JPH111563A - Production of resin dispersion and colorant and electrophtographic developer, coating, printing ink and ink jet ink using the resin dispersion and colorant - Google Patents
Production of resin dispersion and colorant and electrophtographic developer, coating, printing ink and ink jet ink using the resin dispersion and colorantInfo
- Publication number
- JPH111563A JPH111563A JP17104797A JP17104797A JPH111563A JP H111563 A JPH111563 A JP H111563A JP 17104797 A JP17104797 A JP 17104797A JP 17104797 A JP17104797 A JP 17104797A JP H111563 A JPH111563 A JP H111563A
- Authority
- JP
- Japan
- Prior art keywords
- colorant
- resin dispersion
- carboxylic acid
- aliphatic carboxylic
- unsaturated aliphatic
- 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
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、樹脂分散液及びそ
の製造方法、着色剤及びその製造方法、並びに樹脂分散
液又は着色剤を用いた電子写真現像剤、塗料、印刷イン
キ、又はインクジェット用インキに関する。The present invention relates to a resin dispersion and a method for producing the same, a colorant and a method for producing the same, and an electrophotographic developer, a paint, a printing ink or an ink-jet ink using the resin dispersion or the colorant. About.
【０００２】[0002]
【従来の技術】従来、ジエチレングリコールジメタクリ
レートなどの多官能性（メタ）アクリル酸エステルとラ
ウリルアクリレートのような重合性モノマーを脂肪族炭
化水素、トルエン、ベンゼン、キシレン等の芳香族炭化
水素溶媒中で、重合開始剤の存在下で重合反応させて共
重合体樹脂分散液を製造する方法が知られている（特開
昭５６−１４５９１１号、特開昭５６−７９１１２
号）。しかし、この製造方法により得られる樹脂分散液
は、芳香族炭化水素溶媒を使用するので、含まれている
樹脂の架橋が進み易く、又重合反応を進める間に生成す
る樹脂がゲル化したり、保存中に、樹脂が固化する等の
問題があった。また、この非水系樹脂を塗料や接着剤用
として用いる場合に、保存中に固化するので接着力の低
下をきたす。そこでこれらの問題点を解決するために、
多価グリコールジアクリレート等の多官能性アクリル酸
エステル又はメタクリル酸エステルの使用量を２重量％
以下に抑える必要があった。確かに、２重量％以下にす
ることにより従来の問題が解消されるが、その結果、樹
脂は芳香族溶媒に可溶のものとなり、塗料として用いた
場合は、顔料への樹脂の吸着量が少なく、接着力が不足
する結果となる。特に、電着塗料として用いる場合は顔
料が樹脂に吸着されないので、塗料として望ましくない
ものであった。更に、この方法で使用される芳香族溶媒
は毒性及び引火性が強く、環境衛生上問題があるばかり
でなく、火災の危険も多いという問題も有することが指
摘されていた。本発明者らは以上のような問題点を解決
すべく、非水系樹脂からなる分散液の製造方法を開発し
た。この方法は脂肪族炭化水素又はハロゲン化脂肪族炭
化水素を主成分とする溶媒中で、重合開始剤の存在下
に、前述のような多官能性のアクリル酸エステル又はメ
タクリル酸エステルと、不飽和カルボン酸のような極性
モノマー及びラウリルアクリレートのような重合前も重
合後も前記溶媒と溶媒和し得るモノマーとを重合反応さ
せる方法である（特開昭５６−７９１１２号）。しか
し、この方法では架橋剤として用いる多官能性のアクリ
ル酸エステル又はメタクリル酸エステルの架橋性が高
く、即ち、架橋速度が速くなるために、（１）重合時の
反応制御が困難となり、製品である分散樹脂にバラツキ
が生じ易い、（２）重合が均一に行なわれないので、粒
度分布の広い製品しか得られず、又（３）製品の分散安
定性がよくない等の欠点がある他に、多官能性アクリル
酸又はメタクリル酸モノマーは極性基を持っていないの
で、（４）着色剤を分散する能力が低く、たとえ極性基
を有するモノマーを併用したとても共重合性が悪く、均
一な重合ができないという問題点がある。2. Description of the Related Art Hitherto, a polyfunctional (meth) acrylate such as diethylene glycol dimethacrylate and a polymerizable monomer such as lauryl acrylate have been used in an aromatic hydrocarbon solvent such as an aliphatic hydrocarbon, toluene, benzene, or xylene. A method of producing a copolymer resin dispersion by carrying out a polymerization reaction in the presence of a polymerization initiator is known (JP-A-56-145911, JP-A-56-79112).
issue). However, since the resin dispersion obtained by this production method uses an aromatic hydrocarbon solvent, the crosslinking of the contained resin is easy to proceed, and the resin generated during the progress of the polymerization reaction is gelled or stored. There were problems such as solidification of the resin. In addition, when the non-aqueous resin is used for a paint or an adhesive, the non-aqueous resin is solidified during storage, resulting in a decrease in adhesive strength. So, in order to solve these problems,
2% by weight of polyfunctional acrylate or methacrylate such as polyhydric glycol diacrylate
It was necessary to keep it below. Certainly, the conventional problem can be solved by setting the content to 2% by weight or less, but as a result, the resin becomes soluble in an aromatic solvent, and when used as a paint, the amount of the resin adsorbed on the pigment is reduced. Less, resulting in poor adhesion. In particular, when used as an electrodeposition paint, the pigment is not adsorbed by the resin, which is not desirable as a paint. Furthermore, it has been pointed out that the aromatic solvent used in this method has high toxicity and flammability, and has not only a problem in environmental health, but also a problem of a great risk of fire. The present inventors have developed a method for producing a dispersion comprising a non-aqueous resin in order to solve the above problems. In this method, a polyfunctional acrylic ester or methacrylic ester as described above is mixed with an unsaturated hydrocarbon or a halogenated aliphatic hydrocarbon as a main component in the presence of a polymerization initiator. This is a method in which a polar monomer such as carboxylic acid and a solvable monomer such as lauryl acrylate are subjected to a polymerization reaction with the solvent before and after the polymerization (JP-A-56-79112). However, in this method, the polyfunctional acrylate or methacrylate used as a cross-linking agent has a high cross-linking property, that is, a high cross-linking rate, so that (1) reaction control during polymerization becomes difficult, and In addition to the drawbacks that certain dispersion resins tend to vary, (2) the polymerization is not uniform, only products with a wide particle size distribution can be obtained, and (3) the dispersion stability of the products is poor. Since polyfunctional acrylic acid or methacrylic acid monomer does not have a polar group, (4) the ability to disperse a colorant is low, and even if a monomer having a polar group is used in combination, it has very poor copolymerizability and uniform polymerization. There is a problem that can not be.
【０００３】[0003]
【発明が解決しようとする課題】本発明の課題は、バラ
ツキが少なく、分散安定性に優れた樹脂分散液及び着色
剤の製造方法を提供すること並びにこれら樹脂分散液及
び着色剤を用いた電子写真現像剤、塗料、印刷インキ、
インクジェット用インキを提供することである。SUMMARY OF THE INVENTION An object of the present invention is to provide a method for producing a resin dispersion and a colorant which are less scattered and have excellent dispersion stability, and an electronic method using the resin dispersion and the colorant. Photo developers, paints, printing inks,
An object of the present invention is to provide an inkjet ink.
【０００４】[0004]
【課題を解決するための手段】本発明によれば、非水溶
媒の存在下に、α，β不飽和脂肪族カルボン酸とα−オ
レフィン共重合体、α，β不飽和脂肪族カルボン酸エス
テルとα−オレフィン共重合体、又はα，β不飽和脂肪
族カルボン酸とα，β不飽和脂肪族カルボンエステルと
α−オレフィン共重合体から選ばれる共重合体樹脂を、
６０〜１５０℃に加熱し、架橋剤により架橋させて樹脂
分散液を得る樹脂分散液の製造方法が提供される。According to the present invention, an α, β unsaturated aliphatic carboxylic acid and an α-olefin copolymer, an α, β unsaturated aliphatic carboxylic acid ester are prepared in the presence of a non-aqueous solvent. And α-olefin copolymer, or a copolymer resin selected from α, β unsaturated aliphatic carboxylic acid, α, β unsaturated aliphatic carboxylic ester and α-olefin copolymer,
There is provided a method for producing a resin dispersion, which is heated to 60 to 150 ° C. and crosslinked with a crosslinking agent to obtain a resin dispersion.
【０００５】[0005]
【発明の実施の形態】本発明では、αオレフイン／α，
β不飽和カルボン酸共重合体、αオレフイン／α，β不
飽和脂肪族カルボン酸エステル共重合体、αオレフイン
／α，β不飽和脂肪族カルボン酸／α，β不飽和脂肪族
カルボン酸エステルを対象にして、架橋するものであ
る。これらの具体例としては、次のものが示される。エ
チレン／アクリル酸共重合体、エチレン／メタクリル酸
共重合体、エチレン／無水マレイン酸共重合体、エチレ
ン／ラウリルメタクリレート、メタクリル酸共重合体、
プロピレン／スチレンジビニルベンゼン／２−エチルヘ
キシルアクリレート／マレイン酸共重合体、エチレン／
グリシジルメタクリレート／メタクリル酸共重合体、ブ
テン／アクリル酸／エチレングリコールジメタクリレー
ト重合体等。これらは、ランダム、ブロック、グラフト
の共重合体を用いることができる。これらの共重合体で
は、αオレフインが、共重合体全体の３０〜９５重量
％、好ましくは５０〜８０重量％であり、α，β不飽和
脂肪族カルボン酸が３０〜０．１重量％、好ましくは１
５〜１重量％、α，β不飽和脂肪族カルボン酸エステル
が７０〜３重量％、好ましくは５０〜１０重量％であ
る。DETAILED DESCRIPTION OF THE INVENTION In the present invention, α-olefin / α,
β-unsaturated carboxylic acid copolymer, α-olefin / α, β-unsaturated aliphatic carboxylic acid ester copolymer, α-olefin / α, β-unsaturated aliphatic carboxylic acid / α, β-unsaturated aliphatic carboxylic acid ester It is intended to crosslink. The following are shown as specific examples of these. Ethylene / acrylic acid copolymer, ethylene / methacrylic acid copolymer, ethylene / maleic anhydride copolymer, ethylene / lauryl methacrylate, methacrylic acid copolymer,
Propylene / styrenedivinylbenzene / 2-ethylhexyl acrylate / maleic acid copolymer, ethylene /
Glycidyl methacrylate / methacrylic acid copolymer, butene / acrylic acid / ethylene glycol dimethacrylate polymer and the like. These can be random, block, or graft copolymers. In these copolymers, α-olefin is 30 to 95% by weight, preferably 50 to 80% by weight of the whole copolymer, and α, β unsaturated aliphatic carboxylic acid is 30 to 0.1% by weight; Preferably 1
It is 5 to 1% by weight, and the α, β unsaturated aliphatic carboxylic acid ester is 70 to 3% by weight, preferably 50 to 10% by weight.
【０００６】本発明では、非水溶媒の存在下に架橋が行
われる。非水溶媒としては、ケロシン、リグロイン、ｎ
−ヘキサン、ｎ−オクタン、ｉ−ドデカン、トルエン、
キシレン、シリコーンオイル、脂肪酸エステル、低分子
量オレフイン化合物、フッ素化オイルなどが用いられ
る。市販商品名としては、エクソン社製、アイソパー
Ｇ、アイソパーＨ、アイソパーＬ、アイソパーＭが用い
られる。In the present invention, crosslinking is carried out in the presence of a non-aqueous solvent. Non-aqueous solvents include kerosene, ligroin, n
-Hexane, n-octane, i-dodecane, toluene,
Xylene, silicone oil, fatty acid ester, low molecular weight olefin compound, fluorinated oil and the like are used. As commercial names, Exoper G, Isopar H, Isopar L, and Isopar M are used.
【０００７】架橋に際しては、共重合体を上記非水溶媒
と混合し、６０〜１５０℃、好ましくは９０〜１２０℃
に加熱し、ポリマーを溶解、溶融または分散状態を保持
する。At the time of crosslinking, the copolymer is mixed with the above non-aqueous solvent, and the mixture is mixed at 60 to 150 ° C., preferably 90 to 120 ° C.
To maintain the dissolved, molten or dispersed state of the polymer.
【０００８】架橋剤としては、金属又は金属化合物架橋
剤、有機化合物、及び有機アミンを用いることができ
る。金属又は金属化合物架橋剤としては、水酸化ベリリ
ウム、水酸化マグネシウム、水酸化バリウム、亜鉛、カ
ルシウム、ストロンチウム、酸化亜鉛、酸化チタン、炭
酸カルシウムを挙げることができ、有機アミンとして
は、ｎ−ヘキシルアミン、ヘキサメチレンジアミン、ト
リエチルアミン、ピリジン、トリエタノールアミン、メ
タキシレンジアミン等を挙げることができ、有機アミン
は金属架橋剤と併用することができる。共重合体中のカ
ルボキシル基が前記架橋剤により架橋されるものであ
る。As the crosslinking agent, a metal or metal compound crosslinking agent, an organic compound, and an organic amine can be used. Examples of the metal or metal compound crosslinking agent include beryllium hydroxide, magnesium hydroxide, barium hydroxide, zinc, calcium, strontium, zinc oxide, titanium oxide, and calcium carbonate. As the organic amine, n-hexylamine , Hexamethylenediamine, triethylamine, pyridine, triethanolamine, metaxylenediamine and the like, and the organic amine can be used in combination with a metal crosslinking agent. The carboxyl groups in the copolymer are crosslinked by the crosslinking agent.
【０００９】架橋時に共重合体を非水溶媒中で加熱する
ことにより、これらの共重合体に含まれる成分は非水溶
媒である、ケロシン、トルエン、シリコーンオイル、フ
ッ素オイル等の非水溶媒に溶媒和する。溶媒和する共重
合体の成分はα，β不飽和カルボン酸エステルであり、
溶媒和した結果、得られる樹脂溶媒の分散安定性及び着
色剤の定着性に寄与するものである。非水溶媒に溶媒和
するモノマーとしてはラウリルメタクリレート、２−エ
チルヘキシル、メチルメタクリレート、メタクリル変性
シリコーンモノマー、アクリル変性フッ素モノマーなど
が挙げられる。By heating the copolymer in a non-aqueous solvent at the time of crosslinking, the components contained in these copolymers are converted into non-aqueous solvents such as kerosene, toluene, silicone oil and fluorine oil. Solvate. The component of the copolymer to be solvated is an α, β unsaturated carboxylic acid ester,
As a result of solvation, it contributes to the dispersion stability of the obtained resin solvent and the fixability of the colorant. Monomers solvated in non-aqueous solvents include lauryl methacrylate, 2-ethylhexyl, methyl methacrylate, methacryl-modified silicone monomers, and acryl-modified fluorine monomers.
【００１０】着色剤を製造する場合には、前記共重合体
からなる樹脂を非水溶媒に加え混合撹拌し、さらに顔料
を分散後、架橋剤を加え加熱すると、樹脂中に顔料を含
んだ着色剤が得られる。架橋剤を使用しないと、顔料と
樹脂の結合力が弱く、顔料と樹脂が分離しやすく、定着
性や分散性が劣化するばかりでなく、現像剤の寿命も短
かくなる。架橋剤の種類は前記非水系樹脂分散液を製造
する場合のものと同じである。着色剤の色を特定するた
めに顔料が用いられる。顔料としてはカーボンブラック
やフタロシアニンブルー、ジスアゾイエロー、カーミン
６Ｂ、キナクリドンを挙げることができる。この着色剤
は電子写真用現像剤、塗料、印刷インキ、インクジェッ
ト用インクに用いることができる。In the case of producing a coloring agent, a resin comprising the above-mentioned copolymer is added to a non-aqueous solvent, mixed and stirred, and after a pigment is dispersed, a crosslinking agent is added and heated. Agent is obtained. If a crosslinking agent is not used, the bonding force between the pigment and the resin is weak, the pigment and the resin are easily separated, not only the fixability and dispersibility are deteriorated, but also the life of the developer is shortened. The type of the crosslinking agent is the same as in the case of producing the non-aqueous resin dispersion. Pigments are used to specify the color of the colorant. Examples of the pigment include carbon black, phthalocyanine blue, disazo yellow, carmine 6B, and quinacridone. This colorant can be used for a developer for electrophotography, a paint, a printing ink, and an ink for inkjet.
【００１１】電子写真用現像剤には、乾式用と湿式用が
ある。電子写真用乾式現像剤は、非水溶媒からなる樹脂
分散液にカーボンブラックを添加し、撹拌混合する。次
に、架橋剤を添加して、６０〜１５０℃に加熱して架橋
する。この様にして得られた着色剤を製造した後に、加
熱により溶媒を除去する。得られた固体状の塊を粉砕機
で粉体として、トナーを製造する。トナーの粒径は一般
に０．１〜５μｍである。電子写真用湿式現像剤は、非
水溶媒からなる樹脂分散液にカーボンブラックを添加
し、撹拌混合する。次に、架橋剤を添加して、６０〜１
５０℃に加熱して架橋する。この様にして得られた着色
剤を用いるものである。Electrophotographic developers are classified into dry type and wet type. In the dry developer for electrophotography, carbon black is added to a resin dispersion liquid composed of a non-aqueous solvent, followed by stirring and mixing. Next, a crosslinking agent is added, and the mixture is heated to 60 to 150 ° C. for crosslinking. After producing the coloring agent thus obtained, the solvent is removed by heating. The resulting solid mass is pulverized with a pulverizer to produce a toner. The particle size of the toner is generally from 0.1 to 5 μm. In a wet developer for electrophotography, carbon black is added to a resin dispersion liquid composed of a non-aqueous solvent, followed by stirring and mixing. Next, a crosslinking agent is added, and
Crosslink by heating to 50 ° C. The colorant thus obtained is used.
【００１２】塗料を製造するには、非水溶媒からなる樹
脂分散液に顔料を添加し、撹拌混合後、架橋剤を添加し
て６０〜１５０℃に加熱して架橋する。次に、得られた
生成物にカーボンを添加し、さらに溶剤を添加し、混合
撹拌し、塗料を得る。架橋したことにより塗膜の接着性
及び光沢性が良好であった。In order to produce a paint, a pigment is added to a resin dispersion composed of a non-aqueous solvent, and after stirring and mixing, a crosslinking agent is added and the mixture is heated to 60 to 150 ° C. to perform crosslinking. Next, carbon is added to the obtained product, a solvent is further added, and the mixture is mixed and stirred to obtain a paint. Due to the crosslinking, the adhesiveness and glossiness of the coating film were good.
【００１３】印刷用インキとして使用するには、本発明
の湿式現像剤をそのまま使用することもできる。インク
ジェット用インキとして使用するには、本発明の湿式現
像剤をそのまま使用することもできる。For use as a printing ink, the wet developer of the present invention can be used as it is. For use as an inkjet ink, the wet developer of the present invention can be used as it is.
【００１４】[0014]
【実施例】以下、実施例により本発明を更に詳細に説明
する。The present invention will be described in more detail with reference to the following examples.
【００１５】実施例１ １リットルの四ッ口フラスコにケロシン２００重量部を
とり、オイルバス中で１００℃に加熱した。その中にエ
チレン／メタクリル酸（９０／１０）共重合体１００重
量部を入れ１時間撹拌しつつ溶解せた。この中に、水酸
化亜鉛１０重量部を添加し、１００℃で４０時間撹拌反
応させた。次に得られた生成物を撹拌しながら冷却し、
樹脂分散液を得た。Example 1 200 parts by weight of kerosene was placed in a 1-liter four-necked flask and heated to 100 ° C. in an oil bath. 100 parts by weight of an ethylene / methacrylic acid (90/10) copolymer was added therein and dissolved with stirring for 1 hour. Into this, 10 parts by weight of zinc hydroxide was added, and the mixture was stirred and reacted at 100 ° C. for 40 hours. The resulting product is then cooled while stirring,
A resin dispersion was obtained.
【００１６】実施例２ 実施例１の共重合体の代りに、エチレン／ラウリルメタ
クリレート／メタクリル酸（６０／３０／１０）共重合
体を用いて同様に樹脂分散液を得た。Example 2 A resin dispersion was obtained in the same manner as in Example 1 except that an ethylene / lauryl methacrylate / methacrylic acid (60/30/10) copolymer was used instead of the copolymer of Example 1.
【００１７】実施例３ 実施例１の共重合体の代りに、エチレン／メチルメタク
リレート／アクリル酸（６０／３０／１０）共重合体を
用いて同様に樹脂分散液を得た。Example 3 A resin dispersion was similarly obtained using an ethylene / methyl methacrylate / acrylic acid (60/30/10) copolymer instead of the copolymer of Example 1.
【００１８】実施例４ 実施例３の非水溶媒をケロシンの代りにトルエンでを用
いて同様に樹脂分散液を得た。Example 4 A resin dispersion was obtained in the same manner as in Example 3 except that the non-aqueous solvent was toluene instead of kerosene.
【００１９】実施例５ 実施例１において用いられている架橋剤の水酸化亜鉛に
替えてメタキシレンジアミン１．０重量部と水酸化マグ
ネシウム２．０重量部を加え、同様に樹脂分散液を得
た。Example 5 In place of zinc hydroxide as a crosslinking agent used in Example 1, 1.0 part by weight of metaxylenediamine and 2.0 parts by weight of magnesium hydroxide were added, and a resin dispersion was obtained in the same manner. Was.
【００２０】実施例６ 実施例１の共重合体にケロシンを加え、さらにカーボン
ブラックを２０重量部入れ４時間混合撹拌し、カーボン
をブラック樹脂分散液中に分散させた。次に、水酸化亜
鉛１０重量部を添加し、架橋を１００℃で６時間行って
着色剤を得た。その後、非水溶媒を除去し、粉体化し乾
式トナー平均粒径１０μｍを作成した。Example 6 Kerosene was added to the copolymer of Example 1, and 20 parts by weight of carbon black was further added and mixed and stirred for 4 hours to disperse carbon in the black resin dispersion. Next, 10 parts by weight of zinc hydroxide was added and crosslinking was performed at 100 ° C. for 6 hours to obtain a colorant. Thereafter, the non-aqueous solvent was removed to obtain a powder, and a dry toner having an average particle diameter of 10 μm was prepared.
【００２１】実施例７ ３００ｍｌ内容量のアトライターにイソパラフィン（ア
イソパーＭ、エクソン化学製）１００ｇ、エチレン／ス
テアリルメタクリレート／メタクリル酸（７０／２０／
１０）共重合体５０ｇ、カーボンブラック（三菱化学
製、カーボンＭＡ・１００）１０ｇを加え、９０℃で２
時間撹拌処理分散した。次に、水酸化亜鉛５ｇを加え、
１００℃で１時間混練撹拌分散し、着色剤組成物を得
た。Example 7 100 g of isoparaffin (Isoper M, manufactured by Exxon Chemical), ethylene / stearyl methacrylate / methacrylic acid (70/20 /
10) Add 50 g of the copolymer and 10 g of carbon black (carbon MA100 manufactured by Mitsubishi Chemical Corporation), and add 2 g at 90 ° C.
The mixture was dispersed by stirring for an hour. Next, add 5 g of zinc hydroxide,
The mixture was kneaded, stirred, and dispersed at 100 ° C for 1 hour to obtain a colorant composition.
【００２２】比較例１〜７ 実施例１〜７の実施例で用いている架橋剤を使用するこ
となく、他は同じ条件で処理した。Comparative Examples 1 to 7 The cross-linking agents used in Examples 1 to 7 were not used, and the other conditions were the same.
【００２３】実施例８ 実施例１の樹脂１００ｇ、カーボンブラック（三菱化学
製、ＭＡ−１００）１０ｇ、イソパラフィン（アイソパ
ーＬ、エクソン化学製）１００ｇを１リットルのアトラ
イターに取り、８０℃で６時間分散し、電子写真現像剤
を作成した。この現像液を用いて、湿式複写機（リコピ
ーＦＴ−４００ｉ）でコピーしたところ、画像濃度１．
２８、解像度６．３本／ｍｍ、定着性７８％、定着温度
９０〜１６０℃においてオフセットは再生しなかった。
現像剤の耐久性は２５，０００枚であった。Example 8 100 g of the resin of Example 1, 10 g of carbon black (manufactured by Mitsubishi Chemical Corporation, MA-100) and 100 g of isoparaffin (Isoper L, manufactured by Exxon Chemical) were placed in a 1-liter attritor, and were heated at 80 ° C. for 6 hours. It was dispersed to form an electrophotographic developer. Using this developer, copying was performed with a wet copying machine (Recopy FT-400i).
28, the resolution was 6.3 lines / mm, the fixing property was 78%, and the offset was not reproduced at a fixing temperature of 90 to 160 ° C.
The durability of the developer was 25,000 sheets.
【００２４】実施例２〜５、比較例２〜５についても実
施例１同様に評価したところ、以下の結果を得た。この
結果を表１に示す。Examples 2 to 5 and Comparative Examples 2 to 5 were evaluated in the same manner as in Example 1, and the following results were obtained. Table 1 shows the results.
【００２５】[0025]
【表１】 [Table 1]
【００２６】実施例６の着色剤は乾式トナーとして、リ
コピーＦＴ４０６０、実施例７の着色剤は液体トナーと
してリコピーＦＴ４００ｉで評価したところ、以下の結
果を得た。同様に比較例６及び７についても、表２にそ
の結果を示す。When the colorant of Example 6 was evaluated as dry toner by Ricopy FT4060 and the colorant of Example 7 was evaluated as liquid toner by Ricopy FT400i, the following results were obtained. Table 2 also shows the results of Comparative Examples 6 and 7.
【００２７】[0027]
【表２】 [Table 2]
【００２８】実施例９ 実施例４の樹脂１００ｇに、カーボンブラック（三菱化
学製カーボンＭＡ１００）１０ｇ及びトルエン１００ｇ
を加えてアトライターで分散し、塗料とした。塗料の粒
径は０．２μｍで、塗膜の接着性及び光沢性が良好であ
った。Example 9 10 g of carbon black (carbon MA100 manufactured by Mitsubishi Chemical) and 100 g of toluene were added to 100 g of the resin of Example 4.
Was added and dispersed with an attritor to obtain a paint. The particle size of the paint was 0.2 μm, and the adhesion and gloss of the coating film were good.
【００２９】実施例１０ 実施例７の液体トナーをインクジェットインキに用いた
ところ、画像濃度１．４４、吐出性２５μｍドット、耐
光性１年以上であった。一方、従来のインクジェットイ
ンク（株式会社セイコーエプソンのマッハジェット用イ
ンク）の結果は、画像濃度１．２２、吐出性８０μｍド
ット、耐光性１か月以下であった。Example 10 When the liquid toner of Example 7 was used for an ink jet ink, the image density was 1.44, the ejection property was 25 μm dots, and the light fastness was one year or more. On the other hand, the results of the conventional inkjet ink (ink for Mach Jet manufactured by Seiko Epson Corporation) were 1.22 in image density, 80 μm dots in ejection property, and 1 month or less in light fastness.
【００３０】実施例１１ 実施例７を同様に印刷インキに用いたところ、印刷物の
定着性、光沢、画像濃度の高いものが得られた。Example 11 When Example 7 was used in the same manner as the printing ink, a printed matter having high fixability, gloss and image density was obtained.
【００３１】[0031]
【発明の効果】本発明による樹脂分散液又は着色剤を用
いた電子写真液体現像剤及び電子写真乾式現像剤は、画
像濃度、解像度、電着性、耐久性にすぐれる。また、熱
ローラー定着におけるオフセットの発生も少ないもので
ある。また、塗料、印刷インク、インジェット用インキ
に用いた場合は、高画像濃度で、解像度、定着性、光
沢、インキの吐出性、耐光性が良好である結果が得られ
る。The electrophotographic liquid developer and the electrophotographic dry developer using the resin dispersion or the colorant according to the present invention are excellent in image density, resolution, electrodeposition and durability. Further, the occurrence of offset in the heat roller fixing is small. In addition, when used in paints, printing inks, and inks for ink jets, it is possible to obtain results with high image density and good resolution, fixability, gloss, ink ejection properties, and light fastness.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 ＦＩ Ｃ０９Ｄ 133/00 Ｃ０９Ｄ 133/00 Ｇ０３Ｇ 9/12 Ｇ０３Ｇ 9/12 ──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 6 Identification code FI C09D 133/00 C09D 133/00 G03G 9/12 G03G 9/12
Claims (8)
族カルボン酸とα−オレフィン共重合体、α，β不飽和
脂肪族カルボン酸エステルとα−オレフィン共重合体、
又はα，β不飽和脂肪族カルボン酸とα，β不飽和脂肪
族カルボン酸エステルとαオレフィン共重合体から選ば
れる共重合体樹脂を、６０〜１５０℃に加熱し、架橋剤
を添加して、前記樹脂を架橋させて樹脂分散液を得るこ
とを特徴とする樹脂分散液の製造方法。1. An α, β unsaturated aliphatic carboxylic acid and an α-olefin copolymer, an α, β unsaturated aliphatic carboxylic acid ester and an α-olefin copolymer, in the presence of a non-aqueous solvent.
Alternatively, a copolymer resin selected from α, β unsaturated aliphatic carboxylic acid, α, β unsaturated aliphatic carboxylic acid ester and α olefin copolymer is heated to 60 to 150 ° C., and a crosslinking agent is added. A method for producing a resin dispersion, characterized in that a resin dispersion is obtained by crosslinking the resin.
族カルボン酸とα−オレフィン共重合体、α，β不飽和
脂肪族カルボン酸エステルとα−オレフィン共重合体、
又はα，β不飽和脂肪族カルボン酸とα，β不飽和脂肪
族カルボン酸エステルとα−オレフィン共重合体から選
ばれる共重合体樹脂を、６０〜１５０℃に加熱し、顔料
と架橋剤を添加し、混合することによりし着色剤を製造
することを特徴とする着色剤の製造方法。2. An α, β unsaturated aliphatic carboxylic acid and an α-olefin copolymer, an α, β unsaturated aliphatic carboxylic acid ester and an α-olefin copolymer, in the presence of a non-aqueous solvent.
Alternatively, a copolymer resin selected from an α, β unsaturated aliphatic carboxylic acid, an α, β unsaturated aliphatic carboxylic acid ester and an α-olefin copolymer is heated to 60 to 150 ° C. to form a pigment and a crosslinking agent. A method for producing a colorant, characterized by producing a colorant by adding and mixing.
β不飽和脂肪族カルボン酸エステル成分を非水溶媒に溶
媒和させて樹脂分散液又は着色剤を得ることを特徴とす
る樹脂分散液又は着色剤の製造方法。3. The copolymer according to claim 1 or 2, wherein α,
A method for producing a resin dispersion or a colorant, wherein a β-unsaturated aliphatic carboxylic acid ester component is solvated with a non-aqueous solvent to obtain a resin dispersion or a colorant.
剤、又は有機アミンから選ばれる請求項１〜３の樹脂分
散液又は着色剤の製造方法。4. The method for producing a resin dispersion or a colorant according to claim 1, wherein the crosslinking agent is selected from a crosslinking agent containing a metal or a metal compound, and an organic amine.
分散液又は着色剤を用いた電子写真用現像剤。5. An electrophotographic developer using the resin dispersion or the colorant obtained in any one of claims 1 to 4.
分散液又は着色剤を用いた塗料。6. A paint using a resin dispersion or a colorant obtained in any one of claims 1 to 4.
樹脂分散液又は着色剤を用いた印刷用インキ。7. A printing ink using a resin dispersion or a colorant obtained according to claim 1.
樹脂分散液又は着色剤を用いたインクジェット用イン
キ。8. An ink-jet ink using the resin dispersion or the colorant obtained according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17104797A JP3566034B2 (en) | 1997-06-12 | 1997-06-12 | Colorant and electrophotographic developer, paint, printing ink and ink-jet ink using the colorant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17104797A JP3566034B2 (en) | 1997-06-12 | 1997-06-12 | Colorant and electrophotographic developer, paint, printing ink and ink-jet ink using the colorant |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003321996A Division JP4064324B2 (en) | 2003-09-12 | 2003-09-12 | Composition and method for producing the composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH111563A true JPH111563A (en) | 1999-01-06 |
| JP3566034B2 JP3566034B2 (en) | 2004-09-15 |
Family
ID=15916106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17104797A Expired - Fee Related JP3566034B2 (en) | 1997-06-12 | 1997-06-12 | Colorant and electrophotographic developer, paint, printing ink and ink-jet ink using the colorant |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3566034B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001281935A (en) * | 2000-03-30 | 2001-10-10 | Ricoh Co Ltd | Electrophotographic liquid developer and image forming method |
| JP4621901B2 (en) * | 2008-12-24 | 2011-02-02 | 独立行政法人海上技術安全研究所 | Antifouling paint composition and substrate antifouling method |
| US10196531B2 (en) | 2013-12-30 | 2019-02-05 | E I Du Pont De Nemours And Company | Pigmented inkjet ink comprising dispersed polyurethane and olefin ionic copolymer |
-
1997
- 1997-06-12 JP JP17104797A patent/JP3566034B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001281935A (en) * | 2000-03-30 | 2001-10-10 | Ricoh Co Ltd | Electrophotographic liquid developer and image forming method |
| JP4621901B2 (en) * | 2008-12-24 | 2011-02-02 | 独立行政法人海上技術安全研究所 | Antifouling paint composition and substrate antifouling method |
| US10196531B2 (en) | 2013-12-30 | 2019-02-05 | E I Du Pont De Nemours And Company | Pigmented inkjet ink comprising dispersed polyurethane and olefin ionic copolymer |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3566034B2 (en) | 2004-09-15 |
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