JPH06240171A - Modification of pigment - Google Patents
Modification of pigmentInfo
- Publication number
- JPH06240171A JPH06240171A JP5508793A JP5508793A JPH06240171A JP H06240171 A JPH06240171 A JP H06240171A JP 5508793 A JP5508793 A JP 5508793A JP 5508793 A JP5508793 A JP 5508793A JP H06240171 A JPH06240171 A JP H06240171A
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- sulfuric acid
- acid solution
- solution
- modification
- 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
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、粗顔料中の不純物を除
去するとともに、微細な粒径の顔料を得る顔料の改質法
に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for modifying a pigment to remove impurities in a crude pigment and obtain a pigment having a fine particle size.
【０００２】[0002]
【従来の技術】顔料は汎用性塗料をはじめとしてさまざ
まな用途に使用されている。これらの顔料は粗顔料がそ
のまま用いられているのではなく、色味を均質にした
り、光沢性、着色力、分散性を向上させる等の改質処理
を施したものが使用されている。2. Description of the Related Art Pigments are used in various applications including general-purpose paints. As these pigments, crude pigments are not used as they are, but those that have been subjected to a modification treatment such as homogenizing the tint or improving glossiness, coloring power and dispersibility are used.
【０００３】従来粗顔料を分散し得る状態に改質する方
法として、顔料合成条件の改良、あるいは合成後の特定
処理などがある。合成後の処理としては粗顔料を無機塩
や粉砕助材と混合・磨砕する方法、界面活性剤を添加し
た系で粉砕処理する方法、フタロシアニン顔料において
はアシッドペースト法・アシッドスラリー法等が知られ
ている。また、顔料の精製には溶媒抽出が一般に用いら
れている。Conventionally, as a method for modifying a crude pigment into a dispersible state, there are improvements in pigment synthesis conditions or a specific treatment after synthesis. As the post-synthesis treatment, a method of mixing and grinding a crude pigment with an inorganic salt or a grinding aid, a method of grinding with a system containing a surfactant, and a phthalocyanine pigment known as an acid paste method or an acid slurry method are known. Has been. Further, solvent extraction is generally used for the purification of the pigment.
【０００４】[0004]
【発明が解決しようとする課題】最近は顔料独自の吸収
波長を利用して、光電変換素子、電子写真用感光体、光
記録媒体等に顔料を使用している。これらの機能性顔料
においては不純物による特性の経時変化、あるいは粒径
の不均一による特性のばらつき等が問題となっている。
たとえば電子写真用感光体の電荷発生物質に顔料を用い
る場合、合成後の一次粒径が大きいため分散性が低い、
あるいは場所によって感度がばらつくという問題があっ
た。さらに不純物を多く含む場合には吸収波長で光感度
を有しても帯電能が低い、暗減衰が大きいなどの初期特
性、あるいは繰り返し使用による感度シフト、帯電能の
低下などの問題があった。これらの問題を解決するた
め、上記のような改質処理が施されているが、顔料を十
分に精製、微粒化するには至っていない。Recently, pigments have been used in photoelectric conversion elements, electrophotographic photoreceptors, optical recording media, etc. by utilizing the absorption wavelength unique to the pigments. In these functional pigments, there are problems such as changes in characteristics due to impurities over time, and variations in characteristics due to uneven particle size.
For example, when a pigment is used as the charge generating substance of the electrophotographic photoreceptor, the dispersibility is low because the primary particle size after synthesis is large,
Alternatively, there was a problem that the sensitivity varied depending on the place. Further, when a large amount of impurities are contained, there are problems such as initial characteristics such as low charging ability and large dark decay even if it has photosensitivity at the absorption wavelength, or sensitivity shift due to repeated use, and deterioration of charging ability. In order to solve these problems, the above-described modification treatment has been carried out, but the pigment has not been sufficiently refined and atomized.
【０００５】そこで本発明の目的は、顔料を十分に精
製、微粒化することのできる顔料の改質法を提供するこ
とである。Therefore, an object of the present invention is to provide a method for modifying a pigment, which is capable of sufficiently purifying and atomizing the pigment.
【０００６】本発明の顔料の改質法は、顔料を硫酸に溶
解し硫酸溶液とした後に、硫酸溶液を水添することを特
徴とするものである。The method for modifying the pigment of the present invention is characterized in that the pigment is dissolved in sulfuric acid to form a sulfuric acid solution, and then the sulfuric acid solution is hydrogenated.
【０００７】また、本発明の顔料の改質法は、顔料を硫
酸に溶解し硫酸溶液とした後に、硫酸に不活性な水溶性
有機溶剤と硫酸溶液とを混合し、混合液を水添すること
を特徴とするものである。In the method for modifying the pigment of the present invention, the pigment is dissolved in sulfuric acid to form a sulfuric acid solution, and then a water-soluble organic solvent inert to sulfuric acid and a sulfuric acid solution are mixed, and the mixed solution is hydrogenated. It is characterized by that.
【０００８】さらに、本発明の顔料の改質法は、顔料を
硫酸に溶解し硫酸溶液とした後、硫酸に不活性な水溶性
有機溶剤の水溶液と硫酸溶液とを混合することを特徴と
するものである。Further, the method for modifying a pigment of the present invention is characterized in that the pigment is dissolved in sulfuric acid to prepare a sulfuric acid solution, and then an aqueous solution of a water-soluble organic solvent inert to sulfuric acid and a sulfuric acid solution are mixed. It is a thing.
【０００９】[0009]
【作用】本発明の改質法を施した顔料は、粒径が微細で
分散安定性が高く、さらに水溶性有機溶剤を用いる場合
には、改質過程において親油性、親水性の不純物を除去
することができる。The pigment subjected to the modification method of the present invention has a fine particle size and high dispersion stability, and when a water-soluble organic solvent is used, it removes lipophilic and hydrophilic impurities during the modification process. can do.
【００１０】本発明の改質法に用いられる顔料は、硫酸
に可溶で、かつ硫酸中で分解反応を起こさない顔料であ
れば使用できる。その一例としてフタロシアニン顔料、
スクエアリウム顔料、ペリレン顔料、アゾ顔料、キナク
リドン顔料等が挙げられる。The pigment used in the modifying method of the present invention may be any pigment that is soluble in sulfuric acid and does not cause a decomposition reaction in sulfuric acid. As an example, a phthalocyanine pigment,
Squarium pigment, perylene pigment, azo pigment, quinacridone pigment and the like can be mentioned.
【００１１】硫酸に不活性な水溶性有機溶剤としては、
水に可溶な低級アルコール、グリコール、グリコールエ
ーテル、カルボン酸等が挙げられる。As the water-soluble organic solvent inert to sulfuric acid,
Examples thereof include water-soluble lower alcohols, glycols, glycol ethers and carboxylic acids.
【００１２】[0012]
【実施例】以下、本発明の実施例にしたがって説明す
る。EXAMPLES Examples will be described below according to the present invention.
【００１３】（実施例１）スクエアリック酸とＮ，Ｎ−
ジメチルアニリンをｎ−ブタノールとトルエンの混合溶
媒中で加熱し、共沸反応にて脱水することにより化１に
示すスクエアリウム化合物を合成した。次に溶媒抽出に
より精製した。このときのスクエアリウム化合物の電子
顕微鏡写真を図２に示す（倍率２０００倍）。続いて硫
酸１０ｇに対し１ｇのスクエアリウム化合物を加え、得
られた硫酸溶液をジエチレングリコールジメチルエーテ
ル中に氷浴下で滴下した。その後水１００ｇをゆっくり
添加することによりスクエアリウム化合物の改質を行っ
た。このようにして得られたスクエアリウム化合物の電
子顕微鏡写真を図１に示す（倍率２００００倍）。これ
らの図面から、本発明の改質法により顔料の粒径が非常
に細かくなり、粒径も均一化されていることがわかる。(Example 1) Squaric acid and N, N-
Dimethylaniline was heated in a mixed solvent of n-butanol and toluene and dehydrated by an azeotropic reaction to synthesize the squarylium compound shown in Chemical formula 1. It was then purified by solvent extraction. An electron micrograph of the squarylium compound at this time is shown in FIG. 2 (magnification: 2000 times). Subsequently, 1 g of the squarylium compound was added to 10 g of sulfuric acid, and the resulting sulfuric acid solution was added dropwise to diethylene glycol dimethyl ether in an ice bath. After that, 100 g of water was slowly added to modify the squarium compound. An electron micrograph of the thus obtained squarainium compound is shown in FIG. 1 (magnification: 20000 times). From these drawings, it can be seen that the particle size of the pigment is made extremely fine and the particle size is made uniform by the modification method of the present invention.
【００１４】[0014]
【化１】 [Chemical 1]
【００１５】（実施例２）実施例１にて改質したスクエ
アリウム化合物２ｇとポリエステル樹脂１８ｇをシクロ
ヘキサノン１８０ｇに溶解したポリマー溶液を混合し、
振とう式分散機で３時間分散した。本発明の改質法を施
したスクエアリウム化合物は分散性が高く、容易に分散
させることができる。得られた溶液をＡｌ蒸着ポリエス
テルフィルム上にワイヤーバーで塗布し、乾燥後の膜厚
が０．５μｍでスクエアリウム化合物濃度１０ｗｔ％の
電荷発生層を形成した。(Example 2) 2 g of the squarylium compound modified in Example 1 and 18 g of polyester resin dissolved in 180 g of cyclohexanone were mixed in a polymer solution,
Dispersion was carried out for 3 hours with a shaking type disperser. The squarylium compound subjected to the modification method of the present invention has high dispersibility and can be easily dispersed. The resulting solution was applied onto an Al vapor-deposited polyester film with a wire bar to form a charge generation layer having a dried film thickness of 0.5 μm and a squarylium compound concentration of 10 wt%.
【００１６】次に、ポリカーボネート樹脂１２ｇをシク
ロヘキサノン１０８ｇに溶解させたポリマー溶液に、電
荷輸送物質として化２に示すヒドラゾン化合物を１０ｇ
溶解させた。得られた溶液を電荷発生層上にワイヤーバ
ーで塗布し、膜厚が１７μｍの電荷輸送層を形成して電
子写真用感光体を作製した。Next, in a polymer solution prepared by dissolving 12 g of polycarbonate resin in 108 g of cyclohexanone, 10 g of the hydrazone compound shown in Chemical formula 2 as a charge transport substance is added.
Dissolved. The obtained solution was applied onto the charge generation layer with a wire bar to form a charge transport layer having a thickness of 17 μm, to prepare an electrophotographic photoreceptor.
【００１７】[0017]
【化２】 [Chemical 2]
【００１８】このようにして作製した電子写真用感光体
を、まず暗所にて−６ＫＶでコロナ帯電し、次いで照度
２．５μＷ／ｃｍ2 のＷランプで２０秒間露光し感光体
特性を調べた。感光体特性としては、帯電後初期帯電電
位Ｖ0 、表面電位が−６２０Ｖから−６００Ｖまで暗減
衰するのに要する時間ｔD 、−６００Ｖから−３００Ｖ
に光減衰するのに必要な露光量Ｅ1 / 2 、２０秒光照射
後の残留電位Ｖｒを測定した。さらに、この電子写真用
感光体に同様の操作を繰り返し１０００回後のＶ0 （１
０００）、ｔD （１０００）、Ｅ1 / 2 （１０００）、
Ｖｒ（１０００）を測定し、耐久性を調べた。結果は下
記の通りであった。The electrophotographic photoreceptor thus prepared was first corona-charged at -6 KV in a dark place, and then exposed to a W lamp having an illuminance of 2.5 μW / cm 2 for 20 seconds to examine the characteristics of the photoreceptor. . As the characteristics of the photoconductor, the initial charging potential V 0 after charging, the time t D required for the surface potential to dark decay from −620 V to −600 V, and −600 V to −300 V.
The residual electric potential Vr after irradiation with light for 20 seconds and the amount of exposure E 1/2 required for light attenuation was measured. Further, the same operation was repeated for this electrophotographic photosensitive member, and V 0 (1
000), t D (1000), E 1/2 (1000),
Vr (1000) was measured and durability was investigated. The results were as follows.
【００１９】Ｖ0 ＝−７３２Ｖ ｔD ＝１２秒 Ｅ1 / 2 ＝０．４６μＪ／ｃｍ2 Ｖｒ＝−４７Ｖ Ｖ0 （１０００）＝−７２８Ｖ ｔD （１０００）＝１０秒 Ｅ1 / 2 （１０００）＝０．４２μＪ／ｃｍ2 Ｖｒ（１０００）＝−５０ＶV 0 = -732 V t D = 12 seconds E 1/2 = 0.46 μJ / cm 2 Vr = -47 V V 0 (1000) =-728 V t D (1000) = 10 seconds E 1/2 (1000 ) = 0.42 μJ / cm 2 Vr (1000) = − 50V
【００２０】（実施例３）スクエアリック酸とＮ，Ｎ−
ジメチルアニリンをｎ−ブタノールとトルエンの混合溶
媒中で加熱し、共沸反応にて脱水することにより化１に
示したスクエアリウム化合物を合成した。続いて硫酸１
０ｇに対し１ｇのスクエアリウム化合物を加え、得られ
た硫酸溶液をジエチレングリコールジメチルエーテルの
水溶液に滴下することにより、スクエアリウム化合物の
改質を行った。このようにして得られたスクエアリウム
化合物を電子顕微鏡にて観察したところ実施例１と同様
の粒径であった。また、分散性も良好であり、実施例２
と同様の条件で電子写真用感光体を作製することがで
き、感光体特性は実施例２と同様であった。(Example 3) Squaric acid and N, N-
Dimethylaniline was heated in a mixed solvent of n-butanol and toluene and dehydrated by an azeotropic reaction to synthesize the squarylium compound shown in Chemical formula 1. Then sulfuric acid 1
The squarium compound was modified by adding 1 g of the squarium compound to 0 g and dropping the resulting sulfuric acid solution into an aqueous solution of diethylene glycol dimethyl ether. When the thus-obtained squarylium compound was observed with an electron microscope, the particle size was the same as in Example 1. Further, the dispersibility is also good, and Example 2
An electrophotographic photosensitive member could be produced under the same conditions as in 1. and the photosensitive member characteristics were the same as in Example 2.
【００２１】（実施例４）スクエアリック酸とＮ，Ｎ−
ジメチルアニリンをｎ−ブタノールとトルエンの混合溶
媒中で加熱し、共沸反応にて脱水することにより化１に
示したスクエアリウム化合物を合成した。続いて硫酸１
０ｇに対し１ｇのスクエアリウム化合物を加え、得られ
た硫酸溶液を水中に滴下することにより、スクエアリウ
ム化合物の改質を行った。このようにして得られたスク
エアリウム化合物を電子顕微鏡にて観察したところ実施
例１と同様の粒径であった。また、分散性も良好であ
り、実施例２と同様の条件で電子写真用感光体を作製す
ることができ、感光体特性は実施例２と同様であった。(Example 4) Squaric acid and N, N-
Dimethylaniline was heated in a mixed solvent of n-butanol and toluene and dehydrated by an azeotropic reaction to synthesize the squarylium compound shown in Chemical formula 1. Then sulfuric acid 1
The squarium compound was modified by adding 1 g of the squarium compound to 0 g and dropping the obtained sulfuric acid solution into water. When the thus-obtained squarylium compound was observed with an electron microscope, the particle size was the same as in Example 1. The dispersibility was also good, and an electrophotographic photoreceptor could be prepared under the same conditions as in Example 2, and the photoreceptor characteristics were the same as in Example 2.
【００２２】（比較例１）実施例１において溶媒抽出ま
で行い、硫酸溶解以降の処理を施さなかったスクエアリ
ウム化合物を、電荷発生物質として使用するほかは実施
例２と同様の条件で電子写真用感光体を作製した。感光
体特性は下記の通りであった。Comparative Example 1 For electrophotography under the same conditions as in Example 2 except that a squarylium compound which was subjected to solvent extraction in Example 1 but was not treated after dissolution with sulfuric acid was used as the charge generating substance. A photoconductor was prepared. The photoconductor characteristics were as follows.
【００２３】Ｖ0 ＝−７２７Ｖ ｔD ＝１０秒 Ｅ1 / 2 ＝０．７３μＪ／ｃｍ2 Ｖｒ＝−５１Ｖ Ｖ0 （１０００）＝−７１５Ｖ ｔD （１０００）＝８秒 Ｅ1 / 2 （１０００）＝０．６８μＪ／ｃｍ2 Ｖｒ（１０００）＝−５６ＶV 0 = -727V t D = 10 seconds E 1/2 = 0.73 μJ / cm 2 Vr = -51V V 0 (1000) =-715V t D (1000) = 8 seconds E 1/2 (1000 ) = 0.68 μJ / cm 2 Vr (1000) = − 56V
【００２４】（実施例５）化３に示すペリレン顔料１ｇ
を硫酸１５ｇに加え、得られた硫酸溶液をジエチレング
リコールジメチルエーテルの水溶液に滴下した。このよ
うにして得られたペリレン顔料を電子顕微鏡にて観察し
たところ、処理前のものに比べて、粒径が非常に細か
く、均一であった。(Example 5) 1 g of perylene pigment shown in Chemical formula 3
Was added to 15 g of sulfuric acid, and the resulting sulfuric acid solution was added dropwise to an aqueous solution of diethylene glycol dimethyl ether. Observation of the thus-obtained perylene pigment with an electron microscope revealed that the particle size was very fine and uniform as compared with that before treatment.
【００２５】[0025]
【化３】 [Chemical 3]
【００２６】このペリレン顔料５ｇとポリエステル樹脂
２０ｇをシクロヘキサノン１８０ｇに溶解したポリマー
溶液を混合し、振とう式分散機で３時間分散した。得ら
れた溶液をＡｌ蒸着ポリエステルフィルム上にワイヤー
バーで塗布し、乾燥後の膜厚が１７μｍの感光層を形成
した。A polymer solution prepared by dissolving 5 g of this perylene pigment and 20 g of polyester resin in 180 g of cyclohexanone was mixed and dispersed for 3 hours with a shaking type disperser. The resulting solution was applied onto an Al vapor-deposited polyester film with a wire bar to form a photosensitive layer having a film thickness after drying of 17 μm.
【００２７】このようにして作製した電子写真用感光体
を、まず暗所にて−６ＫＶでコロナ帯電し、次いで照度
２．５μＷ／ｃｍ2 、５００ｎｍの光で２０秒間露光し
感光体特性を調べた。感光体特性としては、帯電後初期
帯電電位Ｖ0 、表面電位が−６２０Ｖから−６００Ｖま
で暗減衰するのに要する時間ｔD 、−６００Ｖから−３
００Ｖに光減衰するのに必要な露光量Ｅ1 / 2 、２０秒
光照射後の残留電位Ｖｒを測定した。さらに、この電子
写真用感光体に同様の操作を繰り返し１０００回後のＶ
0 （１０００）、ｔD （１０００）、Ｅ1 / 2 （１００
０）、Ｖｒ（１０００）を測定し、耐久性を調べた。結
果は下記の通りであった。The electrophotographic photoreceptor thus prepared was first corona-charged at -6 KV in a dark place, and then exposed to light of 2.5 μW / cm 2 and 500 nm for 20 seconds to examine the characteristics of the photoreceptor. It was As the characteristics of the photoconductor, the initial charging potential V 0 after charging, the time t D required for dark decay of the surface potential from −620 V to −600 V, and −600 V to −3.
The amount of exposure E 1/2 required for light attenuation to 00 V and the residual potential Vr after 20 seconds of light irradiation were measured. Further, the same operation was repeated for this electrophotographic photosensitive member, and V after 1000 times
0 (1000), t D (1000), E 1/2 (100
0) and Vr (1000) were measured and durability was investigated. The results were as follows.
【００２８】Ｖ0 ＝−７６２Ｖ ｔD ＝１８秒 Ｅ1 / 2 ＝９．８９μＪ／ｃｍ2 Ｖｒ＝−５７Ｖ Ｖ0 （１０００）＝−７５８Ｖ ｔD （１０００）＝１７秒 Ｅ1 / 2 （１０００）＝９．４３μＪ／ｃｍ2 Ｖｒ（１０００）＝−６９ＶV 0 = -762 V t D = 18 seconds E 1/2 = 9.89 μJ / cm 2 Vr = -57 V V 0 (1000) =-758 V t D (1000) = 17 seconds E 1/2 (1000 ) = 9.43 μJ / cm 2 Vr (1000) = − 69V
【００２９】（比較例２）電荷発生物質として、実施例
６で用いたペリレン顔料で本発明の改質法を施さないも
のを用いた以外は実施例６と同様の条件で電子写真用感
光体を作製した。感光体特性は下記の通りであった。Comparative Example 2 An electrophotographic photoreceptor under the same conditions as in Example 6 except that the perylene pigment used in Example 6 which was not subjected to the modification method of the present invention was used as the charge generating substance. Was produced. The photoconductor characteristics were as follows.
【００３０】Ｖ0 ＝−７４６Ｖ ｔD ＝１５秒 Ｅ1 / 2 ＝２１．４７μＪ／ｃｍ2 Ｖｒ＝−２３２Ｖ Ｖ0 （１０００）＝−６５８Ｖ ｔD （１０００）＝１３秒 Ｅ1 / 2 （１０００）＝１８．２６μＪ／ｃｍ2 Ｖｒ（１０００）＝−２４８ＶV 0 = -746 V t D = 15 seconds E 1/2 = 21.47 μJ / cm 2 Vr = -232 V V 0 (1000) =-658 V t D (1000) = 13 seconds E 1/2 (1000 ) = 18.26 μJ / cm 2 Vr (1000) = − 248V
【００３１】[0031]
【発明の効果】本発明の改質法により、非常に粒径が細
かく、均一で、分散性に優れる顔料を得ることができ
る。さらに電子写真用感光体の電荷発生物質として用い
た場合に光感度が高く繰り返しによる特性の経時変化が
少ないという結果から、純度の高い顔料が得られること
がわかる。By the modification method of the present invention, it is possible to obtain a pigment having a very fine particle size, a uniform particle size, and excellent dispersibility. Further, when it is used as a charge generating substance for an electrophotographic photoreceptor, the photosensitivity is high and there is little change in characteristics over time due to repetition, which indicates that a pigment with high purity can be obtained.
【図１】本発明の改質法を施した顔料の電子顕微鏡写真
である。FIG. 1 is an electron micrograph of a pigment that has been subjected to the modifying method of the present invention.
【図２】本発明の改質法を施す前の顔料の電子顕微鏡写
真である。FIG. 2 is an electron micrograph of a pigment before being subjected to the modifying method of the present invention.
─────────────────────────────────────────────────────
─────────────────────────────────────────────────── ───
【手続補正書】[Procedure amendment]
【提出日】平成６年２月３日[Submission date] February 3, 1994
【手続補正１】[Procedure Amendment 1]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】図面の簡単な説明[Name of item to be corrected] Brief description of the drawing
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【図面の簡単な説明】[Brief description of drawings]
【図１】本発明の改質法を施した顔料の粒子構造を表す
電子顕微鏡写真である。FIG. 1 is an electron micrograph showing a particle structure of a pigment subjected to a modification method of the present invention.
【図２】本発明の改質法を施す前の顔料の粒子構造を表
す電子顕微鏡写真である。FIG. 2 is an electron micrograph showing a particle structure of a pigment before the modification method of the present invention.
Claims (3)
に、該硫酸溶液を水添することを特徴とする顔料の改質
法。1. A method for modifying a pigment, which comprises dissolving the pigment in sulfuric acid to form a sulfuric acid solution, and then hydrogenating the sulfuric acid solution.
に、前記硫酸に不活性な水溶性有機溶剤と前記硫酸溶液
とを混合し、該混合液を水添することを特徴とする顔料
の改質法。2. A pigment which is prepared by dissolving a pigment in sulfuric acid to prepare a sulfuric acid solution, mixing the water-soluble organic solvent inert to the sulfuric acid with the sulfuric acid solution, and hydrogenating the mixed solution. Modification method.
前記硫酸に不活性な水溶性有機溶剤の水溶液と前記硫酸
溶液とを混合することを特徴とする顔料の改質法。3. The pigment is dissolved in sulfuric acid to prepare a sulfuric acid solution,
A method for modifying a pigment, which comprises mixing an aqueous solution of a water-soluble organic solvent inert to sulfuric acid with the sulfuric acid solution.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP05508793A JP3297128B2 (en) | 1993-02-19 | 1993-02-19 | Pigment modification method |
| GB9311425A GB2274848A (en) | 1993-02-05 | 1993-06-03 | Modification of pigment and electrophotographic photoreceptor containing modified pigment |
| US08/071,475 US5403687A (en) | 1993-02-05 | 1993-06-04 | Modification of pigment and electrophotographic photoreceptor with modified pigment |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP05508793A JP3297128B2 (en) | 1993-02-19 | 1993-02-19 | Pigment modification method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06240171A true JPH06240171A (en) | 1994-08-30 |
| JP3297128B2 JP3297128B2 (en) | 2002-07-02 |
Family
ID=12988949
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP05508793A Expired - Fee Related JP3297128B2 (en) | 1993-02-05 | 1993-02-19 | Pigment modification method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3297128B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020132706A (en) * | 2019-02-15 | 2020-08-31 | Dic株式会社 | Method for producing surface-treated organic pigment |
-
1993
- 1993-02-19 JP JP05508793A patent/JP3297128B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020132706A (en) * | 2019-02-15 | 2020-08-31 | Dic株式会社 | Method for producing surface-treated organic pigment |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3297128B2 (en) | 2002-07-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69531590T2 (en) | Titanyl phthalocyanine crystals, methods of manufacturing the same, and electrophotographic photoreceptors using the same | |
| JPH0629976B2 (en) | Single layer type electrophotographic photoreceptor | |
| JPH05202309A (en) | Production of titanyl phthalocyanine | |
| FR2551561A1 (en) | ELECTROPHOTOGRAPHIC CLICHES | |
| DE3823363C2 (en) | Electrophotographic recording material and process for its production | |
| JPH06240171A (en) | Modification of pigment | |
| US7998650B2 (en) | Method for preparing oxytitanium phthalocyanine charge generating material and the new-type oxytitanium phthalocyanine charge generating material therefrom | |
| JPH06279704A (en) | Preparation of iv type oxytitanium phthalocyanine | |
| JP2873627B2 (en) | Method for producing titanyl phthalocyanine crystal | |
| KR100203312B1 (en) | Oxy-titanium pthalocyanine crystal | |
| DE19925647A1 (en) | New crystal modifications of oxytitanium phthalocyanine useful in electrophotographic photoreceptor | |
| JP3248638B2 (en) | Electrophotographic photoreceptor | |
| JPH0352056B2 (en) | ||
| JP4164970B2 (en) | Pigment particles, production method thereof, electrophotographic photoreceptor using the same, and electrophotographic image forming method | |
| JP3259414B2 (en) | Photoconductive material and electrophotographic photoreceptor | |
| JP2973055B2 (en) | Titanyl phthalocyanine crystal dispersion | |
| JP3072778B2 (en) | Method for producing oxytitanium phthalocyanine crystal | |
| JP2532795B2 (en) | Method for manufacturing electrophotographic photoreceptor | |
| JP2830417B2 (en) | Electrophotographic photoreceptor and coating solution for organic electrophotographic photoreceptor | |
| JPH01291256A (en) | Electrophotographic sensitive body | |
| JP2560481B2 (en) | Method for manufacturing electrophotographic photoreceptor | |
| JP3230173B2 (en) | Electrophotographic photoreceptor | |
| US5403687A (en) | Modification of pigment and electrophotographic photoreceptor with modified pigment | |
| JPH0823705B2 (en) | Photoconductor | |
| JP3230179B2 (en) | Electrophotographic photoreceptor |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |