JP2009031823A - Toner for electrostatic image development - Google Patents
Toner for electrostatic image development Download PDFInfo
- Publication number
- JP2009031823A JP2009031823A JP2008291651A JP2008291651A JP2009031823A JP 2009031823 A JP2009031823 A JP 2009031823A JP 2008291651 A JP2008291651 A JP 2008291651A JP 2008291651 A JP2008291651 A JP 2008291651A JP 2009031823 A JP2009031823 A JP 2009031823A
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- JP
- Japan
- Prior art keywords
- toner
- particle size
- meth
- particles
- acrylate
- 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.)
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Landscapes
- Developing Agents For Electrophotography (AREA)
Abstract
【課題】 高解像度化及び高階調化に対する静電荷像現像用トナーを提供する
【解決手段】 少なくともスチレン−(メタ）アクリレート系共重合体である結着樹脂と着色剤と下記一般式（Ｉ）で表されるケトン化合物を含有するトナー用樹脂組成物からなり、体積平均粒径が４〜９μｍであり、且つ、体積平均粒径の４０％以下の粒径を有する粒子数の全粒子数に占める割合が９．０％以下であり、重合法により製造されることを特徴とする静電荷像現像用トナー。
【化１】
［式（Ｉ）中、Ｒ１はアルキル基、又はアルコキシ基を示し、Ｒ２はアルキル基、又はアルキルカルボニルオキシアルキル基を示す。］
【選択図】 なし
PROBLEM TO BE SOLVED: To provide a toner for developing an electrostatic charge image for high resolution and high gradation. SOLUTION: At least a binder resin and a colorant which are styrene- (meth) acrylate copolymers, and the following general formula (I) The total number of particles having a volume average particle size of 4 to 9 μm and a particle size of 40% or less of the volume average particle size. A toner for developing an electrostatic charge image, wherein the toner accounts for 9.0% or less and is produced by a polymerization method.
[Chemical 1]
[In formula (I), R 1 represents an alkyl group, or an alkoxy group, R 2 represents an alkyl group, or an alkylcarbonyloxy group. ]
[Selection figure] None
Description
本発明は、電子写真方式の画像形成方法における静電荷潜像を現像するための静電荷現像用トナーに関する。 The present invention relates to an electrostatic charge developing toner for developing an electrostatic latent image in an electrophotographic image forming method.
従来より、電子写真方式の画像形成方法として、光導電性物質からなる感光体を一様に帯電させ、次いで、露光せしめた後、露光された部分の電荷を消散させて静電荷潜像を形成し、露光されていない部分に荷電させたトナーを付着させることによってその静電荷潜像を可視化させて現像し、得られた可視像を転写紙等の転写材に転写せしめ、加熱、加圧等によってその可視像を転写材に定着させる方法が多用されている。 Conventionally, as an electrophotographic image forming method, a photoconductor made of a photoconductive material is uniformly charged, then exposed to light, and then the exposed portion of the charge is dissipated to form an electrostatic charge latent image. Then, the electrostatic latent image is visualized and developed by attaching a charged toner to an unexposed portion, and the resulting visible image is transferred to a transfer material such as transfer paper, and heated and pressed. For example, a method of fixing the visible image on a transfer material by a method such as the above is widely used.
そして、近年のコンピューターの普及、能力向上に伴い、文字画像等にとどまらず写真画像も取り扱われるに及び、それに対応して複写機やプリンターにおいては高解像度化や高階調化が求められているが、装置面での対応には限界があり、現像剤としてのトナー面での対応に期待が寄せられている。 With the recent spread of computers and improved capabilities, not only text images, but also photographic images are handled, and in response to this, copiers and printers are required to have higher resolution and higher gradation. However, there is a limit to the correspondence on the apparatus side, and expectation is expected on the correspondence on the toner side as a developer.
一方、従来のトナーの製造方法としては、結着樹脂と着色剤、或いは更に離型剤、帯電制御剤等を溶融混練した樹脂組成物を、粉砕し、分級することによる粉砕法が主として採られているが、この方法は、得られるトナー粒子の形状が不定形となって、高解像度化や高階調化には必ずしも適しておらず、又、小粒径化には限度があり、更に、分級工程が必要であることから経済的に不利であるという側面もあった。 On the other hand, as a conventional toner production method, a pulverization method by pulverizing and classifying a resin composition obtained by melt-kneading a binder resin and a colorant, or a release agent, a charge control agent, etc. is mainly employed. However, this method makes the shape of the obtained toner particles indefinite, and is not necessarily suitable for high resolution and high gradation, and there is a limit to reducing the particle size. There was also an aspect of being economically disadvantageous because a classification process was necessary.
これに対して、結着樹脂成分モノマーを着色剤等の存在下に懸濁重合する懸濁重合法、又は、結着樹脂成分モノマーを乳化重合して得られたエマルジョンを、着色剤等の存在下に攪拌することによって乳化粒子を凝集（会合）させる乳化重合凝集法等が用いられているが、前者懸濁重合法では、重合後の樹脂粒子の形状は真球であると共にトナーに適した粒径となって高画質化には適しているものの、粒径分布の制御が困難であって高解像度化及び高階調化には対応し得てはおらず、又、後者乳化重合凝集法では、高解像度化及び高階調化には一応の対応は可能であるものの、重合条件や凝集条件等による粒径分布が必ずしも安定しておらず、往々にして高解像度化及び高階調化に対応し得ない場合が発生するという問題があった。
本発明は、前述の従来技術に鑑みてなされたもので、従って、本発明は、高解像度化及び高階調化に対応し得る静電荷現像用トナーを提供することを目的とする。 The present invention has been made in view of the above-described prior art, and therefore, an object of the present invention is to provide an electrostatic charge developing toner that can cope with higher resolution and higher gradation.
本発明者等は、前記課題を解決すべく鋭意検討した結果、トナーの平均粒径を特定の範囲とすると共に、微小粒子の個数を特定の範囲とすることにより、前記目的が達成できることを見出し本発明を完成したもので、即ち、本発明は、少なくともスチレン−(メタ）アクリレート系共重合体である結着樹脂と着色剤と下記一般式（Ｉ）で表されるケトン化合物を含有するトナー用樹脂組成物からなり、体積平均粒径が４〜９μｍであり、且つ、体積平均粒径の４０％以下の粒径を有する粒子数の全粒子数に占める割合が９．０％以下であり、重合法により製造されることを特徴とする静電荷像現像用トナー、を要旨とする。
［式（Ｉ）中、Ｒ １ はアルキル基、又はアルコキシ基を示し、Ｒ ２ はアルキル基、又はアルキルカルボニルオキシアルキル基を示す。］
As a result of intensive studies to solve the above problems, the present inventors have found that the above object can be achieved by setting the average particle size of the toner within a specific range and the number of fine particles within a specific range. The present invention has been completed. That is, the present invention is a toner containing at least a binder resin that is a styrene- (meth) acrylate copolymer, a colorant, and a ketone compound represented by the following general formula (I). The volume average particle size is 4 to 9 μm, and the ratio of the number of particles having a particle size of 40% or less of the volume average particle size to the total number of particles is 9.0% or less. The gist of the toner is an electrostatic charge image developing toner produced by a polymerization method .
[In Formula (I), R 1 represents an alkyl group or an alkoxy group, and R 2 represents an alkyl group or an alkylcarbonyloxyalkyl group. ]
本発明によれば、高解像度化及び高階調化に対応し得る静電荷現像用トナーを提供することができる。 According to the present invention, it is possible to provide an electrostatic charge developing toner that can cope with higher resolution and higher gradation.
本発明において、トナー用樹脂組成物を構成する結着樹脂としては、特に限定されるものではなく、スチレン系樹脂、ポリエステル系樹脂、ポリアミド系樹脂、ポリカーボネート系樹脂、ポリ塩化ビニル系樹脂、ポリオレフィン系樹脂、ポリフェニレンエーテル系樹脂、ポリビニルブチラール系樹脂、ケトン系樹脂、アクリル系樹脂、フッ素系樹脂、ウレタン系樹脂、エポキシ系樹脂等、結着樹脂として一般に用いられている各種樹脂を用いることができる。中で、本発明においては、スチレン−（メタ）アクリレート系共重合体に代表されるスチレン系樹脂、及びポリエステル系樹脂が好ましい。 In the present invention, the binder resin constituting the resin composition for toner is not particularly limited, and is a styrene resin, polyester resin, polyamide resin, polycarbonate resin, polyvinyl chloride resin, polyolefin resin. Various resins that are generally used as binder resins, such as resins, polyphenylene ether resins, polyvinyl butyral resins, ketone resins, acrylic resins, fluorine resins, urethane resins, and epoxy resins, can be used. Among them, in the present invention, styrene resins represented by styrene- (meth) acrylate copolymers and polyester resins are preferable.
尚、結着樹脂は、ガラス転移温度が４０〜８０℃であるものが好ましく、５５〜７０℃であるのが更に好ましく、５８〜６５℃であるのが特に好ましい。ガラス転移温度が前記範囲未満では、トナーとしての保存安定性が低下する傾向となり、一方、前記範囲超過では、画像の転写材への定着が不良となったり、透明性の良好な画像を得ることが困難な傾向となる。 The binder resin preferably has a glass transition temperature of 40 to 80 ° C, more preferably 55 to 70 ° C, and particularly preferably 58 to 65 ° C. If the glass transition temperature is less than the above range, the storage stability as a toner tends to be reduced. On the other hand, if the glass transition temperature is above the above range, fixing of an image to a transfer material becomes poor or an image with good transparency can be obtained. Tends to be difficult.
また、本発明において、トナー用樹脂組成物を構成する着色剤としても、特に限定されるものではなく、トナー用着色剤として一般に用いられている各種の有機及び無機顔料、染料等を用いることができる。 In the present invention, the colorant constituting the toner resin composition is not particularly limited, and various organic and inorganic pigments, dyes and the like generally used as toner colorants may be used. it can.
例えば、ブラックトナーに用いられる着色剤としては、例えば、カーボンブラック、マグネタイト、アニリンブラック等が挙げられ、非磁性トナー用としてはカーボンブラックが、磁性トナー用としてはマグネタイトが、それぞれ好ましい。 For example, examples of the colorant used in the black toner include carbon black, magnetite, and aniline black. Carbon black is preferable for the non-magnetic toner, and magnetite is preferable for the magnetic toner.
尚、カーボンブラックとしては、ファーネス法で製造されたものが好ましく、ＢＥＴ法での窒素吸着による比表面積が２０〜５００ｍ２／ｇで、ジブチルフタレート（ＤＢＰ）吸油量が３０〜１５０ｍｌ／１００ｇのものが好ましい。又、非磁性一成分系負荷電性トナー用としては、純水中で沸騰させた後のカーボンブラック懸濁液のｐＨが６以下の酸性カーボンブラックが好ましい。 Carbon black produced by the furnace method is preferred, the specific surface area by nitrogen adsorption by the BET method is 20 to 500 m 2 / g, and the oil absorption of dibutyl phthalate (DBP) is 30 to 150 ml / 100 g. Is preferred. For non-magnetic one-component negatively charged toner, acidic carbon black having a pH of 6 or less after carbon black suspension after boiling in pure water is preferable.
また、イエロートナー用としては、例えば、Ｃ．Ｉ．ピグメント・イエロー１、同３、同７４、同９７、同９８等のアセト酢酸アリールアミド系モノアゾ黄色顔料、Ｃ．Ｉ．ピグメント・イエロー１２、同１３、同１４、同１７等のアセト酢酸アリールアミド系ジスアゾ黄色顔料、Ｃ．Ｉ．ピグメント・イエロー９３、同１５５等の縮合モノアゾ系黄色顔料、Ｃ．Ｉ．ピグメント・イエロー１０９、同１１０、同１３７、同１７３等のイソインドリン系顔料、Ｃ．Ｉ．ピグメント・イエロー１５０、同１８０、同１８５等のその他黄色顔料、及びＣ．Ｉ．ソルベント・イエロー１９、同７７、同７９、Ｃ．Ｉ．ディスパース・イエロー１６４等の黄色染料等が挙げられ、中で、Ｃ．Ｉ．ピグメント・イエロー１３、同１７、同７４、同９３、同１５０、同１５５、同１８０、同１８５の黄色顔料が好適である。 For yellow toner, for example, C.I. I. Pigment Yellow 1, 3, 74, 97, 98, etc. acetoacetic acid arylamide monoazo yellow pigments, C.I. I. Pigment Yellow 12, 13, 13, 14, etc., acetoacetic acid arylamide disazo yellow pigments, C.I. I. Condensed yellow pigments such as CI Pigment Yellow 93 and 155, C.I. I. Pigment Yellow 109, 110, 137, 173 and the like, isoindoline pigments such as C.I. I. Other yellow pigments such as C.I. Pigment Yellow 150, 180 and 185, and C.I. I. Solvent Yellow 19, 77, 79, C.I. I. Yellow dyes such as disperse yellow 164 and the like. I. Pigment Yellow 13, 17, 74, 93, 150, 155, 180, and 185 are preferred.
また、マゼンタトナー用としては、例えば、Ｃ．Ｉ．ピグメント・レッド４８、同４９：１、同５３：１、同５７、同５７：１、同８１、同１２２、同５、同１４６、同１８４、同２３８、Ｃ．Ｉ．ピグメント・バイオレット１９等の赤色若しくは紅色顔料、及びＣ．Ｉ．ソルベント・レッド４９、同５２、同５８、同８等の赤色染料等が挙げられ、中で、Ｃ．Ｉ．ピグメント・レッド５７：１、同１２２、同１４６、同１８４、同２３８、Ｃ．Ｉ．ピグメント・バイオレット１９等の赤色若しくは紅色顔料が好適である。 For magenta toner, for example, C.I. I. Pigment Red 48, 49: 1, 53: 1, 57, 57: 1, 81, 122, 5, 146, 184, 238, C.I. I. Red or red pigments such as CI Pigment Violet 19, and C.I. I. And red dyes such as Solvent Red 49, 52, 58, 8 and the like. I. Pigment Red 57: 1, 122, 146, 184, 238, C.I. I. Red or red pigments such as CI Pigment Violet 19 are preferred.
また、シアントナー用としては、例えば、Ｃ．Ｉ．ピグメント・ブルー１５：３、同１５：４等の銅フタロシアニン又はその誘導体系青色顔料、及びＣ．Ｉ．ピグメント・グリーン７、同３６（フタロシアニングリーン）等の緑色顔料等が挙げられ、中で、Ｃ．Ｉ．ピグメント・ブルー１５：３、同１５：４の青色顔料が好適である。 For cyan toner, for example, C.I. I. Pigment Blue 15: 3, 15: 4, etc., copper phthalocyanine or its derivative-based blue pigment, and C.I. I. And green pigments such as CI Pigment Green 7 and 36 (phthalocyanine green). I. Pigment blue 15: 3 and 15: 4 blue pigments are preferred.
尚、トナー用樹脂組成物における前記着色剤の含有量は、前記結着樹脂１００重量部に対して１〜１５重量部であるのが好ましく、２〜１０重量部であるのが更に好ましい。 The content of the colorant in the toner resin composition is preferably 1 to 15 parts by weight, and more preferably 2 to 10 parts by weight with respect to 100 parts by weight of the binder resin.
また、本発明におけるトナー用樹脂組成物は、少なくとも前記結着樹脂と前記着色剤を含有するが、更に、離型剤としてワックス類を含有するのが好ましく、そのワックス類としては、例えば、低分子量ポリエチレン、低分子量ポリプロピレン、エチレン−プロピレン共重合体等のポリオレフィン系ワックス、パラフィン系ワックス、ステアリン酸エステル、ベヘン酸エステル、モンタン酸エステル等の長鎖脂肪族基を有するエステル系ワックス、水添ヒマシ油、カルナバワックス等の植物系ワックス、ジステアリルケトン等の長鎖アルキル基を有するケトン、アルキル基を有するシリコーン、ステアリン酸等の高級脂肪酸、長鎖脂肪族アルコール、ペンタエリスリトール等と長鎖脂肪酸との（部分）エステル体、オレイン酸アミド、ステアリン酸アミド等の高級脂肪酸アミド等、公知のものを用いることができる。 Further, the toner resin composition in the present invention contains at least the binder resin and the colorant, and preferably contains a wax as a release agent. Polyolefin wax such as molecular weight polyethylene, low molecular weight polypropylene, ethylene-propylene copolymer, paraffin wax, ester wax having a long chain aliphatic group such as stearic acid ester, behenic acid ester, montanic acid ester, hydrogenated castor Oils, plant waxes such as carnauba wax, ketones having a long chain alkyl group such as distearyl ketone, silicones having an alkyl group, higher fatty acids such as stearic acid, long chain fatty alcohols, pentaerythritol and the like and long chain fatty acids (Partial) ester, oleic acid amide, steer Higher fatty acid amides, such as phosphate amides, can be a known.
本発明においては、これらの中で、下記一般式（Ｉ）で表されるケトン化合物が特に好ましい。
［式（Ｉ）中、Ｒ１はアルキル基、又はアルコキシ基を示し、Ｒ２はアルキル基、又はアルキルカルボニルオキシアルキル基を示す。］ [In Formula (I), R 1 represents an alkyl group or an alkoxy group, and R 2 represents an alkyl group or an alkylcarbonyloxyalkyl group. ]
ここで、Ｒ２がアルキルカルボニルオキシアルキル基であるときは、Ｒ１はアルコキシ基であるのが好ましく、又、Ｒ１、Ｒ２のアルキル基としては、炭素数が１０以上であり、１６以上であるのが好ましく、２０以上であるのが更に好ましい。又、Ｒ２のアルキルカルボニルオキシアルキル基としては、アルキルカルボニルオキシ基におけるアルキル基の炭素数は１０以上であり、１６以上であるのが好ましく、２０以上であるのが更に好ましく、カルボニルオキシアルキル基におけるアルキル基は、炭素数６以上の直鎖状であるのが好ましい。 Here, when R 2 is an alkylcarbonyloxyalkyl group, R 1 is preferably an alkoxy group, and the alkyl groups of R 1 and R 2 have 10 or more carbon atoms and 16 or more carbon atoms. It is preferable that it is 20 or more. In addition, as the alkylcarbonyloxyalkyl group of R 2, the alkyl group in the alkylcarbonyloxy group has 10 or more carbon atoms, preferably 16 or more, more preferably 20 or more, and a carbonyloxyalkyl group The alkyl group in is preferably a straight chain having 6 or more carbon atoms.
これらのケトン化合物の具体例としては、例えば、ジ−ｎ−デシルケトン、ジ−ｎ−ドデシルケトン、ジ−ｎ−ステアリルケトン、ジ−ｎ−エイコシルケトン、ジ−ｎ−ベヘニルケトン、ジ−ｎ−テトラコシルケトン等の脂肪族ケトン、セバシン酸ジドシル、セバシン酸ジステアリル、セバシン酸ジベヘニル等の脂肪族ジエステル、ラウリン酸ステアリル、ラウリン酸ベヘニル、ステアリン酸ステアリル、ステアリン酸ベヘニル、ベヘン酸ベヘニル等の脂肪族モノエステル等が挙げられる。尚、これらの中で、示差走査熱量計（ＤＳＣ）による吸熱ピークの半値幅が１５℃以下のものが特に好ましい。 Specific examples of these ketone compounds include, for example, di-n-decyl ketone, di-n-dodecyl ketone, di-n-stearyl ketone, di-n-eicosyl ketone, di-n-behenyl ketone, di-n. -Aliphatic ketones such as tetracosyl ketone, didosyl sebacate, distearyl sebacate, dibehenyl sebacate, etc., stearyl laurate, behenyl laurate, stearyl stearate, behenyl stearate, behenyl behenate, etc. An aliphatic monoester etc. are mentioned. Of these, those having a half-value width of an endothermic peak by a differential scanning calorimeter (DSC) of 15 ° C. or less are particularly preferable.
尚、トナー用樹脂組成物における前記ワックス類の含有量は、前記結着樹脂１００重量部に対して１〜２５重量部であるのが好ましく、５〜１５重量部であるのが更に好ましい。 The content of the wax in the toner resin composition is preferably 1 to 25 parts by weight, more preferably 5 to 15 parts by weight with respect to 100 parts by weight of the binder resin.
また、本発明におけるトナー用樹脂組成物は、必要に応じて、帯電制御剤を含有していてもよく、その帯電制御剤としては、例えば、ニグロシン系染料、４級アンモニウム塩系化合物、トリフェニルメタン系化合物、イミダゾール系化合物、ポリアミン系樹脂等の正荷電性帯電制御剤、又は、クロム、コバルト、アルミニウム、鉄等の金属含有アゾ系染料、サリチル酸若しくはアルキルサリチル酸のクロム、亜鉛、アルミニウム等の金属塩や金属錯体、ベンジル酸の金属塩や金属錯体、アミド化合物、フェノール化合物、ナフトール化合物、フェノールアミド化合物等の負荷電性帯電制御剤等、公知のものを用いることができる。 The toner resin composition of the present invention may contain a charge control agent as necessary. Examples of the charge control agent include nigrosine dyes, quaternary ammonium salt compounds, and triphenyl. Positive charge control agents such as methane compounds, imidazole compounds, polyamine resins, or metal-containing azo dyes such as chromium, cobalt, aluminum and iron, metals such as chromium, zinc and aluminum of salicylic acid or alkylsalicylic acid Known compounds such as negatively charged charge control agents such as salts and metal complexes, metal salts and metal complexes of benzylic acid, amide compounds, phenol compounds, naphthol compounds, and phenolamide compounds can be used.
更に、本発明におけるトナー用樹脂組成物は、トナーの粘着性、凝集性、流動性、帯電性、表面抵抗等の改質を目的として公知の各種内添剤等を更に含有していてもよい。 Furthermore, the resin composition for toner in the present invention may further contain various known internal additives for the purpose of modifying the adhesiveness, cohesiveness, fluidity, chargeability, surface resistance, etc. of the toner. .
本発明の静電荷像現像用トナーは、少なくとも前記結着樹脂と前記着色剤を含有するトナー用樹脂組成物からなり、体積平均粒径が４〜９μｍであり、且つ、体積平均粒径の４０％以下の粒径を有する粒子数の全粒子数に占める割合が９．０％以下であることを必須とし、体積平均粒径が５〜８μｍであるのが好ましく、５〜６μｍであるのが更に好ましく、又、体積平均粒径の４０％以下の粒径を有する粒子数の全粒子数に占める割合が６．０％以下であるのが好ましく、３．０％以下であるのが更に好ましい。 The electrostatic image developing toner of the present invention comprises a resin composition for toner containing at least the binder resin and the colorant, and has a volume average particle diameter of 4 to 9 μm and a volume average particle diameter of 40. It is essential that the ratio of the number of particles having a particle size of not more than% to the total number of particles is 9.0% or less, and the volume average particle size is preferably 5 to 8 μm, and more preferably 5 to 6 μm. More preferably, the ratio of the number of particles having a particle size of 40% or less of the volume average particle size to the total number of particles is preferably 6.0% or less, and more preferably 3.0% or less. .
体積平均粒径が前記範囲超過、又は、体積平均粒径の４０％以下の粒径を有する粒子数の全粒子数に占める割合が前記範囲超過の場合は、トナーとしての解像性、階調性に十分な改良効果を与えることができず、一方、体積平均粒径が前記範囲未満では、トナーとしての流動性が低下することとなる。尚、トナーの前記体積平均粒径及びその粒径分布は、ベックマン・コールター社製マルチサイザーにて測定したものである。 When the volume average particle size exceeds the above range, or the ratio of the number of particles having a particle size of 40% or less of the volume average particle size to the total number of particles exceeds the above range, resolution and gradation as a toner On the other hand, if the volume average particle diameter is less than the above range, the fluidity as a toner is lowered. The volume average particle size and the particle size distribution of the toner are measured with a multisizer manufactured by Beckman Coulter.
本発明の静電荷像現像用トナーの製造方法としては、特に限定されるものではなく、例えば、前記結着樹脂、前記着色剤、及び前記ワックス、前記帯電制御剤等を、例えばヘンシェルミキサー等の混合機により均一に混合した後、一軸又は二軸以上の押出機等の混練機により溶融混練してトナー用樹脂組成物となし、冷却固化させた後、例えばフェザーミル等により粗粉砕或いは更に中粉砕して粗粒子とした後、該粗粒子を、例えばジェットミル等により微粉砕し、得られた粉体を、例えばエルボジェット等の分級機により分級して規定粒度のトナー粒子とする粉砕法、前記結着樹脂成分モノマーを、前記着色剤、及び前記ワックス、前記帯電制御剤等の存在下に懸濁重合させる懸濁重合法、前記結着樹脂成分モノマーを乳化重合させたエモルジョンを、前記着色剤、及び前記ワックス、前記帯電制御剤等の存在下に攪拌して乳化粒子を凝集（会合）させる乳化重合凝集法等をあげることができるが、なかで、後者の重合法によるのが好ましく、その中でも乳化重合凝集法によるのが特に好ましい。 The method for producing the toner for developing an electrostatic image of the present invention is not particularly limited. For example, the binder resin, the colorant, the wax, the charge control agent, etc. After uniformly mixing with a mixer, melt and knead with a kneader such as a single or biaxial extruder to form a toner resin composition, and after cooling and solidifying, for example, coarsely pulverizing or further using a feather mill or the like After pulverizing coarse particles, the coarse particles are finely pulverized by, for example, a jet mill, and the obtained powder is classified by, for example, a classifier such as an elbow jet to obtain toner particles having a specified particle size. A suspension polymerization method in which the binder resin component monomer is subjected to suspension polymerization in the presence of the colorant, the wax, the charge control agent, etc., and an emo obtained by emulsion polymerization of the binder resin component monomer. An emulsion polymerization aggregation method in which John is agitated in the presence of the colorant, the wax, the charge control agent, and the like to agglomerate (aggregate) the emulsion particles. Of these, the emulsion polymerization aggregation method is particularly preferable.
その乳化重合凝集法について、好ましいとするスチレン系樹脂について更に詳述すると、例えば、スチレン、α−メチルスチレン、α−エチルスチレン等のα−置換アルキルスチレン、ｍ−メチルスチレン、ｐ−メチルスチレン、２，５−ジメチルスチレン等の核置換スチレン、ｐ−クロロスチレン、ｐ−ブロモスチレン、ジブロモスチレン等の核置換ハロゲン化スチレン等のスチレン類を単独で、又は、それらのスチレン類と、メチル（メタ）アクリレート、エチル（メタ）アクリレート、プロピル（メタ）アクリレート、ブチル（メタ）アクリレート、ペンチル（メタ）アクリレート、ヘキシル（メタ）アクリレート、２−エチルヘキシル（メタ）アクリレート、グリシジル（メタ）アクリレート、ベンジル（メタ）アクリレート等の単官能アクリレート、エチレングリコールジ（メタ）アクリレート、ジエチレングリコールジ（メタ）アクリレート、プロピレングリコールジ（メタ）アクリレート、テトラメチレングリコールジ（メタ）アクリレート、ネオペンチルグリコールジ（メタ）アクリレート、ヘキサメチレングリコールジ（メタ）アクリレート、トリメチロールプロパンジ（メタ）アクリレート、トリメチロールプロパントリ（メタ）アクリレート、グリセロールジ（メタ）アクリレート、グリセロールトリ（メタ）アクリレート、ペンタエリスリトールジ（メタ）アクリレート、ペンタエリスリトールトリ（メタ）アクリレート、ペンタエリスリトールテトラ（メタ）アクリレート、ジペンタエリスリトールジ（メタ）アクリレート、ジペンタエリスリトールトリ（メタ）アクリレート、ジペンタエリスリトールテトラ（メタ）アクリレート、ジペンタエリスリトールペンタ（メタ）アクリレート、ジペンタエリスリトールヘキサ（メタ）アクリレート、ソルビトールトリ（メタ）アクリレート、ソルビトールテトラ（メタ）アクリレート、ソルビトールペンタ（メタ）アクリレート、ソルビトールヘキサ（メタ）アクリレート等の多官能アクリレート等のアクリレート類、又は、更に（メタ）アクリル酸（尚、以上の例示における「（メタ）アクリル」とは、アクリル及びメタクリルを意味するものとする。）とを、過酸化水素等の重合開始剤の存在下に、カチオン系、アニオン系、又はノニオン系等の界面活性剤を乳化剤として乳化重合或いは共重合せしめ、得られた単独重合体或いは共重合体の乳化液を、前記着色剤、及び前記ワックス、前記帯電制御剤等と共に、所定の温度でディスパーザー等で攪拌することにより、微小１次粒子を凝集（会合）させることにより、トナー粒子を製造するものである。 The styrene resin that is preferred for the emulsion polymerization aggregation method will be described in more detail. For example, α-substituted alkylstyrene such as styrene, α-methylstyrene, α-ethylstyrene, m-methylstyrene, p-methylstyrene, Styrenes such as nucleus-substituted styrenes such as 2,5-dimethylstyrene, nucleus-substituted halogenated styrenes such as p-chlorostyrene, p-bromostyrene, and dibromostyrene are used alone, or these styrenes and methyl (meta ) Acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, glycidyl (meth) acrylate, benzyl (meth) ) Single officers such as acrylate Acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, tetramethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, hexamethylene glycol di (meth) Acrylate, trimethylolpropane di (meth) acrylate, trimethylolpropane tri (meth) acrylate, glycerol di (meth) acrylate, glycerol tri (meth) acrylate, pentaerythritol di (meth) acrylate, pentaerythritol tri (meth) acrylate, Pentaerythritol tetra (meth) acrylate, dipentaerythritol di (meth) acrylate, dipentaerythritol tri (Meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, sorbitol tri (meth) acrylate, sorbitol tetra (meth) acrylate, sorbitol penta (meth) Acrylates, acrylates such as polyfunctional acrylates such as sorbitol hexa (meth) acrylate, or (meth) acrylic acid (in addition, “(meth) acryl” in the above examples means acrylic and methacrylic) In the presence of a polymerization initiator such as hydrogen peroxide, and emulsion polymerization or copolymerization using a cationic, anionic, or nonionic surfactant as an emulsifier, and the resulting homopolymer or Emulsification of copolymer A toner is produced by aggregating (associating) fine primary particles by stirring the liquid together with the colorant, the wax, the charge control agent, and the like with a disperser or the like at a predetermined temperature. It is.
ここで、乳化剤としてのカチオン系界面活性剤としては、例えば、ドデシルアンモニウムクロライド、ドデシルアンモニウムブロマイド、ドデシルトリメチルアンモニウムブロマイド、ドデシルピリジニウムクロライド、ドデシルピリジニウムブロマイド、ヘキサデシルトリメチルアンモニウムブロマイド等が、又、アニオン系界面活性剤としては、例えば、ステアリン酸ナトリウム、ドデカン酸ナトリウム等の脂肪酸石鹸、硫酸ドデシルナトリウム、ドデシルベンゼンスルホン酸ナトリウム等が、又、ノニオン系界面活性剤としては、例えば、ドデシルポリオキシエチレンエーテル、ヘキサデシルポリオキシエチレンエーテル、ノニルフェニルポリオキシエチレンエーテル、ラウリルポリオキシエチレンエーテル、ソルビタンモノオレエートポリオキシエチレンエーテル、スチリルフェニルポリオキシエチレンエーテル、モノデカノイル蔗糖等が挙げられ、これらの中で、アニオン系界面活性剤、又はノニオン系界面活性剤が好ましい。 Here, as the cationic surfactant as an emulsifier, for example, dodecyl ammonium chloride, dodecyl ammonium bromide, dodecyl trimethyl ammonium bromide, dodecyl pyridinium chloride, dodecyl pyridinium bromide, hexadecyl trimethyl ammonium bromide, and the anionic interface Examples of the activator include fatty acid soaps such as sodium stearate and sodium dodecanoate, sodium dodecyl sulfate, sodium dodecylbenzenesulfonate, and the like. Nonionic surfactants include, for example, dodecyl polyoxyethylene ether, hexa Decyl polyoxyethylene ether, nonylphenyl polyoxyethylene ether, lauryl polyoxyethylene ether, sorbitan monoolea Polyoxyethylene ethers, styryl phenyl polyoxyethylene ether, Monodekanoiru sucrose and the like, among these, anionic surfactants, or nonionic surfactants are preferred.
本発明の静電荷像現像用トナーの体積平均粒径、及び体積平均粒径の４０％以下の粒径を有する粒子数の全粒子数に占める割合は、前記製造方法における、乳化重合時の界面活性剤の種類と量、凝集時のｐＨ、攪拌条件、凝集時に必要に応じて用いられる有機溶剤、無機塩等の種類と量、凝集処理時間等で調整することができる。 The ratio of the volume average particle diameter of the toner for developing an electrostatic charge image of the present invention and the number of particles having a particle diameter of 40% or less of the volume average particle diameter to the total number of particles is an interface at the time of emulsion polymerization in the production method. It can be adjusted by the type and amount of the activator, the pH at the time of aggregation, the stirring conditions, the type and amount of the organic solvent and inorganic salt used as necessary at the time of aggregation, the aggregation treatment time, and the like.
尚、本発明の静電荷像現像用トナーは、通常、前記方法で得られたトナー粒子に、トナー用として一般に用いられているシリカ、アルミナ、チタニア等の無機質微粉末を外添剤として添加し、例えばヘンシェルミキサー等の混合機により均一に混合し、トナー粒子の粒子表面にこれらの無機質微粉末を被覆させることにより用いられる。その際の無機質微粉末としては、例えばシランカップリング剤又はシリコーンオイル等で表面処理されたものが好ましく、比表面積が５〜５００ｍ2 ／ｇであるものが更に好ましい。 The toner for developing an electrostatic charge image of the present invention is usually obtained by adding inorganic fine powders such as silica, alumina, and titania generally used for toner as an external additive to the toner particles obtained by the above method. For example, the toner particles are uniformly mixed by a mixer such as a Henschel mixer, and the surface of the toner particles is coated with these inorganic fine powders. As the inorganic fine powder at that time, for example, those treated with a silane coupling agent or silicone oil are preferable, and those having a specific surface area of 5 to 500 m @ 2 / g are more preferable.
また、本発明の静電荷像現像用トナーは、トナーを磁力により静電潜像部に搬送するためのキャリアとしてのフェライト、マグネタイト等の磁性粉を共存させる磁性二成分用、及び、それらの磁性粉をトナー中に含有させた磁性一成分用、トナーに磁性粉を用いない非磁性一成分用のいずれにも用いられるが、非磁性一成分用、又は磁性一成分用として好適に用いられる。 In addition, the electrostatic image developing toner of the present invention is a magnetic two-component toner in which magnetic powders such as ferrite and magnetite coexist as a carrier for conveying the toner to the electrostatic latent image portion by magnetic force, and their magnetic properties. It can be used for either a magnetic one component containing powder in the toner or a non-magnetic one component that does not use magnetic powder in the toner, but is preferably used for a non-magnetic one component or a magnetic one component.
以下、本発明を実施例により更に具体的に説明するが、本発明はその要旨を越えない限り、以下の実施例に限定されるものではない。 EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples. However, the present invention is not limited to the following examples unless it exceeds the gist.
実施例１
ガラス製反応器に、ベヘン酸ベヘニルを主成分とするエステルワックスのエマルジョン（日本油脂社製「ユニスターＭ２２２２ＳＬ」）を固形分として１０重量部、ドデシルベンゼンスルホン酸を０．４重量部、脱イオン水を前記エマルジョン中の分も併せて４００重量部仕込み、窒素気流下で９０℃に昇温した後、スチレン８０重量部、ブチルアクリレート２０重量部、アクリル酸３重量部、トリクロロブロモメタン１重量部、２％過酸化水素水溶液４３重量部、及び２％アスコルビン酸水溶液４３重量部を仕込み、攪拌下に７時間乳化共重合させ、冷却することにより、スチレン−ブチルアクリレート−アクリル酸共重合体の一次粒子エマルジョンを得た。
Example 1
In a glass reactor, 10 parts by weight of an ester wax emulsion (“Unistar M2222SL” manufactured by NOF Corporation) containing behenyl behenate as a main component, 0.4 parts by weight of dodecylbenzenesulfonic acid, deionized water 400 parts by weight together with the amount in the emulsion, heated to 90 ° C. under a nitrogen stream, 80 parts by weight of styrene, 20 parts by weight of butyl acrylate, 3 parts by weight of acrylic acid, 1 part by weight of trichlorobromomethane, Primary particles of styrene-butyl acrylate-acrylic acid copolymer were prepared by charging 43 parts by weight of 2% aqueous hydrogen peroxide solution and 43 parts by weight of 2% ascorbic acid aqueous solution, followed by emulsion copolymerization with stirring for 7 hours and cooling. An emulsion was obtained.
次いで、前記一次粒子エマルジョンを固形分として１２０重量部、青色色素フタロシアニン（大日精化社製）を７重量部、帯電制御剤（オリエント化学社製「ボントロンＥ−８２」（５％分散液））を固形分として１重量部の割合の混合物を、ｐＨ２．６としてディスパーザーで攪拌しながら７０℃に昇温し３時間保持した後、ｐＨを７に調節し、９５℃に昇温して２時間保持した。得られたスラリーを冷却し、濾過、水洗し、４５℃の送風乾燥機で１０時間乾燥させることにより静電荷像現像用トナーを得た。 Next, 120 parts by weight of the primary particle emulsion as a solid content, 7 parts by weight of a blue pigment phthalocyanine (manufactured by Dainichi Seika Co., Ltd.), a charge control agent (“Bontron E-82” (5% dispersion) manufactured by Orient Chemical Co., Ltd.) 1 part by weight of the mixture as a solid content was heated to 70 ° C. while stirring with a disperser at pH 2.6 and held for 3 hours, then the pH was adjusted to 7, and the temperature was raised to 95 ° C. to 2 Held for hours. The obtained slurry was cooled, filtered, washed with water, and dried for 10 hours in a 45 ° C. blow dryer to obtain an electrostatic image developing toner.
得られたトナーについて、ベックマン・コールター社製マルチサイザーを用いて体積平均粒径及びその粒径分布を測定し、その体積平均粒径、及びその体積平均粒径の４０％以下の粒径を有する粒子数の全粒子数に占める割合を算出し、結果を表１に示した。 About the obtained toner, the volume average particle diameter and the particle diameter distribution thereof are measured using a multisizer manufactured by Beckman Coulter, and the volume average particle diameter and the particle diameter is 40% or less of the volume average particle diameter. The ratio of the number of particles to the total number of particles was calculated, and the results are shown in Table 1.
更に、得られたトナーに、シランカップリング剤で表面処理され比表面積が１１０ｍ２／ｇのシリカ（日本アエロジル社製「Ｒ９７２」）をトナー１００重量部当たり０．６重量部添加して、ヘンシェルミキサーで混合して得たトナーを、レーザープリンターの現像機内に入れ、１２００ｄｐｉの細線を１ラインおきに黒・白を繰り返し出力する解像度チャート、及び、１２００ｄｐｉの細線を２ラインずつ黒黒・白白を繰り返し出力する解像度チャートの二種類を出力し、そのチャートの解像度を以下の基準で評価し、結果を表１に示した。 Further, 0.6 parts by weight of silica (“R972” manufactured by Nippon Aerosil Co., Ltd.) having a specific surface area of 110 m 2 / g and surface-treated with a silane coupling agent was added to the obtained toner per 100 parts by weight of the toner. The toner obtained by mixing with a mixer is placed in a developing machine of a laser printer, and a resolution chart that repeatedly outputs black and white every other line of 1200 dpi, and black and white and white and white of 1200 dpi thin lines by two lines. Two types of resolution charts to be output repeatedly were output, the resolution of the charts was evaluated according to the following criteria, and the results are shown in Table 1.
○；細線が完全に分離している。
△；細線の分離が不完全である。
×；細線が分離していない。
○: Fine lines are completely separated.
Δ: Fine line separation is incomplete.
X: Fine lines are not separated.
実施例２〜９、比較例１〜２実施例１において得られた一次粒子エマルジョンを攪拌、凝集させるにおける温度と時間を変更することにより、表１に示す各種の体積平均粒径、及びその体積平均粒径の４０％以下の粒径を有する粒子数の全粒子数に占める割合を有するトナーを製造し、得られた各トナーを用いて実施例１と同様にして、解像度を評価し、結果を表１に示した。 Examples 2 to 9 and Comparative Examples 1 and 2 By changing the temperature and time for stirring and aggregating the primary particle emulsions obtained in Example 1, various volume average particle diameters shown in Table 1, and their volumes A toner having a ratio of the number of particles having a particle size of 40% or less of the average particle size to the total number of particles was produced, and the resolution was evaluated in the same manner as in Example 1 using each of the obtained toners. Is shown in Table 1.
Claims (5)
［式（Ｉ）中、Ｒ １ はアルキル基、又はアルコキシ基を示し、Ｒ ２ はアルキル基、又はアルキルカルボニルオキシアルキル基を示す。］ It comprises a resin composition for toner containing at least a binder resin that is a styrene- (meth) acrylate copolymer, a colorant, and a ketone compound represented by the following general formula (I), and has a volume average particle size of 4 to 4 An electrostatic charge characterized by being produced by a polymerization method , wherein the proportion of the number of particles having a particle size of 9 μm and a volume average particle size of 40% or less to the total number of particles is 9.0% or less. Toner for image development.
[In Formula (I), R 1 represents an alkyl group or an alkoxy group, and R 2 represents an alkyl group or an alkylcarbonyloxyalkyl group. ]
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| JP36238999A Division JP2001175024A (en) | 1999-12-21 | 1999-12-21 | Toner for developing electrostatic images |
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| JPH1184737A (en) * | 1997-09-03 | 1999-03-30 | Minolta Co Ltd | Negatively electrostatic-chageable toner |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0822138A (en) * | 1994-07-05 | 1996-01-23 | Toshiba Corp | Non-magnetic one-component developer and developing method using the same |
| JPH08184989A (en) * | 1994-12-27 | 1996-07-16 | Canon Inc | Magnetic toner and image forming method |
| JPH0934170A (en) * | 1995-07-21 | 1997-02-07 | Mitsubishi Chem Corp | Toner for developing electrostatic images |
| JPH0996920A (en) * | 1995-07-21 | 1997-04-08 | Mitsubishi Chem Corp | Toner for developing electrostatic images |
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| JPH10309531A (en) * | 1997-05-08 | 1998-11-24 | Mitsubishi Chem Corp | Powder classification method |
| JPH1165172A (en) * | 1997-08-21 | 1999-03-05 | Minolta Co Ltd | Yellow developer |
| JPH1172946A (en) * | 1997-08-29 | 1999-03-16 | Minolta Co Ltd | Image forming method and toner used for that method |
| JPH1184737A (en) * | 1997-09-03 | 1999-03-30 | Minolta Co Ltd | Negatively electrostatic-chageable toner |
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