WO1992011581A1 - Photoelectrographic imaging with near-infrared sensitizing dyes - Google Patents

Photoelectrographic imaging with near-infrared sensitizing dyes Download PDF

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Publication number
WO1992011581A1
WO1992011581A1 PCT/US1991/009078 US9109078W WO9211581A1 WO 1992011581 A1 WO1992011581 A1 WO 1992011581A1 US 9109078 W US9109078 W US 9109078W WO 9211581 A1 WO9211581 A1 WO 9211581A1
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acid
photoelectrographic
group
copper
dye
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PCT/US1991/009078
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French (fr)
Inventor
Douglas Eugene Bugner
William Mey
Dennis Reed Kamp
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Eastman Kodak Company
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    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02Charge-receiving layers
    • G03G5/026Layers in which during the irradiation a chemical reaction occurs whereby electrically conductive patterns are formed in the layers, e.g. for chemixerography

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

Abstract

The present invention relates to a photoelectrographic element having a conductive layer in electrical contact with an acid photogenerating layer which is free of photopolymerizable materials and contains an electrically insulating binder and acid photogenerator. A dye which absorbs near-infrared radiation is included in the photoelectrographic element so that the element, when used in electrostatic copying, can be exposed with near-infrared radiation. A method for forming images with this element is also disclosed.

Description

PHOTOELECTROGRAPHIC IMAGING
WITH NEAR-INFRARED SENSITIZING DYES
FIELD OF THE INVENTION
This invention relates to new
photoelectrographic elements and an imaging method of exposing such elements with near-infrared radiation.
BACKGROUND OF THE INVENTION
Acid photogenerators are known for use in photoresist imaging elements. In imaging processes utilizing such elements, the acid photogenerator is coated on a support and imagewise exposed to actinic radiation. The layer containing the acid photogenerator is then contacted with a photopolymerizable or curable composition such as epoxy and epoxy-containing resins. In the exposed areas, the acid photogenerator generates protons which catalyze polymerization or curing of the photopolymerizable composition. Acid photogenerators are disclosed, for example, in U.S. Patent Nos.
4,081,276, 4,058,401, 4,026,705, 2,807,648, 4,069,055, and 4,529,490.
Acid photogenerators have been employed in photoelectrographic elements to be exposed with actinic or undefined radiation as shown, for example, in U.S. Patent No. 3,316,088. Photoelectrographic elements have been found useful where multiple copies from a single exposure are desired. See e.g., U.S. Patent
Nos. 4,661,429, 3,681,066 as well as German Democratic Republic Patent No. 226,067 and Japanese Patent
No. 105,260. Sensitizer dyes have been disclosed with regard to such elements, but not for sensitization in the near-IR portion of the spectrum. See, for example, in U.S. Patent No. 3,525,612 and Japanese Patent
No. 280,793. SUMMARY OF THE INVENTION
The present invention relates to a
photoelectrographic element comprising a conductive layer in electrical contact with an acid photogenerating layer. The acid photogenerating layer is free of photopolymerizable materials and includes an
electrically insulating binder and an acid
photogenerator in accordance with U.S. Patent
No. 4,661,429. The present invention constitutes an improvement over U.S. Patent No. 4,661,429 by
incorporating a dye in the photoelectrographic element which absorbs near-infrared radiation. As a result, the element can be sensitized with such radiation.
The present invention also provides a photoelectrographic imaging method which utilizes the above-described photoelectrographic element. This process comprises the steps of: exposing the acid photogenerating layer imagewise to near-infrared
radiation without prior charging to create a latent conductivity pattern and printing by a sequence
comprising: charging to create an electrostatic latent image, developing the electrostatic latent image with charged toner particles, transferring the toned image to a suitable receiver, and cleaning any residual,
untransferred toner from the photoelectrographic element.
The imaging method and elements of the present invention use acid photogenerators in thin layers coated over a conductive layer to form images. This imaging technigue or method takes advantage of the discovery that exposure of the acid generator significantly
increases the conductivity in the exposed area of the layer. Imagewise radiation of the acid photogenerator layer creates a persistent differential conductivity between exposed and unexposed areas. This allows for the subsequent use of the element for printing multiple copies from a single exposure with only multiple charging, developing, transferring, and cleaning steps. This is different from electrophotographic imaging techniques where the electrophotographic element must generally be charged electrostatically followed by imagewise exposure for each copy produced. As a result, maximum throughput tends to be limited, and energy consumption is likely to be greater.
The charged toner may have the same sign as the electrographic latent image or the opposite sign. In the former case, a negative image is developed, while a positive image is developed in the latter.
By incorporating a dye which absorbs
near-infrared radiation in the photoelectrographic element containing an acid generating layer, such elements are no longer limited to exposure with
ultraviolet and visible radiation. Such dyes instead permit exposure with radiation in the near-infrared region of the spectrum (having wavelengths of 650 to 1,000 nm). The use of near-infrared radiation is advantageous, because laser diodes, which emit in this part of the spectrum, are relatively inexpensive and consume little energy. Dyes absorbing near-infrared radiation can be included in the same layer as the acid photogenerating compound or as a separate layer adjacent to the acid photogenerating layer. Certain copper (II) salts, which are known to catalyze the thermal
decomposition of iodonium salts especially when used in conjunction with compounds containing secondary hydroxyl groups, may also be included in the acid photogenerating layer.
DESCRIPTION OF THE PREFERRED EMBODlMENTS As already noted, the present invention relates to a photoelectrographic element comprising a conductive layer in electrical contact with an acid photogenerating layer which is free of photopolymerizable materials and includes an electrically insulating binder and an acid photogenerator. In this element, the improvement resides in the use of a dye which absorbs near-infrared radiation so that the element can be exposed with such radiation during electrostatic imaging or printing processes.
In preparing acid photogenerating layers, the acid photogenerator, the electrically insulating binder, and the dye are co-dissolved in a suitable solvent, and the resulting solution is coated over the electrically conductive support.
Solvents of choice for preparing acid photogenerator coatings include a number of solvents including aromatic hydrocarbons such as toluene;
ketones, such as acetone or 2-butanone; esters, such as ethyl acetate or methyl acetate, chlorinated
hydrocarbons such as ethylene dichloride,
trichloroethane, and dichloromethane, ethers such as tetrahydrofuran; or mixtures of these solvents.
The acid photogenerating layers are coated on a conducting support in any well-known manner such as by doctor-blade coating, swirling, dip-coating, and the like.
The acid photogenerating materials should be selected to impart little or no conductivity before irradiation with the conductivity increasing after exposure. Useful results are obtained when the coated layer contains at least about 1 weight percent of the acid photogenerator. The upper limit of acid
photogenerator is not critical as long as no deleterious effect on the initial conductivity of the film is
encountered. A preferred weight range for the acid photogenerator in the coated and dried composition is from 15 weight percent to about 30 weight percent.
The thicknesses of the acid photogenerator layer can vary widely with dry coating thicknesses ranging from about 0.1 μm to about 50 μm. Coating thicknesses outside these ranges may also be useful.
Although there are many known acid
photogenerators useful with ultraviolet and visible radiation, the utility of their exposure with
near-infrared radiation is unpredictable. Potentially useful aromatic onium salt acid photogenerators are disclosed in U.S. Patent Nos. 4,661,429, 4,081,276, 4,529,490, 4,216,288, 4,058,401, 4,069,055, 3,981,897, and 2,807,648 which are hereby incorporated by
reference. Such aromatic onium salts include Group Va, Group Via, and Group Vila elements. The ability of triarylselenonium salts, aryldiazonium salts, and triarylsulfonium salts to produce protons upon exposure to ultraviolet and visible light is also described in detail in "UV Curing, Science and Technology",
Technology Marketing Corporation, Publishing Division, 1978.
A representative portion of useful Group Va onium salts are:
Figure imgf000008_0001
A representative portion of useful Group VIa onium salts, including sulfonium and selenonium salts, are:
Figure imgf000009_0001
Figure imgf000010_0001
Figure imgf000011_0001
A representative portion of the useful Group VIIa onium salts, including iodonium salts, are the following:
Figure imgf000012_0001
Figure imgf000013_0001
Also useful as acid photogenerating compounds are:
1. Aryldiazonium salts such as disclosed in U.S. Patent Nos. 3,205,157; 3,711,396; 3,816,281;
3,817,840 and 3,829,369. The following salts are representative:
Figure imgf000014_0001
2. 6-Substituted-2,4-bis(trichloromethyl)- 5-triazines such as disclosed in British Patent
No. 1,388,492. The following compounds are
representative:
Figure imgf000015_0001
A particularly preferred class of acid photogenerators are the diaryliodonium salts, especially di-(4-t-butylphenyl)iodonium trifluoromethanesulfonate ("ITF").
Useful electrically insulating binders for the acid photogenerating layers include polycarbonates, polyesters, polyolefins, phenolic resins, and the like. Desirably, the binders are film forming. Such polymers should be capable of supporting an electric field in excess of 1 × 105 V/cm and exhibit a low dark decay of electrical charge.
Preferred binders are styrene-butadiene copolymers; silicone resins; styrene-alkyd resins;
soya-alkyd resins; poly(vinyl chloride); poly(vinylidene chloride); vinylidene chloride, acrylonitrile
copolymers; poly(vinyl acetate); vinyl acetate, vinyl chloride copolymers; poly(vinyl acetals), such as poly(vinyl butyral); polyacrylic and methacrylic esters, such as poly(methyl methacrylate), poly(n-butyl
methacrylate), poly(isobutyl methacrylate), etc;
polystyrene; nitrated polystyrene;
poly(vinylphenol)polymethylstyrene; isobutylene
polymers; polyesters, such as phenol formaldehyde resins; ketone resins; polyamides; polycarbonates; etc. Methods of making resins of this type have been
described in the prior art, for example, styrene-alkyd resins can be prepared according to the method described in U.S. Patent Nos. 2,361,019 and 2,258,423. Suitable resins of the type contemplated for use in the
photoactive layers of this invention are sold under such tradenames as Vitel PE 101-X, Cymac, Piccopale 100, Saran F-220. Other types of binders which can be used include such materials as paraffin, mineral waxes, etc. Particularly preferred binders are aromatic esters of polyvinyl alcohol polymers and copolymers, as disclosed in pending U.S. Patent Application Serial No. 509,119, entitled "Photoelectrographic Elements".
The binder is present in the element in a concentration of 30 to 98 weight %, preferably 55 to 80 weight %.
Useful conducting layers include any of the electrically conducting layers and supports used in electrophotography. These include, for example, paper (at a relative humidity above about 20 percent);
aluminum paper laminates; metal foils, such as aluminum foil, zinc foil, etc.; metal plates, such as aluminum, copper, zinc, brass, and galvanized plates; regenerated cellulose and cellulose derivatives; certain polyesters, especially polyesters having a thin electroconductive layer (e.g., cuprous iodide) coated thereon; etc.
While the acid photogenerating layers of the present invention can be affixed, if desired, directly to a conducting substrate or support, it may be desirable to use one or more intermediate subbing layers between the conducting layer or substrate and the acid photogenerating layer to improve adhesion to the conducting substrate and/or to act as an electrical and/or chemical barrier between the acid
photogenerating layer and the conducting layer or substrate.
Such subbing layers, if used, typically have a dry thickness in the range of about 0.1 to about 5 μm. Useful subbing layer materials include film-forming polymers such as cellulose nitrate, polyesters, copolymers or poly(vinyl pyrrolidone) and vinylacetate, and various vinylidene chloride-containing polymers including two, three and four component polymers prepared from a polymerizable blend of monomers or prepolymers containing at least 60 percent by weight of vinylidene chloride. Other useful subbing materials include the so-called tergels which are described in Nadeau et al, U.S. Patent No. 3,501,301.
Optional overcoat layers are useful with the present invention, if desired. For example, to improve surface hardness and resistance to abrasion, the surface layer of the photoelectrographic element of the invention may be coated with one ore more organic polymer coatings or inorganic coatings. A number of such coatings are well known in the art and accordingly an extended discussion thereof is unnecessary. Several such overcoats are described, for example, in Research Disclosure. "Electrophotographic Elements, Materials, and Processes", Vol. 109, page 63, Paragraph V, May 1973, which is incorporated herein by reference.
The dye which absorbs near-infrared radiation can be any such material possessing this property but must not adversely interfere with the operation of the acid photogenerating layer. Suitable dyes include those selected from the cyanine dye family. A particularly preferred dye is 1,3,3-trimethyl-2-[7-(l,3,3-trimethyl-5-nitroindolenin-2-yl)-4-chloro-3,5-trimethylene-1,3,5-heptatrienylidene]-5-nitroindolium hexafluorophosphate ("TTNTHNH") having the following formula:
Figure imgf000018_0001
This dye, when included in the photoelectrographic element of the present invention at concentrations between 0.1 and 2.0% by weight of the element, gives rise to an absorption between about 600-900 nm, with a maximum near 820 nm. A typical element containing 1 wt% of this dye and measuring 10 μm in thickness exhibits an optical density ("OD") of about 3.54 at 818 nm.
When the acid generating layer contains iodonium salts, it may be advantageous to include in that layer a compound with secondary hydroxyl groups and a copper (II) salt which, when used together, are known to catalyze thermal decomposition of iodonium salts. Suitable copper (II) salts are disclosed by J. V.
Crivello, T. P. Lockhart, and J. L. Lee, J. Polym. Sci., Polym. Chem. Ed.. 21, 97 (1983). These include copper (II) arylates, copper (II) alkanoates, copper (II) acetonates, copper (II) acetoacetates, and mixtures thereof.
A particularly preferred example of a copper (II) salt useful for this invention is copper (II) ethyl acetoacetate. This salt is soluble in organic solvents such as dichloromethane and can be homogeneously
incorporated at concentrations as high as 18% by weight of the dry photoelectrographic element.
The compound with secondary hydroxyl groups include those which contain dialkyl-, diaryl-,
alkylaryl-, and hydroxymethane moieties. A particularly preferred compound with secondary hydroxyl groups is the binder polymer having the following formula:
Figure imgf000019_0001
This is a copolymer of bisphenol A and epichlorohydrin, and may be obtained from Aldrich Chemical Company,
Milwaukee, Wisconsin under the trade name PHENOXY RESIN. The dye can either be included in the acid photogenerating layer or in an adjacent separate layer.
When the dye is incorporated in the acid photogenerating layer, the acid generating layer contains .1 to 30, preferably 1-15, weight percent of dye. If a copper (II) salt and a compound with
secondary hydroxyl groups are included in this layer, the copper (II) salt is present in an amount of 1 to 20, preferably 10-15, weight percent and, except when
PHENOXY RESIN is used, the compound with secondary hydroxyl groups is present in an amount of 1 to 10, preferably 2-4, weight percent. When PHENOXY RESIN is used as the compound with secondary hydroxyl groups, it is also functioning as the binder and then is used in a concentration of 30-98 weight %, preferably 55 to 80 weight %. The thickness of the acid generating layer ranges from 1 to 30 μm, preferably 5 to 10 μm.
If the dye is utilized as a separate layer, that layer is positioned adjacent to the acid
photogenerating layer, preferably between the conductive layer and the acid photogenerating layer. Preferably, the dye containing layer has a thickness of .05 to 5, preferably .5 to 2.0, μm.
In some cases, it may be optionally desirable to incorporate a near-ultraviolet radiation (250 to 450 nm) sensitizer in the photoelectrographic element. This gives the element the capability of being exposed either with traditional near-ultraviolet radiation or with near-infrared radiation from a laser diode. The amount of near-ultraviolet radiation sensitizer used varies widely, depending upon the type and thickness of the acid photogenerator used as well as the particular sensitizer used. Generally, the near-ultraviolet
radiation sensitizer can be present in an amount of up to about 30 percent by weight of the acid generating composition. Iodonium salt acid photogenerators may be sensitized for near-ultraviolet radiation with ketones such as xanthones, indandiones, indanones,
thioxanthones, acetophenones, benzophenones, or other aromatic compounds such as anthracenes,
dialkoxyanthracenes, perylenes, phenothiazines, etc.
Triarylsulfonium salt acid photogenerators may be sensitized for near-ultraviolet radiation by aromatic hydrocarbons, anthracenes, perylenes, pyrenes, and phenothiazines.
The photoelectrographic elements of the present invention are employed in the photoelectrographic process summarized above. This process involves a
2-step sequence ╌ i.e. an exposing phase followed by a printing phase.
In the exposing phase, the acid photogenerating layer is exposed imagewise to near-infrared radiation without prior charging to create a latent conductivity pattern. Once the exposing phase is completed, a persistent latent conductivity pattern exists on the element, and no further exposure is needed. The element can then be subjected to the printing phase either immediately or after some period of time has passed.
In the printing phase, the element is given a blanket electrostatic charge, for example, by passing it under a corona discharge device, which uniformly charges the surface of the acid photogenerator layer. The charge is dissipated by the layer in the exposed areas, creating an electrostatic latent image. The
electrostatic latent image is developed with charged toner particles, and the toned image is transferred to a suitable receiver (e.g., paper). The toner particles can be fused either to a material (e.g., paper) on which prints are actually made or to an element to create an optical master or a transparency for overhead
projection. Any residual, untransferred toner is then cleaned away from the photoelectrographic element. The toner particles are in the form of a dust, a powder, a pigment in a resinous carrier, or a liquid developer in which the toner particles are carried in an electrically insulating liquid carrier. Methods of such development are widely known and described as, for example, in U.S. Patent Nos. 2,296,691, 3,893,935,
4,076,857, and 4,546,060.
By the above-described process, multiple prints from a single exposure can be prepared by subjecting the photoelectrographic element only once to the exposing phase and then subjecting the element to the printing phase once for each print made.
The photoelectrographic layer can be developed with a charged toner having the same polarity as the latent electrostatic image or with a charged toner having a different polarity from the latent
electrostatic image. In one case, a positive image is formed. In the other case, a negative image is formed. Alternatively, the photoelectrographic layer can be charged either positively or negatively, and the
resulting electrostatic latent images can be developed with a toner of given polarity to yield either a
positive or negative appearing image.
The photoelectrographic element of the present invention can be imaged with a laser which emits
radiation most efficiently at near-infrared
wavelengths. For example, a laser diode with about
200mW peak power output at 827 nm and a spot size of about 40 μm can be used to image the photoelectrographic element. In a typical device, the element is mounted on a rotating drum, and the laser is stepped across the length of the drum in lines about 25 μm from center to center. The image is written by modulating the output of the laser in an imagewise manner. When
photoelectrographic elements of the present invention are imaged in this manner, an imagewise conductivity pattern is formed from which toned images can be produced, as described above.
The invention is further illustrated by the following examples which include preferred embodiments thereof.
EXAMPLES
In the examples which follow, the preparation of representative materials, the formulation of
representative film packages, and the characterization of these films are described. These examples are provided to illustrate the usefulness of the
photoelectrographic element of the present invention and are by no means intended to exclude the use of other elements which fall within the above disclosure.
Example 1
A polyester support was coated successively with solutions of (i) cuprous iodide (3.4 wt%) and poly(vinyl formal) (0.32 wt%) in acetonitrile (96.3 wt%), and (ii) cellulose nitrate (6 wt%) in 2-butanone (94 wt%), such that the layer formed from solution (i) is about 0.5 μm thick, and the layer formed by solution (ii) is about 1.5 μm thick. A formulation consisting of ITF (1.5 wt%), copper (II) ethyl acetoacetate (0.91 wt%), TTNTHNH (0.10 wt%), and PHENOXY RESIN (7.49 wt%) in dichloromethane ("DCM") (90 wt%) was completely dissolved and coated over the layer formed from solution (ii) with a 5 mil coating blade under ambient
conditions. The resulting photoelectrographic element was dried in a convection oven for 20 min at 60ºC.
Cross-section and optical microscopy of a sample of this element show it to be approx. 7.4 μm thick. Optical spectroscopy reveals an absorption maximum at 816 nm with an OD of 1.08. A sample of this film was evaluated for sensitivity to near-IR irradiation in the following manner. The film was exposed on a breadboard equipped with a 200 mW IR laser diode (827 nm output), and the output beam focused to a 40 μm spot. The breadboard consists of a rotating drum, upon which the film is mounted, and a translation stage which moves the laser beam along the drum length. The drum rotation, the laser beam location, and the laser beam intensity are all controlled by an IBM-AT computer. The drum was rotated at a speed of 120 rpm, and the film was exposed to an electronically generated graduated exposure consisting of 11 exposure steps. The line spacing (distance between scan lines in the continuous tone step-wedge) was 25 μm, and the maximum intensity was about 100 mW with an exposure time of about
30 μsec/pixel. Within one-half hour after exposure, the sample was mounted and tested on a separate linear breadboard. The sample was corona charged with a grid controlled charger set at a grid potential of +500 V. The surface potential was then measured at 1 sec and 15 sec after charging.
The data for this and the other examples are tabulated below in Table 1. The delta V's reported in this table represent the difference in potential between an unexposed area of the film and an area receiving maximum exposure. Several samples were also charged with the charger set at -500 V, and identical results were obtained, thus illustrating the bipolarity of the inventive element.
Example 2
An element was prepared in the same manner as that described in Example 1, except that 0.2 wt% of TTNTHNH and 7.39 wt% of PHENOXY RESIN were used. This film was found to be 6.2 μm thick and to exhibit an absorption maximum at 817 nm with OD = 2.46. Data for this film is set forth in Table 1.
Example 3
An element was prepared in the same manner as that described in Example 1, except that no TTNTHNH was added and 7.59 wt% of PHENOXY RESIN was used. This photoelectrographic element was found to be 7.8 μm thick and did not exhibit any absorption at wavelengths greater than 450 nm. Data for this element is listed in Table 1. This element displayed no photoelectrographic activity. It is thus apparent that a near-IR absorbing species must be present in the element. Example 4
An element was prepared in the same manner as that described in Example 1, except that no copper (II) salt was added, and 8.4 wt% PHENOXY RESIN was used.
This photoelectrographic element was 9.8 μm thick and exhibited an absorption maximum at 818 nm with OD =
3.54. Data for this element is set forth in Table 1.
Example 5
This element was coated in the same manner as that described in Example 4, except that 2.5 wt% of ITF and 7.4 wt% of PHENOXY RESIN were used. This element was 9.8 μm thick and had an absorption maximum of 817 nm with OD = 3.86. Data for this element is set forth in Table 1.
Example 6
A photoelectrographic element was prepared as described in Example 2, except that 2.50 wt% of ITF, 1.52 wt% of the copper (II) salt, and 5.78 wt% of
PHENOXY RESIN were used. The top coating was 5.8 μm thick and had an absorption maximum of 816 nm with OD = 2.48. Data for this element is set forth in Table 1. This element was also exposed to an
electronically-generated continuous-tone image. The photoelectrographic element was subsequently charged and toned, and the toned image was transferred to paper.
TABLE 1 EXAMPLE DELTA V's
1 sec 15 sec
1 40 100 2 60 190 3 30 30 4 75 160 5 100 225 6 150 235

Claims

We Claim:
1. A photoelectrographic element for electrostatic imaging comprising a conductive layer in electrical contact with an acid photogenerating layer which is free of photopolymerizable materials and comprises an electrically insulating binder and an acid photogenerator, wherein the improvement comprises:
a dye in said photoelectrographic element which absorbs near-infrared radiation, thereby making said photoelectrographic element capable of being exposed with near-infrared radiation.
2. A photoelectrographic element according to claim 1, wherein the acid photogenerator is selected from the group consisting of 6-substituted-2,4- bis(trichloromethyl)-5-triazines, aromatic onium salts containing elements selected from the group consisting of Group Va, Group VIa, and Group VIIa elements, and diazonium salts.
3. A photoelectrographic element according to claim 2 , wherein the acid photogenerator is di(4-t-butylphenyl iodonium trifluoromethanesulfonate).
4. A photoelectrographic element according to claim 1, wherein the binder is selected from the group consisting of polycarbonates, polyesters,
polyolefinn, phenolic resins, paraffins, and mineral waxes.
5. A photoelectrographic element according to claim 1, wherein the dye is a cyanine dye.
6. A photoelectrographic element according to claim 5, wherein the dye is 1,3,3-trimethyl-2-[7-(1,3,3-trimethyl-5-nitroindolenin-2-yl)-4 chloro-3,5- trimethylene-1,3,5-neptatrienylidene]-5-nitroindolium hexafluorophosphate.
7. A photoelectrographic element according to claim 1, wherein the acid photogenerating layer further comprises:
a copper (II) salt and a compound containing secondary hydroxyl groups.
8. A photoelectrographic element according to claim 7 , wherein the copper (II) salt is selected from the group consisting of copper (II) arylates, copper (II) alkanoates, copper (II) acetonates, copper (II) acetoacetates, and mixtures thereof.
9. A photoelectrographic element according to claim 8, wherein the copper (II) salt is copper (II) ethyl acetoacetate and the compound containing
secondary hydroxyl groups has the formula:
Figure imgf000029_0001
10. A photoelectrographic element according to claim 1 further comprising:
a near-ultraviolet radiation sensitizer.
11. A photoelectrographic method for
printing using a photoelectrographic element comprising a conductive layer in electrical contact with an acid photogenerating layer which is free of
photopolymerizable materials and comprises an
electrically insulating binder, an acid photogenerator, and a dye capable of absorbing near-infrared radiation, said method comprising: exposing the acid photogenerating layer imagewise to near infrared radiation without prior charging to create a permanent latent conductivity pattern and
printing an image from the latent conductivity pattern, said printing comprising:
charging said element with the acid photogenerating layer having a latent conductivity pattern to create an electrostatic latent image;
developing the electrostatic latent image by applying charged toner particles to said element to produce a toned image; and
transferring the toned image to a suitable receiver, wherein said printing is carried out one time for each print made.
12. A method according to claim 11, wherein the acid photogenerator is selected from the group consisting of 6-substituted-2,4-bis(trichloromethyl)-5- triazines, aromatic onium salts containing elements selected from the group consisting of Group Va, Group VIa, and Group VIIa elements, and diazonium salts.
13. A method according to claim 11, wherein the acid photogenerator is di-(4-t-butylphenyliodonium trifluoromethanesulfonate).
14. A method according to claim 11, where the dye is a cyanine dye.
15. A method according to claim 11, wherein the acid photogenerating layer further comprises:
a copper (II) salt and a compound containing secondary hydroxyl groups.
PCT/US1991/009078 1990-12-21 1991-12-10 Photoelectrographic imaging with near-infrared sensitizing dyes WO1992011581A1 (en)

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US5401607A (en) * 1991-04-17 1995-03-28 Polaroid Corporation Processes and compositions for photogeneration of acid
US5582956A (en) * 1994-04-25 1996-12-10 Polaroid Corporation Process for fixing an image, and medium for use therein

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EP0201725A2 (en) * 1985-04-17 1986-11-20 Hoechst Aktiengesellschaft Electrophotographic registration material
US4661429A (en) * 1986-04-28 1987-04-28 Eastman Kodak Company Photoelectrographic elements and imaging method
EP0401782A2 (en) * 1989-06-06 1990-12-12 Nec Corporation Titanyl phthalocyanine crystal, method of manufacture thereof and its use for electrophotographic photosensitive material

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5401607A (en) * 1991-04-17 1995-03-28 Polaroid Corporation Processes and compositions for photogeneration of acid
WO1993003426A1 (en) * 1991-07-29 1993-02-18 Eastman Kodak Company Near-infrared radiation sensitive photoelectrographic master
US5240800A (en) * 1991-07-29 1993-08-31 Eastman Kodak Company Near-infrared radiation sensitive photoelectrographic master and imaging method
US5582956A (en) * 1994-04-25 1996-12-10 Polaroid Corporation Process for fixing an image, and medium for use therein
US5741630A (en) * 1994-04-25 1998-04-21 Polaroid Corporation Process for fixing an image, and medium for use therein

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EP0516794A1 (en) 1992-12-09

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