CN1594330A - Method for preparing micrometer Y crystalline form oxotitanium phthalocyanine - Google Patents
Method for preparing micrometer Y crystalline form oxotitanium phthalocyanine Download PDFInfo
- Publication number
- CN1594330A CN1594330A CN 200410019964 CN200410019964A CN1594330A CN 1594330 A CN1594330 A CN 1594330A CN 200410019964 CN200410019964 CN 200410019964 CN 200410019964 A CN200410019964 A CN 200410019964A CN 1594330 A CN1594330 A CN 1594330A
- Authority
- CN
- China
- Prior art keywords
- tiopc
- crystal formation
- micron order
- preparation
- solution
- 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
Landscapes
- Photoreceptors In Electrophotography (AREA)
Abstract
The invention provides a method for preparing micrometer Y crystalline form oxotitanium phthalocyanine which consists of, dissolving the oxotitanium phthalocyanine into concentrated sulfuric acid, dropping the solution into aqueous solution of polyethylene glycol, agitating so as to form suspending liquid, charging crystal form conditioning agent into the suspending liquid, agitating into colloidal solution, charging low carbon alcohols, stewing and filtering, scouring filter cake to neutral, charging PVB resin and dispersing agent methyl ethyl ketone for ball grinding.
Description
Technical field
The present invention relates to the preparation method of TiOPc (Y-TiOPc), be specifically related to the preparation method of micron order Y crystal formation TiOPc.
Background technology
In recent years, along with the raising of people, strengthen organic light-guide (Organic Photoconductive the is called for short OPC) photosensitive property of material and become the direction of people's research image taking speed in the Xeroxing and image quality requirement.Charge generating material affects the performance of OPC to a great extent as the important component part of organic photoconductor.Wherein, TiOPc (TiOPc) is a kind of good organic light-guide material, and it is strong with low toxicity, inexpensive, thermostability and light stability, (700～850nm) have the extensive concern that very strong absorption, current carrier production rate advantages of higher have been subjected to people in the near-infrared region.Therefore, the photosensitivity of raising light-guide material becomes the focus that people pay close attention to.By discovering, TiOPc and other phthalocyanine compound are similar, have multiple different crystallized form: α type, β type, γ type, m type, I type, Y type etc., wherein Y-TiOPc shows best photosensitivity, is the ideal organic light-guide material.Simultaneously, the size of particles of material has very important influence to its photosensitive property.Therefore, preparation micron Y-TiOPc is an effective means of improving its photosensitive property.
At present, in existing micron order Y crystal formation TiOPc technology of preparing, normally the acid of TiOPc being stuck with paste drips of solution adds in the water that contains tensio-active agent and forms amorphous sediment, should precipitate again through washing-suction filtration step repeatedly until reaching neutral, then filter cake is dispersed in and carries out the crystalline form conversion in two-phase (as water/orthodichlorobenzene) or the heterogeneous solvent (as water/ethylene glycol/propyl carbinol/chlorobenzene), final formation has micron order TiOPc definite crystal formation, that photoconductivity is arranged, as J.P.No04,264,450, CN 1342729, and CN 1150261.
Above-mentioned preparation process not only the time long, and the forward and backward washing leaching cake that needs that makes the transition is to neutral, washing process is loaded down with trivial details.
Summary of the invention
The object of the present invention is to provide a kind of preparation method of micron order Y crystal formation TiOPc, this procedure is simple, and preparation time is short.
The present invention is realized by following technical proposals.A kind of preparation method of micron order Y crystal formation TiOPc, it is characterized in that comprising following process: TiOPc is dissolved in the vitriol oil, with the mass concentration that contains of-5～5 ℃ of this drips of solution addings is 0.01～0.1% polyoxyethylene glycol aqueous solution, stirs and forms TiOPc suspension; Add the crystalline form conditioning agent under 0～20 ℃ in suspension, crystal structure adjusting agent was by ethanol, propyl carbinol, ethylene glycol, chlorobenzene and emulsifying agent 10: 10: 10 by volume: 2: 1～.5, stir and form colloidal solution; Add low-carbon alcohol according to colloidal solution volume ratio 1～10%, leave standstill the back suction filtration, washing leaching cake gets Y crystal formation TiOPc solid to neutral; The Y crystal formation TiOPc that makes added the PVB resin in 1: 1 by mass percentage, and carried out ball milling by every gram TiOPc adding dispersion agent butanone 50～70mL, made high sensitivity micron order Y crystal formation TiOPc coating fluid.
Above-mentioned emulsifying agent is polyoxyethylene nonylphenol ether, fatty alcohol-polyoxyethylene ether or tween;
Above-mentioned low-carbon alcohol is methyl alcohol, ethanol or propyl alcohol.
Description of drawings
Fig. 1 is a Y crystal formation TiOPc x-ray diffraction pattern.
Fig. 2 is Y crystal formation TiOPc photoelectric properties curves.
Embodiment
Embodiment 1:
1g TiOPc is dissolved in 98% vitriol oil of 16mL, and under ice-water bath (0 ℃) condition, the concentrated sulfuric acid solution of TiOPc is added drop-wise under agitation condition to contain mass concentration be in the 0.05% polyoxyethylene glycol aqueous solution, forms the suspension of TiOPc.Then, under 0 ℃,, under agitation slowly be added dropwise in the suspension of TiOPc, stir more than the 24h, leave standstill the mixed solution of 20mL ethanol, 20mL propyl carbinol, 20mL ethylene glycol, 4mL chlorobenzene and 2mLOP-10 (polyoxyethylene nonylphenol ether).Add 20mL ethanol then, leave standstill the 30min after-filtration, filter cake washing through vacuum lyophilization, gets particle diameter 220nmY-TiOPc to neutral.
Embodiment 2:
1g TiOPc is dissolved in 98% vitriol oil of 16mL, and under 3 ℃, the concentrated sulfuric acid solution of TiOPc is added drop-wise under agitation condition to contain mass concentration be in the 0.02% polyoxyethylene glycol aqueous solution, form the suspension of TiOPc.Then, under 10 ℃,, under agitation slowly be added dropwise in the suspension of TiOPc, stir more than the 24h, leave standstill the mixed solution of 20mL ethanol, 20mL propyl carbinol, 20mL second two glycol, 4mL chlorobenzene and 5mLOS-15 (fatty alcohol-polyoxyethylene ether).Add 15mL ethanol then, leave standstill the 30min after-filtration, filter cake washing through vacuum lyophilization, gets particle diameter 250nmY-TiOPc to neutral.
Embodiment 3:
1g TiOPc is dissolved in 98% vitriol oil of 16mL, and under ice-water bath (0 ℃) condition, the concentrated sulfuric acid solution of TiOPc is added drop-wise under agitation condition to contain mass concentration be in the 0.08% polyoxyethylene glycol aqueous solution, form the suspension of TiOPc.Then, under 20 ℃,, under agitation slowly be added dropwise in the suspension of TiOPc, stir more than the 24h, leave standstill the mixed solution of 20mL ethanol, 20mL propyl carbinol, 20mL ethylene glycol, 4mL chlorobenzene and 10mLOP-10 (polyoxyethylene nonylphenol ether).Add 10mL methyl alcohol then, leave standstill the 30min after-filtration, filter cake washing through vacuum lyophilization, gets particle diameter 280nmY-TiOPc to neutral.
Adopt X-ray powder diffraction instrument to characterize the TiOPc crystalline form that makes among the embodiment 1, consistent with standard Y-TiOPc crystallogram.In grinding in ball grinder, rotating speed 500rpm forms suspension, obtains high sensitivity micron order Y-TiOPc coating fluid with product and polyvinyl butyral acetal (PVB resin) and butanone.Above-mentioned coating fluid is coated on precoated layer aluminium base, and through the test of static paper analyser, charging voltage is 840V, luminous sensitivity E
1/2Be 1.0lxs.
Claims (3)
1, a kind of preparation method of micron order Y crystal formation TiOPc, it is characterized in that comprising following process: TiOPc is dissolved in the vitriol oil, with the mass concentration that contains of-5～5 ℃ of this drips of solution addings is 0.01～0.1% polyoxyethylene glycol aqueous solution, stirs and forms TiOPc suspension; Add the crystalline form conditioning agent under 0～20 ℃ in suspension, crystal structure adjusting agent was by ethanol, propyl carbinol, ethylene glycol, chlorobenzene and emulsifying agent 10: 10: 10 by volume: 2: 1～.5, stir and form colloidal solution; Add low-carbon alcohol according to colloidal solution volume ratio 1～10%, leave standstill the back suction filtration, washing leaching cake gets Y crystal formation TiOPc solid to neutral; The Y crystal formation TiOPc that makes added the PVB resin in 1: 1 by mass percentage, and carried out ball milling by every gram TiOPc adding dispersion agent butanone 50～70mL, made high sensitivity micron order Y crystal formation TiOPc coating fluid.
2, by the preparation method of the described micron order Y of claim 1 crystal formation TiOPc, it is characterized in that: emulsifying agent is polyoxyethylene nonylphenol ether, fatty alcohol-polyoxyethylene ether or tween.
3, by the preparation method of the described micron order Y of claim 1 crystal formation TiOPc, it is characterized in that: low-carbon alcohol is methyl alcohol, ethanol or propyl alcohol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100199647A CN1314694C (en) | 2004-07-12 | 2004-07-12 | Method for preparing micrometer Y crystalline form oxotitanium phthalocyanine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100199647A CN1314694C (en) | 2004-07-12 | 2004-07-12 | Method for preparing micrometer Y crystalline form oxotitanium phthalocyanine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1594330A true CN1594330A (en) | 2005-03-16 |
| CN1314694C CN1314694C (en) | 2007-05-09 |
Family
ID=34663123
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2004100199647A Active CN1314694C (en) | 2004-07-12 | 2004-07-12 | Method for preparing micrometer Y crystalline form oxotitanium phthalocyanine |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1314694C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102653679A (en) * | 2011-03-04 | 2012-09-05 | 北京大学 | Y-type titanyl phthalocyanine nano-particles and preparation method and application thereof |
| WO2013102657A1 (en) | 2012-01-05 | 2013-07-11 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Process for preparing particles of titanium oxide containing a phthalocyanine derivative, said particles and uses thereof |
| CN103613598A (en) * | 2013-11-28 | 2014-03-05 | 天津大学 | Method for preparing polymorphism photosensitivity TiOPc nano particle and application thereof in organic photoconductor |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08134372A (en) * | 1994-11-04 | 1996-05-28 | Matsushita Electric Ind Co Ltd | Production of oxotitanium phthalocyanine crystal and electrophotographic receptor |
| CN1068029C (en) * | 1995-11-01 | 2001-07-04 | 中国科学院化学研究所 | nm-class phthalocyanines organic light-guide material and preparing process and use thereof |
| JP2000063696A (en) * | 1998-08-21 | 2000-02-29 | Matsushita Electric Ind Co Ltd | Production of oxotitanium phthalocyanine crystal, and laminate-type electrophotographic photoreceptor obtained by using same |
| CN1117821C (en) * | 2000-09-14 | 2003-08-13 | 中国科学院化学研究所 | Process for preparing nm-class Y-type phthalocyanine titanium oxide in batch |
-
2004
- 2004-07-12 CN CNB2004100199647A patent/CN1314694C/en active Active
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102653679A (en) * | 2011-03-04 | 2012-09-05 | 北京大学 | Y-type titanyl phthalocyanine nano-particles and preparation method and application thereof |
| CN102653679B (en) * | 2011-03-04 | 2014-07-02 | 北京大学 | Y-type titanyl phthalocyanine nano-particles and preparation method and application thereof |
| WO2013102657A1 (en) | 2012-01-05 | 2013-07-11 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Process for preparing particles of titanium oxide containing a phthalocyanine derivative, said particles and uses thereof |
| FR2985510A1 (en) * | 2012-01-05 | 2013-07-12 | Commissariat Energie Atomique | PROCESS FOR THE PREPARATION OF TITANIUM OXIDE PARTICLES CONTAINING A PHTHALOCYANINE DERIVATIVE, THE SAID PARTICLES AND USES THEREOF |
| CN103613598A (en) * | 2013-11-28 | 2014-03-05 | 天津大学 | Method for preparing polymorphism photosensitivity TiOPc nano particle and application thereof in organic photoconductor |
| CN103613598B (en) * | 2013-11-28 | 2016-09-14 | 天津大学 | The preparation method of polymorphic heliosensitivity TiOPc nanoparticle and the application in organic photoconductor thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1314694C (en) | 2007-05-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1068027C (en) | Crystalline titanyl phthalocyanines and use thereof | |
| JP4581781B2 (en) | Electrophotographic photosensitive member and method for manufacturing the same, process cartridge, and electrophotographic apparatus | |
| CN102053512A (en) | Electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus | |
| CN102637748A (en) | Sensibilizer for solar cell and solar cell with the same | |
| CN109482206A (en) | A kind of visible and near infrared light response CQDs-ZnIn2S4The preparation method of-BiOCl ternary heterojunction | |
| CN110451615A (en) | A kind of preparation method of metal-organic framework carbon nano-tube hybridization desalination electrode | |
| CN1237182A (en) | Zirconium compounds and electrophotographic toner containing the same | |
| CN104668572A (en) | Silver powder and silver paste for back electrode of solar cell and solar cell | |
| CN1314694C (en) | Method for preparing micrometer Y crystalline form oxotitanium phthalocyanine | |
| CN102653679B (en) | Y-type titanyl phthalocyanine nano-particles and preparation method and application thereof | |
| CN102446632B (en) | Optical anode slurry for dye-sensitized solar cell and preparation method thereof as well as optical anode for dye-sensitized solar cell and dye-sensitized solar cell | |
| CN103739011B (en) | Method for preparing three-dimensional multistage titanium dioxide slurry with micro-nano structure by one-pot method | |
| CN1068029C (en) | nm-class phthalocyanines organic light-guide material and preparing process and use thereof | |
| CN102500402A (en) | Method for synthesizing silver bromide-titanium dioxide (AgBr-TiO2) nano heterostructure photocatalyst with similar micro-emulsion system | |
| CN1876227A (en) | Process for preparing cation sorbent and its application | |
| CN1117821C (en) | Process for preparing nm-class Y-type phthalocyanine titanium oxide in batch | |
| CN1308775C (en) | Monolayer organic light receptor positive charged as well as dedicated material and preparation method | |
| DE10146653B4 (en) | Toner for optical fixing and imaging device using the same | |
| CN107983377A (en) | Silver/iodate silver composite material of cadmium tungstate modification and its preparation method and application | |
| CN104874369B (en) | Modified polyvinyl alcohol microparticles of a kind of coloring functionization and preparation method and application | |
| CN103992328A (en) | Phthalocyanine copper dispersion system and preparation method thereof | |
| CN109876742B (en) | Red fluorescent microcapsule for electronic ink display and preparation method thereof | |
| CN113714500A (en) | Method for purifying superfine silver nanowires | |
| JPH05333575A (en) | Electrophotographic sensitive body | |
| CN107866561B (en) | Extract solution from aloe separates single size In4The method of Ni nanosphere |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |