GB1603279A

GB1603279A – Electrophotographic materials
– Google Patents

GB1603279A – Electrophotographic materials
– Google Patents
Electrophotographic materials

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Publication number
GB1603279A

GB1603279A
GB22412/78A
GB2241278A
GB1603279A
GB 1603279 A
GB1603279 A
GB 1603279A
GB 22412/78 A
GB22412/78 A
GB 22412/78A
GB 2241278 A
GB2241278 A
GB 2241278A
GB 1603279 A
GB1603279 A
GB 1603279A
Authority
GB
United Kingdom
Prior art keywords
chlorendate
photoconductive
poly
binder
photoconductor
Prior art date
1977-05-25
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.)

Expired

Application number
GB22412/78A
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.)

Eastman Kodak Co

Original Assignee
Eastman Kodak Co
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.)
1977-05-25
Filing date
1978-05-25
Publication date
1981-11-25

1978-05-25
Application filed by Eastman Kodak Co
filed
Critical
Eastman Kodak Co

1981-11-25
Publication of GB1603279A
publication
Critical
patent/GB1603279A/en

Status
Expired
legal-status
Critical
Current

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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

G03G5/02—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

G03G5/0601—Acyclic or carbocyclic compounds

G03G5/0603—Acyclic or carbocyclic compounds containing halogens

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

G03G5/0601—Acyclic or carbocyclic compounds

G03G5/0605—Carbocyclic compounds

G03G5/0607—Carbocyclic compounds containing at least one non-six-membered ring

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

G03G5/0601—Acyclic or carbocyclic compounds

G03G5/062—Acyclic or carbocyclic compounds containing non-metal elements other than hydrogen, halogen, oxygen or nitrogen

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

G03G5/07—Polymeric photoconductive materials

G03G5/071—Polymeric photoconductive materials obtained by reactions only involving carbon-to-carbon unsaturated bonds

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

G03G5/07—Polymeric photoconductive materials

G03G5/071—Polymeric photoconductive materials obtained by reactions only involving carbon-to-carbon unsaturated bonds

G03G5/072—Polymeric photoconductive materials obtained by reactions only involving carbon-to-carbon unsaturated bonds comprising pending monoamine groups

G03G5/073—Polymeric photoconductive materials obtained by reactions only involving carbon-to-carbon unsaturated bonds comprising pending monoamine groups comprising pending carbazole groups

Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC

Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

Y10S522/00—Synthetic resins or natural rubbers — part of the class 520 series

Y10S522/904—Monomer or polymer contains initiating group

Description

PATENT SPECIFICATION ( 11) 1 603 279
2 ( 21) Application No 22412/78 ( 22) Filed 25 May 1978 ( 19) s ( 31) Convention Application No 800594 ( 32) Filed 25 May 1977 in I ( 33) United States of America (US) < ( 44) Complete Specification Published 25 Nov 1981 ú ( 51) INT CL 3 G 03 G 5/09 ( 52) Index at Acceptance G 2 C 1014 1015 1023 1046 1047 C 17 C 8 ( 72) Inventors: JOHN M McCABE WILLIAM E YOERGER ( 54) ELECTROPHOTOGRAPHIC MATERIALS ( 71) We EASTMAN KODAK COMPANY, a Company organized under the Laws of the State of New Jersey United States of America of 343 State Street, Rochester, New York 14650, United States of America do hereby declare the invention for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement: 5 This invention relates to electrophotographic materials with chemical sensitizing polymers containing appended chlorendate radicals to increase the speed of the material. Various photoconductive insulating materials have been used in the manufacture of electrophotographic materials For example, vapours of selenium and vapours of selenium alloys deposited on a suitable support have been used Particles of photoconductive zinc 10 oxide dispersed in resinous, film-forming binder have found wide application in the present-day document copying applications For example, inorganic photoconductors are dispersed in such binders as polymerized butyl methacrylates, or vinyl polymers such as polymers of styrene, vinyl chloride, and vinyl acetate When inorganic photoconductors are dispersed in acrylic polymer binders, the technical literature indicates that it is preferred to 15 employ acrylic terpolymers and acrylic polymers free of acid groups This is because the light sensitivity of acrylic homopolymers, acrylic copolymers, or acrylic polymers is lowered when they contain acid groups (See Photographic Science and Engineering, Volume 16, Number 5, September-October 1972 pp 354-358) In photoconductive insulating lavers in which organic photoconductors are used, the 20 photoconductor is usually not polymeric It is usually used in combination with a binder which can form a film Typical binders are polymeric materials having fairly high dielectric strength such as phenolic resins, ketone resins, acrylic ester resins, polystyrenes The photoconductor can be dissolved with the binder to prepare a homogeneous photoconductive composition in a common solvent In another aspect, it can be provided as a dispersion 25 of small particles in the binder to prepare a heterogeneous photoconductive layer. Heterogeneous organic photoconductive layers can be advantageous, especially in the preparation of electrophotographic materials on which visible images will be provided. Such materials are lighter in weight than materials having inorganic photoconductors such as zinc oxide, and can be prepared to resemble bond paper However, they have not 30 enjoyed in such applications the popularity of photoconductive insulating layers comprising inorganic photoconductors This is largely due to the unacceptable photoconductivity of heterogeneous layers or organic photoconductors. To improve the photoconductivity of photoconductive layers using organic photoconductors, a variety of compounds and polymers have been studied for use as socalled chemical 35 sensitizers or activators When added to photoconductive layers it is intended that such materials enhance the photoconductivity of the layer at least within the electromagnetic wavelength region in which the photoconductor is intrinsically sensitive If successful, the photoconductor is said to be chemically sensitized or activated It should be pointed out, however, that chemical sensitizers are often specific in their utility That is, they may have 40 utility in homogeneous systems or heterogeneous systems but not generally in both. Materials which do serve as sensitizers for both systems, accordingly, are rare and highly desirable. Choice of binder in a heterogeneous photoconductive layer having a dispersed organic photoconductive layer having a dispersed organic photoconductor can affect the ability of 45 av 7,U'J, 2 the layer to be sensitized In the case of acrylic polymer binders, this is especially true. Despite references in the prior art to layers comprising polymers including acrylic polymers as binders for dispersed organic photoconductors, attempts to improve the photoconductivity of such layers by using known chemical sensitizers have been largely unsuccessful. Selection of a proper chemical sensitizer for a given photoconductor is further 5 complicated by other requirements of an electrophotographic process A material using a chemically sensitized photoconductive layer as defined herein must, for example, readily accept and hold an electrostatic charge until it is imagewise illuminated Many photoconductive layers using materials screened for use as sensitizers, although acceptably photoconductive, fail to accept a charge which is high enough to merit further study Layers 10 so failing are said to be "charge saturated" Some layers may be unable to retain an applied charge for reasonable periods of time in the dark Such layers are said to have too much "dark decay". According to the present invention there is provided an electrophotographic material comprising an electrically conductive support carrying a photoconductive insulating layer 15 containing an organic photoconductor chemically sensitized with a polymer containing appended chlorendate groups. Preferred polymers containing appended chlorendate radicals are vinyl, acrylic or cellulosic polymers It has been found that such polymers are valuable chemical sensitizers for organic photoconductors independent of the type of binder that is used to bind the 20 photoconductor to the substrate One or more of such polymeric chemical sensitizers can be used to replace the usual binder in heterogeneous photoconductive layers. Heterogeneous organic photoconductive layers comprising acrylic binders which are normally not sensitized by monomeric chlorendic anhydride are chemically sensitized with notable success using the present polymeric chlorendate sensitizers 25 In one embodiment of the invention, the presence of the polymeric chlorendate sensitizers in a heterogeneous organic photoconductive layer permits the use of one or more additional chemical sensitizers. Photoconductive insulating layers having an organic photoconductor dispersed or dissolved in an electrically insulating binder are chemically sensitized with a polymer to 30 which is appended chlorendate groups. Use of polymeric chlorendate sensitizers in accordance with this invention makes possible a wide latitude in the choice of electrophotographic materials, especially materials of the type resembling plain paper (both in feel and appearance) Use of such polymeric chlorendate sensitizers can raise the photoconductivity of an otherwise conventional 35 organic photoconductive layer to a level comparable to that of a layer using inorganic photoconductors such as zinc oxide This is accomplished without the disadvantages, such as excessive weight, glossiness and "coining" propensity which are typically encountered when inorganic photoconductors are used The sensitizing ability of chlorendate-containing polymers is relatively independent of the binder selected for use in the photoconductive 40 layers Hence the use of tough, resinous materials such as acrylic polymers in a broader range of photoconductor layers is made possible by this invention Also, the polymeric chlorendate sensitizers can be used in place of conventional binders in the manufacture of photoconductive layers and become binder-sensitizers for organic photoconductors. The advantages offered by the invention appear to stem from the presence of chlorendate 45 groups appended to the polymer backbone Preferably such polymers are vinyl, acrylic or cellulosic polymers Chlorendate-containing polymers, in accordance with the present invention can be used both in heterogeneous photoconductive layers (see example 52) and in homogeneous photoconductive layers (see example 61). Chlorendate groups, as referred to herein, can be structurally depicted as: 50 cl O Cl \ /\ 55 GL C = O 60 Cli Cl 65 1 Afnl 17 X I