JPH03105350A - Toner for electrophotographic and production thereof - Google Patents
Toner for electrophotographic and production thereofInfo
- Publication number
- JPH03105350A JPH03105350A JP1241797A JP24179789A JPH03105350A JP H03105350 A JPH03105350 A JP H03105350A JP 1241797 A JP1241797 A JP 1241797A JP 24179789 A JP24179789 A JP 24179789A JP H03105350 A JPH03105350 A JP H03105350A
- Authority
- JP
- Japan
- Prior art keywords
- toner
- betaine
- compd
- weight
- manufactured
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000000178 monomer Substances 0.000 claims abstract description 24
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 6
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical group C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 claims 2
- 238000000034 method Methods 0.000 abstract description 39
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical group C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 abstract description 33
- 229960003237 betaine Drugs 0.000 abstract description 19
- 239000011347 resin Substances 0.000 abstract description 18
- 229920005989 resin Polymers 0.000 abstract description 18
- 239000011230 binding agent Substances 0.000 abstract description 17
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract description 10
- 239000000203 mixture Substances 0.000 abstract description 10
- 239000003086 colorant Substances 0.000 abstract description 7
- 239000006229 carbon black Substances 0.000 abstract description 6
- 230000001877 deodorizing effect Effects 0.000 abstract description 6
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 235000019645 odor Nutrition 0.000 description 28
- -1 betaine compound Chemical class 0.000 description 16
- 239000000126 substance Substances 0.000 description 13
- 239000003205 fragrance Substances 0.000 description 10
- 238000011161 development Methods 0.000 description 9
- 239000002245 particle Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000000975 dye Substances 0.000 description 5
- 239000012212 insulator Substances 0.000 description 5
- 230000005291 magnetic effect Effects 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 229960003403 betaine hydrochloride Drugs 0.000 description 2
- HOPSCVCBEOCPJZ-UHFFFAOYSA-N carboxymethyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)=O HOPSCVCBEOCPJZ-UHFFFAOYSA-N 0.000 description 2
- 239000012986 chain transfer agent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000002781 deodorant agent Substances 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000010558 suspension polymerization method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 238000009834 vaporization Methods 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- CYLVUSZHVURAOY-UHFFFAOYSA-N 2,2-dibromoethenylbenzene Chemical compound BrC(Br)=CC1=CC=CC=C1 CYLVUSZHVURAOY-UHFFFAOYSA-N 0.000 description 1
- CISIJYCKDJSTMX-UHFFFAOYSA-N 2,2-dichloroethenylbenzene Chemical compound ClC(Cl)=CC1=CC=CC=C1 CISIJYCKDJSTMX-UHFFFAOYSA-N 0.000 description 1
- YSULOORXQBDPCU-UHFFFAOYSA-N 2-(trimethylazaniumyl)ethanehydrazonate;hydrochloride Chemical compound [Cl-].C[N+](C)(C)CC(=O)NN YSULOORXQBDPCU-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 229920006222 acrylic ester polymer Polymers 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- QJVOZXGJOGJKPT-UHFFFAOYSA-N albine Natural products C12CC(=O)C=CN2CC2CNC(CC=C)C1C2 QJVOZXGJOGJKPT-UHFFFAOYSA-N 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- SXKNCCSPZDCRFD-UHFFFAOYSA-N betaine aldehyde Chemical compound C[N+](C)(C)CC=O SXKNCCSPZDCRFD-UHFFFAOYSA-N 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-UHFFFAOYSA-N 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000010556 emulsion polymerization method Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 230000005294 ferromagnetic effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000006249 magnetic particle Substances 0.000 description 1
- 239000006247 magnetic powder Substances 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- HDBWAWNLGGMZRQ-UHFFFAOYSA-N p-Vinylbiphenyl Chemical compound C1=CC(C=C)=CC=C1C1=CC=CC=C1 HDBWAWNLGGMZRQ-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920005792 styrene-acrylic resin Polymers 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
Landscapes
- Developing Agents For Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
〔概 要〕
電子写真用トナーに関し、
トナーを溶融させて定着を行う時に不快臭を伴わない電
子写真用トナーを提供することを目的とし、
ベタイン構造を有する化合物を含有するように〔産業上
の利用分野〕
本発明は電子写真用トナーに関し、さらに詳しく述べる
と、電子写真法において静電潜像を現像するために用い
られかつ現像後の定着時に不快臭を伴わない電子写真用
トナーに関する。本発明のトナーは、カスケード現像法
、磁気プラン現像法等のような電子写真現像法において
有利に用いることができる。本発明はまた、上記のよう
な電子写真用トナーの製造方法にも関する。[Detailed Description of the Invention] [Summary] The purpose of this invention is to provide an electrophotographic toner that does not produce an unpleasant odor when the toner is melted and fixed, and contains a compound having a betaine structure. [Field of Industrial Application] The present invention relates to a toner for electrophotography, and more specifically, it relates to a toner for electrophotography that is used to develop an electrostatic latent image in electrophotography and that does not produce an unpleasant odor when fixed after development. Regarding toner for electrophotography. The toner of the present invention can be advantageously used in electrophotographic development methods such as cascade development, magnetic plan development, and the like. The present invention also relates to a method of manufacturing an electrophotographic toner as described above.
電子写真法としては米国特許第２． ２９７． ６９１
号などに記載された方式が周知である。この方式は、一
般には光導電性絶縁体（フォトコンドラムなど）を利用
し、コロナ放電などにより光導電性絶縁体上に一様な静
電荷を与え、様々な手段により光導電性絶縁体上に光像
を照射することによって静電潜像を形戊し、次いで、潜
像をトナーと呼ばれる微粉末を用いて現像可視化し、必
要に応じて紙等にトナー画像を転写した後、加圧、加熱
、溶剤蒸気、光等により該トナー画像を溶融させて紙等
に定着させ、印刷物を得るものである。静電潜像を現像
するトナーとしては、従来より天然または合或高分子物
質よりなるバインダ樹脂中に染料、カーボンブラックな
どの着色剤等を分散させたものを１〜３０ｐＭ程度に微
粉砕した粒子が用いられている。かかるトナーは、通常
、トナー単体で用いられるかもしくは鉄粉、ガラスビー
ズなどの担体物′ｉｔ．（キャリア）と混合され、静電
潜像の現像に用いられる。As an electrophotographic method, US Patent No. 2. 297. 691
The method described in this issue is well known. This method generally utilizes a photoconductive insulator (such as a photocondrum), applies a uniform electrostatic charge on the photoconductive insulator by means of corona discharge, etc. An electrostatic latent image is formed by irradiating the image with a light image, and then the latent image is developed and visualized using fine powder called toner. After transferring the toner image to paper etc. as necessary, pressure is applied. The toner image is melted and fixed on paper or the like by heating, solvent vapor, light, etc. to obtain a printed matter. Toners for developing electrostatic latent images have conventionally been made by finely pulverizing particles of about 1 to 30 pM of colorants such as dyes and carbon black dispersed in a binder resin made of natural or synthetic polymeric substances. is used. Such toner is usually used alone or with a carrier such as iron powder or glass beads. (carrier) and used for developing electrostatic latent images.
トナー単体を現像に供する場合（一或分現像方法）、ト
ナーは通常、磁性粉を含有しており、現像装置の壁面や
ブレードやマグネットロールなどの現像装置内の部材と
摩擦されることにより摩擦帯電し、さらに、マグネット
ロールの磁力により、マグネットロール上に保持され、
マグネットロールが回転することによりトナーが光導電
性絶縁体上の潜像部分に運ばれ、帯電したトナーのみが
電気的吸引力により潜像に付着することによって現像が
行われる。また、キャリアとトナーを混合して用いる場
合（二戒分現像方法）、トナーとキャリアとからなる現
像剤は現像装置内で混合撹拌されることにより摩擦帯電
し、トナーがキャリアに担持された状態で光導電性絶縁
体上の潜像部分に運ばれ、帯電したトナーのみが電気的
吸引力により選択的に潜像に付着することによって現像
が行われる。この場合、通常キャリアとしては鉄粉もし
くは他の強磁性体粒子を用いることが多く、この場合、
磁性体粒子が、現像装置内のマグネットロールにより保
持され磁気ブラシを形或し、該マグネットロールが回転
することにより磁気ブラシが光導電性絶縁体上の潜像部
分に運ばれることにより潜像部分へのトナーの運搬が行
われる。When the toner alone is used for development (one-minute development method), the toner usually contains magnetic powder, and friction occurs when it rubs against the walls of the developing device, blades, magnet rolls, and other internal components of the developing device. It is charged and held on the magnet roll by the magnetic force of the magnet roll.
The rotation of the magnetic roll transports the toner to the latent image area on the photoconductive insulator, and development occurs when only the charged toner adheres to the latent image due to electrical attraction. In addition, when using a mixture of carrier and toner (two-command development method), the developer consisting of toner and carrier is mixed and stirred in the developing device and is frictionally charged, so that the toner is supported on the carrier. The toner is transported to the latent image area on the photoconductive insulator, and development is performed by selectively adhering only the charged toner to the latent image by electrical attraction. In this case, iron powder or other ferromagnetic particles are usually used as the carrier;
Magnetic particles are held by a magnet roll in a developing device to form a magnetic brush, and rotation of the magnet roll carries the magnetic brush to the latent image area on the photoconductive insulator, thereby forming a latent image area. Toner is transported to.
上記のようにして静電潜像をトナーで現像可視化した後
、トナー画像を定着する。ここで、トナーの定着方法と
しは、加圧によりトナーを塑性変形させて定着を行う圧
力定着方法、トナーに熱を加えてトナーを溶融させて定
着を行う熱ロール定着方法やオーブン定着方法、有機溶
剤によりトナーを溶融させて定着を行う溶剤定着方法、
光を照射してそのエネルギーでトナーを溶融させて定着
を行う光定着方法などの方式がある。このなかで最も簡
便な定着方法は加圧によりトナーを定着する圧力定着方
式である。しかし、圧力定着方式の場合、十分な定着性
を得難いなどの問題がある。After the electrostatic latent image is developed and visualized with toner as described above, the toner image is fixed. Here, toner fixing methods include a pressure fixing method in which the toner is plastically deformed by applying pressure, a heated roll fixing method and an oven fixing method in which heat is applied to the toner to melt the toner, and an oven fixing method. A solvent fixing method that fixes toner by melting it with a solvent;
There are methods such as an optical fixing method in which toner is irradiated with light and the energy is used to melt the toner. Among these, the simplest fixing method is a pressure fixing method in which toner is fixed by applying pressure. However, in the case of the pressure fixing method, there are problems such as difficulty in obtaining sufficient fixing performance.
したがって現在、最も広く用いられている定着法は、ト
ナーをいったん溶融させて定着を行う熱ロール定着法や
光定着法である。しかし、これらの方法によって定着を
行う場合、トナーの溶融時にバイダ樹脂の熱分解や重合
体中の微量の単量体及び／又はそれらの酸化物の気化す
ること等によって悪臭を伴う問題がある。上記欠点の対
策案として特開昭４８−６５９４５号公報、特開昭５２
−１１３７３７号公報、特開昭６０−２８６８５６号公
報などに記載されているように、あらかじめトナー原料
に香料を添加し、混練、粉砕、分級によってトナーを得
る方法がある。しかし、これらの方法の場合、香料が少
ないとほとんど効果がなく、香料を漸次増やすと香料の
芳香と悪臭が混ざった複雑な匂いとなり、不快臭に対し
て必ずしも満足できるものではなかった。Therefore, the most widely used fixing methods at present are the hot roll fixing method and the optical fixing method, in which the toner is once melted and then fixed. However, when fixing is carried out by these methods, there is a problem that a bad odor is generated due to thermal decomposition of the binder resin and vaporization of trace amounts of monomers and/or their oxides in the polymer when the toner is melted. As a countermeasure for the above-mentioned drawbacks, Japanese Patent Application Laid-Open No. 48-65945 and Japanese Patent Application Laid-open No. 52
As described in Japanese Patent Laid-open No. 113737 and Japanese Patent Application Laid-Open No. 60-286856, there is a method of adding a fragrance to toner raw materials in advance and obtaining a toner by kneading, crushing, and classifying. However, these methods have little effect when the amount of fragrance is small, and when the amount of fragrance is gradually increased, a complex odor is produced, which is a mixture of the aroma of the fragrance and bad odor, and they are not always satisfactory in terms of unpleasant odors.
本発明の目的は、トナーを溶融させて定着を行う時に不
快臭を伴わない電子写真用トナーを提供することにある
。An object of the present invention is to provide an electrophotographic toner that does not produce an unpleasant odor when the toner is melted and fixed.
本発明の目的は、また、上記のような電子写真用トナー
の製造方法を提供することにある。Another object of the present invention is to provide a method for manufacturing the electrophotographic toner as described above.
上記した目的は、本発明によれば、ベタイン構造を有す
る化合物を含有することを特徴とする電子写真用トナー
によって達或することができる。According to the present invention, the above object can be achieved by an electrophotographic toner characterized by containing a compound having a betaine structure.
本発明による電子写真用トナーでは、トナーの溶融時に
バインダ樹脂の熱分解や重合体中の微量の単量体および
／またはそれらの酸化物の気化すること等によって生じ
る悪臭を除去するため、ベタイン構造を有する化合物（
以下、「ベタイン化合物」と記す）をバインダ樹脂に添
加する。ベタイン化合物は、従来の香料添加の場合のよ
うに香料の芳香によって不快臭をマスキングするのでは
なくて、それ自体が不快臭を反応吸着させる脱臭効果を
持つため、微量で効果を上げることができる。ベクイン
化合物は、次のようなベタイン骨格：ｃｏＨｒ Ｒ３Ｎ
″ＣＨ．ＣＯＯＨ またはその水化物Ｒ３〜”ＣＨ２
Ｃ（］（）−を有していることを特徴としており、グリ
シンベタイン、γ−プチロベタイン、ベタインアルデヒ
ド、リシンベタイン、オキシノリンペタイン、トリメチ
ルグリシンベタイン、トリメチルグリコルルベタイン、
ベタインヒドロクロライド、ベタインヒドラザイドクロ
ライド等を例示することができる。これらのベタイン化
合物はトナーの溶融時に発生する悪臭を除去するのに有
効な量で用いられ、その有効量は一般に約０． ００５
〜５重量％の微量、好ましくは約０．０１〜０、１重量
％である。上記した範囲よりも微量では脱臭の効果が得
られず、反対に多量ではトナー自体の作用に悪影響を及
ぼすであろう。The electrophotographic toner according to the present invention has a betaine structure in order to remove bad odors caused by thermal decomposition of the binder resin and vaporization of trace amounts of monomers and/or their oxides in the polymer when the toner is melted. A compound having (
Hereinafter, a "betaine compound") is added to the binder resin. Betaine compounds do not mask unpleasant odors with the aroma of fragrances as in the case of conventional fragrance additions, but rather have a deodorizing effect that reacts and adsorbs unpleasant odors, so they can be effective even in small amounts. . Bequine compounds have the following betaine skeleton: coHr R3N
"CH.COOH or its hydrate R3~"CH2
It is characterized by having C(]()-, and includes glycine betaine, γ-putilobetaine, betaine aldehyde, lysine betaine, oxynoline petaine, trimethylglycine betaine, trimethylglycolubetaine,
Examples include betaine hydrochloride and betaine hydrazide chloride. These betaine compounds are used in an amount effective to eliminate malodors generated during toner melting, and the effective amount is generally about 0. 005
Trace amounts of ~5% by weight, preferably about 0.01-0.1% by weight. If the amount is smaller than the above-mentioned range, no deodorizing effect will be obtained, and if the amount is too large, it will adversely affect the action of the toner itself.
本発明のトナーにおいて、この技術分野においてバイン
ダとして一般的に用いられているものをバインダ樹脂と
して用いることができる。適当なバインダ樹脂として、
熱可型性樹脂、例えばスチレン樹脂、アクリル酸エステ
ル重合体、スチレンとアクリル酸エステルの共重合体、
塩化ビニル重合体、酢酸ビニル重合体、ポリエチレン、
ボリブロビレン、ポリエステル樹脂、エポキシ樹脂、フ
ェノール樹脂、マレイン酸樹脂、ウレタン樹脂、スチロ
ール樹脂等が挙げられる。これらの重合体は単独もしく
は混合して使用することができる。In the toner of the present invention, binder resins that are commonly used as binders in this technical field can be used. As a suitable binder resin,
Thermoplastic resins, such as styrene resins, acrylic ester polymers, styrene and acrylic ester copolymers,
Vinyl chloride polymer, vinyl acetate polymer, polyethylene,
Examples include boribropylene, polyester resin, epoxy resin, phenol resin, maleic acid resin, urethane resin, styrene resin, and the like. These polymers can be used alone or in combination.
バインダ樹脂の使用量は任意であるが、約９０〜９６重
量％が好ましい。The amount of binder resin used is arbitrary, but is preferably about 90 to 96% by weight.
本発明のトナーにおいて、上記したバインダ樹脂及びベ
タイン化合物のほかこの技術分野において一般的に用い
られている添加剤を任意に用いることができる。適当な
添加剤の１つとして染料、カーボンブラック等の着色剤
があり、その使用量は好ましくは０．５〜１０重量％で
ある。その他の添加剤としては帯電制御剤、ワックス、
重合開始剤などがあり、必要に応じて香料などを併用し
てもよい。In the toner of the present invention, in addition to the binder resin and betaine compound described above, any additives commonly used in this technical field can be used. Suitable additives include colorants such as dyes and carbon black, the amount of which is preferably from 0.5 to 10% by weight. Other additives include charge control agents, wax,
There are polymerization initiators and the like, and fragrances and the like may be used in combination if necessary.
本発明のトナーは、この技術分野において一般的な手法
を用いて、あるいは以下に詳述するように新規な本発明
方法を用いて、調製することができる。前者に従うと、
上記したようなトナー或分を入念に混合し、加熱混練し
、その後粉砕し、そして分級する。The toners of the present invention can be prepared using techniques common in the art or using the novel method of the present invention as detailed below. Following the former,
A portion of the toner as described above is carefully mixed, heated and kneaded, then ground and classified.
さらにまた、上記した目的は、本発明によれば、ベタイ
ン化合物をトナーの溶融時に発生する悪臭を除去するの
に有効な量で含有する電子写真用トナーを製造するに当
って、アクリル系もしくはメタクリル系単量体及び／又
はラジカル重合可能なビニル系単量体中に前記ベタイン
化合物の有効量を分散せしめた後に前記単量体を重合せ
しめてトナーを調製することを特徴とする電子写真用ト
ナーの製法によって達或することができる。Furthermore, according to the present invention, the above-mentioned object is to produce an electrophotographic toner containing a betaine compound in an amount effective to remove the bad odor generated when the toner is melted. An electrophotographic toner, characterized in that the toner is prepared by dispersing an effective amount of the betaine compound in a monomer and/or a radically polymerizable vinyl monomer, and then polymerizing the monomer. It can be achieved by the manufacturing method.
ここで、得られるトナー自体は上記した本発明のトナー
の範囲に包含されるものであり、但し、さらに製造方法
に特徴がある。すなわち、以下に詳述するように、本発
明方法では従来の粉砕、分級等の煩雑な処理工程を省略
することができるので、プロセス的に多くのメリットが
ある。Here, the obtained toner itself falls within the scope of the toner of the present invention described above, however, it is further characterized by the manufacturing method. That is, as will be described in detail below, the method of the present invention can omit conventional complicated processing steps such as pulverization and classification, and therefore has many advantages in terms of process.
理解されるように、本発明方法では、アクリル系もしく
はメタクリル系単量体及び／又はラジカル重合可能なビ
ニル系単量体をバインダ樹脂提供物質として用い、この
物質を重合させて得た重合体をバインダ樹脂として用い
るものである。バインダ樹脂提供物質となるビニル系単
量体としては公知のものが利用できる。具体例を挙げれ
ば、スチレン、α−メチルスチレン、０−メチルスチレ
ン、ｍ−メチルスチレン、ｐ−メチルスチレン、ｐ−メ
トキシスチレン、クロロスチレン、プロモスチレン、ジ
クロロスチレン、ジブロモスチレン、ｐ−フェニルスチ
レン、ｔｅｒｔ−プチルスチレン、メチルメタクリレー
ト、ｎ−プチルメタクリレート、ｎ−才クチルメタクリ
レート、メチルアクリレート、ジビニルベンゼン、ジア
リルフタレート、マレイン酸、マレイン酸ハーフエステ
ル、アクリ口ニトリル、エチレングリコールジメタクリ
レート、エチレングリコールジアクリレー゜ト、トリメ
チロールプロパントリメタクリレート等がある。As will be understood, in the method of the present invention, an acrylic or methacrylic monomer and/or a radically polymerizable vinyl monomer is used as a binder resin providing material, and the polymer obtained by polymerizing this material is It is used as a binder resin. As the vinyl monomer serving as the binder resin providing substance, known ones can be used. Specific examples include styrene, α-methylstyrene, 0-methylstyrene, m-methylstyrene, p-methylstyrene, p-methoxystyrene, chlorostyrene, promostyrene, dichlorostyrene, dibromostyrene, p-phenylstyrene, tert-butyl styrene, methyl methacrylate, n-butyl methacrylate, n-butyl methacrylate, methyl acrylate, divinylbenzene, diallyl phthalate, maleic acid, maleic acid half ester, acrylic nitrile, ethylene glycol dimethacrylate, ethylene glycol diacrylate and trimethylolpropane trimethacrylate.
これらの単量体は単独もしくは混合して使用することが
できる。These monomers can be used alone or in combination.
本発明方法を実施するには、公知の懸濁重合または乳化
重合法を用いて行う。すなわち、単量体組成物に着色剤
、帯電制御剤、ワックス、重合開始剤およびベタイン化
合物をよく混合する。この際、重合を制御するために四
塩化炭素やチオール系化合物を連鎖移動剤として更に添
加してもよい。The method of the invention is carried out using known suspension polymerization or emulsion polymerization methods. That is, a colorant, a charge control agent, a wax, a polymerization initiator, and a betaine compound are thoroughly mixed into the monomer composition. At this time, carbon tetrachloride or a thiol compound may be further added as a chain transfer agent in order to control the polymerization.
また必要に応じて香料なども併用できる。この混合物を
分散剤及び／又は乳化剤入りの水中に分散し、温浴にて
５０〜９０℃に加熱することによって重合を完結し、ト
ナーを分散する。したがって、本発明方法の好ましい１
態様として、アクリル系もしくはメタクリル系単量体及
び／又はラジカル重合可能なビニル系単量体中に、０．
００５〜５．０重量％のベタイン化合物、および０．
５〜１０重量％の着色剤を分散せしめた後、該単量体を
懸濁重合法も゛シ＜は乳比重合法により、重合させてト
ナーを調製することを特徴とする電子写真用トナーの製
造方法があげられる。Additionally, fragrances can be added if necessary. This mixture is dispersed in water containing a dispersant and/or emulsifier, and heated to 50 to 90° C. in a hot bath to complete polymerization and disperse the toner. Therefore, a preferred method of the present invention
In one embodiment, the acrylic or methacrylic monomer and/or the radically polymerizable vinyl monomer contains 0.
0.005 to 5.0% by weight of a betaine compound, and 0.005 to 5.0% by weight of a betaine compound;
After dispersing 5 to 10% by weight of a colorant, the monomers are polymerized either by a suspension polymerization method or by a milk specific polymerization method to prepare a toner. Examples include manufacturing methods.
本発明の電子写真用トナーではベタイン構造を有する化
合物がバインダ樹脂に添加される。このベタイン化合物
は、従来用いられている香料のようにその芳香によって
不快臭をマスキングするのではなく、それ自体が不快臭
を反応吸着させる脱臭効果を持つため、完全に悪臭を除
去することができ、しかも微量の添加でもって満足すべ
き効果を得ることができる。In the electrophotographic toner of the present invention, a compound having a betaine structure is added to the binder resin. This betaine compound does not mask unpleasant odors with its fragrance like conventional fragrances, but it itself has a deodorizing effect that reacts and adsorbs unpleasant odors, so it cannot completely remove bad odors. Moreover, satisfactory effects can be obtained even with the addition of a small amount.
次いで、本発明をいくつかの実施例によって説明する。 Next, the invention will be explained by some examples.
なお、本発明はこれらの実施例によって限定されないこ
とを理解されたい。However, it should be understood that the present invention is not limited by these examples.
例ｌ
バインダ樹脂として、エボキシ樹脂（エピクロンＥＸＡ
−１１９１ ；大日本インキ化学工業製）７０重量部と
スチレンーアクリル樹脂（ＳＢＭ６０ ；三洋化或製）
３０重量部を用い、着色剤としてカーボンブラック（ブ
ラックバールズＬ；平均粒径２４ｍμ、比表面積１３８
ｍ’／ｇ ；キャボット社製）５重量部、ニグロシン染
料（オイルブラックＢＹ１オリエント化学製）３重量部
、さらに脱臭剤としてグリシンベタイン（東京化或製）
０．２重量部を加え、加圧二−ダにより１３０℃，３０
分溶融混練し、トナー塊を得た。冷却したトナー塊をロ
ートブレックス粉砕機により約〜２０］ｍの粗トナーと
した。次いで、粗トナーをジェットミル（ＰＪＭ粉砕機
、日本ニューマチック工業製）を用いて微粉砕を行い、
粉砕物を風力分級機（アルビネ社製）により分級し、粒
径５〜２０μのトナーを得た。トナー５重量部、キャリ
アとしての不定形鉄粉ＴＳＶＩＯＯ／２００ （日本鉄
粉製）９５重量部からなる現像剤を調製し、フラッシュ
定着方式を採用しているＦＡＣＯＭ−６７１５０レーザ
プリンタを用いて臭気試験を行った。ＩＯ人のパネラー
によって不快臭の有無をチェックしたけれども、１０人
中１人として不快臭を認めなかった。Example l As the binder resin, epoxy resin (Epicron EXA
-1191; manufactured by Dainippon Ink and Chemicals) 70 parts by weight and styrene-acrylic resin (SBM60; manufactured by Sanyo Chemical)
Using 30 parts by weight, carbon black (Black Burls L; average particle size 24 mμ, specific surface area 138
m'/g; manufactured by Cabot Corporation) 5 parts by weight, nigrosine dye (Oil Black BY1 manufactured by Orient Chemical Co., Ltd.) 3 parts by weight, and as a deodorizing agent glycine betaine (manufactured by Tokyo Kaoru Co., Ltd.)
Add 0.2 parts by weight and heat at 130℃, 30
The mixture was melted and kneaded to obtain a toner mass. The cooled toner mass was reduced to approximately 20]m of coarse toner using a Rotobrex mill. Next, the coarse toner was pulverized using a jet mill (PJM pulverizer, manufactured by Nippon Pneumatic Industries).
The pulverized product was classified using an air classifier (manufactured by Albine Co., Ltd.) to obtain toner having a particle size of 5 to 20 μm. A developer consisting of 5 parts by weight of toner and 95 parts by weight of irregular iron powder TSVIOO/200 (manufactured by Nippon Steel Powder) as a carrier was prepared, and an odor test was conducted using a FACOM-67150 laser printer that uses a flash fixing method. I did it. A panel of IO people checked for the presence of unpleasant odors, but not one out of 10 found any unpleasant odors.
例２ 本例は比較例である。Example 2 This example is a comparative example.
前記例１に記載の手法を繰り返したけれども、本例では
、比較のため、脱臭剤としてのグリシンベタインを添加
しなかった。得られた現像剤を臭気試験に供したところ
、パネラー１０人中８人において不快臭が認められた。The procedure described in Example 1 above was repeated, but in this example, for comparison, no glycine betaine was added as a deodorant. When the obtained developer was subjected to an odor test, 8 out of 10 panelists recognized an unpleasant odor.
例 ３
下記のトナー或分：
モノマ
スチレン（和光純薬製）１００重量部
プチルメタクリレート４０重量部
（和光純薬製）
着色剤
グラフト化カーボンブラック ２重量部（デグサ
社製）
ニグロシン染料 ２重量部（オイル
ブラックＢＹ；オリエント社製）開始剤
２，２′−アゾイソブチロニトリル １重量部（和光純
薬製）
過酸化ベンゾイル（日本油脂製） １重量部脱臭剤
グリシンベタイン（東京化或製） ０．０５重量部を
ディスバーサ（ヤマト科学製〉を用い、３分間撹拌し、
単量体組戒物を調製した。次に、分散剤としてのポリビ
ニルアルコール（和光純薬社製〉０．０２％を含む蒸留
水５００重量部中に前記単量体組或物を加え、５０℃で
ディスバーサ（２４． ００Ｏｒ． ｐ． ｍ）を用い
て３分間撹拌し、その後ディスバーサを１０Ｏ ｒ．ｐ
．ｍに変え、９時間重合を続けた。次に、水に分敗した
生戊トナーを遠心分離し、ろ別した。Example 3 The following toner parts: 100 parts by weight of monomastyrene (manufactured by Wako Pure Chemical Industries) 40 parts by weight of butyl methacrylate (manufactured by Wako Pure Chemical Industries, Ltd.) 2 parts by weight of colorant grafted carbon black (manufactured by Degussa) 2 parts by weight of nigrosine dye (manufactured by Degussa) Oil black BY; manufactured by Orient) Initiator 2,2'-azoisobutyronitrile 1 part by weight (manufactured by Wako Pure Chemical Industries) Benzoyl peroxide (manufactured by NOF) 1 part by weight Deodorizer glycine betaine (manufactured by Tokyo Kaoru) 0.05 parts by weight was stirred for 3 minutes using Disversa (manufactured by Yamato Scientific),
A monomer compound was prepared. Next, the monomer assembly was added to 500 parts by weight of distilled water containing 0.02% polyvinyl alcohol (manufactured by Wako Pure Chemical Industries, Ltd.) as a dispersant, and the monomer assembly was added to 500 parts by weight of distilled water containing 0.02% polyvinyl alcohol (manufactured by Wako Pure Chemical Industries, Ltd.) as a dispersant, and the mixture was heated at 50° C. using a disperser (24.00 Or. p. m) for 3 minutes, then the disperser was turned to 100 r.p.
．． The polymerization was continued for 9 hours. Next, the raw toner separated into water was centrifuged and filtered.
このトナーをｌ）Ｈが８以下になるまで水洗を３回繰り
返し、平均粒径５．６μの球形トナー粒子を得た。This toner was washed with water three times until l)H became 8 or less to obtain spherical toner particles with an average particle size of 5.6 μm.
得られたトナー３重量部、キャリアとしての不定形鉄扮
ＴＳＶＩＯＯ／２００ （日本鉄粉製）９７重量部から
なる現像剤を調製し、フラッシュ定着方式を採用してい
るＦＡＣＯＭ−６７１５０レーザプリンタを用いて定着
を行い、臭気試験を行った。前記例１の場合と同様に１
０人のパネラーによって不快臭の有無をチェックしたけ
れども、１０人中１人として不快臭をδ忍めなかった。A developer consisting of 3 parts by weight of the obtained toner and 97 parts by weight of amorphous iron TSVIOO/200 (manufactured by Nippon Tetsuko Powder) as a carrier was prepared, and a FACOM-67150 laser printer employing a flash fixing method was used. After fixing, an odor test was conducted. 1 as in Example 1 above
Although the presence or absence of unpleasant odor was checked by 0 panelists, 1 out of 10 could not bear the unpleasant odor.
例 ４
下記のトナー或分：
モノマ
スチレン（和光純薬製）１００重量部
プチルアクリレート（和光純薬製）４０重量部着色剤
グラフト化カーボンブラック ２重量部（デグサ
社製）
ニグロシン染料 ２重量部〈オイル
ブラックＢＹ；オリエント社製〉開始剤
２，２′−アゾイソブチロニトリル １重量部（和光純
薬製）
過酸化ベンゾイル（日本油脂製〉 １重量部連鎖移
動剤
ｔ−ドデシルメル力ブタン ０，５重量部脱臭剤
ベタインヒドロクロライド ０，０５重量部（東京
化或製）
をディスバーサ（ヤマト科学製）を用い、３分間撹拌し
、単量体組成物を調製した。次に、分散剤としてのポリ
ビニルアルコール（和光純薬社製〉０．０２％を含む蒸
留水５００重量部中に前記単量体組或物を加え、５０℃
でディスバーサ（２４． ００Ｏｒ． ｐ． ｍ）を用
いて３分間撹拌し、その後ディスパーサを１００ ｒ，
ｐ，ｍに変え、９時間重合を続けた。次に、水に分散し
た生或トナーを遠心分離し、ろ別した。Example 4 The following toner parts: 100 parts by weight of monomastyrene (manufactured by Wako Pure Chemical Industries) 40 parts by weight of butyl acrylate (manufactured by Wako Pure Chemical Industries) 2 parts by weight of colorant grafted carbon black (manufactured by Degussa) 2 parts by weight of nigrosine dye Oil Black BY: Orient Co., Ltd. Initiator 2,2'-azoisobutyronitrile 1 part by weight (Wako Pure Chemical Industries) Benzoyl peroxide (NOF Co., Ltd.) 1 part by weight Chain transfer agent t-dodecyl mer-butane 0, A monomer composition was prepared by stirring 5 parts by weight of a deodorizing agent betaine hydrochloride (manufactured by Tokyo Chemical Co., Ltd.) for 3 minutes using a disperser (manufactured by Yamato Kagaku Co., Ltd.). The monomer composition was added to 500 parts by weight of distilled water containing 0.02% polyvinyl alcohol (manufactured by Wako Pure Chemical Industries, Ltd.), and the mixture was heated at 50°C.
Stir for 3 minutes using a disperser (24.00 Or. p.m), then turn the disperser at 100 r,
p and m, and polymerization was continued for 9 hours. Next, the raw toner dispersed in water was centrifuged and filtered.
このトナーをｐＨが８以下になるまで水洗を３回繰り返
し、平均粒径５、６一の球形トナー粒子を得た。This toner was washed three times with water until the pH became 8 or less to obtain spherical toner particles with an average particle size of 5.6.
得られたトナー３重量部、キャリアとしての不定形鉄粉
ＴＳＶＩＯＯ／２００ （日本鉄粉製）９７重量部から
なる現像剤を調製し、フラッシュ定着方式を採用してい
るＦＡＣＯＭ−６７１５Ｄ レーザプリンタを用いて定
着を行い、臭気試験を行った。臭気試験の結果、前記例
３と同じく不快臭は認められなかった。A developer consisting of 3 parts by weight of the obtained toner and 97 parts by weight of amorphous iron powder TSVIOO/200 (manufactured by Nippon Steel Powder) as a carrier was prepared, and a FACOM-6715D laser printer employing a flash fixing method was used. After fixing, an odor test was conducted. As a result of the odor test, no unpleasant odor was observed as in Example 3 above.
例５ 本例は比較例である。Example 5 This example is a comparative example.
前記例３に記載の手法を繰り返したけれども、本例では
、比較のため、脱臭剤としてのグリシンベタインを添加
しなかった。得られた現像剤を臭気試験に供したところ
、パネラー１０人中８人において不快臭が認められた。The procedure described in Example 3 above was repeated, but in this example, for comparison, no glycine betaine was added as a deodorant. When the obtained developer was subjected to an odor test, 8 out of 10 panelists recognized an unpleasant odor.
本発明によれば、バインダ樹脂に対してベタイン化合物
を添加することによって、トナー画像の定着時に不快臭
を示さない電子写真用トナーを提供することができる。According to the present invention, by adding a betaine compound to the binder resin, it is possible to provide an electrophotographic toner that does not exhibit an unpleasant odor when a toner image is fixed.
Claims (1)
とする電子写真用トナー。 ２、請求項１に記載の電子写真用トナーを製造するに当
って、アクリル系もしくはメタクリル系単量体及び／又
はラジカル重合可能なビニル系単量体中に前記のベタイ
ン構造を有する化合物の有効量を分散せしめた後に前記
単量体を重合せしめてトナーを調製することを特徴とす
る電子写真用トナーの製法。[Scope of Claims] 1. An electrophotographic toner containing a compound having a betaine structure. 2. In producing the electrophotographic toner according to claim 1, the effectiveness of the compound having the betaine structure in the acrylic or methacrylic monomer and/or the radically polymerizable vinyl monomer. 1. A method for producing a toner for electrophotography, characterized in that the toner is prepared by polymerizing the monomers after dispersing the monomers.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1241797A JPH03105350A (en) | 1989-09-20 | 1989-09-20 | Toner for electrophotographic and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1241797A JPH03105350A (en) | 1989-09-20 | 1989-09-20 | Toner for electrophotographic and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03105350A true JPH03105350A (en) | 1991-05-02 |
Family
ID=17079655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1241797A Pending JPH03105350A (en) | 1989-09-20 | 1989-09-20 | Toner for electrophotographic and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03105350A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7399567B2 (en) | 2005-02-09 | 2008-07-15 | Fuji Xerox Co., Ltd. | Toner for electrostatic latent image development, electrostatic latent image developer containing the toner, and image formation method using the developer |
| US7514194B2 (en) | 2005-07-07 | 2009-04-07 | Fuji Xerox Co., Ltd. | Toner for developing electrostatic latent image and production method thereof, electrostatic latent image developer, image forming method, and image forming apparatus |
| JP2010149613A (en) * | 2008-12-24 | 2010-07-08 | Kanto Auto Works Ltd | Seat of automobile |
-
1989
- 1989-09-20 JP JP1241797A patent/JPH03105350A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7399567B2 (en) | 2005-02-09 | 2008-07-15 | Fuji Xerox Co., Ltd. | Toner for electrostatic latent image development, electrostatic latent image developer containing the toner, and image formation method using the developer |
| US7514194B2 (en) | 2005-07-07 | 2009-04-07 | Fuji Xerox Co., Ltd. | Toner for developing electrostatic latent image and production method thereof, electrostatic latent image developer, image forming method, and image forming apparatus |
| JP2010149613A (en) * | 2008-12-24 | 2010-07-08 | Kanto Auto Works Ltd | Seat of automobile |
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