JPH06122725A - Fine polymer particle and its production - Google Patents
Fine polymer particle and its productionInfo
- Publication number
- JPH06122725A JPH06122725A JP4273111A JP27311192A JPH06122725A JP H06122725 A JPH06122725 A JP H06122725A JP 4273111 A JP4273111 A JP 4273111A JP 27311192 A JP27311192 A JP 27311192A JP H06122725 A JPH06122725 A JP H06122725A
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- vinylformamide
- monomer
- units derived
- mol
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F26/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F26/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a single or double bond to nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Developing Agents For Electrophotography (AREA)
- Polymerisation Methods In General (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は官能性モノマーであるＮ
−ビニルホルムアミドをモノマー成分として含むポリマ
ー微粒子に関するものである。該ポリマー微粒子は、電
子写真用のトナー、液晶表示板ギャップ調節剤、高性能
イオン交換樹脂、クロマトグラフィー用カラム充填剤、
免疫診断用担体、化粧品、および塗料用の充填剤等の用
途が期待される。FIELD OF THE INVENTION The present invention relates to N which is a functional monomer.
-It relates to fine polymer particles containing vinylformamide as a monomer component. The polymer fine particles are used as a toner for electrophotography, a liquid crystal display panel gap adjusting agent, a high performance ion exchange resin, a column packing material for chromatography,
Applications such as immunodiagnostic carriers, cosmetics, and fillers for paints are expected.
【０００２】また、本発明のポリマー微粒子は、さらに
化学反応により、表面にビニルアミン単位を持つ反応性
粒子に変えることができるので、各種の機能性物質を担
持させて高機能の粒子として利用することもできる。Further, the polymer fine particles of the present invention can be converted into reactive particles having a vinylamine unit on the surface by a chemical reaction, so that various functional substances can be supported and used as highly functional particles. You can also
【０００３】[0003]
【従来の技術】従来、ポリマー粒子の製造方法としては
多くの報告がされているが、ポリＮ−ビニルホルムアミ
ドに関しては、Ｎ−ビニルホルムアミドモノマーおよび
生成するポリマーのいずれにも溶解しない溶媒中で、該
モノマーの水溶液を乳化または分散重合する方法が知ら
れているにすぎない。2. Description of the Related Art Conventionally, many reports have been made as to a method for producing polymer particles, but regarding poly-N-vinylformamide, in a solvent that is insoluble in neither the N-vinylformamide monomer nor the polymer produced, Only a method of emulsion- or dispersion-polymerizing an aqueous solution of the monomer is known.
【０００４】例えば、特開昭６３−９０５１３および特
開平２−２２２４０４記載の乳化重合方法で得られたポ
リマーは、分解溶媒中の分散物を反転用の界面活性剤の
存在下、含水状態のまま水に溶解して凝集剤や石油回収
用等の用途に水溶液として利用することを目的とし、粒
子の均一性、性質、形状および生成物を単離する操作
上、本願の上記用途には適さない。さらに、特開昭６３
−１０５００９記載の高分子分散剤を使用する分散重合
法によれば球状のポリマーが得られるが微粒子を製造す
ることはできない。For example, a polymer obtained by the emulsion polymerization method described in JP-A-63-90513 and JP-A-2-222404 remains in a water-containing state in the presence of a surfactant for reversing a dispersion in a decomposition solvent. It is not suitable for the above applications of the present application in terms of uniformity of particles, properties, shape, and isolation of products for the purpose of being dissolved in water and used as an aqueous solution for applications such as flocculants and oil recovery. . Furthermore, JP-A-63
According to the dispersion polymerization method using the polymer dispersant described in -1050909, spherical polymers can be obtained, but fine particles cannot be produced.
【０００５】[0005]
【発明が解決しようとする課題】本発明は電子写真用の
トナー、液晶表示板ギャップ調節剤、高性能イオン交換
樹脂、クロマトグラフィー用カラム充填剤、免疫診断用
担体、化粧品、および塗料用の充填剤等の用途に適した
ポリマー微粒子を提供することを目的とする。SUMMARY OF THE INVENTION The present invention is a toner for electrophotography, a liquid crystal display panel gap regulator, a high-performance ion exchange resin, a column filler for chromatography, an immunodiagnostic carrier, a cosmetic, and a filler for paints. It is an object of the present invention to provide polymer fine particles suitable for applications such as agents.
【０００６】[0006]
【課題を解決するための手段】本発明のポリマー微粒子
は、モノマー構造単位としてＮ−ビニルホルムアミドを
１〜１００モル％、Ｎ−ビニルホルムアミドと共重合可
能な１種または２種以上のビニル化合物を９９〜０モル
％含有するポリマーであって、その粒子径が０．１〜２
０μｍ、好ましくは０．２〜１０μｍのポリマー微粒子
である。The polymer fine particles of the present invention contain 1 to 100 mol% of N-vinylformamide as a monomer structural unit and one or more vinyl compounds copolymerizable with N-vinylformamide. A polymer containing 99 to 0 mol% and having a particle size of 0.1 to 2
Polymer fine particles having a size of 0 μm, preferably 0.2 to 10 μm.
【０００７】本発明のポリマー微粒子は従来公知のＮ−
ビニルホルムアミドの重合方法で得られる微粒子と異な
り、その形状が球状で均一であるために、電子写真用の
トナー、液晶表示板ギャップ調節剤、高性能イオン交換
樹脂、クロマトグラフィー用カラム充填剤、免疫診断用
担体、化粧品、および塗料用の充填剤に利用できるとい
う特徴を有する。The polymer fine particles of the present invention are N-
Unlike fine particles obtained by the polymerization method of vinylformamide, its shape is spherical and uniform, so toner for electrophotography, liquid crystal display panel gap regulator, high-performance ion exchange resin, column filler for chromatography, immunity It has a feature that it can be used as a filler for diagnostic carriers, cosmetics, and paints.
【０００８】本発明のポリマー微粒子の製造方法に使用
されるモノマーは、Ｎ−ビニルホルムアミド１〜１００
モル％、およびＮ−ビニルホルムアミドと共重合可能な
１種または２種以上のビニル化合物９９〜０モル％含有
するからなるモノマーである。Ｎ−ビニルホルムアミド
の含有量は、好ましくは５モル％以上、特に好ましくは
１０モル％以上である。Ｎ−ビニルホルムアミドと共重
合可能なビニル化合物としては、Ｎ−ビニルホルムアミ
ドと共重合可能な物質のいずれも使用することができ
る。特に、以下の１種または２種以上の物質との混合物
が例示される。The monomer used in the method for producing fine polymer particles of the present invention is N-vinylformamide 1-100.
It is a monomer consisting of mol% and 99-0 mol% of one or more vinyl compounds copolymerizable with N-vinylformamide. The content of N-vinylformamide is preferably 5 mol% or more, particularly preferably 10 mol% or more. As the vinyl compound copolymerizable with N-vinylformamide, any substance copolymerizable with N-vinylformamide can be used. Particularly, a mixture with the following one or more substances is exemplified.
【０００９】１）非イオン性モノマー：エチレン、プロ
ピレン、ブチレン、イソブチレン、ブタジエン、αーオ
レフィン類、スチレン、ビニルトルエン、アクリロニト
リル、アクリルアミド、メタクリルアミド、Ｎ−置換ア
クリルアミド、Ｎ−置換メタクリルアミド、Ｎ−ビニル
ピロリドン、アクリル酸エステル、メタクリル酸エステ
ル、酢酸ビニル、プロピオン酸ビニル、ビニルエーテル ２）カチオン性のモノマー：アミノアルキルアクリルア
ミド、アミノアルキルメタクリルアミド、アリルアミ
ン、ジアリルジアミン、Ｎ−アルキルアリルアミン、こ
れらの塩および第４級アンモニウム塩、ジアルキルジア
リルアンモニウム塩 ３）アニオン性モノマー：アクリル酸、メタクリル酸、
イタコン酸、ビニルスルホン酸、アリルスルホン酸、メ
タリルスルホン酸、アクリルアミドアルカンスルホン
酸、およびこれらのアルカリ金属塩1) Nonionic monomers: ethylene, propylene, butylene, isobutylene, butadiene, α-olefins, styrene, vinyltoluene, acrylonitrile, acrylamide, methacrylamide, N-substituted acrylamide, N-substituted methacrylamide, N-vinyl. Pyrrolidone, acrylic acid ester, methacrylic acid ester, vinyl acetate, vinyl propionate, vinyl ether 2) Cationic monomers: aminoalkylacrylamide, aminoalkylmethacrylamide, allylamine, diallyldiamine, N-alkylallylamine, salts thereof and the fourth. Primary ammonium salt, dialkyl diallyl ammonium salt 3) Anionic monomer: acrylic acid, methacrylic acid,
Itaconic acid, vinyl sulfonic acid, allyl sulfonic acid, methallyl sulfonic acid, acrylamido alkane sulfonic acid, and their alkali metal salts
【００１０】本発明のポリマー微粒子およびその製造方
法に使用される溶媒は、Ｎ−ビニルホルムアミド、およ
びＮ−ビニルホルムアミドと共重合可能な１種または２
種以上のビニル化合物の混合物を含有するモノマーを溶
解し、生成するポリマーを溶解しない溶媒のいずれもが
使用される。Ｎ−ビニルホルムアミドは極めて多くの有
機溶媒に溶解し、しかもそのポリマーはほとんどの溶媒
に溶解しないという性質を有するもので、モノマーとし
てＮ−ビニルホルムアミドを単独で用いる場合は極めて
広い範囲の有機溶剤が使用できる。好ましい溶媒として
以下の物質が例示される。The polymer fine particles of the present invention and the solvent used in the method for producing the same are N-vinylformamide and one or two copolymerizable with N-vinylformamide.
Any solvent that dissolves the monomer containing a mixture of one or more vinyl compounds and not the resulting polymer is used. N-vinylformamide has the property of being soluble in an extremely large number of organic solvents, and its polymer is insoluble in most solvents. When N-vinylformamide alone is used as a monomer, an extremely wide range of organic solvents can be used. Can be used. The following substances are exemplified as preferable solvents.
【００１１】１）芳香族炭化水素：ベンゼン、トルエ
ン、キシレン、エチルベンゼン、ブチルベンゼン ２）ハロゲン化芳香族炭化水素：クロルベンゼン、ジク
ロルベンゼン、ブロムベンゼン ３）ハロゲン化炭化水素：塩化メチル、塩化メチレン、
クロロホルム、四塩化炭素、各種塩素化エチレン、各種
塩素化プロパン ４）アルコール類：メタノール、エタノール、プロパノ
ール、ブタノール、ペンタノール、ヘキサノール、シク
ロヘキサノール、２−エチルヘキサノール、エチレング
リコール、プロピレングリコール、ベンジルアルコー
ル、メトキシエタノール、ブトキシエタノール ５）エステル類：蟻酸メチル、蟻酸エチル、蟻酸ブチ
ル、酢酸メチル、酢酸エチル、酢酸イソブチル、酢酸ブ
チル、酢酸イソブチル、酢酸アミル、酢酸イソアミル、
酢酸シクロヘキシル、プロピオン酸メチル、プロピオン
酸ブチル ６）エーテル類：ジエチルエーテル、ジイソプロピルエ
ーテル、ジブチルエーテル、テトラヒドロフラン、ジオ
キサン、エチレングリコールジメチルエーテル、エチレ
ングリコールジエチルエーテル、エチレングリコールジ
ブチルエーテル ７）ケトン類：アセトン、メチルエチルケトン、メチル
イソブチルケトン、シクロヘキサノン ８）含窒素溶媒：アセトニトリル、ニトロメタン、ニト
ロエタン、ホルムアミド、ジメチルホルムアミド、ジメ
チルアセトアミド、Ｎ−メチルピロリドン、 ９）含硫黄化合物：ジメチルホルムアミド、二硫化炭素 必要により水またはこれらの溶媒を相互に混合すること
ができる。1) Aromatic hydrocarbons: benzene, toluene, xylene, ethylbenzene, butylbenzene 2) Halogenated aromatic hydrocarbons: chlorobenzene, dichlorobenzene, bromobenzene 3) Halogenated hydrocarbons: methyl chloride, methylene chloride ,
Chloroform, carbon tetrachloride, various chlorinated ethylene, various chlorinated propane 4) Alcohols: methanol, ethanol, propanol, butanol, pentanol, hexanol, cyclohexanol, 2-ethylhexanol, ethylene glycol, propylene glycol, benzyl alcohol, Methoxyethanol, butoxyethanol 5) Esters: methyl formate, ethyl formate, butyl formate, methyl acetate, ethyl acetate, isobutyl acetate, butyl acetate, isobutyl acetate, amyl acetate, isoamyl acetate,
Cyclohexyl acetate, methyl propionate, butyl propionate 6) Ethers: diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether 7) Ketones: acetone, methyl ethyl ketone, Methyl isobutyl ketone, cyclohexanone 8) Nitrogen-containing solvent: acetonitrile, nitromethane, nitroethane, formamide, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, 9) Sulfur-containing compound: dimethylformamide, carbon disulfide If necessary, water or these solvents may be added. It can be mixed with one another.
【００１２】溶媒は、Ｎ−ビニルホルムアミド単独また
はＮ−ビニルホルムアミドと他のビニル化合物の混合物
からなるモノマーの濃度が、通常１〜４０重量％、好ま
しくは５〜３０重量％となる条件で使用される。溶媒は
その沸点が３０〜１８０℃であることが好ましく、特に
好ましくは、６０〜１５０℃の溶媒である。本発明のポ
リマー粒子の製造に使用する高分子分散剤は、重合に用
いる溶媒に溶解するポリマーのいずれも使用することが
できるが、炭化水素以外のヘテロ元素を含有する高極性
のポリマーまたは該ポリマー成分を側鎖にもつマクロマ
ーが好ましく、特に非イオン性の酸素および／または窒
素を含有する高極性ポリマーおよびそのマクロマーが好
ましい。特に好ましい高分子分散剤としては、ポリエチ
レングリコール、ポリプロピレングリコール、ポリビニ
ルメチルエーテル、ポリ酢酸ビニル、ポリビニルアルコ
ール、ポリＮ−ビニルピロリドン、ポリ（２−メチル−
２−オキサゾリン）、ポリ（２−エチル−２−オキサゾ
リン）およびこれらのポリマー成分を含有するマクロマ
ーが例示される。特に好ましくはポリ（２−オキサゾリ
ン）誘導体である。高分子分散剤の使用量は、モノマー
に対して０．０５〜１００重量％、好ましくは０．２〜
５０重量％である。特にマクロマーを使用する場合０．
２〜５重量％で優れた効果を奏する。The solvent is used under the condition that the concentration of the monomer consisting of N-vinylformamide alone or a mixture of N-vinylformamide and other vinyl compounds is usually 1 to 40% by weight, preferably 5 to 30% by weight. It The solvent preferably has a boiling point of 30 to 180 ° C, particularly preferably 60 to 150 ° C. As the polymer dispersant used in the production of the polymer particles of the present invention, any of the polymers soluble in the solvent used for the polymerization can be used, but a highly polar polymer containing a hetero element other than hydrocarbon or the polymer Macromers having a component in the side chain are preferable, and particularly highly polar polymers containing nonionic oxygen and / or nitrogen and macromers thereof are preferable. Particularly preferred polymer dispersants are polyethylene glycol, polypropylene glycol, polyvinyl methyl ether, polyvinyl acetate, polyvinyl alcohol, poly N-vinylpyrrolidone, poly (2-methyl-).
2-oxazoline), poly (2-ethyl-2-oxazoline) and macromers containing these polymer components are exemplified. Particularly preferred is a poly (2-oxazoline) derivative. The amount of polymer dispersant used is 0.05 to 100% by weight, preferably 0.2 to
It is 50% by weight. Especially when a macromer is used.
An excellent effect is achieved at 2 to 5% by weight.
【００１３】Ｎ−ビニルホルムアミド単独またはＮ−ビ
ニルホルムアミドと他のビニル化合物の混合物からなる
モノマーは分散剤の存在下溶媒中で不活性ガスの雰囲気
下重合されるが、その重合法としては、通常公知のラジ
カル重合法のいずれもが用いられ、攪拌または振盪等の
条件下、公知の分離方法により単離される。ラジカル重
合開始剤としては、２，２′−アゾビスイソブチロニト
リル、２，２′−アゾビス（２，４−ジメチルバレロニ
トリル）、２，２′−アゾビス−２−アミジノプロパン
の塩酸塩、４，４′−アゾビス−４−シアノ吉草酸のナ
トリウム塩などのアゾ化合物、ベンゾイルパーオキシ
ド、ラウリルパーオキシド、ｔ−ブチルハイドロパーオ
キシド、ｔ−ブチルパーオクトエイトなどの過酸化物が
例示され、必要によりレドックス系の重合開始剤を併用
する重合法も利用できる。A monomer composed of N-vinylformamide alone or a mixture of N-vinylformamide and another vinyl compound is polymerized in the presence of a dispersant in a solvent in an inert gas atmosphere. The polymerization method is usually Any known radical polymerization method is used, and isolation is carried out by a known separation method under conditions such as stirring or shaking. As the radical polymerization initiator, 2,2′-azobisisobutyronitrile, 2,2′-azobis (2,4-dimethylvaleronitrile), 2,2′-azobis-2-amidinopropane hydrochloride, Examples include azo compounds such as sodium salt of 4,4′-azobis-4-cyanovaleric acid, and peroxides such as benzoyl peroxide, lauryl peroxide, t-butyl hydroperoxide and t-butyl peroctoate. If necessary, a polymerization method in which a redox type polymerization initiator is used in combination can also be used.
【００１４】重合温度は０℃〜２００℃の範囲で実施さ
れるが、操作上４０〜１２０℃であることが好ましい。
重合反応はその操作法、および添加順序に制限されない
が、通常、不活性雰囲気下、モノマー、分散剤および重
合開始剤を溶媒に溶解し、攪拌条件下、所定温度で重合
し、得られた微粒子状の生成物を遠心分離する。本発明
のＮ−ビニルホルムアミドを成分として有するポリマー
微粒子は、さらに酸性またはアルカリ性の条件下、加水
分解または加アルコール分解等、ポリＮ−ビニルホルム
アミドを変性する公知の方法により、表面にビニルアミ
ン単位を持つ反応性粒子に変えることができるので、各
種の機能性物質を担持させて高機能の粒子として利用す
ることもできる。The polymerization temperature is 0 ° C. to 200 ° C., but it is preferably 40 ° C. to 120 ° C. in operation.
The polymerization reaction is not limited to the operation method and the addition order, but usually, the monomer, the dispersant and the polymerization initiator are dissolved in a solvent under an inert atmosphere, and the particles are polymerized at a predetermined temperature under stirring conditions to obtain fine particles. The product of the form is centrifuged. The polymer fine particles having N-vinylformamide as a component of the present invention further have vinylamine units on the surface thereof by a known method of modifying poly N-vinylformamide such as hydrolysis or alcoholysis under acidic or alkaline conditions. Since it can be changed to reactive particles, it can be used as highly functional particles by supporting various functional substances.
【００１５】[0015]
【実施例】以下、実施例により本発明を説明するが、本
発明はこれら実施例に限定されるものではない。 実施例１〜６ アルゴンガス雰囲気下、３０ｍｌのガラス管に表−１に
示すモノマー１ｇ、同じく表−１に示す分散剤０．２ｇ
（実施例５は０．０２ｇ）、２，２′−アゾビス（２，
４−ジメチルバレロニトリル）０．０２ｇ、およびメタ
ノール９ｇを入れ封管した。封管を５６℃の水浴中に入
れ、毎分１５０回振盪しつつ２４時間重合した。冷却後
遠心分離により生成したポリマーを分離後、乾燥し、収
率および粒子径を測定し、表−１に示した。EXAMPLES The present invention will be described below with reference to examples, but the present invention is not limited to these examples. Examples 1 to 6 In a 30 ml glass tube under an argon gas atmosphere, 1 g of the monomer shown in Table 1 and 0.2 g of the dispersant shown in Table 1 were used.
(Example 5 is 0.02 g), 2,2'-azobis (2,2
4-Dimethylvaleronitrile) (0.02 g) and methanol (9 g) were put into a sealed tube. The sealed tube was placed in a water bath at 56 ° C. and polymerized for 24 hours while shaking 150 times per minute. After cooling, the polymer produced by centrifugation was separated and dried, and the yield and particle size were measured and shown in Table 1.
【００１６】[0016]
【表１】 ＮＶＦ：Ｎ−ビニルホルムアミド Ｓｔ：スチレン ＰＥｔＯＺＯ：ポリ（２−エチル−２−オキサゾリン）
（分子量：５０万） ＰＶＭＥ：ポリビニルメチルエーテル（分子量：４．６
万） ＰＥＧ：ポリエチレングリコール（分子量：５万） ＰＮＶＰ：ポリＮ−ビニルピロリドン（分子量：３６
万） ＰＭｅＯＺＯＭ：ポリ（２−メチル−２−オキサゾリ
ン）マクロマー（重合性基：スチリル基、分子量：４８
００）[Table 1] NVF: N-vinylformamide St: Styrene PEtOZO: Poly (2-ethyl-2-oxazoline)
(Molecular weight: 500,000) PVME: Polyvinyl methyl ether (Molecular weight: 4.6
10,000) PEG: polyethylene glycol (molecular weight: 50,000) PNVP: poly N-vinylpyrrolidone (molecular weight: 36)
10,000) PMeOZOM: poly (2-methyl-2-oxazoline) macromer (polymerizable group: styryl group, molecular weight: 48)
00)
【００１７】[0017]
【発明の効果】本発明のポリマー微粒子は、電子写真用
のトナー、液晶表示板ギャップ調節剤、高性能イオン交
換樹脂、クロマトグラフィー用カラム充填剤、免疫診断
用担体、化粧品、および塗料用の充填剤等の用途が期待
される。表面の化学反応によりビニルアミン単位を持つ
反応性粒子に変えることができるので、各種の機能性物
質を担持した高機能の粒子として利用することもでき
る。The polymer fine particles of the present invention are used for toners for electrophotography, liquid crystal display panel gap regulators, high-performance ion exchange resins, column fillers for chromatography, carriers for immunodiagnosis, cosmetics, and fillers for paints. Applications such as agents are expected. Since it can be converted into a reactive particle having a vinylamine unit by a chemical reaction on the surface, it can also be used as a highly functional particle carrying various functional substances.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｇ０３Ｇ 9/087 ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification code Internal reference number FI technical display location G03G 9/087
Claims (3)
ムアミドを１〜１００モル％、Ｎ−ビニルホルムアミド
と共重合可能な１種または２種以上のビニル化合物を９
９〜０モル％含有するポリマーであって、その粒子径が
０．１〜２０μｍであるポリマー微粒子。1. A monomer structural unit comprising 1 to 100 mol% of N-vinylformamide and 9 or more of one or more vinyl compounds copolymerizable with N-vinylformamide.
Polymer fine particles containing 9 to 0 mol% and having a particle diameter of 0.1 to 20 μm.
ル％、およびＮ−ビニルホルムアミドと共重合可能な１
種または２種以上のビニル化合物を９９〜０モル％含有
するモノマーを、高分子分散剤の存在下、該モノマーを
溶解するが、生成するポリマーを溶解しない溶媒中で重
合することを特徴とする粒子径が０．１〜２０μｍであ
るポリマー微粒子の製造方法。2. N-vinylformamide in an amount of 1 to 100 mol%, and 1 copolymerizable with N-vinylformamide.
Characterized in that a monomer containing 99 to 0 mol% of one or two or more vinyl compounds is polymerized in the presence of a polymer dispersant in a solvent which dissolves the monomer but does not dissolve the produced polymer. A method for producing fine polymer particles having a particle diameter of 0.1 to 20 μm.
オキサゾリン）またはそのマクロマーである請求項２の
ポリマー微粒子の製造方法。3. The polymer dispersant is poly (2-methyl-2-).
The method for producing polymer fine particles according to claim 2, which is an oxazoline) or a macromer thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27311192A JP3273064B2 (en) | 1992-10-12 | 1992-10-12 | Polymer fine particles and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27311192A JP3273064B2 (en) | 1992-10-12 | 1992-10-12 | Polymer fine particles and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06122725A true JPH06122725A (en) | 1994-05-06 |
| JP3273064B2 JP3273064B2 (en) | 2002-04-08 |
Family
ID=17523287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27311192A Expired - Lifetime JP3273064B2 (en) | 1992-10-12 | 1992-10-12 | Polymer fine particles and method for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3273064B2 (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996003969A1 (en) * | 1994-08-05 | 1996-02-15 | National Starch And Chemical Investment Holding Corporation | Hair care compositions containing polymeric n-vinyl formamide and methods of treating hair |
| US5977274A (en) * | 1998-03-09 | 1999-11-02 | National Starch And Chemical Investment Holding Corporation | Method for making polymers from N-vinyl formamide monomer |
| US6231876B1 (en) | 1996-09-30 | 2001-05-15 | Basf Aktiengesellschaft | Use of water-soluble copolymers as active ingredients in cosmetics |
| US6271327B1 (en) | 1996-07-31 | 2001-08-07 | Basf Aktiengesellschaft | Water-soluble polymers and their use in cosmetic formulations |
| WO2010047305A1 (en) * | 2008-10-22 | 2010-04-29 | 東亞合成株式会社 | Process for producing polymer microparticles |
| WO2010047287A1 (en) * | 2008-10-22 | 2010-04-29 | 東亞合成株式会社 | Process for producing polymer microparticles |
| JP2016024430A (en) * | 2014-07-24 | 2016-02-08 | 富士ゼロックス株式会社 | Positive charging toner, liquid developer, developer, developer cartridge, process cartridge, and image forming apparatus |
| WO2016043225A1 (en) * | 2014-09-18 | 2016-03-24 | 東亞合成株式会社 | Polymer microparticles and method for producing same |
-
1992
- 1992-10-12 JP JP27311192A patent/JP3273064B2/en not_active Expired - Lifetime
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996003969A1 (en) * | 1994-08-05 | 1996-02-15 | National Starch And Chemical Investment Holding Corporation | Hair care compositions containing polymeric n-vinyl formamide and methods of treating hair |
| AU696302B2 (en) * | 1994-08-05 | 1998-09-03 | National Starch And Chemical Investment Holding Corporation | Hair care compositions containing polymeric N-vinyl formamide and methods of treating hair |
| US6271327B1 (en) | 1996-07-31 | 2001-08-07 | Basf Aktiengesellschaft | Water-soluble polymers and their use in cosmetic formulations |
| US6231876B1 (en) | 1996-09-30 | 2001-05-15 | Basf Aktiengesellschaft | Use of water-soluble copolymers as active ingredients in cosmetics |
| US5977274A (en) * | 1998-03-09 | 1999-11-02 | National Starch And Chemical Investment Holding Corporation | Method for making polymers from N-vinyl formamide monomer |
| WO2010047305A1 (en) * | 2008-10-22 | 2010-04-29 | 東亞合成株式会社 | Process for producing polymer microparticles |
| WO2010047287A1 (en) * | 2008-10-22 | 2010-04-29 | 東亞合成株式会社 | Process for producing polymer microparticles |
| JP5578080B2 (en) * | 2008-10-22 | 2014-08-27 | 東亞合成株式会社 | Method for producing polymer fine particles |
| JP5630266B2 (en) * | 2008-10-22 | 2014-11-26 | 東亞合成株式会社 | Method for producing polymer fine particles |
| JP2016024430A (en) * | 2014-07-24 | 2016-02-08 | 富士ゼロックス株式会社 | Positive charging toner, liquid developer, developer, developer cartridge, process cartridge, and image forming apparatus |
| WO2016043225A1 (en) * | 2014-09-18 | 2016-03-24 | 東亞合成株式会社 | Polymer microparticles and method for producing same |
| JP2016060824A (en) * | 2014-09-18 | 2016-04-25 | 東亞合成株式会社 | Polymer fine particle and method for producing the same |
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| Publication number | Publication date |
|---|---|
| JP3273064B2 (en) | 2002-04-08 |
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