JPH03206067A - Quaternization of n,n-dialkylaminoalkyl (meth)acrylates - Google Patents
Quaternization of n,n-dialkylaminoalkyl (meth)acrylatesInfo
- Publication number
- JPH03206067A JPH03206067A JP2002067A JP206790A JPH03206067A JP H03206067 A JPH03206067 A JP H03206067A JP 2002067 A JP2002067 A JP 2002067A JP 206790 A JP206790 A JP 206790A JP H03206067 A JPH03206067 A JP H03206067A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- acrylate
- alkylating agent
- meth
- raw material
- 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.)
- Pending
Links
- 150000001252 acrylic acid derivatives Chemical class 0.000 title claims description 13
- 238000005956 quaternization reaction Methods 0.000 title claims description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- 229940100198 alkylating agent Drugs 0.000 claims abstract description 16
- 239000002168 alkylating agent Substances 0.000 claims abstract description 16
- 239000002994 raw material Substances 0.000 claims abstract description 9
- 239000012736 aqueous medium Substances 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 12
- YTLYLLTVENPWFT-UPHRSURJSA-N (Z)-3-aminoacrylic acid Chemical group N\C=C/C(O)=O YTLYLLTVENPWFT-UPHRSURJSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 11
- 230000035484 reaction time Effects 0.000 abstract description 7
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 abstract description 6
- -1 salt compound Chemical class 0.000 abstract description 5
- 229940050176 methyl chloride Drugs 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 abstract description 3
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 abstract description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 description 13
- 239000003112 inhibitor Substances 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 150000003839 salts Chemical group 0.000 description 5
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical group [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229960003750 ethyl chloride Drugs 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229940102396 methyl bromide Drugs 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- QHVBLSNVXDSMEB-UHFFFAOYSA-N 2-(diethylamino)ethyl prop-2-enoate Chemical compound CCN(CC)CCOC(=O)C=C QHVBLSNVXDSMEB-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- KDAHUGMXOVGQGC-UHFFFAOYSA-N 2-(ethylamino)propyl prop-2-enoate Chemical compound CCNC(C)COC(=O)C=C KDAHUGMXOVGQGC-UHFFFAOYSA-N 0.000 description 1
- QGXMPHBQJFXJCI-UHFFFAOYSA-N 4-(dimethylamino)butyl prop-2-enoate Chemical compound CN(C)CCCCOC(=O)C=C QGXMPHBQJFXJCI-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- AGWGLQAQTSTART-UHFFFAOYSA-N [3-(dimethylamino)-2-hydroxypropyl] prop-2-enoate Chemical compound CN(C)CC(O)COC(=O)C=C AGWGLQAQTSTART-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 230000003311 flocculating effect Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000010842 industrial wastewater Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000005518 polymer electrolyte Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Landscapes
- Separation Of Suspended Particles By Flocculating Agents (AREA)
- Treatment Of Sludge (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
〔産業上の利用分野〕
本発明は、Ｎ，Ｎ−ジアルキルアミノアルキル（メタ）
アクリレート類の４級化方法の改良に関するものである
．
〔従来の技術〕
（１）背景
Ｎ，Ｎ−ジアルキルアミノアルキル（メタ）アクリレー
ト類の４級塩（以下、“第４級アミノアクリレート塩”
と総称する．）を、単独で又は他のビニルモノマーと共
重合させると、容易に高分子量の水溶性ポリマーが得ら
れる．このポリマーは、カチオン性の高分子電解質であ
って、コロイドや懸濁粒子に対して優れた凝集性を示す
ため高分子凝集剤として有用であり、特に、下水，Ｒ床
及び産業廃水の活性汚泥処理で生じる有機性汚泥の遠心
濾過、圧搾濾過などの脱水促進に優れた効果を発揮する
．
（２）従来技術の問題点
上記第４級アミノアクリレート塩の製造法としては、第
３級アミノ（メタ）アクリレート（以下，“第３級アク
リレート”とも云う）と７ルキルハライドを水性媒質中
で反応させる方法が知られているが、この反応では、副
反応として起こるアクリレートの加水分解を避けるため
、可及的低温（５０℃以下、好ましくは１０〜３０℃）
で行なう必要があり、このため反応に長時間（例えば反
応に８時間、熟威１６時間）を必要とする（特開昭５１
−７６２１６号；「（メタ）アクリロイルオキシエチル
トリアルキルアンモニウム塩の製這法」参照）．以上の
欠点は、原料第３級アクリレートの濃度を高めることに
よりある程度解決できるが（初期濃度を８０％以上、好
ましくは８５％以上、反応時間６時間；特開昭５２−３
１０１７号「４級化方法」参照）、反面、反応液及び生
或物の粘度が高くなり、攪拌及び輪送に問題を生じる他
、生或物が重合する可能性がある．
〔発明が解決しようとする課題〕
本発明は，第３級アクリレートと７ルキルハライドを水
性媒質中で反応させる方法において，アルキル化剤の添
加方法と反応温度を工夫することによって、既知方法に
比べて，反応時間を著しく短縮した、工業的な第４級ア
ミノアクリレート塩の製造法を開発することを目的とす
る．（以下余白）[Industrial Application Field] The present invention relates to N,N-dialkylaminoalkyl (meth)
This paper relates to improvements in the quaternization method for acrylates. [Prior Art] (1) Background Quaternary salts of N,N-dialkylaminoalkyl (meth)acrylates (hereinafter referred to as "quaternary aminoacrylate salts")
Collectively called. ), alone or copolymerized with other vinyl monomers, can easily yield high molecular weight water-soluble polymers. This polymer is a cationic polymer electrolyte and exhibits excellent flocculating properties for colloids and suspended particles, making it useful as a polymer flocculant, especially for activated sludge in sewage, R-beds, and industrial wastewater. It exhibits excellent effects in promoting dewatering of organic sludge generated during processing, such as centrifugal filtration and press filtration. (2) Problems with the prior art The method for producing the above-mentioned quaternary amino acrylate salt involves reacting tertiary amino (meth)acrylate (hereinafter also referred to as "tertiary acrylate") with 7-alkyl halide in an aqueous medium. However, this reaction is carried out at the lowest possible temperature (50°C or lower, preferably 10 to 30°C) in order to avoid hydrolysis of the acrylate that occurs as a side reaction.
Therefore, the reaction requires a long time (for example, 8 hours for reaction and 16 hours for ripening) (Japanese Patent Laid-Open No. 51
No.-76216; see ``Method for producing (meth)acryloyloxyethyl trialkylammonium salt''). The above drawbacks can be solved to some extent by increasing the concentration of the raw material tertiary acrylate (initial concentration 80% or more, preferably 85% or more, reaction time 6 hours; JP-A-52-3
On the other hand, the viscosity of the reaction solution and the raw material increases, causing problems in stirring and conveyance, and there is a possibility that the raw material may polymerize. [Problems to be Solved by the Invention] The present invention provides a method for reacting tertiary acrylate and 7-alkyl halide in an aqueous medium, which is improved compared to known methods by devising the method of adding an alkylating agent and the reaction temperature. The purpose of this paper is to develop an industrial method for producing quaternary amino acrylate salts that significantly shortens the reaction time. (Margin below)
〔課題を解決するための手段〕
（１）概念
本発明者は、上記課題の解決を目指して，第３級アクリ
レートの第４級化方法につき系統的な検討を加えた結果
、
■ 原料第３級アミノアクリレートの反応初期濃度を７
０〜８０％好まし〈は７０〜７５％とすることにより、
多量の重合禁止剤を添加しなくとも事実上重合を防止し
うること．
■ アルキル化剤を２０℃以下の低温度下に短時間以内
に添加することにより、反応初期の加水分解を回避でき
ること．
■ ４級化反応を４５〜７５℃、好ましくは４８〜５５
℃の比較的高温度下に実施することにより反応所要時間
を大幅に短縮できること．
を見出した．
（２）概要
本発明は以上の知見に基〈もので、その要旨はＮ，Ｎ−
ジアルキルアミノアルキル（メタ）アクリレート類を水
性媒質中アルキル化剤により４級化するに当り、原料第
３級アミノアクリレートの初期濃度を７０〜８０％とし
てアルキル化剤を２０℃以下低温下に急速に添加すると
共に、反応を４５〜７０℃で行なわせることを特徴とす
るＮ，Ｎ−ジアルキルアミノアルキル（メタ）アクリレ
ート類の４級化方法に存する．
以下、発明の構或に関連する主要な事項につき項分けし
て説明する．
（３）第３級アクリレート類
本発明の原料となる第３級アクリレート類としては，ジ
メチルアミノエチルアクリレート、ジメチルアミノプロ
リルアクリレート、ジメチルアミノブチルアクリレート
、メチルエチルアミノエチルアクリレート，ジエチルア
ミノエチルアクリレート、３−ジメチルアミノ−２−ビ
ドロキシプロビルアクリレート、ジブチルアミノエチル
アクリレート等が挙げられる．
初期反応時の第３級アクリレート類の濃度は、７０〜８
０％，殊に７０〜７５％であるのが好ましい．加木分解
抑制のためには高濃度が望ましいが、８５％以上になる
と，４級化反応中に重合等の障害が起こり易い．
（４）アルキル化剤
４級化反応を短時間内に完結させるため、アルキル化剤
としては、塩化メチル、塩化エチル、臭化メチル、臭化
エチル、ジメチル硫酸、沃化エチル、塩化ベンジル、モ
ノクロル酢酸エステル等が例示できるが、特に４級化反
応の速度が遅い塩化メチルが好ましい．
以上のアルキル化剤は、１５〜２０℃の低温度下に反応
系中に急速に添加されることが加水分解抑制ため効果的
である．従って、塩化メチル、塩化エチル、臭化メチル
又は臭化エチルのような揮発性のアルキル化剤は、加圧
下に反応系へ導入されるのがよい．
（５）重合禁止剤
メルカブタン等の重合禁止剤の添加は、重合抑制のため
効果的ではあるが、過剰の場合は、４級化反応の進行を
妨げると共に、得られた４級化物を重合させる際、誘導
期間（時間）を長くしたり，未反応のモノマー量を増加
させたりする．好適な重合禁止剤の量は、８００〜１５
００ｐｐ＋ｍ ，殊に１０００〜１２００ｐｐｍである
．
（８）反応時間
本発明の反応に必要な時間は、既知の方法より著しく短
〈、通常２時間以内，殊に１００分以内に完結する．
〔作用〕
第３級アクリレート類を水媒体中でアルキル化剤との反
応において，加水分解反応は反応初期に起こり，反応の
中期及び終期には殆ど起こらない．一般に、反応初期段
階での加水分解を抑制する方法として低温度での反応及
び高濃度溶液中での反応があるが、反応温度が低下し、
反応終了まで極めて長時間を要する．一方、高濃度反応
では、反応液の粘度上昇が問題となる．
本発明は，第３級アクリレート類の濃度を調整すると共
に、低温下にアルキル化剤を急速に加え、かつ反応温度
を一定範囲内の高温に保つことによって、反応所要時間
を２時間以内に短縮するのに戒功したものである．
〔実施例〕
以下実施例により発明実施の態様につき述べるが、例示
は単に説明用のものであって，発明思想の限定又は制限
を意図したものではない・Ｘ簾負ユ
攪拌機を備えた容量５１のオートクレープ反応槽に，ジ
メチルアミノエチルメタクリレート３０００ ｇ、水１
１３２ｇ及び重合禁止剤１２０Ｏｐｐ鵬を仕込み（初期
濃度７２．６％），回転数２５０ ｒｐ＋ｓで攪拌混合
した．全体を冷水で循環させたジャケット内に入れ、内
温を１８℃に保ちながら塩化メチル１０１２ｇ （第３
級メタクリレートに対し，モル比１．０５）を圧力２
ｋｇ／ｃｍ２で６０秒以内に液体の形で添加した．次い
でジャケットに５０℃の温水を通じて内音を４８〜５２
℃に昇湿させた（内温５０℃の時、ゲージ圧５ｋｇ／ｃ
ｍ２） ．反応中、最高７０℃まで昇湿しても重合は起
こらなかった．４級化反応が進行するにつれ、圧力は低
下した， １００分間反応させた後，ジャケットに冷水
を通じて２５℃まで冷却し、反応物を取り出した．得ら
れた４級化物の濃度は７９％，遊離塩素分１４％、４級
塩の濃度は８２％であった．
罠菓史ヱ
前例の反応において，重合禁止剤を２０００ｐｐｍに増
量した以外同様に実施した．
得られた４級化物濃度は７８．２％，遊離塩素分１３．
６％、４級塩濃度７９．５％であった．重合禁止剤の増
量により，４級塩の濃度が前例より２．５％下回った．
Ｘ簾忽ユ
実施例ｌにおける重合禁止剤２０００ｐｐｍに，反応時
間を３００分に，夫々変更した以外は同例と同様に実施
した．得られた４級化物の濃度は７８．５％遊離塩素分
１３．４％、４級塩濃度７８．３％であった．[Means for Solving the Problems] (1) Concept Aiming to solve the above problems, the present inventor conducted a systematic study on a method for quaternizing tertiary acrylates, and found that ■ Raw material 3 The initial reaction concentration of grade aminoacrylate was set to 7.
0 to 80% preferably 70 to 75%,
Polymerization can be virtually prevented without adding a large amount of polymerization inhibitor. ■ By adding the alkylating agent within a short time at a low temperature of 20°C or less, hydrolysis in the early stage of the reaction can be avoided. ■ Quaternization reaction at 45-75℃, preferably 48-55℃
The time required for the reaction can be significantly shortened by carrying out the reaction at a relatively high temperature of ℃. I found out. (2) Overview The present invention is based on the above knowledge, and its gist is
In quaternizing dialkylaminoalkyl (meth)acrylates with an alkylating agent in an aqueous medium, the initial concentration of the raw tertiary aminoacrylate is 70 to 80%, and the alkylating agent is rapidly added at a low temperature of 20°C or lower. A method for quaternizing N,N-dialkylaminoalkyl (meth)acrylates, characterized in that the reaction is carried out at 45 to 70°C. Below, the main matters related to the structure of the invention will be explained in sections. (3) Tertiary acrylates Examples of tertiary acrylates used as raw materials for the present invention include dimethylaminoethyl acrylate, dimethylaminoprolyl acrylate, dimethylaminobutyl acrylate, methylethylaminoethyl acrylate, diethylaminoethyl acrylate, 3- Examples include dimethylamino-2-hydroxypropyl acrylate and dibutylaminoethyl acrylate. The concentration of tertiary acrylates during the initial reaction is 70-8
It is preferably 0%, especially 70 to 75%. A high concentration is desirable in order to suppress the decomposition of oxidation, but if it exceeds 85%, problems such as polymerization are likely to occur during the quaternization reaction. (4) Alkylating agent In order to complete the quaternization reaction within a short time, the alkylating agent is methyl chloride, ethyl chloride, methyl bromide, ethyl bromide, dimethyl sulfate, ethyl iodide, benzyl chloride, monochloride, etc. Examples include acetic acid ester, but methyl chloride is particularly preferred because of its slow quaternization reaction rate. It is effective for the above alkylating agents to be rapidly added to the reaction system at a low temperature of 15 to 20°C to suppress hydrolysis. Therefore, volatile alkylating agents such as methyl chloride, ethyl chloride, methyl bromide or ethyl bromide are preferably introduced into the reaction system under pressure. (5) Polymerization inhibitor Addition of a polymerization inhibitor such as mercabutane is effective for inhibiting polymerization, but if it is in excess, it will hinder the progress of the quaternization reaction and cause the resulting quaternized product to polymerize. In this case, the induction period (time) may be lengthened or the amount of unreacted monomer may be increased. A suitable amount of polymerization inhibitor is 800 to 15
00pp+m, especially 1000-1200ppm. (8) Reaction time The time required for the reaction of the present invention is significantly shorter than that of known methods, and is usually completed within 2 hours, particularly within 100 minutes. [Function] When tertiary acrylates are reacted with an alkylating agent in an aqueous medium, hydrolysis reaction occurs at the beginning of the reaction and hardly occurs during the middle and final stages of the reaction. Generally, methods for suppressing hydrolysis in the initial stage of the reaction include reactions at low temperatures and reactions in high concentration solutions;
It takes an extremely long time to complete the reaction. On the other hand, in high-concentration reactions, increased viscosity of the reaction solution becomes a problem. The present invention reduces the reaction time to less than 2 hours by adjusting the concentration of tertiary acrylates, rapidly adding an alkylating agent at low temperature, and maintaining the reaction temperature within a certain range. It is something that I practiced practice to do. [Example] The mode of carrying out the invention will be described below with reference to Examples, but the examples are merely for illustration purposes and are not intended to limit or restrict the idea of the invention. Into an autoclave reactor, 3000 g of dimethylaminoethyl methacrylate and 1 portion of water were added.
132g of polymerization inhibitor and 120g of polymerization inhibitor were added (initial concentration 72.6%), and the mixture was stirred and mixed at a rotational speed of 250 rpm+s. The whole was placed in a jacket circulated with cold water, and while maintaining the internal temperature at 18℃, 1012g of methyl chloride (3.
methacrylate, molar ratio 1.05) at a pressure of 2
kg/cm2 within 60 seconds in liquid form. Next, heat the jacket with warm water at 50℃ to reduce the internal sound to 48~52℃.
The humidity was raised to ℃ (when the internal temperature was 50℃, the gauge pressure was 5kg/c)
m2). During the reaction, no polymerization occurred even when the humidity was raised to a maximum of 70°C. As the quaternization reaction progressed, the pressure decreased. After reacting for 100 minutes, the reactant was cooled to 25°C by passing cold water through the jacket, and the reactant was taken out. The concentration of the obtained quaternary product was 79%, the free chlorine content was 14%, and the concentration of quaternary salt was 82%. Trakkashi: The reaction was carried out in the same manner as in the previous example except that the amount of polymerization inhibitor was increased to 2000 ppm. The resulting quaternized product concentration was 78.2%, and the free chlorine content was 13.
6%, and the quaternary salt concentration was 79.5%. Due to the increased amount of polymerization inhibitor, the concentration of quaternary salt was 2.5% lower than in the previous example. The same procedure as in Example 1 was carried out except that the polymerization inhibitor in Example 1 was changed to 2000 ppm and the reaction time was changed to 300 minutes. The concentration of the obtained quaternized product was 78.5%, the free chlorine content was 13.4%, and the quaternary salt concentration was 78.3%.
以上説明し、かつ実証した通り，本発明は，第３級アク
リレートと７ルキルハライドを水性媒質中で反応させる
方法において、反応時間を著し〈短縮した、
工業的な第４級アミノアクリレート塩
の製造法を開発できたことにより、
関連産業界に
対し貢献しうる．As explained and demonstrated above, the present invention provides an industrial method for producing quaternary amino acrylate salts by significantly shortening the reaction time in a method of reacting a tertiary acrylate and a 7-alkyl halide in an aqueous medium. By developing this method, we can contribute to related industries.
Claims (1)
レート類を水性媒質中アルキル化剤により４級化するに
当り、原料第３級アミノアクリレートの初期濃度を７０
〜８０％としてアルキル化剤を２０℃以下低温下に急速
に添加すると共に、反応を４５〜７０℃で行なわせるこ
とを特徴とするＮ，Ｎ−ジアルキルアミノアルキル（メ
タ）アクリレート類の４級化方法。1 When quaternizing N,N-dialkylaminoalkyl (meth)acrylates with an alkylating agent in an aqueous medium, the initial concentration of the raw material tertiary aminoacrylate was set to 70%
Quaternization of N,N-dialkylaminoalkyl (meth)acrylates characterized by rapidly adding an alkylating agent at a concentration of ~80% at a low temperature of 20°C or lower and carrying out the reaction at 45 to 70°C. Method.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002067A JPH03206067A (en) | 1990-01-08 | 1990-01-08 | Quaternization of n,n-dialkylaminoalkyl (meth)acrylates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002067A JPH03206067A (en) | 1990-01-08 | 1990-01-08 | Quaternization of n,n-dialkylaminoalkyl (meth)acrylates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03206067A true JPH03206067A (en) | 1991-09-09 |
Family
ID=11519002
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002067A Pending JPH03206067A (en) | 1990-01-08 | 1990-01-08 | Quaternization of n,n-dialkylaminoalkyl (meth)acrylates |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03206067A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011091197A3 (en) * | 2010-01-21 | 2011-12-29 | Nalco Company | Continuous production of quaternary salts |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5143712A (en) * | 1974-08-23 | 1976-04-14 | Rhone Poulenc Ind |
-
1990
- 1990-01-08 JP JP2002067A patent/JPH03206067A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5143712A (en) * | 1974-08-23 | 1976-04-14 | Rhone Poulenc Ind |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011091197A3 (en) * | 2010-01-21 | 2011-12-29 | Nalco Company | Continuous production of quaternary salts |
| JP2013518047A (en) * | 2010-01-21 | 2013-05-20 | ナルコ カンパニー | Continuous production of quaternary salt |
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