CA2551441A1 - Imaging members - Google Patents
Imaging members Download PDFInfo
- Publication number
- CA2551441A1 CA2551441A1 CA002551441A CA2551441A CA2551441A1 CA 2551441 A1 CA2551441 A1 CA 2551441A1 CA 002551441 A CA002551441 A CA 002551441A CA 2551441 A CA2551441 A CA 2551441A CA 2551441 A1 CA2551441 A1 CA 2551441A1
- Authority
- CA
- Canada
- Prior art keywords
- imaging member
- integer
- group
- formula
- polysiloxane composition
- 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
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Classifications
-
- 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
- G03G5/14—Inert intermediate or cover layers for charge-receiving layers
- G03G5/147—Cover layers
-
- 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
- G03G5/14—Inert intermediate or cover layers for charge-receiving layers
- G03G5/147—Cover layers
- G03G5/14708—Cover layers comprising organic material
- G03G5/14713—Macromolecular material
- G03G5/14747—Macromolecular material obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- G03G5/14773—Polycondensates comprising silicon atoms in the main chain
-
- 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
- G03G5/14—Inert intermediate or cover layers for charge-receiving layers
- G03G5/147—Cover layers
- G03G5/14708—Cover layers comprising organic material
- G03G5/14713—Macromolecular material
- G03G5/14786—Macromolecular compounds characterised by specific side-chain substituents or end groups
Abstract
A silicone overcoat (SOC) layer having a crosslinked polysiloxane composition comprising a perfluoropolyether segment are disclosed. The polysiloxane composition is the product of the hydrolysis and condensation of a SOC formulation comprising a perfluoropolyether compound, an aromatic silicon-containing compound, and a silicon-containing hole transport compound. An electrophotographic imaging member having such a SOC layer has improved properties.
Claims (20)
1. An electrophotographic imaging member having a silicone overcoat (SOC) layer, the SOC layer including a crosslinked polysiloxane composition comprising a perfluoropolyether segment.
2. The imaging member of claim 1, wherein the perfluoropolyether segment is represented by -(C n F 2n O)x-, or a copolymer comprised thereof, wherein n is an integer from 1 to about 6, and x is the number of repeating units ranging from about 2 to about 500.
3. The imaging member of claim 2, wherein the perfluoropolyether segment is selected from the group consisting of poly(difluoromethylene oxide), poly(tetrafluoroethylene oxide), poly(hexafluoropropylene oxide), poly(tetrafluoro-ethylene oxide-co-difluoromethylene oxide), poly(hexafluoropropylene oxide-co-difluoromethylene oxide), and poly(tetrafluoroethylene oxide-co-hexafluoropropylene oxide-co-difluoromethylene oxide).
4. The imaging member of claim 1, wherein the perfluoropolyether segment has a number average molecular weight of from about 100 to about 50,000.
5. The imaging member of claim 1, wherein the perfluoropolyether segment is present in the amount of from about 0.01 to about 10 wt%, based on the total weight of the crosslinked polysiloxane composition.
6. The imaging member of claim 1, wherein the crosslinked polysiloxane composition is the product of the hydrolysis and condensation of a SOC
formulation comprising a perfluoropolyether compound represented by Formula (I), an aromatic silicon-containing compound represented by Formula (II), and a silicon-containing hole transport compound represented by Formula (III):
wherein f is an integer from 1 to about 6; x is an integer from about 2 to about 500; G is a functional group connected to the end of the perfluoropolyether chain or grafted to the polymer backbone thereof; p is an integer from 1 to about 100; and G is selected from the group consisting of -OH, -CH2OH, -CH2(OCH2CH2)k OH, -CH2OCH2CH(OH)CH2OH, -CO2H, -SiE q(Y)3-q, and -( CH2)d SiE q(Y)3-q, where E is alkyl having from 1 to 6 carbon atoms, q is an integer from 0 to 2, d is an integer from 1 to about 6, and Y is selected from the group consisting of hydroxy, acetoxy, alkoxy having from 1 to 6 carbon atoms, and halide; A is a multiple-valent organic group; B
is a hole transport moiety; L is a divalent linkage; R is selected from alkyl, arylalkyl, aryl, and alkylaryl; X is a hydrolytic group; m is an integer from 1 to 6; n is an integer from 0 to 2;
and the m, n, L, R, and X of Formulas (II) and (III) are independently selected.
formulation comprising a perfluoropolyether compound represented by Formula (I), an aromatic silicon-containing compound represented by Formula (II), and a silicon-containing hole transport compound represented by Formula (III):
wherein f is an integer from 1 to about 6; x is an integer from about 2 to about 500; G is a functional group connected to the end of the perfluoropolyether chain or grafted to the polymer backbone thereof; p is an integer from 1 to about 100; and G is selected from the group consisting of -OH, -CH2OH, -CH2(OCH2CH2)k OH, -CH2OCH2CH(OH)CH2OH, -CO2H, -SiE q(Y)3-q, and -( CH2)d SiE q(Y)3-q, where E is alkyl having from 1 to 6 carbon atoms, q is an integer from 0 to 2, d is an integer from 1 to about 6, and Y is selected from the group consisting of hydroxy, acetoxy, alkoxy having from 1 to 6 carbon atoms, and halide; A is a multiple-valent organic group; B
is a hole transport moiety; L is a divalent linkage; R is selected from alkyl, arylalkyl, aryl, and alkylaryl; X is a hydrolytic group; m is an integer from 1 to 6; n is an integer from 0 to 2;
and the m, n, L, R, and X of Formulas (II) and (III) are independently selected.
7. The imaging member of claim 6, wherein G is selected from the group consisting of -SiE q(Y)3-q, and -( CH2)d SiE q(Y)3-q, where E is alkyl having from 1 to 6 carbon atoms, q is an integer from 0 to 2, d is an integer from 1 to about 6, and Y is alkoxy having from 1 to 6 carbon atoms.
8. The imaging member of claim 6, wherein the X of Formulas (II) and (III) are independently selected from the group consisting of hydroxyl, alkoxy having from 1 to 6 carbon atoms, acetoxy, and halide.
9. The imaging member of claim 8, wherein X is independently selected from methoxy, ethoxy, propoxy, or isopropoxy.
10. The imaging member of claim 6, wherein the R of Formulas (II) and (III) are independently selected from the group consisting of alkyl having from 1 to about 6 carbon atoms and phenyl.
11. The imaging member of claim 10, wherein R is independently selected from methyl or ethyl.
12. The imaging member of claim 6, wherein the L of Formulas (II) and (III) are independently selected from the group consisting of:
wherein y is an integer from 1 to about 6 and z is an integer from 1 to about 6.
wherein y is an integer from 1 to about 6 and z is an integer from 1 to about 6.
13. The imaging member of claim 6, wherein A is selected from the group consisting of:
14. The imaging member of claim 13, wherein the aromatic silicon-containing compound of Formula (II) is selected from the group consisting of the following Formulas (II-1), (II-2), and (II-3):
wherein R' is alkyl having from 1 to about 4 carbon atoms.
wherein R' is alkyl having from 1 to about 4 carbon atoms.
15. The imaging member of claim 6, wherein the aromatic silicon-containing compound of Formula (II) is present in the crosslinked polysiloxane composition in an amount of from about 10 to about 80 wt%, based on the total weight of the crosslinked polysiloxane composition.
16. The imaging member of claim 6, wherein B is a tertiary aromatic amine represented by Formula (IV):
wherein Ar1, Ar2, Ar3, and Ar4 are independently any substituted or unsubstituted aryl group; Ar5 is a substituted or unsubstituted aryl or arylene group; i is 0 or 1; and at least one of Ar1, Ar2, Ar3, Ar4, and Ar5 offers a bonding site to connect with the silyl component of Formula (III).
wherein Ar1, Ar2, Ar3, and Ar4 are independently any substituted or unsubstituted aryl group; Ar5 is a substituted or unsubstituted aryl or arylene group; i is 0 or 1; and at least one of Ar1, Ar2, Ar3, Ar4, and Ar5 offers a bonding site to connect with the silyl component of Formula (III).
17. The imaging member of claim 16, wherein the silicon-containing hole transport compound of Formula (III) is selected from the group consisting of:
18. The imaging member of claim 6, wherein the silicon-containing hole transport compound of Formula (III) is present in the crosslinked polysiloxane composition in an amount from about 20 to about 90 wt%, based on the total weight of the crosslinked polysiloxane composition.
19. An imaging method comprising:
generating a latent electrostatic image on the electrostatographic imaging member of claim 1;
developing the latent image; and transferring the developed electrostatic image to a suitable substrate.
generating a latent electrostatic image on the electrostatographic imaging member of claim 1;
developing the latent image; and transferring the developed electrostatic image to a suitable substrate.
20. An electrophotographic imaging member comprising a substrate, a charge generating layer, a charge transport layer, and a SOC layer;
wherein the SOC layer includes a crosslinked polysiloxane composition which is the product of the hydrolysis and condensation of a SOC formulation comprising:
a perfluoropolyether compound represented by Formula (I):
Formula (I) wherein f is an integer from 1 to about 6; x is an integer from about 2 to about 500; G is a functional group connected to the end of the perfluoropolyether chain or grafted to the polymer backbone thereof; p is an integer from 1 to about 100; and G
is selected from the group consisting of-SiE q(Y)3-q, and -(CH2)d SiE q(Y)3-q, where E is alkyl having from 1 to 6 carbon atoms, q is an integer from 0 to 2, d is an integer from 1 to about 6, and Y is alkoxy having from 1 to 6 carbon atoms;
wherein the perfluoropolyether compound is present in an amount of from about 0.1 to about 3 wt% based on the total weight of the crosslinked polysiloxane composition;
an aromatic silicon-containing compound selected from the group consisting of the following Formulas (II-1), (II-2), and (II-3):
wherein R' is alkyl having from 1 to about 4 carbon atoms; and the aromatic silicon-containing compound is present in an amount of from about 30 to about 70 wt%, based on the total weight of the crosslinked polysiloxane composition; and the silicon-containing hole transport compound represented by Formula (III-1):
wherein the silicon-containing hole transport compound is present in an amount of from about 40 to about 60 wt%, based on the total weight of the crosslinked polysiloxane composition.
wherein the SOC layer includes a crosslinked polysiloxane composition which is the product of the hydrolysis and condensation of a SOC formulation comprising:
a perfluoropolyether compound represented by Formula (I):
Formula (I) wherein f is an integer from 1 to about 6; x is an integer from about 2 to about 500; G is a functional group connected to the end of the perfluoropolyether chain or grafted to the polymer backbone thereof; p is an integer from 1 to about 100; and G
is selected from the group consisting of-SiE q(Y)3-q, and -(CH2)d SiE q(Y)3-q, where E is alkyl having from 1 to 6 carbon atoms, q is an integer from 0 to 2, d is an integer from 1 to about 6, and Y is alkoxy having from 1 to 6 carbon atoms;
wherein the perfluoropolyether compound is present in an amount of from about 0.1 to about 3 wt% based on the total weight of the crosslinked polysiloxane composition;
an aromatic silicon-containing compound selected from the group consisting of the following Formulas (II-1), (II-2), and (II-3):
wherein R' is alkyl having from 1 to about 4 carbon atoms; and the aromatic silicon-containing compound is present in an amount of from about 30 to about 70 wt%, based on the total weight of the crosslinked polysiloxane composition; and the silicon-containing hole transport compound represented by Formula (III-1):
wherein the silicon-containing hole transport compound is present in an amount of from about 40 to about 60 wt%, based on the total weight of the crosslinked polysiloxane composition.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/179,943 | 2005-07-12 | ||
| US11/179,943 US7439002B2 (en) | 2005-07-12 | 2005-07-12 | Imaging members |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2551441A1 true CA2551441A1 (en) | 2007-01-12 |
| CA2551441C CA2551441C (en) | 2010-09-28 |
Family
ID=37143742
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2551441A Expired - Fee Related CA2551441C (en) | 2005-07-12 | 2006-07-04 | Imaging members |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7439002B2 (en) |
| EP (1) | EP1744220B1 (en) |
| JP (1) | JP4880389B2 (en) |
| KR (1) | KR20070008424A (en) |
| CN (1) | CN1896878B (en) |
| BR (1) | BRPI0602651A (en) |
| CA (1) | CA2551441C (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7795462B2 (en) * | 2005-01-13 | 2010-09-14 | Xerox Corporation | Crosslinked siloxane outmost layer having aromatic silicon-containing compounds for photoreceptors |
| US7592110B2 (en) * | 2007-02-13 | 2009-09-22 | Xerox Corporation | Polyhydroxy siloxane photoconductors |
| JP5031408B2 (en) * | 2007-03-09 | 2012-09-19 | キヤノン株式会社 | Electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus |
| JP5469313B2 (en) * | 2008-03-26 | 2014-04-16 | 大阪瓦斯株式会社 | Silicon compound having a fluorene skeleton |
| JP5297079B2 (en) * | 2008-05-07 | 2013-09-25 | 大阪瓦斯株式会社 | Silicon compound having fluorene skeleton and polymerizable composition thereof |
| JP5571979B2 (en) * | 2010-03-11 | 2014-08-13 | 大阪ガスケミカル株式会社 | Novel fluorene compound and its metal oxide complex |
| JP5577149B2 (en) * | 2010-05-10 | 2014-08-20 | 大阪ガスケミカル株式会社 | Novel fluorene compound, method for producing the same, and metal oxide composite thereof |
| US9523928B2 (en) * | 2014-09-26 | 2016-12-20 | Xerox Corporation | Fluorinated structured organic film photoreceptor layers |
| US9651878B2 (en) | 2014-12-26 | 2017-05-16 | Samsung Electronics Co., Ltd. | Organic photoconductor and electrophotographic apparatus and process cartridge including the organic photo conductor |
| ES2682598T3 (en) * | 2015-12-17 | 2018-09-21 | Henkel Ag & Co. Kgaa | Titanium complexes as vulcanization catalysts |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3121006A (en) * | 1957-06-26 | 1964-02-11 | Xerox Corp | Photo-active member for xerography |
| US3590000A (en) * | 1967-06-05 | 1971-06-29 | Xerox Corp | Solid developer for latent electrostatic images |
| US3849182A (en) * | 1969-06-19 | 1974-11-19 | Xerox Corp | Highly shape-classified oxidized low carbon hypereutectoid electrostatographic steel carrier particles |
| US3900588A (en) * | 1974-02-25 | 1975-08-19 | Xerox Corp | Non-filming dual additive developer |
| AU8393475A (en) * | 1974-09-30 | 1977-02-17 | Bakelite Xylonite Ltd | Polymer films |
| US4298697A (en) * | 1979-10-23 | 1981-11-03 | Diamond Shamrock Corporation | Method of making sheet or shaped cation exchange membrane |
| US4338390A (en) * | 1980-12-04 | 1982-07-06 | Xerox Corporation | Quarternary ammonium sulfate or sulfonate charge control agents for electrophotographic developers compatible with viton fuser |
| US4558108A (en) * | 1982-12-27 | 1985-12-10 | Xerox Corporation | Aqueous suspension polymerization process |
| EP0114056B1 (en) * | 1983-01-15 | 1987-11-19 | Hoechst Aktiengesellschaft | Sample stand |
| US4560635A (en) * | 1984-08-30 | 1985-12-24 | Xerox Corporation | Toner compositions with ammonium sulfate charge enhancing additives |
| JP2666314B2 (en) * | 1988-01-07 | 1997-10-22 | 富士ゼロックス株式会社 | Electrophotographic photoreceptor |
| US5368967A (en) * | 1993-12-21 | 1994-11-29 | Xerox Corporation | Layered photoreceptor with overcoat containing hydrogen bonded materials |
| EP0890138A1 (en) * | 1996-03-28 | 1999-01-13 | Minnesota Mining And Manufacturing Company | Perfluoroether release coatings for organic photoreceptors |
| US5702854A (en) * | 1996-09-27 | 1997-12-30 | Xerox Corporation | Compositions and photoreceptor overcoatings containing a dihydroxy arylamine and a crosslinked polyamide |
| US5681679A (en) * | 1996-09-27 | 1997-10-28 | Xerox Corporation | Overcoated electrophotographic imaging member with resilient charge transport layer |
| US5709974A (en) * | 1996-09-27 | 1998-01-20 | Xerox Corporation | High speed electrophotographic imaging member |
| JP4445146B2 (en) * | 2001-03-15 | 2010-04-07 | 株式会社リコー | Electrostatic latent image liquid developing device |
| US6797444B2 (en) * | 2001-07-18 | 2004-09-28 | Konica Corporation | Electrophotographic photoreceptor and production method of the same |
| JP2003066642A (en) * | 2001-08-28 | 2003-03-05 | Fuji Xerox Co Ltd | Electrophotographic photoreceptor and method for manufacturing the same |
| JP4039182B2 (en) * | 2002-08-28 | 2008-01-30 | 富士ゼロックス株式会社 | Electrophotographic photosensitive member, process cartridge, and image forming apparatus |
| JP2004109917A (en) * | 2002-09-20 | 2004-04-08 | Fuji Xerox Co Ltd | Image forming apparatus |
| US7205079B2 (en) * | 2004-07-09 | 2007-04-17 | Xerox Corporation | Imaging member |
| US7795462B2 (en) * | 2005-01-13 | 2010-09-14 | Xerox Corporation | Crosslinked siloxane outmost layer having aromatic silicon-containing compounds for photoreceptors |
-
2005
- 2005-07-12 US US11/179,943 patent/US7439002B2/en not_active Expired - Fee Related
-
2006
- 2006-06-13 EP EP06115389A patent/EP1744220B1/en not_active Expired - Fee Related
- 2006-07-04 CA CA2551441A patent/CA2551441C/en not_active Expired - Fee Related
- 2006-07-10 BR BRPI0602651-6A patent/BRPI0602651A/en not_active IP Right Cessation
- 2006-07-11 CN CN2006101015387A patent/CN1896878B/en not_active Expired - Fee Related
- 2006-07-11 KR KR1020060065000A patent/KR20070008424A/en active IP Right Grant
- 2006-07-12 JP JP2006191703A patent/JP4880389B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1744220B1 (en) | 2012-08-22 |
| US20070015072A1 (en) | 2007-01-18 |
| US7439002B2 (en) | 2008-10-21 |
| CN1896878A (en) | 2007-01-17 |
| BRPI0602651A (en) | 2007-03-06 |
| CA2551441C (en) | 2010-09-28 |
| JP2007025676A (en) | 2007-02-01 |
| KR20070008424A (en) | 2007-01-17 |
| EP1744220A3 (en) | 2009-03-25 |
| JP4880389B2 (en) | 2012-02-22 |
| EP1744220A2 (en) | 2007-01-17 |
| CN1896878B (en) | 2010-12-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20140704 |