JP4064324B2 - Composition and method for producing the composition - Google Patents
Composition and method for producing the composition Download PDFInfo
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Description
本発明は、樹脂分散液及び樹脂分散液の製造方法に関する。
The present invention relates to a resin dispersion and a method for producing the resin dispersion .
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(特許文献1、特許文献2)。
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(特許文献3)。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。
Conventionally, a polyfunctional (meth) acrylic acid ester such as diethylene glycol dimethacrylate and a polymerizable monomer such as lauryl acrylate in an aromatic hydrocarbon solvent such as aliphatic hydrocarbon, toluene, benzene, xylene, etc. A method of producing a copolymer resin dispersion by carrying out a polymerization reaction in the presence is known (Patent Document 1, Patent Document 2).
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 produced during the polymerization reaction is gelled or stored. There were problems such as solidification of the resin. Further, when this non-aqueous resin is used for a paint or an adhesive, it is solidified during storage, resulting in a decrease in adhesive strength. Therefore, in order to solve these problems, it was necessary to suppress the amount of polyfunctional acrylic acid ester or methacrylic acid ester such as polyvalent glycol diacrylate to 2% by weight or less. Certainly, the conventional problems are solved by setting it 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 adsorption of the resin to the pigment is small. As a result, the adhesive strength is insufficient. In particular, when used as an electrodeposition paint, the pigment is not adsorbed by the resin, which is undesirable as a paint.
Furthermore, it has been pointed out that the aromatic solvent used in this method is not only toxic and flammable, but also has a problem of not only environmental hygiene but also a high risk of fire.
In order to solve the above problems, the present inventors have developed a method for producing a dispersion comprising a non-aqueous resin. In this method, a polyfunctional acrylic acid ester or methacrylic acid ester as described above is unsaturated with an unsaturated hydrocarbon or a halogenated aliphatic hydrocarbon in the presence of a polymerization initiator in the presence of a polymerization initiator. In this method, a polar monomer such as carboxylic acid and a monomer such as lauryl acrylate, which can be solvated with the solvent, are polymerized before and after polymerization (Patent Document 3). However, in this method, the polyfunctional acrylic acid ester or methacrylic acid ester used as a cross-linking agent has high cross-linkability, that is, the cross-linking speed is high, so that (1) it is difficult to control the reaction at the time of polymerization. In addition to the disadvantages that certain dispersion resins are likely to vary, (2) because the polymerization is not performed uniformly, 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 monomers do not have polar groups, (4) low ability to disperse colorants, even if monomers with polar groups are used together, the copolymerization is very poor and uniform polymerization There is a problem that can not be.
本発明の課題は、バラツキが少なく、分散安定性に優れた組成物、組成物の製造方法を提供することである。 An object of the present invention is to provide a composition having little dispersion and excellent dispersion stability, and a method for producing the composition.
本発明によれば、以下の発明が提供される。
(1)非水溶媒の存在下に樹脂を60〜150℃に加熱し、架橋剤を添加し、該樹脂を架橋することにより得られる樹脂分散液であって、該樹脂は、α,β−不飽和脂肪族カルボン酸エステルとα−オレフィンの共重合体、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−オレフィンの共重合体から選ばれ、該樹脂中の、α,β−不飽和脂肪族カルボン酸エステル成分を該非水溶媒に溶媒和させて得られることを特徴とする樹脂分散液。
(2)前記架橋剤が、金属若しくは金属化合物を含む架橋剤、又は有機アミンから選ばれるものであることを特徴とする(1)記載の樹脂分散液。
(3)非水溶媒の存在下に樹脂を60〜150℃に加熱し、架橋剤を添加し、該樹脂を架橋することにより樹脂分散液を製造する樹脂分散液の製造方法であって、該樹脂は、α,β−不飽和脂肪族カルボン酸とα−オレフィンの共重合体、α,β−不飽和脂肪族カルボン酸エステルとα−オレフィンの共重合体、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−オレフィンの共重合体から選ばれることを特徴とする樹脂分散液の製造方法。
(4)前記樹脂は、前記α,β−不飽和脂肪族カルボン酸エステルとα−オレフィンの共重合体、又は前記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−オレフィンの共重合体から選ばれ、前記樹脂中の、α,β−不飽和脂肪族カルボン酸エステル成分を該非水溶媒に溶媒和させて架橋することを特徴とする(3)記載の樹脂分散液の製造方法。
(5)前記架橋剤が、金属若しくは金属化合物を含む架橋剤、又は有機アミンから選ばれるものであることを特徴とする(3)記載の樹脂分散液の製造方法。
According to the present invention, the following inventions are provided.
(1) A resin dispersion obtained by heating a resin to 60 to 150 ° C. in the presence of a non-aqueous solvent, adding a crosslinking agent, and crosslinking the resin, wherein the resin is α, β- It is selected from a copolymer of an unsaturated aliphatic carboxylic acid ester and an α-olefin, or a copolymer of an α, β-unsaturated aliphatic carboxylic acid, an α, β-unsaturated aliphatic carboxylic acid ester and an α-olefin. A resin dispersion obtained by solvating an α, β-unsaturated aliphatic carboxylic acid ester component in the resin with the non-aqueous solvent.
(2) The resin dispersion according to (1), wherein the crosslinking agent is selected from a crosslinking agent containing a metal or a metal compound, or an organic amine.
(3) A method for producing a resin dispersion by heating a resin to 60 to 150 ° C. in the presence of a nonaqueous solvent, adding a crosslinking agent, and crosslinking the resin to produce a resin dispersion, The resin is a copolymer of α, β-unsaturated aliphatic carboxylic acid and α-olefin, a copolymer of α, β-unsaturated aliphatic carboxylic acid ester and α-olefin, or α, β-unsaturated fat. A method for producing a resin dispersion characterized by being selected from copolymers of aliphatic carboxylic acids, α, β-unsaturated aliphatic carboxylic acid esters and α-olefins.
(4) The resin is a copolymer of the α, β-unsaturated aliphatic carboxylic acid ester and an α-olefin, or the α, β-unsaturated aliphatic carboxylic acid and an α, β-unsaturated aliphatic carboxylic acid. It is selected from a copolymer of an acid ester and an α-olefin , and the α, β-unsaturated aliphatic carboxylic acid ester component in the resin is solvated in the non-aqueous solvent and crosslinked (3) The manufacturing method of the resin dispersion of description.
(5) The method for producing a resin dispersion according to (3), wherein the crosslinking agent is selected from a crosslinking agent containing a metal or a metal compound, or an organic amine.
本発明によれば、バラツキが少なく、分散安定性に優れた樹脂分散液が得られる。
According to the present invention, a resin dispersion having little dispersion and excellent dispersion stability can be obtained.
本発明では、α−オレフィン/α,β−不飽和脂肪族カルボン酸共重合体、α−オレフィン/α,β−不飽和脂肪族カルボン酸エステル共重合体、α−オレフィン/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共重合体を対象にして、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−オレフィンが、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15〜1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。
In the present invention, alpha --olefin fin / alpha, beta - unsaturated aliphatic carboxylic acid copolymers, alpha --olefin fin / alpha, beta - unsaturated aliphatic carboxylic acid ester copolymer, alpha --olefin fin / alpha, beta - unsaturated aliphatic carboxylic acid / alpha, beta - in the interest of unsaturated aliphatic carboxylic acid ester copolymer, is intended to crosslinking. Specific examples thereof are as follows. Ethylene / acrylic acid copolymer, ethylene / methacrylic acid copolymer, ethylene / maleic anhydride copolymer, ethylene / lauryl methacrylate / methacrylic acid copolymer, propylene / styrene divinylbenzene / 2-ethylhexyl acrylate / maleic acid copolymer Polymer, ethylene / glycidyl methacrylate / methacrylic acid copolymer, butene / acrylic acid / ethylene glycol dimethacrylate polymer, and the like.
These may be random, block or graft copolymers.
In these copolymers, alpha --olefin fin is 30 to 95 wt% of the total copolymer, preferably 50 to 80 wt%, alpha, beta - unsaturated aliphatic carboxylic acid 30-0. 1wt%, preferably from 15 to 1 wt%, alpha, beta - unsaturated aliphatic carboxylate ester 70-3% by weight, preferably 50 to 10 wt%.
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 performed in the presence of a non-aqueous solvent.
As the non-aqueous solvent, 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 the commercial product names, Exxon Corporation, Isopar G, Isopar H, Isopar L, and Isopar M are used.
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。 For crosslinking, the copolymer is mixed with the non-aqueous solvent and heated to 60 to 150 ° C., preferably 90 to 120 ° C., to maintain the polymer in a dissolved, molten or dispersed state.
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 cross-linking agent include beryllium hydroxide, magnesium hydroxide, barium hydroxide, zinc, calcium, strontium, zinc oxide, titanium oxide, calcium carbonate, and organic amine includes n-hexylamine. , Hexamethylenediamine, triethylamine, pyridine, triethanolamine, metaxylenediamine and the like, and an organic amine can be used in combination with a metal crosslinking agent. The carboxyl group in the copolymer is crosslinked by the crosslinking agent.
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−不飽和脂肪族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 cross-linking, the components contained in these copolymers are solvated in a non-aqueous solvent such as kerosene, toluene, silicone oil, or fluorine oil. .
Component of the copolymer solvation alpha, beta - an unsaturated aliphatic carboxylic acid esters, solvated result, which contributes to fixing of the dispersion stability and coloring agents of the resulting resin solvent.
Monomers that solvate in the non-aqueous solvent include lauryl methacrylate, 2-ethylhexyl, methyl methacrylate, methacryl-modified silicone monomers, acrylic-modified fluorine monomers, and the like.
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。
When producing a colorant, the resin comprising the above copolymer is added to a non-aqueous solvent, mixed and stirred, and after the pigment is dispersed, a crosslinking agent is added and heated to obtain a colorant containing the pigment in the resin. It is done. If a crosslinking agent is not used, the binding force between the pigment and the resin is weak, the pigment and the resin are easily separated, the fixing property and dispersibility are deteriorated, and the life of the developer is also shortened. The kind of the crosslinking agent is the same as that in the case of producing the non-aqueous resin dispersion.
A pigment is 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 in electrophotographic developers, paints, printing inks and inkjet inks.
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、60〜150℃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。
There are two types of electrophotographic developers: dry type and wet type.
In the electrophotographic dry developer, carbon black is added to a resin dispersion composed of a non-aqueous solvent and mixed with stirring. Next, a crosslinking agent is added, and it crosslinks by heating to 60-150 degreeC. After producing the colorant thus obtained, the solvent is removed by heating. The obtained solid lump is powdered with a pulverizer to produce a toner. The particle size of the toner is generally 0.1 to 5 μm.
In the electrophotographic wet developer, carbon black is added to a resin dispersion composed of a non-aqueous solvent and mixed with stirring. Next, a crosslinking agent is added, and it crosslinks by heating to 60-150 degreeC. The colorant thus obtained is used.
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 heated to 60 to 150 ° C. for crosslinking. Next, carbon is added to the obtained product, a solvent is further added, and the mixture is stirred to obtain a paint. Due to the crosslinking, the adhesion and gloss of the coating were good.
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。
When used as a printing ink, the wet developer of the present invention can be used as it is.
For use as an ink jet ink, the wet developer of the present invention can be used as it is.
以下、実施例により本発明を更に詳細に説明する。 Hereinafter, the present invention will be described in more detail with reference to examples.
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 put therein and dissolved while stirring for 1 hour. In this, 10 weight part of zinc hydroxide was added, and it was made to react by stirring at 100 degreeC for 40 hours. Next, the obtained product was cooled with stirring to obtain a resin dispersion.
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 using an ethylene / lauryl methacrylate / methacrylic acid (60/30/10) copolymer instead of the copolymer of Example 1.
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 obtained in the same manner using an ethylene / methyl methacrylate / acrylic acid (60/30/10) copolymer instead of the copolymer of Example 1.
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 using the non-aqueous solvent of Example 3 with toluene instead of kerosene.
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
Instead of the cross-linking agent zinc hydroxide used in Example 1, 1.0 part by weight of metaxylenediamine and 2.0 parts by weight of magnesium hydroxide were added to obtain a resin dispersion in the same manner.
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, 20 parts by weight of carbon black was added, and the mixture was stirred for 4 hours to disperse the 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 and pulverized to prepare a dry toner average particle size of 10 μm.
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
300 ml capacity attritor, isoparaffin (Isopar M, manufactured by Exxon Chemical) 100 g, ethylene / stearyl methacrylate / methacrylic acid (70/20/10) copolymer 50 g, carbon black (Mitsubishi Chemical, carbon MA • 100) 10 g The mixture was stirred and dispersed at 90 ° C. for 2 hours. Next, 5 g of zinc hydroxide was added, and the mixture was kneaded and dispersed at 100 ° C. for 1 hour to obtain a colorant composition.
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 1-7
The others were processed under the same conditions without using the crosslinking agent used in the examples of Examples 1-7.
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, MA-100) and 100 g of isoparaffin (Isopar L, manufactured by Exxon Chemical) are placed in a 1 liter attritor, dispersed at 80 ° C. for 6 hours, and electrophotographic development An agent was created. When this developer was used for copying with a wet copying machine (Recopy FT-400i), the offset was regenerated at an image density of 1.28, resolution of 6.3 lines / mm, fixability of 78%, and a fixing temperature of 90-160 ° C. I did not.
The durability of the developer was 25,000 sheets.
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 also evaluated in the same manner as Example 1, and the following results were obtained. The results are shown in Table 1.
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 a dry toner using Recopy FT4060 and the colorant of Example 7 as a liquid toner evaluated using Recopy FT400i, the following results were obtained. Similarly, the results of Comparative Examples 6 and 7 are shown in Table 2.
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, 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.
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 inkjet ink, it had an image density of 1.44, an ejection property of 25 μm dots, and a light resistance of 1 year or longer.
On the other hand, the results of the conventional ink-jet ink (Seiko Epson Co., Ltd. Machjet ink) were 1.22 in image density, 80 µm dots in ejection performance, and 1 month or less in light resistance.
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 similarly used as a printing ink, a printed matter having high fixability, gloss and image density was obtained.
Claims (5)
該樹脂は、α,β−不飽和脂肪族カルボン酸エステルとα−オレフィンの共重合体、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−オレフィンの共重合体から選ばれ、
該樹脂中の、α,β−不飽和脂肪族カルボン酸エステル成分を該非水溶媒に溶媒和させて得られることを特徴とする樹脂分散液。
A resin dispersion obtained by heating a resin to 60 to 150 ° C. in the presence of a nonaqueous solvent, adding a crosslinking agent, and crosslinking the resin,
The resin is a copolymer of α, β-unsaturated aliphatic carboxylic acid ester and α-olefin, or α, β-unsaturated aliphatic carboxylic acid and α, β-unsaturated aliphatic carboxylic acid ester and α- Selected from olefin copolymers ,
A resin dispersion obtained by solvating an α, β-unsaturated aliphatic carboxylic acid ester component in the resin with the non-aqueous solvent.
該樹脂は、α,β−不飽和脂肪族カルボン酸とα−オレフィンの共重合体、α,β−不飽和脂肪族カルボン酸エステルとα−オレフィンの共重合体、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−オレフィンの共重合体から選ばれることを特徴とする樹脂分散液の製造方法。 A method for producing a resin dispersion in which a resin dispersion is produced by heating a resin to 60 to 150 ° C. in the presence of a nonaqueous solvent, adding a crosslinking agent, and crosslinking the resin,
The resin, alpha, beta - copolymers of unsaturated aliphatic carboxylic acids and α- olefin, alpha, beta - copolymers of unsaturated aliphatic carboxylic acid esters and α- olefin or alpha, beta - unsaturated aliphatic carboxylic acid alpha, beta - method for producing a resin dispersion, wherein is selected from copolymers of unsaturated aliphatic carboxylic acid esters and α- olefin.
前記樹脂中の、α,β−不飽和脂肪族カルボン酸エステル成分を該非水溶媒に溶媒和させて架橋することを特徴とする請求項3記載の樹脂分散液の製造方法。
The resin is a copolymer of the α, β-unsaturated aliphatic carboxylic acid ester and an α-olefin, or the α, β-unsaturated aliphatic carboxylic acid and the α, β-unsaturated aliphatic carboxylic acid ester. selected from α-olefin copolymers,
The method for producing a resin dispersion according to claim 3, wherein the α, β-unsaturated aliphatic carboxylic acid ester component in the resin is cross-linked by solvating the non-aqueous solvent.
The method for producing a resin dispersion according to claim 3 , wherein the crosslinking agent is selected from a crosslinking agent containing a metal or a metal compound, or an organic amine.
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