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
  • G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
  • G03G5/0528—Macromolecular bonding materials
  • G03G5/0557—Macromolecular bonding materials obtained otherwise than by reactions only involving carbon-to-carbon unsatured bonds
  • G03G5/0567—Other polycondensates comprising oxygen atoms in the main chain; Phenol resins
• • 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
  • G03G5/043—Photoconductive layers characterised by having two or more layers or characterised by their composite structure
  • G03G5/047—Photoconductive layers characterised by having two or more layers or characterised by their composite structure characterised by the charge-generation layers or charge transport 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
  • G03G5/02—Charge-receiving layers
  • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
  • G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
  • G03G5/0528—Macromolecular bonding materials
  • G03G5/0557—Macromolecular bonding materials obtained otherwise than by reactions only involving carbon-to-carbon unsatured bonds
  • G03G5/0575—Other polycondensates comprising nitrogen atoms with or without oxygen 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
  • G03G5/02—Charge-receiving layers
  • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
  • G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
  • G03G5/0528—Macromolecular bonding materials
  • G03G5/0592—Macromolecular compounds characterised by their structure or by their chemical properties, e.g. block polymers, reticulated polymers, molecular weight, acidity

Definitions

• the present invention relates to photosensitive recording materials suitable for use in electrophotography.
• photoconductive materials are used to form a latent electrostatic charge image that is developable with finely divided colouring material, called toner.
• the developed image can then be permanently affixed to the photoconductive recording material, e.g. a photoconductive zinc oxide-binder layer, or transferred from the photoconductor layer, e.g. a selenium or selenium alloy layer, onto a receptor material, e.g. plain paper and fixed thereon.
• the photoconductive recording material is reusable.
• a photoconductor layer has to be used that rapidly loses its charge on photo—exposure and also rapidly regains its insulating state after the exposure to receive again a sufficiently high electrostatic charge for a next image formation.
• the failure of a material to return completely to its relatively insulating state prior to succeeding charging/imaging steps is commonly known in the art as "f tigue".
• the fatigue phenomenon has been used as a guide in the selection of commercially useful photoconductive materials, since the fatigue of the photoconductive layer limits the copying rates achievable.
• active layer is meant a layer that plays a role in the formation of the electrostatic charge image.
• Such a layer may be the layer responsible for charge carrier generation, charge carrier transport or both.
• Such layers may have a homogeneous structure or heterogeneous structure.
• Examples of active layers in said photoconductive recording material having a homogeneous structure are layers made of vacuum- deposited photoconductive selenium, doped silicon, selenium alloys and homogeneous photoconducting polymer coatings, e.g. of poly(vinylcarbazole) or polymeric binder(s) molecularly doped with an electron (negative charge carrier) transporting compound or a hole (positive charge carrier) transporting compound such as particular hydrazones, amines and heteroaromatic compounds sensitized by a dissolved dye, so that in said layers both charge carrier generation and charge carrier transport take place.
• an electron (negative charge carrier) transporting compound or a hole (positive charge carrier) transporting compound such as particular hydrazones, amines and heteroaromatic compounds sensitized by a dissolved dye
• a charge generating and charge transporting layer are combined in contiguous relationship.
• Layers which serve only for the charge transport of charge generated in an adjacent charge generating layer are e.g. plasma-deposited inorganic layers, photoconducting polymer layers, e.g. on the basis of poly(N-vinylcarbazole) or layers made of low molecular weight organic compounds molecularly distributed in a polymer binder or binder mixture.
• tetrabenzoporphyrins and tetranaphthaloporphyrins e.g. U2 ⁇ phthalocyanine in X-crystal form (X-I ⁇ Pc) described in US-P 3,357,989, metal phthalo ⁇ yanines, e.g. CuPc C.I. 74 160 described in DBP 2 239 924, indium phthalocyanine described in US-P 4,713,312 and tetrabenzoporphyrins described in
• EP 428,214A and naphthalocyanines having siloxy groups bonded to the central metal silicon described in published EP—A 243,205; f) indigo- and thioindigo dyes, e.g. Pigment Red 88, C.I. 73 312 described in DBP 2 237 680; g) benzothioxanthene derivatives as described e.g. in Deutsches Auslegungsschrift (DAS) 2 355 075; h) perylene 3,4, 9,10-tetracarboxylic acid -derived pigments including condensation products with o-diamines as described e.g.
• DAS Deutsches Auslegungsschrift
• polyazo-pigments including bisazo-, trisazo- and tetrakisazo- pigments, e.g. Chlordiane Blue C.I. 21 180 described in DAS 2 635 887, trisazo-pigments, e.g. as described in US-P 4,990 421 and bisazo-pigments described in Deutsches Offenlegungsschrift (DOS) 2 919 791, DOS 3 026 653 and DOS 3 032 117; j) squarylium dyes as described e.g. in DAS 2 401 220; k) polymethine dyes;
• R and R 1 are either identical or different and denote hydrogen, C- -C ⁇ alkyl, alkoxy, halogen, nitro or hydroxyl or together denote a fused aromatic ring system; m) triarylmethane dyes; and n) dyes containing 1, 5— diamino-anthraquinone groups, o) inorganic photoconducting pigments e. g. Se, Se alloys, s2S ⁇ 3,
• polymeric positive hole charge carrier transporting substances examples include poly(N-vinylcarbazole) , N-vinylcarbazole copolymers, polyvinyl anthracene and the condensation products of an aldehyde with two or more 1,2-dihydroquinoline molecules as described in US-P 5,043,238.
• Preferred non-polymeric materials for positive charge transport are : a) hydrazones e.g. a p-diethylaminobenzaldehyde diphenyl hydrazone as described in US-P 4,150,987; and other hydrazones described in US-P 4,423,129; US-P 4,278,747, US-P 4,365,014, EP 448,843 A and EP 452,569 A, e.g. T191 from Takasago
• aromatic amines e.g. N,N'-diphenyl, N,N-bis-m-tolyl benzidine as described in US-P 4,265,990, tris (p-tolyl) mine as described in US P 3,189,730 :
• CGL charge generating layer
• CGM charge generating pigment
• CTL charge transport layer
• Interfacial mixing between the CGL and the CTL can be avoided by using a CGL-binder or binders, which is/are insoluble in the solvent used for dissolving the CTL-binders in which CTM's exhibit optimum charge transport properties is limited as is the range of solvents in which efficient CTM' s are soluble.
• the range of solvents in which both CTL-binders and CTM's are soluble is thus extremely narrow and often limited to chlorohydrocarbons such as methylene chloride.
• Methylene chloride is an extremely powerful solvent and the range of CGL-binders which is totally insoluble in methylene chloride is extremely limited, unless the CGL-binder is crosslinked in a subsequent hardening process.
• Hardening is here considered as a treatment which renders the binder of a charge generating layer of the photoconductive recording material insoluble in methylene chloride.
• a photoconductive recording material comprising a support and a charge generating layer (CGL) in contiguous relationship with a charge transporting layer (CTL) containing a p-charge transporting material (p-CTM) , wherein the binder of said charge generating layer (CGL) has been made insoluble in methylene chloride by crosslinking, and said binder is composed essentially of at least one resin (1) and/or at least one resin (2) crosslinked with at least one polyisocyanate, said resin (1) before its crosslinking corresponding to the following general formula (I) :
• each of R and R° represents hydrogen, an alkyl group, an aryl group or together represents the necessary atoms to close a cycloaliphatic ring, e.g. cyclohexane ring, and n is zero or an integer; and said resin (2) before its crosslinking being a dialkanolamine- modified epoxy resin.
• the polyisocyanate may be set free in the recording layer in situ, e.g. by heat, from a blocked polyisocyanate also called a polyisocyanate precursor.
• resin (1) may proceed as described for bisphenol-epichlorhydrin resins (ref. "The Chemistry of Organic Film Formers” by D. H. Solomon, John Wiley & Sons, Inc. New York (1967), p. 179-189) using as reaction ingredients a bisphenol, e.g. bisphenol A, and epichlorhydrin.
• Preferred bisphenol-epichlorhydrin resins are derived from bisphenol A (4,4'-isopropylidenediphenol) and epichlorhydrin.
• a photoconductive recording material of the present invention has a charge generating layer containing as the sole binder one or more of said polyhydroxy resins with the general formula (I) and/or at least one of said dialkanolamine- modified epoxy resins ⁇ rosslinked with at least one polyisocyanate.
• a photoconductive recording material of the present invention has a charge generating layer containing one or more resins obtained by the crosslinking with said polyisocyanate(s) of (i) polymeric compounds according to said general formula (I) and/or of (ii) at least one said dialkanolamine- modified epoxy resin having a total free HO-group content in an equivalent ratio from 3.0:1 to 1:2.0 with respect to free isocyanate groups of said polyisocyanate(s) .
• a photoconductive recording material has a charge generating layer containing at least 30 wt% of charge generating material (s) (C ⁇ l's) and one or more resins with the general formula (I) and/or dialkanolamine-modified epoxy resins hardened with one or more of said polyisocyanates .
• Resins according to said general formula (I) are e.g. phenoxy resins of UNION CARBIDE CORP., U.S.A. sold under the following tradenames :
• Dialkanolamine-modified epoxy resins can be prepared from commercially available epoxy resins with dialkanolamines in the melt or in a solvent mixture under reflux.
• polyisocyanates and blocked polyisocyanates used for hardening resins with general formula (I) and dialkanolamine- modified epoxy resins according to the present invention are derived from polyisocyanates or mixtures thereof e.g. 1,6-hexane diiso ⁇ yanate (HDI) ; toluylene diiso ⁇ yanate (TDI) ; diphenylmethane-4,4'-diiso ⁇ yanate (MDI) ; isophorondiisocyanate (IPDI) ; triphenylmethane-4,4' ,4" triisocyanate thiophosphoric acid tris (p-isocyanatophenyl ester)
• HDI 1,6-hexane diiso ⁇ yanate
• TDI toluylene diiso ⁇ yanate
• MDI diphenylmethane-4,4'-diiso ⁇ yanate
• IPDI isophorondiisocyan
• DESMODUR N3200 a biuret HDI (lower viscosity than DESMODUR
• DESMODUR N3390 a 90 % solution of an HDI isocyanurate
• DESMODUR IL 1351 a TDI-polyisocyanate
• DESMODUR HL a TDI/HDI-polyisocyanate
• DESMODUR BL3175 a blocked HDI-type crosslinking stoving urethane resin
• DESMODUR BL100 a blocked TDI-type crosslinking stoving urethane resin.
• a suitable polyisocyanate precursor, also called a blocked polyisocyanate compound, for use according to the present invention has the following structural formula P :
• Said polyisocyanate precursor has a good stability at room temperature (20 °C) and generates free polyisocyanate in the temperature range of 100 to 150 °C.
• a polyester resin particularly suitable for use in combination with said crosslinked resins is DYNAPOL L 206 (registered trade mark of Dynamit Nobel) for a copolyester of terephthali ⁇ a ⁇ id and isophthali ⁇ a ⁇ id with ethylene gly ⁇ ol and neopentyl gly ⁇ ol, the molar ratio of tere- to isophthali ⁇ a ⁇ id being 3/2) .
• Said polyester resin improves the adheren ⁇ e to aluminium that may form a ⁇ ondu ⁇ tive ⁇ oating on the support of the re ⁇ ording material.
• Aromatic polycarbonates having a molecular weight in the range of 10,000 to 200,000 are preferred. " Suitable polycarbonates having such a high molecular weight are sold under the registered trade mark MAKROLON of Bayer AG, W-Germany.
• MAKROLON CD 2000 (registered trade mark) is a bisphenol A polycarbonate with molecular weight in the range of 12,000 to 25,000
• MAKROLON 5700 (registered trade mark) is a bisphenol A poly ⁇ arbonate with molecular weight in the range of 50,000 to
• Suitable electroni ⁇ ally ina ⁇ tive binder resins for use in a ⁇ tive layers of the present photo ⁇ ondu ⁇ tive re ⁇ ording material not containing said resins hardened with polyiso ⁇ yanates are e.g. the above mentioned polyester and poly ⁇ arbonates, but also cellulose esters, a ⁇ rylate and metha ⁇ rylate resins, e.g. ⁇ yanoa ⁇ rylate resins, polyvinyl ⁇ hloride, copolymers of vinyl chloride, e.g. copolyvinyl chloride/acetate and ⁇ opolyvinyl ⁇ hloride/malei ⁇ anhydride.
• binder resins for an active layer are sili ⁇ one resins, polystyrene and copolymers of styrene and malei ⁇ anhydride and copolymers of butadiene and styrene.
• Charge transport layers in the photocondu ⁇ tors of the present invention preferably have a thickness in the range of 5 to 50 ⁇ m, more preferably in range of 5 to 30 ⁇ m. If these layers ⁇ ontain low molecular weight charge transport molecules, such compounds will preferably be present in concentrations of 30 to 70 % by weight. The presence of one or more spectral sensitizing agents can have , an advantageous effect on the charge transport. In that ⁇ onne ⁇ tion reference is made to the methine dyes and xanthene dyes described in US-P 3,832,171.
• these dyes are used in an amount not substantially redu ⁇ ing the transparen ⁇ y in the visible light region (420-750 nm) of the ⁇ harge transporting layer so that the charge generating layer still can receive a substantial amount of the exposure light when exposed through the charge transporting layer.
• the charge transporting layer may contain compounds substituted with electron-acceptor groups forming an intermolecular charge transfer complex, i.e. donor-ac ⁇ eptor complex when electron donor charge transport compounds are present.
• Useful compounds having electron-accepting groups are nitrocellulose and aromatic nitro-compounds such as nitrated fluorenone-9 derivatives, nitrated 9-dicyanomethylene fluorenone derivatives, nitrated naphthalenes and nitrated naphthalic acid anhydrides or imide derivatives.
• the preferred con ⁇ entration range of said compounds having electron acceptor groups is such that the donor/acceptor weight ratio is 2.5:1 to 1,000:1.
• UV-stabilizers are benztriazoles.
• any of the organi ⁇ pigments belonging to one of the following classes and able to transfer ele ⁇ trons to ele ⁇ tron transporting materials may be used :
• polynu ⁇ lear quinones e.g. anthanthrones su ⁇ h as C.I. 59 300 des ⁇ ribed in DBP 2,237,678, ⁇ ) quina ⁇ ridones, e.g. C.I. 46 500 des ⁇ ribed in DBP 2,237,679, d) naphthalene 1,4,5,8-tetra ⁇ arboxyli ⁇ a ⁇ id derived pigments in ⁇ luding the perinones, e.g. Orange GR, C.I.
• polyazo-pigments in ⁇ luding bisazo-, trisazo- and tetrakisazo- pigments e.g. Chlordiane Blue C.I. 21 180 des ⁇ ribed in DAS 2,
• R' and R" have the meaning des ⁇ ribed in said GB-P do ⁇ ument.
• Inorgani ⁇ substances suited for photogenerating negative charges in a recording material ac ⁇ ording to the present invention are e.g. amorphous selenium and selenium alloys e.g. selenium-tellurium, selenium-tellurium-arseni ⁇ and selenium-arseni ⁇ and inorgani ⁇ photoconductive crystalline compounds such as cadmium sulphoselenide, cadmiumselenide, cadmium sulphide and mixtures thereof as disclosed in US-P 4,140,529.
• the thickness of the charge generating layer is preferably not more than 10 ⁇ m, more preferably not more than 5 ⁇ m.
• an adhesive layer or barrier layer may be present between the ⁇ harge generating layer and the support or the ⁇ harge transport layer and the support.
• Useful for that purpose are e.g. a polyamide layer, nitro ⁇ ellulose layer, hydrolysed silane layer, or aluminium oxide layer a ⁇ ting as a blo ⁇ king layer preventing positive or negative charge injection from the support side.
• the thickness of said barrier layer is preferably not more than 1 micron.
• the condu ⁇ tive support may be made of any suitable ⁇ ondu ⁇ tive material.
• Typi ⁇ al ⁇ ondu ⁇ tors in ⁇ lude aluminum, steel, brass and paper and resin materials in ⁇ orporating or ⁇ oated with ⁇ ondu ⁇ tivity enhan ⁇ ing substances.
• An insulating support such as a resin support is e.g. provided with a condu ⁇ tive ⁇ oating e.g. va ⁇ uum-deposited metal su ⁇ h as aluminium, dispersed ⁇ arbon bla ⁇ k, graphite and ⁇ ondu ⁇ tive monomeri ⁇ salts or a ⁇ onductive polymer, e.g. a polymer containing quaternized nitrogen atoms as in Calgon Conductive polymer 261 (trade mark of Calgon Corporation, Inc., Pittsburgh, Pa., U.S.A.) described in US-P 3,832,171.
• the support is an insulating resin support provided with an aluminium layer forming a condu ⁇ tive ⁇ oating.
• the support may be in the form of a foil, web or be part of a drum.
• An ele ⁇ trophotographi ⁇ recording process ac ⁇ ording to the present invention comprises the steps of :
• the photo ⁇ ondu ⁇ tive layer ⁇ ontaining at least one resin a ⁇ ording to general formula (I) and/or alkanolamine-modified epoxy resins hardened with at least one polyiso ⁇ yanate or blo ⁇ ked polyisocyanate;
• the photo-exposure of the charge generating layer proceeds preferably through the charge transporting layer but may be direct if the charge generating layer is uppermost or may proceed likewise through the conductive support if the latter is transparent enough to the exposure light.
• the development of the latent electrostatic image commonly oc ⁇ urs preferably with finely divided ele ⁇ trostati ⁇ ally attractable material, called toner particles that are attracted by ⁇ oulomb force to the electrostatic charge pattern.
• the toner development is a dry or liquid toner development known to those skilled in the art.
• toner particles deposit on those areas of the ⁇ harge ⁇ arrying surfa ⁇ e whi ⁇ h are in positive-positive relation to the original image.
• toner parti ⁇ les migrate and deposit on the recording surface areas whi ⁇ h are in negative-positive image value relation to the original.
• the areas discharged by photo-exposure obtain by induction through a properly biased developing electrode a charge of opposite charge sign with respect to the charge sign of the toner particles so that the toner becomes deposited in the photo-exposed areas that were discharged in the imagewise exposure (ref. : R.M. Schaffert "Ele ⁇ trophotography” - The Fo ⁇ al Press - London, New York, enlarged and revised edition 1975, p. 50-51 and T.P. Ma ⁇ lean "Ele ⁇ troni ⁇ Imaging” A ⁇ ademi ⁇ Press - London, 1979, p. 231) .
• Residual ⁇ harge after toner development may be dissipated before starting a next ⁇ opying cycle by overall exposure and/or alternating current corona treatment.
• Recording materials ac ⁇ ording to the present invention depending on the spe ⁇ tral sensitivity of the ⁇ harge generating layer may be used in ⁇ ombination with all kinds of photon-radiation, e.g. light of the visible spectrum, infra-red light, near ultra-violet light and likewise X-rays when electron-positive hole pairs can be formed by said radiation in the ⁇ harge generating layer.
• photon-radiation e.g. light of the visible spectrum, infra-red light, near ultra-violet light and likewise X-rays when electron-positive hole pairs can be formed by said radiation in the ⁇ harge generating layer.
• the toner image obtained may be fixed onto the re ⁇ ording material or may be transferred to a re ⁇ eptor material to form thereon after fixing the final visible image.
• a re ⁇ ording material a ⁇ ording to the present invention showing a parti ⁇ ularly low fatigue effe ⁇ t ⁇ an be used in recording apparatus operating with rapidly following copying cy ⁇ les in ⁇ luding the sequential steps of overall ⁇ harging, imagewise exposing, toner development and toner transfer to a receptor element.
• the evaluations of electrophotographic properties determined on the recording materials of the following examples relate to the performance of the recording materials in an electrophotographic process with a reusable photore ⁇ eptor.
• the measurements of the performan ⁇ e ⁇ hara ⁇ teristi ⁇ s were ⁇ arried out by using a sensitometri ⁇ measurement in whi ⁇ h the dis ⁇ harge was obtained for 16 different exposures in addition to zero exposure.
• the photo ⁇ ondu ⁇ tive re ⁇ ording sheet material was mounted with its ⁇ ondu ⁇ tive ba ⁇ king on an aluminium drum whi ⁇ h was earthed and rotated at a ⁇ ir ⁇ umferential speed of 10 cm/s.
• Ea ⁇ h measurement relates to 80 ⁇ opying ⁇ y ⁇ les in whi ⁇ h the photo ⁇ ondu ⁇ tor is exposed to the full light sour ⁇ e intensity for the first 5 ⁇ ycles, then sequentially to the light source the light output of whi ⁇ h is moderated by grey filters of opti ⁇ al densities 0.2, 0.38, 0.55, 0.73, 0.92, 1.02, 1.20, 1.45, 1.56, 1.70, 1.95, 2.16, 2.25, 2.51 and 3.21, ea ⁇ h for 5 ⁇ ycles and finally to zero light intensity for the last 5 cy ⁇ les.
• the ele ⁇ tro-opti ⁇ al results quoted in the EXAMPLES 1 to 43 and COMPARATIVE EXAMPLES 1 to 3 hereinafter refer to charging level at zero light intensity (CL) and to discharge at a light intensity corresponding to the light source intensity moderated by a grey filter to the exposure indicated to a residual potential RP.
• the % discharge is :
• the ⁇ harging level CL is only dependent upon the thi ⁇ kness of the ⁇ harge transport layer and its spe ⁇ ific resistivity.
• practi ⁇ e CL expressed in volts should be preferably
• d is the thickness in ⁇ m of the charge transport layer.
• Said dispersion was prepared by mixing 2 g of metal-free X-phthalocyanine (FASTOGEN BLUE 812OB tradename from Dainippon Ink and Chemi ⁇ als In ⁇ .); 0.3 g of PHENOXY PKHH (tradename for a bisphenol A—epi ⁇ hlorhydrin phenoxy resin from Union Carbide) ; and 26.45 g of methylene chloride for 40 hours in a ball mill.
• metal-free X-phthalocyanine FASTOGEN BLUE 812OB tradename from Dainippon Ink and Chemi ⁇ als In ⁇ .
• PHENOXY PKHH tradename for a bisphenol A—epi ⁇ hlorhydrin phenoxy resin from Union Carbide
• PHENOXY PKHH (tradename), 9.36 g of butan-2-one, 26.58 g of methylene chloride and 1.09 g of DESMODUR N75 (tradename for a a 75 % solution of a hexamethylene diisocyanate-type hardener in 1:1 xylene:l-methoxy ⁇ ropyla ⁇ etate-2 from Bayer AG.), were then added to the dispersion and the dispersion mixed for a further 15 minutes.
• the applied layer was dried and thermally hardened for 2 hours at 100°C and then over ⁇ oated using a do ⁇ tor-blade ⁇ oater with a filtered solution ⁇ onsisting of 3 g of the CTM PI; 3 g of MAKROLON 5700 (tradename for a bisphenol A poly ⁇ arbonate from Bayer AG) ; and 44 g of methylene ⁇ hloride to a dried thi ⁇ kness of 14.1 ⁇ . This layer was dried at 50°C for 16 hours.
• the photo ⁇ ondu ⁇ tive re ⁇ ording materials of examples 2 and 3 and ⁇ omparative example 1 were produced as described for example 1 ex ⁇ ept that alternative hardeners were used in the materials of examples 2 and 3 and no hardener was used for the material of ⁇ omparative example 1 and the amounts of PHENOXY PKHH (tradename) and hardener were adjusted to obtain a theoreti ⁇ al degree of hardening of 100 %.
• the weight per ⁇ entages of the PHENOXY PKHH (tradename) and hardener in the CGL's ⁇ al ⁇ ulated on the basis of the solids content of the hardener are given in Table 1 together with the CTL layer thicknesses.
• the photoconductive recording materials of examples 4 to 10 and comparative example 2 were produced as described for example 1 except that DER 684 EK40 (tradename for a high molecular weight bisphenol A-epichlorhydrin epoxy resin from Dow Chemical) , was used instead of PHENOXY PKHH (tradename) with different polyisocyanate hardeners except in the case of comparative example 2 for which no hardener was used.
• the amounts of DER 684 EK40 (tradename) and hardener were adjusted to obtain a theoretical degree of hardening of 100 %.
• the weight percentages of the DER 684 EK40 (tradename) and hardener in the CGL's calculated on the basis of the solids content of the hardener are given in Table 2 together with the CTL layer thi ⁇ knesses.
• Example DER 684 Hardener Hard- I 6 60 t 10 m / ⁇ a2
• the photocondu ⁇ tive re ⁇ ording materials of examples 11 to 16 and ⁇ omparative example 3 were produ ⁇ ed as des ⁇ ribed for example 1 ex ⁇ ept that EPON 1009 (tradename for a bisphenol A-epi ⁇ hlorhydrin epoxy resin from Shell Chemi ⁇ al Co. , was used instead of PHENOXY PKHH (tradename) with different polyiso ⁇ yanate hardeners and no hardener in the ⁇ ase of ⁇ omparative example 3 and in the ⁇ ase of example 15 a hardening temperature of 150°C was used instead of 100°C.
• the amounts of EPON 1009 (tradename) and hardener were adjusted to obtain a theoretical degree of hardening of 100 %.
• the weight per ⁇ entages of the EPON 1009 (tradename) and hardener in the CGL's ⁇ al ⁇ ulated on the basis of the solids content of the hardener are given in Table 3 together with the CTL layer thicknesses
• the photoconductive recording materials of examples 16 to 27 were produced as described for example 1 ex ⁇ ept that different bisphenol A epi ⁇ hlorhydrin epoxy resins from different suppliers with different epoxy equivalent weights were used instead of PHENOXY PKHH.
• the amounts of epoxy resin and DESMODUR N75 were adjusted to obtain a theoreti ⁇ al degree of hardening of 100 %.
• the weight per ⁇ entages of epoxy resin and DESMODUR N75 ⁇ al ⁇ ulated on the basis of the solids ⁇ ontent of DESMODUR N75 are given in Table 4 together with the CTL layer thi ⁇ knesses.
• the photo ⁇ ondu ⁇ tive re ⁇ ording materials of examples 28 and 29 were produced as described for example 1 except that diethanolamine-modified ARALDITE GT 6071 (tradename) and diethanolamine-modified ARALDITE GT 6099 (tradename) were used as hydroxy group-containing resins instead of PHENOXY PKHH (tradename) .
• the amounts of resin and DESMODUR N75 (tradename) were adjusted to obtain a theoretical degree of hardening of 100 %.
• the weight percentages of the resins and DESMODUR N75 (tradename) in the CGL's calculated on the basis of the solids content of the hardener are given in Table 5 together with the CTL layer thi ⁇ knesses.
• the photoconductive recording materials of examples 31 to 34 were produced as described in example 19 except that the amounts of ARALDITE GT7203 (tradename) and DESMODUR N75 (tradename) were adjusted to obtain various theoreti ⁇ al degrees of hardening, as indi ⁇ ated in Table 6.
• the weight percentages of ARALDITE GT7203 (tradename) and DESMODUR N75 (tradename) cal ⁇ ulated on the basis of the solids ⁇ ontents of the rea ⁇ tants are given in Table 6 together with the CTL layer thi ⁇ knesses.
• the photoconductive recording materials of examples 34 to 39 were produced as described for example 10 except that different CTM's were used in the charge transport layer.
• the CTM's used together with the CTM concentrations used in the CTL and the CTL layer thicknesses are given in Table 7.
• the photoconductive recording materials of examples 40 to 43 were produced as described in example 1 except that various CGM' s with different grinding times were used.
• the CGM' s and grinding times used together with the CTL layer thicknesses are summarized in Table 8. 25
• ° CGM 3 metal-free ⁇ -triazotetrabenzoporphyrin x
• CGM 4 4,10-dibromoanthanthrone (ICI) .

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