JPS59155411A - Production of modified vinyl acetate resin - Google Patents
Production of modified vinyl acetate resinInfo
- Publication number
- JPS59155411A JPS59155411A JP58028686A JP2868683A JPS59155411A JP S59155411 A JPS59155411 A JP S59155411A JP 58028686 A JP58028686 A JP 58028686A JP 2868683 A JP2868683 A JP 2868683A JP S59155411 A JPS59155411 A JP S59155411A
- Authority
- JP
- Japan
- Prior art keywords
- vinyl acetate
- meth
- vinyl
- acetate resin
- ether
- 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
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Description
【発明の詳細な説明】
酢酸ビニル樹脂は木質的には水に不溶性の樹脂であるが
、これに少量のエチレン性不飽和カルボン酸アルカリ塩
やアンモニウム塩あるいはエチレン性不飽和スルホン酸
アルカリ塩等を共重合させることによシ、水溶性化が可
能となって糊剤、接着剤、紙加工剤等への水系用途にも
多用されている。[Detailed Description of the Invention] Vinyl acetate resin is a wood-based resin that is insoluble in water, but it can be mixed with a small amount of ethylenically unsaturated carboxylic acid alkali salt, ammonium salt, ethylenically unsaturated sulfonic acid alkali salt, etc. Copolymerization makes it possible to make it water-soluble, and it is widely used in aqueous applications such as pastes, adhesives, and paper processing agents.
しかしかかる水溶性タイプの酢酸ビニル樹脂の用途が拡
大されるにつれＪＭ々な性能が要求される様になシ例え
ばセラミックスバインダー等の用途ではｉ量のアルカリ
金属の存在がセラミックスの性能を劣化させる原因とな
るので該用途への使用が不可能鴫になる等従来の製品で
は到底多岐にわたる性能要求に応じきれない事態となっ
ている。However, as the use of water-soluble vinyl acetate resin expands, various performances are required.For example, in applications such as ceramic binders, the presence of i amount of alkali metal is a cause of deterioration of the performance of ceramics. As a result, conventional products are unable to meet the wide variety of performance requirements, such as making them impossible to use for these purposes.
しかるに本発明者等はかかるアルカリ金属が存在しなく
ても水溶性である酢酸ビニル樹脂を開発すべく鋭意研究
を重ねた結果、オキシアルキレン基を含有する不飽和単
量体と酢酸ビニルとを共重合して得られる変性酢酸ビニ
ル樹脂がその目的を満足することを見出し本発明を完成
するに到った。However, as a result of intensive research to develop a vinyl acetate resin that is water-soluble even in the absence of such alkali metals, the present inventors have found that an unsaturated monomer containing an oxyalkylene group and vinyl acetate are combined together. The present invention was completed by discovering that a modified vinyl acetate resin obtained by polymerization satisfies the purpose.
本発明でいうオキシアルキレン基とは一般式ルキル基、
Ｘは水素、アルキル基、アルキルエステル基、アルキル
アミド基、スルホン酸塩基等の壱機伐基、ｎは１〜１０
０の整数を示す〕で表わされる構造を有すものである。The oxyalkylene group referred to in the present invention is a general formula alkyl group,
X is hydrogen, an alkyl group, an alkyl ester group, an alkylamido group, a sulfonic acid group, etc., and n is 1 to 10.
0 (indicates an integer of 0)].
Ｘは通常は水素である。ｎの故が有利には１〜５０好ま
しくは６〜５０程度のオキシアルキレン基が実用的であ
り、ポリオキシエチレン基、ポリオキシプロピレン基、
ポリオキシブチレン基等が効果的である。X is usually hydrogen. Because n is advantageously 1 to 50, preferably about 6 to 50 oxyalkylene groups are practical, and polyoxyethylene groups, polyoxypropylene groups,
Polyoxybutylene groups and the like are effective.
オキシアルキレン基を有する不飽和単量体としては次の
様なものが例示されるが、本発明ではこれらのみに限定
されるものではない。Examples of the unsaturated monomer having an oxyalkylene group include the following, but the present invention is not limited thereto.
で示されるし但しＲは水素又はメチル基、Ａはアルキレ
ン基、！アルキレン基、フェニレン基、置換フェニレン
基、ｇは０又は１以上の整数、ｎは１〜１００の整数〕
もので、ポリオキシエチレン（メタ）アクリレート、ポ
リオキシプロピレン（メタ）アクリレート、等が挙げら
れる。where R is hydrogen or a methyl group, A is an alkylene group, ! Alkylene group, phenylene group, substituted phenylene group, g is an integer of 0 or 1 or more, n is an integer of 1 to 100]
Examples include polyoxyethylene (meth)acrylate, polyoxypropylene (meth)acrylate, and the like.
（メタ）アクリル酸アミド型
ｊ
デ
で示される〔但しＲ３は本妻又はアルキル基又は同様〕
もので、ポリオキシエチレン−（メタ）アクリル酸ア三
ド、ポリオキシプロピレン（メタ）アクリル酸アミド、
ポリオキシエチレン（１−（メタ）アクリルアミド−１
，１−ジメチルプロピル）エステル等が挙げられる。(Meth)acrylic acid amide type j Shown by de [However, R3 is the original wife or alkyl group or the same]
Polyoxyethylene-(meth)acrylic acid amide, polyoxypropylene(meth)acrylic amide,
Polyoxyethylene (1-(meth)acrylamide-1
, 1-dimethylpropyl) ester and the like.
れるＣＲＸＲ”、Ｒ２、ｎは前記と同様〕ものでポリオ
キシエチレン（メタ）アリルエーテル、ポリオキシプロ
ピレン（メタ）アリルエーテル等が挙げられる。CRXR'', R2, and n are the same as above], such as polyoxyethylene (meth)allyl ether, polyoxypropylene (meth)allyl ether, and the like.
ビニルエーテル型
示される［Ａ、Ｒ１、Ｒ２、ｌ、ｎは前記と同様〕もの
でポリオキシエチレンビニルエーテル、ポリオキシプロ
ピレンビニルエーテル等が挙げられる。Examples of the vinyl ether type (A, R1, R2, l, n are the same as above) include polyoxyethylene vinyl ether and polyoxypropylene vinyl ether.
該不飽和単量体と酢酸ビニルとを共重合するに当って、
特に制限はなく公知の重合方法が任意に用いられるが普
通メタノールあるいはエタノール等のアルコールを溶媒
とする溶液重合が実施される。かかる方法に於て単量体
の仕込み方法としてまず酢酸ビニルの全開と前記不飽和
車上を体の一部を仕込み、重合を開始し、残シの不飽和
単量体を重合期間中に連続的に又は分割的に添加する方
法、両者を一括仕込みする方法等任意の手段を用いて良
い。共重合反応は、アゾビスイソブチロニトリル、過酸
化アセチル、過酸化ベンゾイル、過酸化ラフロイルなど
の公知のラジカル重合触媒を用いて行われる。又反応温
度は５０℃〜沸点程度の範囲から選択きれる。反応後は
常法に従って未反応単量体を除去し目的物を得る。In copolymerizing the unsaturated monomer and vinyl acetate,
Although there are no particular limitations and any known polymerization method may be used, solution polymerization using an alcohol such as methanol or ethanol as a solvent is usually carried out. In this method, the monomer is charged by first fully opening the vinyl acetate and charging a part of the unsaturated monomer onto the unsaturated vehicle to start polymerization, and then continuously adding the remaining unsaturated monomer during the polymerization period. Any method may be used, such as adding them individually or in portions, or adding both at once. The copolymerization reaction is carried out using a known radical polymerization catalyst such as azobisisobutyronitrile, acetyl peroxide, benzoyl peroxide, and lafuroyl peroxide. Further, the reaction temperature can be selected from a range of about 50° C. to boiling point. After the reaction, unreacted monomers are removed according to a conventional method to obtain the desired product.
上記共重合に際しては酢酸ビニル、オキシアルキレン基
含有不飽和単量体の池にこれらと共重合し得る池の単量
体を６０モル％程度以下存在せしめても良い。これらの
単量体を次に例示する。In the above copolymerization, about 60 mol % or less of a monomer that can be copolymerized with vinyl acetate and oxyalkylene group-containing unsaturated monomers may be present. Examples of these monomers are shown below.
互、当：癲と一階ンａ−ザ−そど４二冬２（酢酸ビニル
以外）ギ酸ビニル、グロビオン酸ビニル、醋酸ビニル、
カプリン酸ビニル、ラツリル酸ビニル、パーサティック
酸ビニル、パルミチン酸ビニル、ステアリン酸ビニル等
。Mutual, present: 癲と一KAINA-THE-SODO 4 2winter 2 (other than vinyl acetate) vinyl formate, vinyl globionate, vinyl acetate,
Vinyl caprate, vinyl latulate, vinyl persate, vinyl palmitate, vinyl stearate, etc.
アルキルビニルエーテル
プロビルビニルエーテル、フチルビニルエーテル、ヘキ
シルアリルエーテル、オクチルビニルエーテル、デシル
ビニルエーテル、ドデシルビニルエーテル、テトラデシ
ルビニルエーテル、ヘキサデシルビニルエーテル、オク
タデシルビニルエーテル等。Alkyl vinyl ether probyl vinyl ether, phthyl vinyl ether, hexyl allyl ether, octyl vinyl ether, decyl vinyl ether, dodecyl vinyl ether, tetradecyl vinyl ether, hexadecyl vinyl ether, octadecyl vinyl ether, etc.
Ｌヱまｐｌ」」♀年≦ζ（−−
プロピルアリルエーテル、ブチルアリルエーテル、ヘキ
シルアリルエーテル、オクチルアリルエ−チル、デシル
アリルエーテル、ドデシルアリルエーテル、テトラデシ
ルアリルエーテル、ヘキサデシルアリルエーテル、オク
タデシルアリルエーテル等。♀♀≦ζ(-- Propyl allyl ether, butyl allyl ether, hexyl allyl ether, octyl allyl ether, decyl allyl ether, dodecyl allyl ether, tetradecyl allyl ether, hexadecyl allyl ether, octadecyl Allyl ether etc.
（メタ）アクリル酸メチル、（メタ）アクリル酸エチル
、マレイン酸メチル、マレイン酸エチル、クロトン酸メ
チル、クロトン酸エチル、イタコン酸メチル、イタコン
酸エチル、ソルビン酸メチル、ソルビン酸エチル、（メ
タ）アクリル酸プロピル、（メタ）アクリル酸グチル、
（メタ）アクリル酸ペンチル、（メタ）アクリル酸ヘキ
シル、（メタ）アクリル酸ヘプチル、（メタ）アクリル
酸オクチル、（メタ）アクリル散デシル、（メタ）アク
リル酸ヘキサデシル、（メタ）アクリル酸オクタデシル
、その（也、マレイン酸モノアルキルエステル、マレイ
ン酸ジアルキルエステル、クロトン酸アルキルエステル
、イタコン酸アルキルエステル、ソルビン酸アルキルエ
ステル方しイン酸アルキルエステル等。Methyl (meth)acrylate, ethyl (meth)acrylate, methyl maleate, ethyl maleate, methyl crotonate, ethyl crotonate, methyl itaconate, ethyl itaconate, methyl sorbate, ethyl sorbate, (meth)acrylic propyl acid, butyl (meth)acrylate,
Pentyl (meth)acrylate, hexyl (meth)acrylate, heptyl (meth)acrylate, octyl (meth)acrylate, decyl (meth)acrylate, hexadecyl (meth)acrylate, octadecyl (meth)acrylate, etc. (Also, maleic acid monoalkyl ester, maleic acid dialkyl ester, crotonic acid alkyl ester, itaconic acid alkyl ester, sorbic acid alkyl ester, inic acid alkyl ester, etc.)
−湾榎一吋ノー□せＳびく一即ξ／タ５７−−シー翌−
千−？（オ ４レーステアリン酸アリル、ラフリン酸ア
リル、ヤシ油脂肪酸アリル、オクチル酸アリル、酪酸ア
リル等。-Wan Enoki Ichigo no □se S bikuichi so ξ/ta57--S next day-
Thousand? (O-4 allyl stearate, allyl lafric acid, allyl coconut oil fatty acid, allyl octylate, allyl butyrate, etc.)
怠−二基にヱ、イーイー、−。I'm lazy, I'm lazy.
エチレン、フロピレン、α−ヘキセン、α−オクテン、
α−デセン、α−ドデセン、α−へキサテセン、α−オ
クタデセン等。Ethylene, phlopylene, α-hexene, α-octene,
α-decene, α-dodecene, α-hexatecene, α-octadecene, etc.
エチレン性不飽和カルボン酸
タロトン酸、（メタ）アクリル酸、（無水）マレイン酸
、フマル酸、イタコン酸及びその塩等。Ethylenically unsaturated carboxylic acids tarotonic acid, (meth)acrylic acid, (anhydrous) maleic acid, fumaric acid, itaconic acid and its salts.
その１屯（メタ）アクリルレア三ド、（メタ）アクリロ
ニトリル、（メタ）アリルスルホン酸塩、エチレン性不
飽和スルホン酸塩等の使用もげ能である。One of them is the ability to use (meth)acrylic rare tride, (meth)acrylonitrile, (meth)allyl sulfonate, ethylenically unsaturated sulfonate, and the like.
本発明の酢酸ビニル樹脂中に占めるオキシアルキレン基
含有不飽和単量体の割合は任意に変動出来る。即ち単に
酢酸ビニル４７１脂に水との親和性を付与するだけの目
的であればその割合は比較的少なくて良く、水溶性化ま
で目的とする時はかなり多量の導入が必要である。水溶
性を得るためにば】Ｉノ常１モル％以上の導入が必要と
なる。The proportion of the oxyalkylene group-containing unsaturated monomer in the vinyl acetate resin of the present invention can be varied arbitrarily. That is, if the purpose is simply to impart affinity with water to vinyl acetate 471 fat, the proportion may be relatively small, but if the purpose is to make it water-soluble, a considerably large amount must be introduced. In order to obtain water solubility, it is usually necessary to introduce 1 mol% or more.
該酢酸ビニル樹脂は粉末、ブロック、溶液いずれの形席
でも各種用途に使用出来る。The vinyl acetate resin can be used for various purposes in the form of powder, block, or solution.
それらを次に具体的に挙げる。These are listed below.
（１）成型物関係
繊維、フィルム、シート、パイプ、チューブ、防漏ｌ換
、暫定皮膜、ケミカルレース用水溶性繊維
（２）接着剤関係
木材、紙、アルミ箔、プラスチックス等の接着剤、粘着
剤、再湿剤、不織布用バインダー、繊維状バインダー、
石膏ボードや繊維板等の各種建材用バインダー、各種粉
体造粒用バインダー、セラミックスバインダー、セメン
トやモルタル用添加剤、ホットメルト招接着剤、感圧接
着剤、染料の固名剤
（３）被覆剤関係
紙のクリアーコーティング剤、紙の顔料コーティング剤
、紙の内添サイズ剤、感熱記録紙用バインダー、繊維製
品用サイズ剤、経糸糊剤、繊維加工剤、皮革仕上げ剤、
塗料、防曇剤、金属腐食防止剤、亜鉛メッキ用光沢剤、
帯電防止剤、導電剤、
（４）疎水性樹脂用ブレンド剤関係
疎水性樹脂の帯電防止剤、及び親水性付与剤、複合繊維
、フィルムその沌成型物用添加剤（５）懸濁用分散安定
剤関係
塗料、墨汁、水彩カラー、接着剤等の顔料分散安定剤、
塩化ビニル、塩化ビニリデンスチレン、（メタ゛）アク
リレート、酢酸ビニル等の各種ビニル化合物の懸濁重合
用分散安定剤、及び分散助剤
（６）乳化剤関係
エチレン性不飽和化合物、プクジエン性化合物の乳化重
合用乳化剤、ポリオレフィレ、ポリエステル樹脂等疎水
性樹脂、エポキシ樹脂、パラフィン、ビチュクメン等の
後乳化剤（７）増粘剤関係
各種エマルジョンの増粘剤
（８）凝集剤関係
水中懸濁物および溶存物の凝集剤、パルプスラリーのｐ
水性向上剤
（９）土壌改良剤関係
（ｉ［Ｉ感光剤、感電子剤関係
次に実例を挙げて本発明の方法を更に詐しく説す１する
。(1) Water-soluble fibers for molded products, such as fibers, films, sheets, pipes, tubes, leak-proof lubricants, temporary coatings, and chemical laces (2) Adhesives: Adhesives and adhesives for wood, paper, aluminum foil, plastics, etc. agent, rewetting agent, binder for nonwoven fabrics, fibrous binder,
Binders for various building materials such as gypsum board and fiberboard, binders for various powder granulation, ceramic binders, additives for cement and mortar, hot melt adhesives, pressure sensitive adhesives, dye fixing agents (3) coatings Clear coating agent for paper, pigment coating agent for paper, internal sizing agent for paper, binder for thermal recording paper, sizing agent for textile products, warp sizing agent, textile processing agent, leather finishing agent,
Paints, antifog agents, metal corrosion inhibitors, brighteners for galvanizing,
Antistatic agents, conductive agents, (4) Blend agents for hydrophobic resins Antistatic agents for hydrophobic resins, and hydrophilicity imparting agents, additives for composite fibers, films, and molded products (5) Dispersion stability for suspensions Pigment dispersion stabilizer for agent-related paints, India ink, watercolor colors, adhesives, etc.
Dispersion stabilizer and dispersion aid for suspension polymerization of various vinyl compounds such as vinyl chloride, vinylidene styrene chloride, (meth)acrylate, vinyl acetate, etc. (6) Emulsifier-related For emulsion polymerization of ethylenically unsaturated compounds and peculiar compounds Emulsifiers, polyolefins, hydrophobic resins such as polyester resins, post-emulsifiers such as epoxy resins, paraffin, bitukumen, etc. (7) Thickeners Thickeners for various emulsions (8) Flocculants Flocculants for suspended and dissolved substances in water , p of pulp slurry
Water-based improver (9) Soil conditioner (i [I Photosensitive agent, electrosensitive agent) Next, the method of the present invention will be further explained with examples.
実例１
還流冷却器、滴下ロート、温度計、撹拌器を備えた重合
化に酢酸ビニル９００都、ポリオキシエチレンモノアリ
ルエーテル（ｎ−１５）４１５部、メタノール１０５部
を仕込み撹拌しながら温度を上昇させ６０℃においてア
ゾビスイソブチロニトリル０．１２部をメタノール２０
都に溶解した溶液を投入して重合を開始した。Example 1 900 parts of vinyl acetate, 415 parts of polyoxyethylene monoallyl ether (n-15), and 105 parts of methanol were charged into a polymerization system equipped with a reflux condenser, a dropping funnel, a thermometer, and a stirrer, and the temperature was raised while stirring. Add 0.12 parts of azobisisobutyronitrile to 20 parts of methanol at 60°C.
Polymerization was started by adding a solution dissolved in water.
８時間後、重合率が９６％になった時点で重合を停止し
た。共重合溶液を常法に従って精製しポリオキシエチレ
ンモノアリルエーテル／酢酸ビニル共重合体を得だ。After 8 hours, the polymerization was stopped when the polymerization rate reached 96%. The copolymerization solution was purified according to a conventional method to obtain a polyoxyethylene monoallyl ether/vinyl acetate copolymer.
得られた共重合体の特性値は次の通りであった。The characteristic values of the obtained copolymer were as follows.
ＮＭＲ（δｐｐｍ ）
６．７δｐｐｍ［（−ＣＨ２０Ｈ２０＋のビークが認め
られる。NMR (δppm) 6.7δppm [(-CH20H20+ peak is observed.
実例２
実例１におけるポリオキシエチレンモノアリルエーテル
（ｎ＝１５）に代えてｎ＝５０のポリオキシエチレンモ
ノアリルエーテル４２９部を用いた以外は同例と同様の
方法を行った。Example 2 The same method as in Example 1 was carried out except that 429 parts of polyoxyethylene monoallyl ether (n=50) was used in place of the polyoxyethylene monoallyl ether (n=15) in Example 1.
得られた共重合体の特性値は次の通りであった。The characteristic values of the obtained copolymer were as follows.
ＮＭＲ（δｐｐｍ）は実例１と同一
実例６
実例１におけるポリオキシエチレンモノアリルエーテル
に代えてポリオキシエチレンメタクリレ−ト（ｎ ＝
１０・）を用いた以外は同例に準じて実願を行った。NMR (δppm) is the same as Example 1 Example 6 Polyoxyethylene methacrylate (n =
An actual application was filed in accordance with the same procedure except that 10.) was used.
得られた共重合体の組成は次の通りであった。The composition of the obtained copolymer was as follows.
実例４
実例１におけるポリオキシエチレンモノアリルエーテル
に代えてポリオキシエチレンビニルエーテル（ｎ＝１９
）を用いた以外同側に準じて実欽を行った。Example 4 Polyoxyethylene vinyl ether (n=19) was used instead of polyoxyethylene monoallyl ether in Example 1.
) was performed in the same manner as on the ipsilateral side.
得られた共重合体中のポリオキシエチレンビニルエーテ
ルの含有量１ｌ−ｊ：３．４モル％であった。The content of polyoxyethylene vinyl ether in the obtained copolymer was 1l-j: 3.4 mol%.
Claims (1)
ビニルとを共重合することを特徴とする変性酢酸ビニル
樹脂の製造方法。 ２ オキシアルキレン基として一般式 （−ＣＨ２−ＣＨ２０−４Ｈ［但しｎは１〜１００の整
数〕で示されるオキシエチレン基を含有する不飽和単量
体を使用することを特徴とする特許請求の範囲＠１項記
載の製造方法。[Claims] 1. A method for producing a modified vinyl acetate resin, which comprises copolymerizing an unsaturated monomer containing an oxyalkylene group and vinyl acetate. 2. Claims characterized in that an unsaturated monomer containing an oxyethylene group represented by the general formula (-CH2-CH20-4H [where n is an integer from 1 to 100]) is used as the oxyalkylene group. @The manufacturing method described in item 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58028686A JPS59155411A (en) | 1983-02-22 | 1983-02-22 | Production of modified vinyl acetate resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58028686A JPS59155411A (en) | 1983-02-22 | 1983-02-22 | Production of modified vinyl acetate resin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59155411A true JPS59155411A (en) | 1984-09-04 |
| JPH0368888B2 JPH0368888B2 (en) | 1991-10-30 |
Family
ID=12255366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58028686A Granted JPS59155411A (en) | 1983-02-22 | 1983-02-22 | Production of modified vinyl acetate resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59155411A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6399209A (en) * | 1986-10-15 | 1988-04-30 | Kuraray Co Ltd | Graft copolymer |
| EP0884332A1 (en) * | 1997-06-11 | 1998-12-16 | The Nippon Synthetic Chemical Industry Co., Ltd. | Dispersing stabilizer |
| JP2003096258A (en) * | 2001-09-21 | 2003-04-03 | Nippon Synthetic Chem Ind Co Ltd:The | Melt molding |
| DE19939266B4 (en) * | 1999-07-13 | 2006-11-09 | Clariant Produkte (Deutschland) Gmbh | Aqueous polymer dispersion, its preparation and use |
| DE102006049381A1 (en) * | 2006-10-19 | 2008-04-24 | Süd-Chemie AG | Amphiphilic graft polymers |
| WO2016181873A1 (en) * | 2015-05-08 | 2016-11-17 | 丸善石油化学株式会社 | Alkenyl ether-vinyl ester copolymer |
| CN114426621A (en) * | 2020-10-14 | 2022-05-03 | 中国石油化工股份有限公司 | Nonionic modified polyvinyl alcohol and preparation method thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5535782B2 (en) | 2010-06-16 | 2014-07-02 | 三菱重工業株式会社 | Combustion system |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49130486A (en) * | 1973-04-03 | 1974-12-13 | ||
| JPS5222086A (en) * | 1975-08-08 | 1977-02-19 | Hoechst Ag | Preparation of systhetic resin dispersion |
| JPS53113885A (en) * | 1977-03-15 | 1978-10-04 | Japan Exlan Co Ltd | Preparation of microemulsion |
| JPS5446239A (en) * | 1977-08-29 | 1979-04-12 | Nat Starch Chem Corp | Copolymer latex binderrcontaining composition* and method of using it for making nonwoven material |
| JPS5767672A (en) * | 1980-10-13 | 1982-04-24 | Nippon Oil & Fats Co Ltd | Antifouling coating |
| JPS5920377A (en) * | 1982-07-27 | 1984-02-02 | Nippon Shokubai Kagaku Kogyo Co Ltd | Antifogging agent |
-
1983
- 1983-02-22 JP JP58028686A patent/JPS59155411A/en active Granted
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49130486A (en) * | 1973-04-03 | 1974-12-13 | ||
| JPS5222086A (en) * | 1975-08-08 | 1977-02-19 | Hoechst Ag | Preparation of systhetic resin dispersion |
| JPS53113885A (en) * | 1977-03-15 | 1978-10-04 | Japan Exlan Co Ltd | Preparation of microemulsion |
| JPS5446239A (en) * | 1977-08-29 | 1979-04-12 | Nat Starch Chem Corp | Copolymer latex binderrcontaining composition* and method of using it for making nonwoven material |
| JPS5767672A (en) * | 1980-10-13 | 1982-04-24 | Nippon Oil & Fats Co Ltd | Antifouling coating |
| JPS5920377A (en) * | 1982-07-27 | 1984-02-02 | Nippon Shokubai Kagaku Kogyo Co Ltd | Antifogging agent |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6399209A (en) * | 1986-10-15 | 1988-04-30 | Kuraray Co Ltd | Graft copolymer |
| EP0884332A1 (en) * | 1997-06-11 | 1998-12-16 | The Nippon Synthetic Chemical Industry Co., Ltd. | Dispersing stabilizer |
| DE19939266B4 (en) * | 1999-07-13 | 2006-11-09 | Clariant Produkte (Deutschland) Gmbh | Aqueous polymer dispersion, its preparation and use |
| JP2003096258A (en) * | 2001-09-21 | 2003-04-03 | Nippon Synthetic Chem Ind Co Ltd:The | Melt molding |
| DE102006049381A1 (en) * | 2006-10-19 | 2008-04-24 | Süd-Chemie AG | Amphiphilic graft polymers |
| WO2016181873A1 (en) * | 2015-05-08 | 2016-11-17 | 丸善石油化学株式会社 | Alkenyl ether-vinyl ester copolymer |
| US10570232B2 (en) | 2015-05-08 | 2020-02-25 | Maruzen Petrochemical Co., Ltd. | Alkenyl ether-vinyl ester copolymer |
| CN114426621A (en) * | 2020-10-14 | 2022-05-03 | 中国石油化工股份有限公司 | Nonionic modified polyvinyl alcohol and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0368888B2 (en) | 1991-10-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4600761A (en) | Acrylic emulsion copolymers for thickening aqueous systems and copolymerizable surfactant monomers for use therein | |
| JPS59155408A (en) | Production of modified polyvinyl alcohol | |
| US4743698A (en) | Acrylic emulsion copolymers for thickening aqueous systems and copolymerizable surfactant monomers for use therein | |
| US4616074A (en) | Acrylic-methylene succinic ester emulsion copolymers for thickening aqueous systems | |
| US4916191A (en) | Graft copolymer having dispersion stabilizing effect, a process for producing the same, and a process of emulsion polymerization using the same | |
| CN101809047B (en) | Cross-linkable monomers and polymers and the use thereof | |
| CN102365340B (en) | The surfactant that comprises fluoropolymer | |
| US5849840A (en) | Dispersing stabilizer | |
| USRE33008E (en) | Acrylic emulsion copolymers for thickening aqueous systems and copolymerizable surfactant monomers for use therein | |
| JP3378133B2 (en) | Ceramic molding binder | |
| JPS59155411A (en) | Production of modified vinyl acetate resin | |
| US3386998A (en) | Nu-alkenoyloxy-2-morpholinones and their corresponding hydrolysis products | |
| JPS6412281B2 (en) | ||
| JP2649023B2 (en) | Polyvinyl alcohol-based polymer and method for producing the same | |
| JPS59501268A (en) | Novel aqueous dispersion | |
| US2776951A (en) | Amides of vinyl ethers containing hydroxyl groups and polymers thereof | |
| US3314927A (en) | Copolymers of alkylene polyaminesubstituted alkyl vinyl ethers and thioethers | |
| JPH0199638A (en) | Emulsifier for aqueous resin dispersion | |
| JPS6412282B2 (en) | ||
| JP2925664B2 (en) | Thickener and polymer cement composition containing the same | |
| JPS63183998A (en) | Novel surfactant | |
| JPH04268305A (en) | Production of aqueous self-dispersible vinyl resin | |
| US3350363A (en) | Nu-(acylamidoalkyl)-nu'-vinyl-nu, nu'-alkyleneureas, polymers thereof and methods of making them | |
| JP2968828B2 (en) | Method for producing modified polyvinyl alcohol | |
| JPS6372333A (en) | Novel surface-active agent |