JPS6320365A - Novel titanyl phthalocyanine crystal - Google Patents
Novel titanyl phthalocyanine crystalInfo
- Publication number
- JPS6320365A JPS6320365A JP16333086A JP16333086A JPS6320365A JP S6320365 A JPS6320365 A JP S6320365A JP 16333086 A JP16333086 A JP 16333086A JP 16333086 A JP16333086 A JP 16333086A JP S6320365 A JPS6320365 A JP S6320365A
- Authority
- JP
- Japan
- Prior art keywords
- type
- titanyl phthalocyanine
- crystal
- novel
- alpha
- 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
- SJHHDDDGXWOYOE-UHFFFAOYSA-N oxytitamium phthalocyanine Chemical compound [Ti+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 SJHHDDDGXWOYOE-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 239000013078 crystal Substances 0.000 title claims abstract description 23
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 238000002441 X-ray diffraction Methods 0.000 claims abstract description 6
- 238000010586 diagram Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 239000007900 aqueous suspension Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000049 pigment Substances 0.000 abstract description 6
- 239000000725 suspension Substances 0.000 abstract description 6
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 abstract description 4
- 229940117389 dichlorobenzene Drugs 0.000 abstract description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 230000003287 optical effect Effects 0.000 abstract description 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- 230000007704 transition Effects 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- -1 nonionic Chemical group 0.000 description 1
- 239000002736 nonionic surfactant 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
- 230000001107 psychogenic effect Effects 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
「産業上の利用分野」
本発明は顔料として有用なチタニルフタロシアニンの新
規な結晶の製造法に関する。DETAILED DESCRIPTION OF THE INVENTION "Field of Industrial Application" The present invention relates to a method for producing a novel crystal of titanyl phthalocyanine useful as a pigment.
「従来の技術」
チタニルフタロシアニンに、製造条件により少なくとも
準安定なα型と安定なβ型の２種の結晶型が存在すふこ
とｔｉＰＢ８５］７２等によって知られていふ。これら
のチタニルフタロシアニンの結晶型は機械的ひずみ、有
機溶剤及び熱の影響下に、相互に結晶型が転移すみこと
も知られている。例えばα型チタニルフタロシアニンは
ジクロルベンゼン等の芳香族溶剤の接触によって常温に
おいてもβ型に転移丁ふことは一般によく知られていふ
。"Prior Art" It is known that titanyl phthalocyanine has at least two crystal forms, a metastable α type and a stable β type, depending on the manufacturing conditions. It is also known that these crystal forms of titanyl phthalocyanine undergo mutual transition under the influence of mechanical strain, organic solvents, and heat. For example, it is generally well known that α-type titanyl phthalocyanine can be converted to β-type even at room temperature by contact with an aromatic solvent such as dichlorobenzene.
「発明が解決しようとする問題点」
本発明は従来知られていなかった新規な結晶型を有する
チタニルフタロシアニンの製造法全提供しようとずぶも
のであり、本発明にがかる新規チタニルフタロシアニン
は従来のものと同様に顔料として有用であるのみならず
、結晶転移による光ディスク用記碌材料への応用が期待
されるものである。"Problems to be Solved by the Invention" The present invention is dedicated to providing a complete method for producing titanyl phthalocyanine having a novel crystal form that has not been previously known. Not only is it useful as a pigment, but it is also expected to be used as a recording material for optical discs due to its crystal transition.
「問題点を解決するための手段」
本発明はα型チタニルフタロシアニンの水ａＭ濁液に芳
香族炭化水素溶剤を添加し加熱処理することを特徴とす
るＸ線回析図において、回析角２θが２７．３度に強い
線を示す新規チタニルフタロシアニン結晶の製造法であ
ふ。"Means for Solving the Problems" The present invention provides an X-ray diffraction diagram characterized in that an aromatic hydrocarbon solvent is added to an aqueous aM suspension of α-type titanyl phthalocyanine and heat-treated. The new method for producing titanyl phthalocyanine crystals exhibiting a strong line at 27.3 degrees has been developed.
本発明にいう懸濁液はα型チタニルフタロシアーン顔料
の分散可能な範囲であればよく、好まし〈は顔料分２〜
５０ｗｔ％でろふ。芳香族炭化水素溶剤としてはモノク
ロルベンゼン、ジクロルベンゼン、トリクロルベンゼン
、トルエン、キシレン等があげらｆｉふ。この芳香族炭
化水素溶剤は懸濁液の水に対して５０ｗｔ％以下−好ま
しくは５〜】０ｗｔ％である。又場合によっては懸濁液
に界面活性剤を添加してもよい。界面活性剤はカチオン
系、ノニオン系、アニオン系のいずれでもよくその添７
ｘ＋景はチタニルフタロシアニンの］０ｗｔ％以下、好
甘しくは５〜１ｗｔ％でめふ。The suspension referred to in the present invention may be within a range in which the α-type titanyl phthalocyanine pigment can be dispersed, and preferably the pigment content is 2 to 2.
50wt%. Examples of the aromatic hydrocarbon solvent include monochlorobenzene, dichlorobenzene, trichlorobenzene, toluene, and xylene. The aromatic hydrocarbon solvent is present in an amount of 50 wt% or less, preferably 5 to 0 wt%, based on the water of the suspension. A surfactant may also be added to the suspension depending on the case. The surfactant may be cationic, nonionic, or anionic.
The amount of x+ is less than 0 wt% of titanyl phthalocyanine, preferably 5 to 1 wt%.
本発明を行う際の反応条件の加熱処理温度は室温〜１０
０℃、好甘しくＦｉ５０〜１００℃であり、訓熱処理時
間Ｉ／ｉ３〜５時間あれば充分であみ。The heat treatment temperature of the reaction conditions when carrying out the present invention is room temperature to 10
0°C, preferably Fi 50 to 100°C, and a heating treatment time I/i of 3 to 5 hours is sufficient.
「作用」
本発明方法によればα型チタニルフタロシアニンはβ型
に転移すみことなく添付のＸ線回析図１にみらｆＬるよ
うに、回析角２θが２７．３度に強い線を示すものであ
み。Ｘ線巻→回折図２及び３＃′ｉ夫々α型、β型のチ
タニルフタロシアニンのものである。また本発明の新規
チタニルフタロシアニン結晶はα型及びβ型とは異なつ
念挙動を示すもノテする。例えばジクロルメタン、シク
ロヘキサノン等の有機溶剤に接触させ急場合α型及びβ
型は結晶転移を起石ないが、本発明にかかみものはβ型
に転移すみものである。従って本発明にかかるＴｔｍチ
タニルフタロシアニンは不安定な結晶型と推定される。"Effect" According to the method of the present invention, α-type titanyl phthalocyanine does not undergo any transition to β-type, and as shown in the attached X-ray diffraction diagram 1, a strong line is formed at a diffraction angle 2θ of 27.3 degrees. Ami with what you show. X-ray winding→diffraction diagrams 2 and 3#'i are of α-type and β-type titanyl phthalocyanine, respectively. It is also noted that the novel titanyl phthalocyanine crystal of the present invention exhibits psychogenic behavior different from the α-type and β-type. For example, in case of sudden contact with organic solvents such as dichloromethane and cyclohexanone, α-type and β-type
Although the type does not cause crystal transition, the present invention does cause a crystal transition to the β type. Therefore, the Ttm titanyl phthalocyanine according to the present invention is presumed to be in an unstable crystal form.
「実施例」
実施例にて本発明の詳細な説明するが、これらの例は本
発明を限定するものでＶｉない。実施例中「部」は重１
部である。"Examples" The present invention will be explained in detail in Examples, but these examples do not limit the present invention. In the examples, "part" means 1
Department.
実施例】
通常の酸ペースト法によって得らｆ′Ｌ念含水α型チタ
ニルフタロシアニンペースト（ｆｉ料分２０ｗｔ％）１
０部を水２０部中に懸濁し、ジクロルベンゼン２部を添
加し５０〜６０℃にて１時間熱処理し続いて許過−メタ
ノール洗浄、水洗し乾慄した。Example: f′L-containing α-type titanyl phthalocyanine paste (FI content 20 wt%) obtained by the usual acid paste method 1
0 part was suspended in 20 parts of water, 2 parts of dichlorobenzene was added and heat treated at 50 to 60°C for 1 hour, followed by passing, washing with methanol, washing with water and drying.
こうして得られたチタニルフタロシアニンｌ１ｘｉ回折
図より本処理によりα型からβ型に転移はなく回析角２
θが２７．３度に強い線を示す、新規チタニルフタロシ
アニンであふ。According to the titanyl phthalocyanine l1xi diffraction diagram obtained in this way, there was no transition from α type to β type due to this treatment, and the diffraction angle was 2.
Filled with a new titanyl phthalocyanine that shows a strong line at θ of 27.3 degrees.
実施例２
実施例】に更にノニオン系界面活性剤０．１ｇを添加し
、他は全く同様の処理を行っｔｏこうして得られたチタ
ニルフタロシアニンは実施例】と同様回析角２θが２７
．３度に強い線を示す新規チタニルフタロシアニンであ
る。Example 2 In addition, 0.1 g of nonionic surfactant was added to Example, and the other treatment was carried out in exactly the same manner.The titanyl phthalocyanine thus obtained had a diffraction angle 2θ of 27 as in Example.
．． This is a new titanyl phthalocyanine that shows a strong line at the third degree.
「発明の効果」
本発明Ｆｉ顔料としても有用であり結晶転移性を有すふ
ことがら新規な用途が期待される新しい結晶型を有すふ
チタニルフタロシアニンを、簡単な方法で提供できると
いう効果を示すものであみ。"Effects of the Invention" The effect of the present invention is that it is possible to provide, by a simple method, phthalocyanine having a new crystal type that is useful as an Fi pigment and has crystal transition properties, and is expected to find new uses. Ami with what you show.
第】図はＸ線回析図であり、図中の】は本発明にかかふ
チタニルフタロシアニン結晶の、２及び３ｆｉ夫々公知
のα型及びβ型のチタニルフタロシアニン結晶の図であ
る。The figure shows an X-ray diffraction diagram, and the figures in the figure show the known α-type and β-type titanyl phthalocyanine crystals, 2 and 3fi, respectively, according to the present invention.
Claims (1)
水素溶剤を添加し加熱処理することを特徴とするＸ線回
析図において、回析角２θが２７．３度に強い線を示す
新規チタニルフタロシアニン結晶の製造法。A novel titanyl phthalocyanine that exhibits a strong line at the diffraction angle 2θ of 27.3 degrees in an X-ray diffraction diagram characterized by adding an aromatic hydrocarbon solvent to an aqueous suspension of α-type titanyl phthalocyanine and heat treating it. Method of manufacturing crystals.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61163330A JPH0639575B2 (en) | 1986-07-11 | 1986-07-11 | Method for producing titanyl phthalocyanine crystal |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61163330A JPH0639575B2 (en) | 1986-07-11 | 1986-07-11 | Method for producing titanyl phthalocyanine crystal |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6320365A true JPS6320365A (en) | 1988-01-28 |
| JPH0639575B2 JPH0639575B2 (en) | 1994-05-25 |
Family
ID=15771804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61163330A Expired - Lifetime JPH0639575B2 (en) | 1986-07-11 | 1986-07-11 | Method for producing titanyl phthalocyanine crystal |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0639575B2 (en) |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0384470A2 (en) * | 1989-02-23 | 1990-08-29 | Mitsubishi Chemical Corporation | Process for preparation of crystalline oxytitanium phthalocyanine |
| JPH03134065A (en) * | 1989-10-19 | 1991-06-07 | Canon Inc | Preparation of oxytitanium phthalocyanine crystal |
| JPH03269064A (en) * | 1990-03-20 | 1991-11-29 | Fuji Xerox Co Ltd | Titanylphthalocyanine crystal and electrophotographic photosensitive form using same |
| JPH03269061A (en) * | 1990-03-20 | 1991-11-29 | Fuji Xerox Co Ltd | Production of titanylphthalocyanine crystal |
| US5153094A (en) * | 1990-06-14 | 1992-10-06 | Xerox Corporation | Processes for the preparation of photogenerating pigments |
| US5166339A (en) * | 1990-06-04 | 1992-11-24 | Xerox Corporation | Processes for the preparation of titanium phthalocyanines |
| EP0516433A2 (en) * | 1991-05-28 | 1992-12-02 | Xerox Corporation | Process for the preparation of titanyl phthalocyanines |
| US5183886A (en) * | 1989-05-22 | 1993-02-02 | Mitsubishi Kasei Corporation | Process for preparation of crystalline oxytitanium phthalocyanine showing A,B or C form |
| US5272264A (en) * | 1989-05-22 | 1993-12-21 | Mitsubishi Kasei Corporation | Process for preparation of crystalline oxytitanium phthalocyanine |
| US5290928A (en) * | 1990-11-22 | 1994-03-01 | Fuji Xerox Co., Ltd. | Process for preparing oxytitanium phthalocyanine hydrate crystal |
| JPH0692919A (en) * | 1991-05-22 | 1994-04-05 | Nitto Chem Ind Co Ltd | Stabilization of aqueous solution of acrylamide |
| US5334856A (en) * | 1990-07-03 | 1994-08-02 | Mitsubishi Kasei Corporation | Image readout element with oxytitanium phthalocyanine |
| US5972551A (en) * | 1996-12-26 | 1999-10-26 | Sharp Kabushiki Kaisha | Crystalline titanyl phthalocyanines and use thereof |
| US6210847B1 (en) | 1998-10-28 | 2001-04-03 | Sharp Kabushiki Kaisha | Crystalline oxotitanylphthalocyanine and electrophotographic photoreceptor using the same |
| US6225015B1 (en) | 1998-06-04 | 2001-05-01 | Mitsubishi Paper Mills Ltd. | Oxytitanium phthalocyanine process for the production thereof and electrophotographic photoreceptor to which the oxytitanium phthalocyanine is applied |
| US6291120B1 (en) | 1999-05-14 | 2001-09-18 | Sharp Kabushiki Kaisha | Electrophotographic photoreceptor and coating composition for charge generating layer |
| US6322940B1 (en) | 1999-01-08 | 2001-11-27 | Sharp Kabushiki Kaisha | Electrophotographic photoreceptor and electrophotographic image forming process |
| JP2007233351A (en) * | 2006-01-31 | 2007-09-13 | Yamanashi Electronics Co Ltd | Electrophotographic photoreceptor and electrophotographic device |
| WO2007108488A1 (en) | 2006-03-20 | 2007-09-27 | Mitsubishi Chemical Corporation | Phthalocyanine crystal, electrophotographic photoreceptor utilizing the same, electrophotographic photoreceptor cartridge and image forming apparatus |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6267094A (en) * | 1985-09-18 | 1987-03-26 | Mitsubishi Chem Ind Ltd | Crystalline oxytitanium phthalocyanine and photosensitive material for electrophotography |
-
1986
- 1986-07-11 JP JP61163330A patent/JPH0639575B2/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6267094A (en) * | 1985-09-18 | 1987-03-26 | Mitsubishi Chem Ind Ltd | Crystalline oxytitanium phthalocyanine and photosensitive material for electrophotography |
Cited By (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0384470A2 (en) * | 1989-02-23 | 1990-08-29 | Mitsubishi Chemical Corporation | Process for preparation of crystalline oxytitanium phthalocyanine |
| US5183886A (en) * | 1989-05-22 | 1993-02-02 | Mitsubishi Kasei Corporation | Process for preparation of crystalline oxytitanium phthalocyanine showing A,B or C form |
| US5272264A (en) * | 1989-05-22 | 1993-12-21 | Mitsubishi Kasei Corporation | Process for preparation of crystalline oxytitanium phthalocyanine |
| JPH03134065A (en) * | 1989-10-19 | 1991-06-07 | Canon Inc | Preparation of oxytitanium phthalocyanine crystal |
| JPH03269064A (en) * | 1990-03-20 | 1991-11-29 | Fuji Xerox Co Ltd | Titanylphthalocyanine crystal and electrophotographic photosensitive form using same |
| JPH03269061A (en) * | 1990-03-20 | 1991-11-29 | Fuji Xerox Co Ltd | Production of titanylphthalocyanine crystal |
| US5252417A (en) * | 1990-03-20 | 1993-10-12 | Fuji Xerox Co., Ltd. | Titanyl phthalocyanine crystal and electrophotographic photoreceptor using the same |
| US5166339A (en) * | 1990-06-04 | 1992-11-24 | Xerox Corporation | Processes for the preparation of titanium phthalocyanines |
| US5153094A (en) * | 1990-06-14 | 1992-10-06 | Xerox Corporation | Processes for the preparation of photogenerating pigments |
| US5334856A (en) * | 1990-07-03 | 1994-08-02 | Mitsubishi Kasei Corporation | Image readout element with oxytitanium phthalocyanine |
| US5290928A (en) * | 1990-11-22 | 1994-03-01 | Fuji Xerox Co., Ltd. | Process for preparing oxytitanium phthalocyanine hydrate crystal |
| JPH0692919A (en) * | 1991-05-22 | 1994-04-05 | Nitto Chem Ind Co Ltd | Stabilization of aqueous solution of acrylamide |
| EP0516433A2 (en) * | 1991-05-28 | 1992-12-02 | Xerox Corporation | Process for the preparation of titanyl phthalocyanines |
| EP0516433A3 (en) * | 1991-05-28 | 1995-02-08 | Xerox Corp | Process for the preparation of titanyl phthalocyanines |
| US5972551A (en) * | 1996-12-26 | 1999-10-26 | Sharp Kabushiki Kaisha | Crystalline titanyl phthalocyanines and use thereof |
| US6225015B1 (en) | 1998-06-04 | 2001-05-01 | Mitsubishi Paper Mills Ltd. | Oxytitanium phthalocyanine process for the production thereof and electrophotographic photoreceptor to which the oxytitanium phthalocyanine is applied |
| US6210847B1 (en) | 1998-10-28 | 2001-04-03 | Sharp Kabushiki Kaisha | Crystalline oxotitanylphthalocyanine and electrophotographic photoreceptor using the same |
| US6322940B1 (en) | 1999-01-08 | 2001-11-27 | Sharp Kabushiki Kaisha | Electrophotographic photoreceptor and electrophotographic image forming process |
| US6291120B1 (en) | 1999-05-14 | 2001-09-18 | Sharp Kabushiki Kaisha | Electrophotographic photoreceptor and coating composition for charge generating layer |
| JP2007233351A (en) * | 2006-01-31 | 2007-09-13 | Yamanashi Electronics Co Ltd | Electrophotographic photoreceptor and electrophotographic device |
| WO2007108488A1 (en) | 2006-03-20 | 2007-09-27 | Mitsubishi Chemical Corporation | Phthalocyanine crystal, electrophotographic photoreceptor utilizing the same, electrophotographic photoreceptor cartridge and image forming apparatus |
| JP2013209672A (en) * | 2006-03-20 | 2013-10-10 | Mitsubishi Chemicals Corp | Phthalocyanine crystal, electrophotographic photoreceptor, and electrophotographic photoreceptor cartridge and image forming apparatus using the same |
| US8846282B2 (en) | 2006-03-20 | 2014-09-30 | Mitsubishi Chemical Corporation | Phthalocyanine crystal, and electrophotographic photoreceptor, electrophotographic photoreceptor cartridge and image-forming device using the same |
| US9296899B2 (en) | 2006-03-20 | 2016-03-29 | Mitsubishi Chemical Corporation | Phthalocyanine crystal, and electrophotographic photoreceptor, electrophotographic photoreceptor cartridge and image-forming device using the same |
| US9835961B2 (en) | 2006-03-20 | 2017-12-05 | Mitsubishi Chemical Corporation | Phthalocyanine crystal, and electrophotographic photoreceptor, electrophotographic photoreceptor cartridge and image-forming device using the same |
| US10095135B2 (en) | 2006-03-20 | 2018-10-09 | Mitsubishi Chemical Corporation | Phthalocyanine crystal, and electrophotographic photoreceptor, electrophotographic photoreceptor cartridge and image-forming device using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0639575B2 (en) | 1994-05-25 |
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