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WO1999045074A1 - Phtalocyanine de titane - Google Patents

Phtalocyanine de titane Download PDF

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Publication number
WO1999045074A1
WO1999045074A1 PCT/GB1998/000496 GB9800496W WO9945074A1 WO 1999045074 A1 WO1999045074 A1 WO 1999045074A1 GB 9800496 W GB9800496 W GB 9800496W WO 9945074 A1 WO9945074 A1 WO 9945074A1
Authority
WO
WIPO (PCT)
Prior art keywords
titanyl phthalocyanine
carried out
temperature
sulphonic acid
solid
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.)
Ceased
Application number
PCT/GB1998/000496
Other languages
English (en)
Inventor
Raymond Stephenson Gairns
Elizabeth Shearer Currie Simpson
John Andrew Stewart
Linda Marie Traynor
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Avecia Ltd
Syngenta Ltd
Original Assignee
Zeneca Ltd
Avecia Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Zeneca Ltd, Avecia Ltd filed Critical Zeneca Ltd
Priority to AU62995/98A priority Critical patent/AU6299598A/en
Priority to PCT/GB1998/000496 priority patent/WO1999045074A1/fr
Publication of WO1999045074A1 publication Critical patent/WO1999045074A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
    • C09B67/0016—Influencing the physical properties by treatment with a liquid, e.g. solvents of phthalocyanines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0017—Influencing the physical properties by treatment with an acid, H2SO4
    • C09B67/0019—Influencing the physical properties by treatment with an acid, H2SO4 of phthalocyanines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0025—Crystal modifications; Special X-ray patterns
    • C09B67/0026—Crystal modifications; Special X-ray patterns of phthalocyanine pigments
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0664—Dyes
    • G03G5/0696—Phthalocyanines

Definitions

  • the present invention relates to particular crystalline forms of certain metal phthalocyanines, particularly those of titanium and to the use of such phthalocyanines and compositions comprising such phthalocyanines in electroreprography.
  • Electroreprography is any process in which an image is reproduced by means of electricity and incident radiation, usually electromagnetic radiation more usually visible light. Electroreprography includes the technology of electrophotography which encompasses photocopying and laser printing technologies. In both these technologies a latent electrostatic image in charge is produced by exposure of a photoconductive drum to light. This can be either reflected light from an illuminated image (photocopying) or by scanning the drum with a laser usually under instruction from a computer (laser printing). Once a latent image has been produced in charge it must be developed with colorant so that a visible image can be printed onto paper.
  • Phthalocyanines and their metal complexes have been used for many years in electroreprography because generally they exhibit good photoconduction.
  • organic photoconductors based on various dyes and pigments such as methine, cyanine, pyrylium, phthalocyanine and azo dyes have been used in high speed, high quality printing and copying. Whilst the photoconducting properties of such dyes can be readily tuned for specific applications such dyes are unsuitable because they tend to lack the stability needed for the repeated use required in modern copiers and printers.
  • More recently many crystalline forms of phthalocyanines and their metal complexes have been disclosed and patented but none of these have satisfactorily fulfilled all the requirements necessary to provide charge generating materials.
  • the requirements for a good charge generating material include: i) a high spectral sensitivity to LED's or semiconductor lasers; ii) a high charge acceptance which gives better electrical contrast between charged and uncharged areas and thus provides better print quality; iii) a low dark decay; iv) a high photodischarge sensitivity so the minimum amount of energy may be used to discharge the photoconductor; v) a low residual potential after exposure of the photoconductor to radiation; vi) long term stability of the material to many thousand repeat cycles of charging and discharging.
  • a crystalline form of a titanyl phthalocyanine also abbreviated to TiOPc characterised by having an X-ray diffraction (abbreviated to XRD) pattern showing a maximum peak at a Bragg angle
  • Titanyl phthalocyanines showing the preceding XRD peaks [as well as titanyl phthalocyanine obtained or obtainable as the end product of the process of the present invention comprising steps a) to d) as described below] are referred to herein as "Zeneca type titanyl phthalocyanine" [also abbreviated to TiOPc(Za)].
  • TiOPc(Za) may comprise a previously unknown polymorphic crystal form of titanyl phthalocyanine and/or may comprise an improved form of the titanyl phthalocyanine of the polymorphic crystal form known as Type IV.
  • Preferred titanyl phthalocyanines are those which are unsubstituted or carry fluoro groups on the periphery of the ring structure.
  • An unsubstituted titanyl phthalocyanine is especially preferred.
  • a process for preparing titanyl phthalocyanine comprising the following steps: a) reacting an optionally substituted phthalonitrile with an ammonia in the presence of an alkali metal alkoxide to form a diiminoisoindoline; b) reacting the diiminoisoindoline obtained from step 'a)' with a titanium tetraalkoxide to form a titanyl phthalocyanine of the polymorphic crystal form known as Type I; c) dissolving the Type I titanyl phthalocyanine obtained from step 'b)' in a mixture of an alkane suiphonic acid and a halogenated aliphatic hydrocarbon to form a titanyl phthalocyanine of the polymorphic crystal form known as Type X; and d) treating the Type X titanyl phthalocyanine obtained form step 'c)' with substituted aromatic hydrocarbon until a titanyl phthalocyanine
  • a group which comprises a chain of three or more atoms signifies a group in which the chain may be straight or branched or the chain or part of the chain may form a ring.
  • an alkyl group may comprise: propyl which includes n-propyl and isopropyl; butyl which includes n-butyl, sec-butyl, isobutyl and tert-butyl; and an alkyl group of three or more carbon atoms may comprise a cycloalkyl group.
  • the total number of certain atoms is specified herein for certain substituents, for example C ⁇ alkyl, signifies an alkyl group having from 1 to n carbon atoms.
  • the term ' aryl' as used herein signifies a radical which comprises an aromatic hydrocarbon ring, for example phenyl, naphthyl, anthryl and phenanthryl radicals.
  • the phthalonitrile is preferably unsubstituted.
  • the alkali metal alkoxide may comprise an alkali metal C, - C 6 - alkoxide.
  • the alkali metal alkoxide comprises a sodium alkoxide and/or a potassium alkoxide, more preferably sodium methoxide.
  • the titanium tetraalkoxide may comprise a titanium tetra (C ⁇ - C 6 alkoxide), preferably titanium tetra butoxide.
  • the alkane sulphonic acid may comprise a C, -C 10 - alkane sulphonic acid, preferably a C ⁇ - C 4 - alkane sulphonic acid and more preferably methane sulphonic acid.
  • the halogenated aliphatic hydrocarbon may comprise one or more halo atoms selected from fluoro-, chloro- and bromo- and may comprise different halo atoms on the same molecule.
  • the halogenated aliphatic hydrocarbon comprises a chlorinated aliphatic hydrocarbon, more preferably dichloromethane.
  • the substituted aromatic hydrocarbon may comprise an aryloxybenzene and/or alkoxybenzene, preferably methoxybenzene (also known as anisole).
  • Step 'a)' of the present process may be carried out at a temperature from about
  • the solvent used in step 'a)' may comprise C r C 10 alcohols, preferably C ⁇ ,-C 4 alcohols.
  • the alkali metal alkoxide used will have the same alkoxy group as the alcohol.
  • Step 'b)' of the present process may be carried out at a temperature from about 130°C to about 230.°C, preferably from about 190°C to about 210°C.
  • the solvent used in step 'b)' may comprise suitable high boiling solvents such as aromatic or aliphatic alcohols and/or aromatic or aliphatic hydrocarbons (optionally comprising a hetero atom).
  • the solvent may comprise chloronapthalene, methyl naphthalene and/or quinoline.
  • Step 'c)' of the present process may be carried out at a temperature between -
  • the solvent used in step 'c)' comprises a mixture of methane sulphonic acid and dichloromethane.
  • Step 'd)' of the present process may be carried out at a temperature from about -25°C to about +25°C, preferably from about -10°C to about +10°C, more preferably from about -5°C to about +5°C.
  • step 'd)' is carried under an inert atmosphere, more preferably under nitrogen which is substantially free from water.
  • a preferred method for collecting the solid product from one or more of steps 'b)', 'c)' and/or 'd)' comprises the further steps of: forming a slurry with the solid in a suitable liquid; allowing the solid to settle from the slurry; decanting the mother liquor from the slurry to leave a solid residue, optionally repeating the preceding steps one or more times; dissolving the solid residue in a suitable solvent; and collecting the solid by filtration.
  • This collection method has the advantage that if the process of the present invention uses large quantities collection is quicker than filtration only. Also it has been found that if the solid is initially collected by filtration alone solid impurities (such as tars) in the reaction mixture may settle on the solid during filtration which may impair the electrical properties of the TiOPc collected. Forming a slurry and decanting the mother liquor as described above substantially removes any solid impurities prior to collection of the solid by filtration. Thus TiOPc collected in this way may exhibit improved electrical properties for use in electroreprography and/or is useful as purer starting material for use in subsequent steps in the process of the present invention.
  • solid impurities such as tars
  • a further aspect of the present invention comprises the titanyl phthalocyanine obtained or obtainable as the end product of the process comprising steps a) to d) as described herein.
  • a still further aspect of the present invention provides a charge generating material comprising a Zeneca type titanyl phthalocyanine optionally together with a suitable binder and/or carrier.
  • a photoconductive member comprising a substrate, a charge generating layer and a charge transport layer characterised in that the charge generating layer comprises the charge generating material of the present invention.
  • the charge generating layer comprising the titanyl phthalocyanine is preferably in a binder and is coated on the substrate followed by the charge transport layer which is again preferably in a binder. Coating may be conveniently carried out by dissolving or dispersing the charge generating material or charge transport material as appropriate in a liquid medium followed by evaporating the liquid medium.
  • Suitable liquid media may be selected from one or more of the following and any suitable mixtures thereof: alkylacetates, alkyl propionates, butanol, pentanol, cyclohexanone, cyclopentanone, xylene, toulene, mesitylene and cumene.
  • the charge generating layer may also contain one or more additional charge generating materials which may be selected from one or more of the following and any suitable mixtures thereof: phthalocyanines, polyazo compounds, perylene compounds, dihaloanthanthrone compounds and azonapthol compounds.
  • Suitable binders for the charge generating layer and the charge transport layer may be selected from one or more of the following and any suitable mixtures thereof: polyesters, polycarbonates, polyamides, polyurethanes, polybutyrol, polyester- carbonates), poly (ether-carbonates), polyvinyl acetals, polyvinyl chloride coploymers, stryene-butadiene copolymers, cellulose derivatives, and polyimides.
  • the titanyl phthalocyanine is present in the charge generating layer in an amount of from about 30% to about 80%, more preferably from about 50% to about 75%, by weight of the composition forming the charge generating layer.
  • the binder is present in the charge generating layer in an amount of from about 20% to about 70%, more preferably from about 25% to about 50%, by weight of the composition forming the charge generating layer.
  • the respective weight ratio of the titanyl phthalocyanine to binder in the charge generating layer is from about 3/7 to about 4, more preferably from about 1 to about 3.
  • the substrate for the photoconductive member may be any electrically conducting substrate commonly used in electrophotography.
  • the substrate may be a metal or metallised sheet or the curved surface of a substantially cylindrical drum.
  • Preferred metals comprise aluminium, stainless steel, copper, more preferably aluminium.
  • Metallised sheets preferably comprise aluminised polyester film.
  • the charge transport layer may comprise one or more compounds which may act as a charge transport material selected from one or more of the following and any suitable mixtures thereof: arylamines, aryi hydrazones, stilbenes, pyrazolines, di- and tri- arylmethanes, heterocyclic aminoaryl compounds and oxadiazoles.
  • Preferred charge transport materials comprise arylamines of Formula I;
  • R 1 , R 2 , R 3 and R 4 are each independently H or alkyl.
  • Preferred compounds of Formula I are those in which R 1 and R 2 are each independently C ⁇ 0 alkyl and R 3 and R 4 are both H. More preferred compounds of Formula I are those in which R 1 and R 2 are methyl and R 3 and R 4 are both H.
  • the photoconductive member may also comprise additional layers which improves its electrical, mechanical or stability characteristics. Adhesive layers, blocking layers and/or protective layers may also be added.
  • a further aspect of the present invention comprises an electroreprographic device comprising a Zeneca type titanyl phthalocyanine, a charge generating composition as described herein and/or a photoconductive member as described herein.
  • the electroreprographic device is selected from: a photocopier and a laser printer.
  • a still further aspect of the present invention provides for a method of manufacturing of one of more of the following: a charge generating composition as described herein; a photo-conductive member as described herein; and/or an electroreprographic device as described herein: using a Zeneca type titanyl phthalocyanine.
  • diiminoisoindoline also known as DI 3 - prepared as described in stage 1a
  • the air in the reaction vessel was replaced by dry nitrogen and 340 g of titanium tetrabutoxide was added to the mixture.
  • the mixture was heated to 200°C as rapidly as possible (over 1 hour 30 minutes) using an oil bath and held at that temperature for a further 2 hours 30 minutes whilst the reaction vessel was purged with fast flowing N 2 gas to remove butanol and ammonia gas.
  • the reaction mixture was left to cool to 175°C without being stirred and was allowed to settle for about 20 minutes.
  • the upper mother liquors were decanted to leave a solid residue in the reaction vessel.
  • One litre of boiling dimethylformamide (DMF) was added to this solid whilst heating at 150°C for 15 minutes to form a slurry which was then allowed to settle for 15 minutes and the upper liquors were decanted to leave a solid residue.
  • a slurry was formed from solid residue a further three times as described before, except the third time the DMF slurry was filtered to obtain a pale blue/green filtrate. This filtrate was allowed to cool to room temperature and a purple solid precipitate was formed which was collected by filtration.
  • the purple solid was washed thrice with one litre of DMF at room temperature until the washings were a very pale green colour.
  • the filtrate was diluted by being added drop-wise from a dropping funnel (500 ml at a time to keep the solution cold) over about 1 hour 30 minutes to the centre of the vortex of a stirred cold solution (at -10°C) comprising 10 litres of methanol, 2.5 kg of de-ionised ice and 7.5 kg of de-ionised water.
  • the resultant suspension (at a temperature of -5°C after the dilution was completed) was filtered to collect a blue solid which was then washed with 4 litres of methanol. This blue solid was added to 8 litres of de-ionised water to form a slurry which was heated for 2 hours at 75°C.
  • the XRD pattern of this TiOPc (Za) was measured using a Cu-K ⁇ beam of wavelength 1.541 A and showed a maximum peak at a Bragg angle (2 ⁇ ) of 27.3° and further diffraction peaks in decreasing order of intensity at Bragg angles (2 ⁇ ) of 9.0°, 9.5°, 24.1° and 14.3°.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)

Abstract

L'invention concerne une forme cristalline d'une phtalocyanine de titane, qui se caractérise en ce qu'elle présente un diagramme de diffraction indiquant une crête maximale à un angle de Bragg (2υ±0,2°) d'environ 27,3°, et d'autres crêtes de diffraction par niveaux d'intensité décroissants à des angles de Bragg (2υ±0,2°) d'environ 9,0°, 9,5°, 24,1° et 14,3°. On décrit en outre un procédé de préparation de la phtalocyanine de titane et son utilisation dans des matériaux de génération de charge, dans des éléments photoconducteurs et dans des dispositifs électroreprographiques.
PCT/GB1998/000496 1998-03-05 1998-03-05 Phtalocyanine de titane Ceased WO1999045074A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU62995/98A AU6299598A (en) 1998-03-05 1998-03-05 Titanyl phthalocyanine and its use
PCT/GB1998/000496 WO1999045074A1 (fr) 1998-03-05 1998-03-05 Phtalocyanine de titane

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/GB1998/000496 WO1999045074A1 (fr) 1998-03-05 1998-03-05 Phtalocyanine de titane

Publications (1)

Publication Number Publication Date
WO1999045074A1 true WO1999045074A1 (fr) 1999-09-10

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ID=10825091

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1998/000496 Ceased WO1999045074A1 (fr) 1998-03-05 1998-03-05 Phtalocyanine de titane

Country Status (2)

Country Link
AU (1) AU6299598A (fr)
WO (1) WO1999045074A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006144016A (ja) * 2004-11-18 2006-06-08 Xerox Corp Ｖ型チタニルフタロシアニンの調製方法及び写真画像形成部材
US7629095B2 (en) * 2006-07-19 2009-12-08 Xerox Corporation Electrophotographic photoreceptor
US20100183330A1 (en) * 2007-06-12 2010-07-22 Mitsubishi Chemical Corporation Image-forming apparatus and cartridge

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0409737A1 (fr) * 1989-07-21 1991-01-23 Canon Kabushiki Kaisha Phtalocyanine d'oxytitane, son procédé de fabrication et élément électrophotoconducteur l'utilisant
EP0482922A1 (fr) * 1990-10-24 1992-04-29 Canon Kabushiki Kaisha Procédé de préparation de l'oxytitanephtalocyanine cristalline
US5189155A (en) * 1991-04-11 1993-02-23 Xerox Corporation Titanyl phthalocyanine Type I processes
JPH0572773A (ja) * 1991-09-13 1993-03-26 Mitsubishi Petrochem Co Ltd フタロシアニン系光導電性組成物の製造方法
US5238764A (en) * 1992-02-13 1993-08-24 Eastman Kodak Company Electrophotographic elements containing a titanyl fluorophthalocyanine pigment
US5252417A (en) * 1990-03-20 1993-10-12 Fuji Xerox Co., Ltd. Titanyl phthalocyanine crystal and electrophotographic photoreceptor using the same
US5371213A (en) * 1993-08-23 1994-12-06 Xerox Corporation Titanium phthalocyanine imaging member
DE19505784A1 (de) * 1995-02-08 1996-08-14 Syntec Ges Fuer Chemie Und Tec Verfahren zur Herstellung von elektrofotografisch aktivem Titanylphthalocyanin
EP0810267A2 (fr) * 1996-05-29 1997-12-03 Nec Corporation Cristal d'oxytitanephtalocyanine

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0409737A1 (fr) * 1989-07-21 1991-01-23 Canon Kabushiki Kaisha Phtalocyanine d'oxytitane, son procédé de fabrication et élément électrophotoconducteur l'utilisant
US5252417A (en) * 1990-03-20 1993-10-12 Fuji Xerox Co., Ltd. Titanyl phthalocyanine crystal and electrophotographic photoreceptor using the same
EP0482922A1 (fr) * 1990-10-24 1992-04-29 Canon Kabushiki Kaisha Procédé de préparation de l'oxytitanephtalocyanine cristalline
US5189155A (en) * 1991-04-11 1993-02-23 Xerox Corporation Titanyl phthalocyanine Type I processes
JPH0572773A (ja) * 1991-09-13 1993-03-26 Mitsubishi Petrochem Co Ltd フタロシアニン系光導電性組成物の製造方法
US5238764A (en) * 1992-02-13 1993-08-24 Eastman Kodak Company Electrophotographic elements containing a titanyl fluorophthalocyanine pigment
US5371213A (en) * 1993-08-23 1994-12-06 Xerox Corporation Titanium phthalocyanine imaging member
DE19505784A1 (de) * 1995-02-08 1996-08-14 Syntec Ges Fuer Chemie Und Tec Verfahren zur Herstellung von elektrofotografisch aktivem Titanylphthalocyanin
EP0810267A2 (fr) * 1996-05-29 1997-12-03 Nec Corporation Cristal d'oxytitanephtalocyanine

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 9317, Derwent World Patents Index; Class E23, AN 93-137479, XP002082962 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006144016A (ja) * 2004-11-18 2006-06-08 Xerox Corp Ｖ型チタニルフタロシアニンの調製方法及び写真画像形成部材
EP1672034A1 (fr) * 2004-11-18 2006-06-21 Xerox Corporation Procédé pour la préparation de pigments du type titanyl-phthalocyanines à sensibilité élevée formant une image
US7947417B2 (en) 2004-11-18 2011-05-24 Xerox Corporation Processes for the preparation of high sensitivity titanium phthalocyanines photogenerating pigments
CN1775866B (zh) * 2004-11-18 2011-08-10 施乐公司 高感光度钛酞菁光生颜料的制备方法
US7629095B2 (en) * 2006-07-19 2009-12-08 Xerox Corporation Electrophotographic photoreceptor
US20100183330A1 (en) * 2007-06-12 2010-07-22 Mitsubishi Chemical Corporation Image-forming apparatus and cartridge

Also Published As

Publication number Publication date
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