JP2013133450A5 - - Google Patents
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- JP2013133450A5 JP2013133450A5 JP2011286212A JP2011286212A JP2013133450A5 JP 2013133450 A5 JP2013133450 A5 JP 2013133450A5 JP 2011286212 A JP2011286212 A JP 2011286212A JP 2011286212 A JP2011286212 A JP 2011286212A JP 2013133450 A5 JP2013133450 A5 JP 2013133450A5
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- fine particles
- aqueous dispersion
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- resin fine
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- 229920005989 resin Polymers 0.000 claims description 63
- 239000011347 resin Substances 0.000 claims description 63
- 239000010419 fine particle Substances 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 29
- 239000006185 dispersion Substances 0.000 claims description 29
- 238000004519 manufacturing process Methods 0.000 claims description 26
- 150000003512 tertiary amines Chemical class 0.000 claims description 19
- 238000004945 emulsification Methods 0.000 claims description 10
- 239000003086 colorant Substances 0.000 claims description 8
- 239000002245 particle Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 239000008346 aqueous phase Substances 0.000 claims description 6
- -1 amino cation Chemical class 0.000 claims description 5
- 239000007771 core particle Substances 0.000 claims description 5
- 230000004927 fusion Effects 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 230000002776 aggregation Effects 0.000 claims description 4
- 239000003945 anionic surfactant Substances 0.000 claims description 4
- 230000015271 coagulation Effects 0.000 claims description 4
- 238000005345 coagulation Methods 0.000 claims description 4
- 239000000839 emulsion Substances 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 4
- IWSZDQRGNFLMJS-UHFFFAOYSA-N 2-(dibutylamino)ethanol Chemical compound CCCCN(CCO)CCCC IWSZDQRGNFLMJS-UHFFFAOYSA-N 0.000 claims description 3
- AKNUHUCEWALCOI-UHFFFAOYSA-N 2-[ethyl(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 claims description 3
- 229940013085 2-diethylaminoethanol Drugs 0.000 claims description 3
- BFSVOASYOCHEOV-UHFFFAOYSA-N Diethylethanolamine Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 3
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical group CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 3
- 238000004220 aggregation Methods 0.000 claims description 3
- DIAIBWNEUYXDNL-UHFFFAOYSA-N N,N-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 claims description 2
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N N,N-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 claims description 2
- OOHAUGDGCWURIT-UHFFFAOYSA-N N,N-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Tris Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 229920001225 Polyester resin Polymers 0.000 claims 1
- 239000004645 polyester resin Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000004432 carbon atoms Chemical group C* 0.000 description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 description 5
- 230000004931 aggregating Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002738 chelating agent Substances 0.000 description 2
- 238000007499 fusion processing Methods 0.000 description 2
- 239000003002 pH adjusting agent Substances 0.000 description 2
- 239000010420 shell particle Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- SWZDQOUHBYYPJD-UHFFFAOYSA-N Tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000001737 promoting Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Description
本発明は、
酸基を有する樹脂、及びアニオン性界面活性剤を混合して混合物を得る混合工程と、
該酸基を有する樹脂のガラス転移点以上の温度で、水系媒体、酸、下記式１で表される３級アミン及び該混合物を撹拌し、樹脂乳化物を得る乳化工程と、
を有する樹脂微粒子の水系分散体の製造方法であって、
該乳化工程において、水相中における、該３級アミンと該酸とから生成するアミノカチオンの濃度が、臨界凝集濃度以下である
ことを特徴とする樹脂微粒子の水系分散体の製造方法である。
ＮＲ１Ｒ２Ｒ３ 式１
［式１において、Ｒ１、Ｒ２、及びＲ３は、それぞれ、ヒドロキシル基を有していてもよい炭素数１以上８以下の炭化水素基を表す。］
また、本発明は、
酸基を有する樹脂、及び該酸基を有する樹脂が可溶な溶剤を混合して混合物を得る混合工程と、
水系媒体、酸、アニオン性界面活性剤、下記式１で表される３級アミン、及び該混合物を撹拌し、樹脂乳化物を得る乳化工程と、
を有する樹脂微粒子の水系分散体の製造方法であって、
該乳化工程において、水相中における、該３級アミンと該酸とから生成するアミノカチオンの濃度が、臨界凝集濃度以下である
ことを特徴とする樹脂微粒子の水系分散体の製造方法である。
ＮＲ １ Ｒ ２ Ｒ ３ 式１
［式１において、Ｒ １ 、Ｒ ２ 、及びＲ ３ は、それぞれ、ヒドロキシル基を有していてもよい炭素数１以上８以下の炭化水素基を表す。］
また、本発明は、
上記樹脂微粒子の水系分散体の製造方法で樹脂微粒子の水系分散体を製造する工程と、
該樹脂微粒子と着色剤とを混合し、該樹脂微粒子及び該着色剤を水系媒体中で凝集させて凝集体を形成する凝集工程と、
前記凝集体を加熱し、融合させる融合工程と、
を有するトナーの製造方法である。
また、本発明は、
上記樹脂微粒子の水系分散体の製造方法で樹脂微粒子の水系分散体を製造する工程と、
樹脂、及び着色剤を含有するコア粒子の表面に、該樹脂微粒子の水系分散体中の該樹脂微粒子を付着させる付着工程と、
を有するトナーの製造方法である。
The present invention
A mixing step of obtaining a resin, and mixed to the mixture of anionic surfactants having an acid group,
An emulsification step of stirring the aqueous medium, the acid, the tertiary amine represented by the following formula 1 and the mixture at a temperature equal to or higher than the glass transition point of the resin having an acid group to obtain a resin emulsion ;
A method of manufacturing an aqueous dispersion of resin fine particles have a,
In emulsification step, in the aqueous phase, the concentration of amino cation generated from the said tertiary amine and the acid is not more than the critical coagulation concentration
Ru manufacturing method der the aqueous dispersion of resin fine particles, characterized in that.
NR 1 R 2 R 3 Formula 1
[In formula 1, R 1, R 2, and R 3, respectively, to display the good number 1 to 8 hydrocarbon group carbon atoms which may have a hydroxyl group. ]
The present invention also provides:
A mixing step of mixing a resin having an acid group and a solvent in which the resin having an acid group is soluble;
An emulsification step of stirring a water-based medium, an acid, an anionic surfactant, a tertiary amine represented by the following formula 1, and the mixture to obtain a resin emulsion;
A method for producing an aqueous dispersion of resin fine particles having
In the emulsification step, the concentration of the amino cation generated from the tertiary amine and the acid in the aqueous phase is not more than the critical aggregation concentration.
This is a method for producing an aqueous dispersion of resin fine particles.
NR 1 R 2 R 3 Formula 1
[In Formula 1, R 1 , R 2 , and R 3 each represent a hydrocarbon group having 1 to 8 carbon atoms that may have a hydroxyl group. ]
The present invention also provides:
A step of producing an aqueous dispersion of resin fine particles by the method for producing an aqueous dispersion of resin fine particles,
An aggregating step of mixing the resin fine particles and the colorant, and aggregating the resin fine particles and the colorant in an aqueous medium to form an aggregate;
A fusion step of heating and fusing the aggregates;
A method for producing a toner having the following.
The present invention also provides:
A step of producing an aqueous dispersion of resin fine particles by the method for producing an aqueous dispersion of resin fine particles,
An attachment step of attaching the resin fine particles in the aqueous dispersion of the resin fine particles to the surface of the core particles containing the resin and the colorant;
A method for producing a toner having the following.
本発明に用いられる酸基を有する樹脂は、酸価が１ｍｇＫＯＨ／ｇ以上３０ｍｇＫＯＨ／ｇ以下であることが好ましい。樹脂の酸価が１以上であれば、トナーとした際に帯電性が高く、飛散やかぶりが抑制される。また、酸価が３０以下であれば、樹脂の吸湿が抑制され、温度の異なる環境下においても、トナー特性が変動しにくい。 The resin having an acid group used in the present invention preferably has an acid value of 1 mgKOH / g or more and 30 mgKOH / g or less . When the acid value of the resin is 1 or more, the chargeability is high when the toner is used, and scattering and fogging are suppressed. Further, if the acid value is 30 or less, the moisture absorption of the resin is suppressed, and the toner characteristics hardly change even in environments with different temperatures.
本発明における３級アミンと酸の量は、水相中のアミノカチオンの濃度が臨界凝集濃度以下となればよいが、３級アミンと酸のいずれかの量が多いと、例えば樹脂ポリエステルを使用した場合、水相のｐＨが、塩基性または酸性に偏る場合があり、樹脂の加水分解を促進してしまう。このことから、３級アミンと酸は、等モル量添加することが好ましい。 本発明における乳化工程では、水系媒体、酸、下記式１で表される３級アミン及び混合物の撹拌が行われる。
ＮＲ１Ｒ２Ｒ３ 式１
［式１において、Ｒ１、Ｒ２、及びＲ３は、それぞれ、ヒドロキシル基を有していてもよい炭素数１以上８以下の炭化水素基を表す。］
In the present invention, the amount of the tertiary amine and the acid may be such that the concentration of the amino cation in the aqueous phase is not more than the critical aggregation concentration. If you, pH of the aqueous phase, may Ru polarized in basic or acidic, thereby promoting the hydrolysis of resin. From this, it is preferable to add equimolar amounts of the tertiary amine and the acid. In the emulsification step in the present invention, an aqueous medium, an acid, a tertiary amine represented by the following formula 1 and a mixture are stirred.
NR 1 R 2 R 3 Formula 1
[In formula 1, R 1, R 2, and R 3, respectively, to display the good number 1 to 8 hydrocarbon group carbon atoms which may have a hydroxyl group. ]
式１におけるＲ１、Ｒ２、Ｒ３は、それぞれ、炭素数１以上８以下の炭化水素基、もしくはヒドロキシル基を有する炭素数１以上３以下の炭化水素基であることが好ましい。また、式１におけるＲ１、Ｒ２、Ｒ３は、それぞれ、炭素数１以上８以下の炭化水素基、もしくはヒドロキシル基を有する炭素数２の炭化水素基であることがより好ましい。３級アミンとしては、具体的には、以下の化合物が挙げられる。２−（ジメチルアミノ）エタノール、２−ジエチルアミノエタノール、２−（ジブチルアミノ）エタノール、Ｎ−エチルジエタノールアミン、トリエタノールアミン、トリエチルアミン、トリプロピルアミン、トリアミルアミン、トリヘキシルアミン、トリ−ｎ−オクチルアミン、トリドデシルアミン。これらの３級アミンの中でも、樹脂微粒子の水系分散体の保存安定性の観点から、２−（ジメチルアミノ）エタノール、２−ジエチルアミノエタノール、２−（ジブチルアミノ）エタノール、Ｎ−エチルジエタノールアミンからなる群から選択される１以上の３級アミンを用いることが特に好ましい。 R 1, R 2, R 3 in Formula 1, respectively, is preferably a hydrocarbon group having 1 to 3 carbon atoms having a hydrocarbon group or a hydroxyl group, having 1 to 8 carbon atoms. R 1 , R 2 and R 3 in Formula 1 are each more preferably a hydrocarbon group having 1 to 8 carbon atoms or a hydrocarbon group having 2 carbon atoms having a hydroxyl group. Specific examples of the tertiary amine include the following compounds. 2- (dimethylamino) ethanol, 2-diethylaminoethanol, 2- (dibutylamino) ethanol, N-ethyldiethanolamine, triethanolamine, triethylamine, tripropylamine, triamylamine, trihexylamine, tri-n-octylamine , Tridodecylamine. Among these tertiary amines, the group consisting of 2- (dimethylamino) ethanol, 2-diethylaminoethanol, 2- (dibutylamino) ethanol, and N-ethyldiethanolamine from the viewpoint of storage stability of the aqueous dispersion of resin fine particles. It is particularly preferred to use one or more tertiary amines selected from
３級アミンは、ＳＰ値が１７以上２８以下であることが好ましく、１９以上２５以下であることがより好ましい。３級アミンのＳＰ値が前記範囲内であることによって、樹脂微粒子の水系分散体の保存安定性が良好となる。 The tertiary amine preferably has an SP value of 17 or more and 28 or less , and more preferably 19 or more and 25 or less . When the SP value of the tertiary amine is within the above range, the storage stability of the aqueous dispersion of resin fine particles is improved.
＜トナーの製造方法＞
本発明で得られた樹脂微粒子の水系分散体は、凝集法等のトナーの製造に用いることが可能である。凝集法によってトナーを製造する場合、上記樹脂微粒子の水系分散体と着色剤とを混合し、樹脂微粒子及び着色剤を水系媒体中で凝集させて凝集体を形成する凝集工程、前記凝集体を加熱し、融合させる融合工程を経て、トナーを得る。以下、トナーの製造方法について詳細に説明するが、本発明におけるトナーの製造方法は下記方法に限定されるものではない。
<Toner production method>
The aqueous dispersion of resin fine particles obtained in the present invention can be used for toner production such as an agglomeration method. When the toner is produced by a coagulation method, by mixing the colorant with an aqueous dispersion of the resin fine particles, aggregating step of forming an aggregate of the resin fine particles and colorant are aggregated in an aqueous medium, heating the aggregates and, through the fusion process Ru fused to obtain toner. Hereinafter, the toner production method will be described in detail, but the toner production method in the present invention is not limited to the following method.
融合工程とは、上記凝集体を、第一の樹脂のガラス転移点（Ｔｇ）以上に加熱し、融合させることで、凝集体表面を平滑化させたトナー粒子（コア粒子）を得る工程である。本工程により、上記凝集体の表面積が減少し、良好な形状のトナー粒子を得ることが可能になる。また、後述の付着工程にてシェル粒子を付着させる場合、シェル粒子が効率的にコア粒子に付着する。一次融合工程に入る前に、トナー粒子間の融着を防ぐため、キレート剤、ｐＨ調整剤、界面活性剤等を適宜投入することができる。 The fusing step, the aggregate, by heating the glass transition point (Tg) or more of the first resin, obtained in Rukoto fused, toner particles aggregate surface was smoothed (core particles) process is there. By this step, the surface area of the agglomerates is reduced, and toner particles having a good shape can be obtained. In addition, when shell particles are attached in the attaching step described later, the shell particles are efficiently attached to the core particles. Before entering the primary fusing step, a chelating agent, a pH adjusting agent, a surfactant and the like can be appropriately added in order to prevent fusion between toner particles.
二次融合工程とは、付着工程により得られたシェル付着体を、酸基を有する樹脂（第一の樹脂）のガラス転移点（Ｔｇ）以上に加熱し、融合させることで、粒子表面を平滑化する工程である。二次融合工程により、コア樹脂とシェル樹脂が十分に固着され、後述の洗浄やろ過等の操作で、シェルがコア粒子から脱離することを抑制する。二次融合工程に入る前に、トナー粒子間の融着を防ぐため、キレート剤、ｐＨ調整剤、界面活性剤等を適宜投入することができる。 The secondary fusing step, the resulting shell adhering member by adhesion process, by heating the glass transition point (Tg) or more of the resin (first resin) having an acid group, in Rukoto fusing, the particle surface This is a smoothing process. The core resin and the shell resin are sufficiently fixed by the secondary fusion process, and the shell is prevented from being detached from the core particles by operations such as washing and filtration described later. Before entering the secondary fusion step, a chelating agent, a pH adjuster, a surfactant, and the like can be appropriately added in order to prevent fusion between toner particles.
Claims (11)
該酸基を有する樹脂のガラス転移点以上の温度で、水系媒体、酸、下記式１で表される３級アミン、及び該混合物を撹拌し、樹脂乳化物を得る乳化工程と、
を有する樹脂微粒子の水系分散体の製造方法であって、
該乳化工程において、水相中における、該３級アミンと該酸とから生成するアミノカチオンの濃度が、臨界凝集濃度以下である
ことを特徴とする樹脂微粒子の水系分散体の製造方法。
ＮＲ１Ｒ２Ｒ３ 式１
［式１において、Ｒ１、Ｒ２、及びＲ３は、それぞれ、ヒドロキシル基を有していてもよい炭素数１以上８以下の炭化水素基を表す。］ A mixing step of obtaining a resin, and mixed to the mixture of anionic surfactants having an acid group,
An emulsification step of stirring the aqueous medium, the acid, the tertiary amine represented by the following formula 1 , and the mixture at a temperature equal to or higher than the glass transition point of the resin having an acid group to obtain a resin emulsion ;
A method of manufacturing an aqueous dispersion of resin fine particles have a,
In emulsification step, in the aqueous phase, the concentration of amino cation generated from the said tertiary amine and the acid is not more than the critical coagulation concentration
A method for producing an aqueous dispersion of resin fine particles.
NR 1 R 2 R 3 Formula 1
[In formula 1, R 1, R 2, and R 3, respectively, to display the good number 1 to 8 hydrocarbon group carbon atoms which may have a hydroxyl group. ]
水系媒体、酸、アニオン性界面活性剤、下記式１で表される３級アミン、及び該混合物を撹拌し、樹脂乳化物を得る乳化工程と、
を有する樹脂微粒子の水系分散体の製造方法であって、
該乳化工程において、水相中における、該３級アミンと該酸とから生成するアミノカチオンの濃度が、臨界凝集濃度以下である
ことを特徴とする樹脂微粒子の水系分散体の製造方法。
ＮＲ１Ｒ２Ｒ３ 式１
［式１において、Ｒ１、Ｒ２、及びＲ３は、それぞれ、ヒドロキシル基を有していてもよい炭素数１以上８以下の炭化水素基を表す。］ A mixing step of mixing a resin having an acid group and a solvent in which the resin having an acid group is soluble;
An emulsification step of stirring a water-based medium, an acid, an anionic surfactant, a tertiary amine represented by the following formula 1 , and the mixture to obtain a resin emulsion ;
A method of manufacturing an aqueous dispersion of resin fine particles have a,
In emulsification step, in the aqueous phase, the concentration of amino cation generated from the said tertiary amine and the acid is not more than the critical coagulation concentration
A method for producing an aqueous dispersion of resin fine particles.
NR 1 R 2 R 3 Formula 1
[In formula 1, R 1, R 2, and R 3, respectively, to display the good number 1 to 8 hydrocarbon group carbon atoms which may have a hydroxyl group. ]
該樹脂微粒子と着色剤とを混合し、該樹脂微粒子及び該着色剤を水系媒体中で凝集させて凝集体を形成する凝集工程と、
前記凝集体を加熱し、融合させる融合工程と、
を有するトナーの製造方法。 A step of producing an aqueous dispersion of resin fine particles by the method of producing an aqueous dispersion of resin fine particles according to any one of claims 1 to 9 ,
And aggregation step of mixing the colorant and the resin particles, the resin particles and the colorant to aggregate in an aqueous medium to form aggregates,
Heating the agglomerates with the fusion step of Ru fused,
A method for producing a toner comprising:
樹脂、及び着色剤を含有するコア粒子の表面に、該樹脂微粒子の水系分散体中の該樹脂微粒子を付着させる付着工程と、
を有するトナーの製造方法。 A step of producing an aqueous dispersion of resin fine particles by the method for producing an aqueous dispersion of resin fine particles according to any one of claims 1 to 9,
Resin, and the surface of the core particles containing a colorant, and a deposition step of urging wearing the resin particles of the aqueous dispersion of the resin fine particles,
A method for producing a toner comprising:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2011286212A JP6021333B2 (en) | 2011-12-27 | 2011-12-27 | Toner production method |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2011286212A JP6021333B2 (en) | 2011-12-27 | 2011-12-27 | Toner production method |
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| Publication Number | Publication Date |
|---|---|
| JP2013133450A JP2013133450A (en) | 2013-07-08 |
| JP2013133450A5 true JP2013133450A5 (en) | 2015-04-09 |
| JP6021333B2 JP6021333B2 (en) | 2016-11-09 |
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| JP6402529B2 (en) * | 2014-08-07 | 2018-10-10 | 藤倉化成株式会社 | Toner and method for producing the same |
| JP6551037B2 (en) * | 2015-08-12 | 2019-07-31 | 富士ゼロックス株式会社 | Method of producing resin particle dispersion, method of producing electrostatic charge image developing toner, electrostatic charge image developer, toner cartridge, process cartridge, image forming method, and image forming apparatus |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4718391B2 (en) * | 2005-08-03 | 2011-07-06 | 三洋化成工業株式会社 | Resin particles |
| JP4634273B2 (en) * | 2005-10-14 | 2011-02-16 | 花王株式会社 | Method for producing resin emulsion |
| JP5230435B2 (en) * | 2007-02-19 | 2013-07-10 | キヤノン株式会社 | Method for producing aqueous dispersion of resin fine particles, aqueous dispersion of resin fine particles, method for producing toner, and toner |
| US20090130579A1 (en) * | 2007-11-15 | 2009-05-21 | Kabushiki Kaisha Toshiba | Developing agent and method for manufacturing the same |
| JP5286207B2 (en) * | 2008-09-17 | 2013-09-11 | 株式会社東芝 | Method for producing developer |
| US8697327B2 (en) * | 2009-05-28 | 2014-04-15 | Canon Kabushiki Kaisha | Toner production process and toner |
| CN102236276A (en) * | 2010-04-26 | 2011-11-09 | 东芝泰格有限公司 | Electrohphotographic toner |
-
2011
- 2011-12-27 JP JP2011286212A patent/JP6021333B2/en active Active
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