25 | 株式会社神戸製鋼所 | Ion bombardment equipment |
| JP5591855B2 (en) | 2012-03-22 | 2014-09-17 | 富士フイルム株式会社 | Polymerizable compound precursor |
| CN107673985B (en) * | 2017-12-05 | 2020-10-02 | 淄博齐塑环保科技有限公司 | Preparation process of high-yield N, N-dimethylacrylamide |
-
1990
- 1990-11-30 JP JP2330595A patent/JP2782383B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH04208258A (en) | 1992-07-29 |
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