JPH01274158A - Toner for electrophotography - Google Patents
Toner for electrophotographyInfo
- Publication number
- JPH01274158A JPH01274158A JP63102491A JP10249188A JPH01274158A JP H01274158 A JPH01274158 A JP H01274158A JP 63102491 A JP63102491 A JP 63102491A JP 10249188 A JP10249188 A JP 10249188A JP H01274158 A JPH01274158 A JP H01274158A
- Authority
- JP
- Japan
- Prior art keywords
- toner
- developer
- charge
- charge control
- over time
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 abstract description 16
- 229920005989 resin Polymers 0.000 abstract description 13
- 239000011347 resin Substances 0.000 abstract description 13
- 230000032683 aging Effects 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 description 21
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 16
- 239000003086 colorant Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 238000013112 stability test Methods 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 4
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000002452 interceptive effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 108091008695 photoreceptors Proteins 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000002123 temporal effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- IRERQBUNZFJFGC-UHFFFAOYSA-L azure blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[S-]S[S-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] IRERQBUNZFJFGC-UHFFFAOYSA-L 0.000 description 1
- 229910052980 cadmium sulfide Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000006247 magnetic powder Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000434 metal complex dye Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- -1 polyethylene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- DZXKSFDSPBRJPS-UHFFFAOYSA-N tin(2+);sulfide Chemical compound [S-2].[Sn+2] DZXKSFDSPBRJPS-UHFFFAOYSA-N 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/097—Plasticisers; Charge controlling agents
- G03G9/09783—Organo-metallic compounds
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Developing Agents For Electrophotography (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は電子写真、静電記録などにおいて静電潜像を現
像するために用いられる電子写真用トナーに間する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to an electrophotographic toner used for developing electrostatic latent images in electrophotography, electrostatic recording, and the like.
静電気を利用した静電記録、静電写真等の画像形成プロ
セスは、セレン、硫化カドミウム、アモルファスシリコ
ン等の光導電性物質をアルミ、紙等の基材上に塗布する
ことによって得られた感光体上に光信号により静電潜像
を形成する過程と、トナーと称される１０−５０μに調
整された着色微粒子を、二成分系現像法では該トナーを
キャリヤー（鉄粉、フェライト粉等）により接触帯電さ
せ、又−成分系現像法では該トナーを直接帯電させたあ
と静電潜像に作用せしめ潜像を顕像化させる過程から構
成されている。Image forming processes such as electrostatic recording and electrostatic photography that utilize static electricity use photoreceptors obtained by coating photoconductive substances such as selenium, cadmium sulfide, and amorphous silicon onto base materials such as aluminum and paper. In the two-component development method, the process of forming an electrostatic latent image using an optical signal, and the process of forming colored fine particles called toner with a size of 10-50μ, are carried out using a carrier (iron powder, ferrite powder, etc.). The toner is charged by contact, and the -component development method is comprised of a process of directly charging the toner and then acting on the electrostatic latent image to make the latent image visible.
尚、トナーは感光体上に形成される静電潜像の極性に対
応した電荷、すなわち正、負のいずれかの電荷が付与さ
れる必要がある。Note that the toner needs to be charged with a charge corresponding to the polarity of the electrostatic latent image formed on the photoreceptor, that is, either positive or negative charge.
一般にトナーと称される着色微粒子はバインダー樹脂と
着色剤を必須成分としその他必要に応じ磁性粉等から構
成されている。トナーに電荷を付与する方法としては荷
電制御剤を用いることなくバインダー樹脂そのものの帯
電特性を利用する事もできるがそれでは経時安定制、耐
湿性が劣り良好な画質を得ることが出来ない。従って通
常トナーの電荷保持、荷電制御の目的で荷電制御剤が加
えられる。トナーに要求される品質特性としては帯電性
、流動性、定着性等が優れている事が挙げられるが、こ
れらの品質特性はトナーに用いられる荷電制御剤によっ
て大きく影響されるものである。Colored fine particles, generally called toner, are composed of a binder resin and a colorant as essential components, and other materials such as magnetic powder as required. As a method of imparting charge to the toner, it is possible to utilize the charging characteristics of the binder resin itself without using a charge control agent, but this method results in poor stability over time and moisture resistance, making it impossible to obtain good image quality. Therefore, a charge control agent is usually added for the purpose of retaining and controlling the charge of the toner. Quality properties required of toner include excellent charging properties, fluidity, fixing properties, etc., and these quality properties are greatly influenced by the charge control agent used in the toner.
従来トナーに添加される荷電制御剤としては（１）有色
の負荷電制御剤としての２：１型含金属錯塩染料（特公
昭４５−２６４７８、特公昭４ｌ−２０１５３１）、フ
タロシアニン顔料（特開昭５２−４５９３１）又、無色
の負荷電制御剤の例としての特公昭５９−７３８４又は
特開昭６１−３１４９等に記載された荷電制御剤などが
あり又、（２）正の荷電制御剤としてのニグロシン系染
料、各種４級アンモニウム塩（静電気学会誌１９８０第
４巻第３号Ｐ−１１４）等が知られているがこれらを荷
電制御剤として含有したトナーは、帯電性、経時安定性
等トナーに要求される品質特性を充分に満足させるもの
ではない。Conventional charge control agents added to toners include (1) 2:1 type metal-containing complex salt dyes as colored negative charge control agents (Japanese Patent Publication No. 45-26478, Japanese Patent Publication No. 41-201531), and phthalocyanine pigments (Japanese Patent Publication No. 45-26478, Japanese Patent Publication No. 41-201531); 52-45931) In addition, as examples of colorless negative charge control agents, there are charge control agents described in Japanese Patent Publication No. 59-7384 or Japanese Patent Application Laid-Open No. 61-3149, etc.; (2) As positive charge control agents, Nigrosine dyes, various quaternary ammonium salts (Journal of the Japan Society of Electrostatics, Vol. 4, No. 3, P-114, 1980), etc. are known, but toners containing these as charge control agents have poor chargeability, stability over time, etc. This does not fully satisfy the quality characteristics required for toner.
例えば負の荷電制御剤として知られる２：１型含金属錯
塩染料を含有したトナーは帯電量の高さにを
ついては一応の水準へ有するものの、２：１型金属錯塩
染料は概してバインダー樹脂に対する分散性が劣るとい
う欠点がある。そのためバインダー樹脂中に均一に分布
せず、得られたトナーの帯電量分布もシャープさに欠け
るものであり得られる画像は諧調が低く画像形成能に劣
るものである。For example, toners containing a 2:1 type metal-containing complex dye known as a negative charge control agent have a certain level of charge, but the 2:1 type metal complex dye is generally dispersed in the binder resin. It has the disadvantage of being inferior in quality. Therefore, the toner is not uniformly distributed in the binder resin, and the charge distribution of the obtained toner lacks sharpness, resulting in images with low gradation and poor image forming ability.
更に、２：１型含金属錯塩染料は黒を中心とした色相を
有している為に、黒を基調とした限定された色相のトナ
ーにしか使用できないという欠点がある。無色に近い負
の荷電制御剤として芳香族ダイカルボン酸の金属錯体が
挙げられるが（特公昭５９−７３８４）このものは完全
に無色とは成りえないという欠点や、その分散性に難点
がある。Furthermore, since the 2:1 type metal-containing complex dye has a hue centered on black, it has the disadvantage that it can only be used in toners with a limited hue based on black. A metal complex of aromatic dicarboxylic acid can be cited as a nearly colorless negative charge control agent (Japanese Patent Publication No. 59-7384), but it has the disadvantage that it cannot be completely colorless and has problems with its dispersibility. .
又、無色の負荷電制御剤としては特開昭６１−３１４９
に紹介された化合物があるがこのものは融点が低い為ト
ナー生産時の熱安定性が悪く安定したトナーを製出する
ことが困難であるという欠点がある。In addition, as a colorless negative charge control agent, JP-A-61-3149
However, this compound has a low melting point and therefore has poor thermal stability during toner production, making it difficult to produce a stable toner.
荷電制御剤のバインダー樹脂に対する分散性が良好で、
トナー中において均一に分布し、諧調性の高い画像を与
えるトナーの開発が望まれている。The charge control agent has good dispersibility in the binder resin,
It is desired to develop a toner that is uniformly distributed in the toner and provides an image with high tonality.
本発明者らは前記したような課題を改良すべく鋭意努力
した結果、下記式（１）化合物をトナーに含有せしめる
事により、トナーの帯電量分布がシャープとなり帯電特
性が大幅に改善されることを見出し本発明を完成させた
。As a result of the inventors' earnest efforts to improve the above-mentioned problems, it was found that by incorporating the compound of the following formula (1) into the toner, the charge amount distribution of the toner becomes sharp and the charging characteristics are significantly improved. They found this and completed the present invention.
ＲＳ−ＣＨ２ＣＯＯＲ’
（但し、式（１）中Ｒ，Ｒ’はそれぞれ独立に置換又は
非置換のアルキル基、置換又は非置換のアリール基、ア
ラルキル基、シクロアルキル基又はアリル基を表す。）
式（１）の化合物は負の荷電制御剤として働くが、この
ものはバインダー樹脂に対する相溶性が上と
良好であり、これを含有せしめたトナーは！帯電量が高
く、その経時安定性も良好であることからトナーを長期
間保存しても静電記録の画像形式において安定して鮮明
な画像を与えるものである。RS-CH2COOR' (However, in formula (1), R and R' each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, an aralkyl group, a cycloalkyl group, or an allyl group.)
The compound of formula (1) works as a negative charge control agent, and this compound has excellent compatibility with the binder resin, so toner containing this compound is! Since the amount of charge is high and the stability over time is good, even if the toner is stored for a long period of time, it provides stable and clear images in the electrostatic recording image format.
本発明で荷電制御剤としてトナーに含有せしめられる式
（１）の化合物の具体例としては次の様なものが挙げら
れる。Specific examples of the compound of formula (1) that can be incorporated into the toner as a charge control agent in the present invention include the following.
（１） Ｃ４Ｈ９５−Ｃ）Ｉ２ＣＯＯＣａＨ＋□
（２） Ｃｊｌｌｓ Ｓ Ｃｌｌ２ＣＯＯＣＨ
２ＣＨ＝Ｃ１ｈ＼／
＼／Ｓｎ
Ｓｎ／＼
／＼Ｃ４１＋９ Ｓ ＣＨ２Ｃ００ＣａＨ＋ｔ
Ｃａ１ｌｓ ５−Ｃ１１２Ｃ００
Ｃ）Ｉ２Ｃ）Ｉ：：ＣＴ。(1) C4H95-C)I2COOCaH+□
(2) Cjlls S Cll2COOCH
2CH=C1h\/
\/Sn
Sn/\
/\C41+9 S CH2C00CaH+t
Calls 5-C112C00
C) I2C) I::CT.
Ｓｎ Ｓ
ｎｎ５ｎ
Ｓｎ ５
ｎＳｎ Ｓｎこれ
らの化合物は公知の方法、例えば有機スズサルファトに
対応するα−メルカプト酢酸エステルを作用せしめ合成
することが出来る。Sn S
nn5n Sn 5
nSn Sn These compounds can be synthesized by known methods, for example, by reacting α-mercaptoacetate corresponding to organotin sulfate.
上ｇａ （１’Ｉの化合物を含有するトナーを製造する
方法としては、式（１）の化合物、着色剤及びバインダ
ー樹脂からなる混合物を加熱ニダー、二本ロール等の加
熱混合処理可能な装置によりバインダー樹脂の溶融下で
混練し、次いで冷却固化したものをジェットミル、ボー
ルミル等の粉砕機により１−３０μ粒径に粉砕すること
によって得る方法、着色剤とバインダー樹脂と式（１）
の化合物を溶媒（例、アセトン、酢酸エチル）に溶解し
、攪拌処理後、水中に投じて再沈澱せしめ、濾過、乾燥
後、ボールミル等の粉砕機により１−３０μ粒径に粉砕
することによって得る方法等がある。(1'I) As a method for producing a toner containing the compound of formula (1), a mixture consisting of the compound of formula (1), a colorant, and a binder resin is heated and mixed in an apparatus capable of heating and mixing, such as a heating nider or two rolls. A method of kneading the binder resin while it is molten, then cooling and solidifying the mixture and pulverizing it to a particle size of 1-30 μm using a pulverizer such as a jet mill or a ball mill. Colorant, binder resin, and formula (1)
It is obtained by dissolving the compound in a solvent (e.g., acetone, ethyl acetate), stirring it, pouring it into water to re-precipitate it, filtering it, drying it, and then grinding it to a particle size of 1-30μ using a grinder such as a ball mill. There are methods etc.
この場合通常バインダー樹脂は９９〜６５％より好まし
くは９８〜８５％、着色剤は１．０〜１５％より好まし
くは１．５〜１０％、荷電制御剤は０゜１〜３０％より
好ましくは０．５〜５％の割合（いずれも重量比）で使
用される。In this case, the binder resin is usually 99-65%, preferably 98-85%, the colorant is 1.0-15%, more preferably 1.5-10%, and the charge control agent is more preferably 0.1-30%. It is used in a proportion of 0.5 to 5% (all weight ratios).
本発明の電子写真用トナーに用いられる着色剤の例とし
ては、カーボンブラック、群青等の無機顔料、 Ｃ，１
，ＰＩＧＭＥＮＴ ＹＥＬＬＯ讐 １、Ｃ，１，ＰＩＧ
ＭＥＮＴＲＥＤ ９、Ｃ，１，ＰＩＧＭＥＮＴ ＢＬＵ
Ｅ １５等の有機顔料、Ｃ０１、５ＯＬＶＥＮＴ ＹＥ
ＬＬＯＷ ９３、Ｃ，１，５ＯＬＶＥＮＴ ＲＥＤ １
４６、Ｃ，１，５ＯＬＶＥＮＴ ＢＬＵＥ ３５、Ｃ，
１，ＤＩＳＰＥＲ５Ｅ ＶＥＬＬＯ讐４２、Ｃ，１，Ｄ
ＩＳＰＥＲ５Ｅ ＲＥＤ ５９、Ｃ，１，［１ＩＳＰＥ
Ｒ５Ｅ ＢＬＵＥ８１等の油溶性染料等従来より公知の
着色剤を挙げる事が出来る。又、バインダー樹脂として
は、ポリスチレン、スチレン−アクリル酸共重合体、ス
チレン−プロピレン共重合体、スチレン−アクリロニト
リル共重合体、アクリル樹脂、スチレン−マレイン酸共
重合体、ポリ塩化ビニル、ポリ酢酸ビニル、オレフィン
樹脂、ポリエステル樹脂、ポリウレタン樹脂、エポキシ
樹脂等が単独又は、混合して使用する事が出来る。Examples of the colorant used in the electrophotographic toner of the present invention include inorganic pigments such as carbon black and ultramarine blue;
, PIGMENT YELLO 1, C, 1, PIG
MENTRED 9, C, 1, PIGMENT BLU
Organic pigments such as E 15, C01, 5OLVENT YE
LLOW 93, C, 1, 5OLVENT RED 1
46,C,1,5OLVENT BLUE 35,C,
1, DISPER5E VELLO 42, C, 1, D
ISPER5E RED 59,C,1,[1ISPE
Conventionally known colorants such as oil-soluble dyes such as R5E BLUE81 can be used. Further, as the binder resin, polystyrene, styrene-acrylic acid copolymer, styrene-propylene copolymer, styrene-acrylonitrile copolymer, acrylic resin, styrene-maleic acid copolymer, polyvinyl chloride, polyvinyl acetate, Olefin resins, polyester resins, polyurethane resins, epoxy resins, etc. can be used alone or in combination.
更に、本発明の電子写真用トナーには酸化珪素の如き流
動剤、鉱物油の如きかぶり防止剤、−成分系用としての
各種磁性体、酸化亜鉛の如き導電性付与剤等を必要に応
じて加えてもよい。Furthermore, the electrophotographic toner of the present invention may contain a flow agent such as silicon oxide, an antifoggant such as mineral oil, various magnetic substances for use in the -component system, a conductivity imparting agent such as zinc oxide, etc., as necessary. May be added.
本発明で得られたトナーは例えば２００ ｍｅｓｈ程度
の鉄粉（キャリアー）と例えば３〜８：９７〜９２（ト
ナー：鉄粉）というような重量比で混合し現像剤となし
電子写真における現像工程に使用されるものである。The toner obtained in the present invention is mixed with, for example, about 200 mesh iron powder (carrier) at a weight ratio of 3 to 8:97 to 92 (toner: iron powder) and used as a developer, which is used in the development process in electrophotography. It is used for.
本発明の電子写真用トナーは、従来の荷電制御剤を用い
たトナーに比ベシャーブな帯電量分布及び良好な経時安
定性を有している。その結果極めて諧調性の高い画像が
得られ且つ反復画像形成能が極めて良好である事が特徴
である。The electrophotographic toner of the present invention has a more uniform charge distribution and better stability over time than toners using conventional charge control agents. As a result, an image with extremely high tonality can be obtained, and the repeatable image forming ability is extremely good.
以下実施例により本発明を具体的に説明する。 The present invention will be specifically explained below using Examples.
実施中、部は特に限定しない限り重量部を表す。In the practice, parts refer to parts by weight unless otherwise specified.
実施例１
スチレン−ブチルアクリレート
共重合体くバインダー） １００部低分子量ポ
リエチレン ３部上記組成の混合物を１
４０℃に調整されたニーダ−にて溶融混合処理（１０分
）した後冷却、固化せしめた。次いて粗粉砕機により粗
粉砕後、ジェットミル粉砕機にて微粉砕を行い、更に気
流式分級機にて分級し粒径８〜２０μのトナーを得た。Example 1 100 parts of styrene-butyl acrylate copolymer (binder) 3 parts of low molecular weight polyethylene 1 part of the mixture having the above composition
After melting and mixing (10 minutes) in a kneader adjusted to 40°C, the mixture was cooled and solidified. Next, the mixture was coarsely pulverized using a coarse pulverizer, finely pulverized using a jet mill pulverizer, and further classified using an air classifier to obtain a toner having a particle size of 8 to 20 μm.
得られたトナーを約２００ ｍｅｓｌ＋の鉄分キャリア
と３：９７（トナー：鉄分キャリア）の重量比で混合し
現像剤Ａを得た。次にブローオフ帯電量測定製置により
この現像剤Ａの初期比帯電量を測定し性に優れ、着色剤
本来の色相を阻害することのない鮮明な黄色の画像が得
られた。又、現像剤Ａを用いて経時安定性試験（帯電量
経時変化試験及び帯電量耐湿経時試Ｍ）を実施したとこ
ろ下記表１の結果を得た。The obtained toner was mixed with about 200 mesl+ iron carrier at a weight ratio of 3:97 (toner:iron carrier) to obtain developer A. Next, the initial specific charge of this developer A was measured by blow-off charge measurement, and a clear yellow image with excellent properties and without interfering with the original hue of the colorant was obtained. Further, when a stability test over time (charge amount change test over time and charge amount moisture resistance test M over time) was carried out using developer A, the results shown in Table 1 below were obtained.
表１
以上の結果の如く現像剤Ａの経時安定性が極めて優れて
いた。Table 1 As shown in the above results, the stability over time of developer A was extremely excellent.
経時安定性試験
（帯電量経時変化試験）
現像剤（トナーと鉄分キャリアーとの混合物）ナーの帯
２ｆ１を測定する。Stability test over time (Test on change in charge amount over time) The developer (mixture of toner and iron carrier) toner band 2f1 is measured.
（帯電量耐湿経時試験）
上記帯電量経時変化試験の方法でポリ容器中にて１時間
帯電させた後、ポリ容器をオーブンの状態にて１００％
湿度の雰囲気中（室温）に１週間放置しトナーの帯？ｌ
ｆｆ１を測定する。(Electrical charge humidity resistance aging test) After charging in a plastic container for 1 hour using the method of the above charge amount aging test, the plastic container was placed in an oven to 100%
Leave the toner band in a humid atmosphere (room temperature) for a week? l
Measure ff1.
実施例２
ポリエステル樹脂（バインダー） １００部上記組成の
混合物を１６０℃に調整されたニーダ−にて溶融混合処
理（１０分）した後冷却、固化せしめた。次いで粗粉砕
機により粗粉砕後′、ジェットミル粉砕機にて微粉砕を
行い、更に気流式分級機にて分級し粒径８〜２０μのト
ナーを得た。Example 2 Polyester resin (binder) 100 parts A mixture having the above composition was melt-mixed (10 minutes) in a kneader adjusted to 160°C, and then cooled and solidified. Next, the mixture was coarsely pulverized using a coarse pulverizer, then finely pulverized using a jet mill pulverizer, and further classified using an air classifier to obtain a toner having a particle size of 8 to 20 μm.
得られたトナーを約２００ ｍｅｓｈの鉄分キャリアと
３：９７（トナー：鉄粉キャリア）の重量比で混合し現
像剤Ｂを得た。次にブローオフ帯１！量測定装置により
この現像剤Ｂの初期化帯を量を測定したところ−１８，
３μｃ／ｇであった。更にこの現像★
剤Ｂを用いて複写へにてコピーしたところ諧調性に優れ
た黒色の鮮明な画像が得られた。The obtained toner was mixed with about 200 mesh iron carrier at a weight ratio of 3:97 (toner: iron powder carrier) to obtain developer B. Next is blow-off zone 1! When the amount of the initialization zone of this developer B was measured using a quantity measuring device, it was found that -18,
It was 3μc/g. Further, when this developer ★ was used for copying, a clear black image with excellent tonality was obtained.
又、現像剤Ｂを用いて実施例１と同様に経時安定性試験
を実施したところ下記表２の結果をえた。Further, when a stability test over time was conducted using developer B in the same manner as in Example 1, the results shown in Table 2 below were obtained.
表２
以上の結果の如く現像剤Ｂの経時安定性が極めて優れて
いた。Table 2 As shown in the above results, the stability of developer B over time was extremely excellent.
実施例３
スチレン−アクリル酸メチル
エステル共重合体（バインダー） １００部低分子量ポ
リブロンピレン ３部Ｃ，１，Ｓｏｌ、
Ｂｌｕｅ １０５ （着色剤） １．５部前記
具体例（３）の化合物 １．５部上上記台物
を１０００部のアセトン、酢酸エチルの混合溶液に溶解
させ、常温にて１時間攪拌した。次いで、この混合液を
１００００部の水中へ、攪拌下に滴下し再沈澱せしめた
。生成した結晶を１１過、乾燥することにより粗粒子の
トナーをえた。Example 3 Styrene-acrylic acid methyl ester copolymer (binder) 100 parts Low molecular weight polybropyrene 3 parts C,1,Sol,
Blue 105 (colorant) 1.5 parts Compound of Specific Example (3) 1.5 parts The above-mentioned material was dissolved in a mixed solution of 1000 parts of acetone and ethyl acetate, and the mixture was stirred at room temperature for 1 hour. Next, this mixed solution was dropped into 10,000 parts of water while stirring to cause reprecipitation. The produced crystals were filtered for 11 days and dried to obtain a coarse particle toner.
次いでジェットミル粉砕機にて微粉砕を行い、更に気流
式分級機にて分級し粒径８〜２０μのトナーを得た。得
られたトナーを約２００ ｎ＋ｅｓｈの鉄粉キャリアと
３：９７（）ナー：鉄粉キャリア）の重量比で混合し現
像剤Ｃを得た。次いでブローオフ帯電量測定装置により
この現像剤Ｃの初期化帯電ころｒＩＩ調性に優れ、着色
剤本来の色相を阻害することのない鮮明な青色の画像が
得られた。Next, the mixture was finely pulverized using a jet mill, and further classified using an air classifier to obtain a toner having a particle size of 8 to 20 μm. The obtained toner was mixed with about 200 n+esh of iron powder carrier at a weight ratio of 3:97 (toner: iron powder carrier) to obtain developer C. Next, using a blow-off charge measuring device, it was found that this developer C had excellent initialization charging roller rII tonality, and a clear blue image was obtained without interfering with the original hue of the colorant.
又、現像剤Ｃを用いて実施例１と同様に経時安定性試験
を実稚したところ下記表３の結果を得た。Further, when a temporal stability test was conducted using Developer C in the same manner as in Example 1, the results shown in Table 3 below were obtained.
表３
以上の結果の如く現像剤Ｃの経時安定性が極めて優れて
いた。Table 3 As shown in the above results, the stability over time of developer C was extremely excellent.
実施例４
エボシキ樹脂（バインダー） １００部Ｃ，ｌ。［１
１５，ＲＥＤ ６０ （着色剤） １．２部Ｃ，１
，０１Ｓ、 Ｖｉｏｌｅｔ １７ （着色剤） ０．３
部前記具体例（４）の化合物 ２．０部上記朝成
の混合物を１００℃に調整された二本ロールにて１ＩＪ
ｄ混合処理した後自然冷却、固化せしめた。次いで粗粉
砕機により粗粉砕後、ジェットミル粉砕機にて微粉砕を
行い、更に気流式分級機にて分級し粒径８〜２０μのト
ナーを得た。Example 4 Eboshiki resin (binder) 100 parts C, l. [1
15, RED 60 (colorant) 1.2 parts C, 1
,01S, Violet 17 (colorant) 0.3
2.0 parts of the compound of the above specific example (4)
d After the mixing treatment, the mixture was naturally cooled and solidified. Next, the mixture was coarsely pulverized using a coarse pulverizer, finely pulverized using a jet mill pulverizer, and further classified using an air classifier to obtain a toner having a particle size of 8 to 20 μm.
得られたトナーを約２００ ｍｅｓｈの鉄粉キャリアと
３：９７（）ナー：鉄粉キャリア）の重量比で混合し現
像剤Ｅを得た。次にブローオフ帯電量測定装置によりこ
の現像剤Ｅの初期比帯電量を測定しに優れ、着色剤本来
の色相を阻害することのない鮮明な赤色の画像が得られ
た。又、現像剤Ｅを用いて実施例１と同様に経時安定性
試験を実施したところ下記表４の結果を得た。The obtained toner was mixed with about 200 mesh of iron powder carrier at a weight ratio of 3:97 (toner: iron powder carrier) to obtain developer E. Next, the initial specific charge amount of this developer E was measured using a blow-off charge amount measuring device, and a clear red image was obtained which did not interfere with the original hue of the colorant. Further, when a temporal stability test was conducted using developer E in the same manner as in Example 1, the results shown in Table 4 below were obtained.
表４
以上の結果の如く現像剤Ｅの経時安定性が極めて優れて
いた。Table 4 As shown in the above results, the stability over time of developer E was extremely excellent.
実施例５〜ｌＯ
表５の「化合物」の欄に示される化合物及び「着色剤」
の欄に示される着色剤を用いて実施例１と同様にして現
像剤を調製し各々の現像剤の初期比帯電量を測定し、実
施例１と同様に経時安定性試験を実施した。Examples 5 to 10 Compounds and “colorants” shown in the “Compound” column of Table 5
Developers were prepared in the same manner as in Example 1 using the colorants shown in the column, the initial specific charge amount of each developer was measured, and the stability test over time was conducted in the same manner as in Example 1.
いずれの化合物を用いたトナーも比帯電量の変現像剤も
諧調性に優れ、着、色剤本来の色相で鮮明な画像が得ら
れた。Toners using any of the compounds and developers with variable specific charge amounts had excellent tonality, and clear images with the original hue of the pigment and colorant were obtained.
本発明で得られた電子写真用トナーは従来の荷電制御剤
を用いたトナーに比べてシャープな帯電量分布と耐湿性
、及び経時安定性を有している。The electrophotographic toner obtained by the present invention has a sharper charge distribution, moisture resistance, and stability over time than toners using conventional charge control agents.
その結果極めて諧調性の高い画像が得られ、且つ反復画
像形成能が極めて良好で有る事が特徴である。又荷電制
御剤自体が本質的に無色であることから、カラートナー
に要求される色相に合わせて任意の着色剤を選定するこ
とが可能であり、且つ染料、顔料が有する本来の色相を
何ら阻害することが無い事も特徴である。As a result, an image with extremely high tonality can be obtained, and it is characterized by an extremely good ability to repeatedly form images. Furthermore, since the charge control agent itself is essentially colorless, it is possible to select any colorant according to the hue required for the color toner, and it does not interfere with the original hue of the dye or pigment. Another characteristic is that there is nothing to do.
Claims (1)
徴とする電子写真用トナー ▲数式、化学式、表等があります▼（１） （但し、式（１）中Ｒ、Ｒ′はそれぞれ独立に置換又は
非置換のアルキル基、置換又 は非置換のアリール基、アラルキル基、 シクロアルキル基又はアリル基を表す。）[Claims] 1. An electrophotographic toner characterized by containing a compound represented by the following formula (1) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (1) (However, formula (1) (R and R' each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, an aralkyl group, a cycloalkyl group, or an allyl group.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63102491A JP2614080B2 (en) | 1988-04-27 | 1988-04-27 | Electrophotographic toner |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63102491A JP2614080B2 (en) | 1988-04-27 | 1988-04-27 | Electrophotographic toner |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01274158A true JPH01274158A (en) | 1989-11-01 |
| JP2614080B2 JP2614080B2 (en) | 1997-05-28 |
Family
ID=14328895
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63102491A Expired - Lifetime JP2614080B2 (en) | 1988-04-27 | 1988-04-27 | Electrophotographic toner |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2614080B2 (en) |
-
1988
- 1988-04-27 JP JP63102491A patent/JP2614080B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2614080B2 (en) | 1997-05-28 |
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