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Electrophotographic Lithograph Printing Plate Material

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Electrophotographic Lithograph Printing Plate Material Europaisches Patentamt European Patent Office © Publication number: 0 488 511 A1 Office europeen des brevets EUROPEAN PATENT APPLICATION © Application number: 91309670.7670.7 © int. ci.5: G03G 5/06, G03G 5/09 @ Date of filing: 18.10.91 © Priority: 26.11.90 JP 317894/90 @ Inventor: Yamana, Masahiro 18.02.91 JP 23138/91 3-13-15, Shiroganedai Minato-ku, Tokyo(JP) © Date of publication of application: Inventor- Sato, Koii 03.06.92 Bulletin 92/23 uo.uo.« duiicuii 4g6 Qakuenhigashi-machi^ , Kodaira-shi, Tokyo(JP) Q*)/c\ Designated~ . , Contracting„ ... States:0.. j \ / DE FR GB © Applicant: OJI PAPER CO. LTD. 0 Representative: Arthur, Bryan Edward et al 1-1, Nishi-Shinjuku 2-chome Shinjuku-ku Withers & Rogers 4 Dyer's Buildings Holborn Tokyo 163(JP) London EC1N 2JT(GB) © Electrophotographic lithograph printing plate material. © An electrophotographic lithograph printing plate material having an enhanced sensitivity to laser rays, an excellent heat resistance and a low dark decay comprises an electroconductive, water-resistant substrate and an electrophotographic layer comprising a photoconductive zinc oxide, a resinous binder and a sensitizing dye material which comprises at least one compound (A) of the formula (I) and at least one compound (B) of the formula (II): V1/^^ NN-^^V ! y© I Rl R2 * >B3,' ®^C-i A2 (B4< «"» \__y —— N N vv_^ 1 I e R3COO(Ml)m (Y2)n° R4COOM2 Iff wherein each of Ai and A2 represents a C5-7 polymethine group non-substituted or substituted with at least one substituent, for example, -CI, the substituted polymethine group may have a cyclic structure, for example, of: 00^ 00 ° / \ Q_ 1 2 1 2 -C=CH-C= Rank Xerox (UK) Business Services EP 0 488 51 1 A1 each of from Bi to is a divalent non-substituted or substituted, benzene or naphthalene group, each of from Xi to X4 is a S, Se, or 0 atom or a -C(CH3)2- group, each of from R1 to is a C1-5 alkyl group, each of Mi and M2 is a metal atom, organic base or hydrogen atom, each of Y1 and Y2 is an anion, and m and n is zero or 1 but when n = 1, m = 1 and when n = 0, m = 0 and -R3COO group adjacent to the (Mi)m group in the formula (II) is anionic, the weight ratio of the compound (A) to the compound (B) being 3:1 to 20:1. 2 EP 0 488 51 1 A1 BACKGROUND OF THE INVENTION 1) Field of the Invention 5 The present invention relates to an electrophotographic lithograph printing plate material. More particularly, the present invention relates to an electrophotographic lithograph printing plate material having an enhanced sensitivity to semiconductor laser rays. 2) Description of the Related Arts 70 Generally, a conventional electrophotographic lithograph printing plate material has a photosensitive electrophotographic layer wherein electroconductive zinc oxide particles are dispersed as an photoconduc- tive material. This type of lithograph printing plate material (known as a zinc oxide offset master material) is widely employed in the light printing industry, because it is cheap and because the process for making a 75 printing plate from the material is simple and easy. In a conventional process for producing a lithograph printing plate from the above-mentioned printing plate material, a visible light-irradiation source, for example, a halogen lamp, is used. In this process, the visible light is irradiated to and reflected on an original image or picture and the reflected rays are irradiated to the photosensitive surface of the printing plate material. This method is referred to as a camera system 20 printing plate-making method. Due to the recent development of various recording machines and the spread of data digitalization, a computer-to-plate type printing plate-making method is now widely used for the electrophotographic material. In this method, laser rays that can be controlled in accordance with computer data are applied to the photosensitive printing plate material surface as a scanning exposure. 25 Among the laser rays, semiconductor laser rays, which can be generated in a small size device and can be directly modulated, are most useful. The zinc oxide offset master usable for the semiconductor laser rays is made from a lithograph printing plate material having a photosensitive electrophotographic layer spectrosensitized by a sensitizing dye and having an enhanced sensitivity at a wave length of 700 to 1000 nm, particularly 780 nm, of the 30 semiconductor laser rays. Zinc oxide per se exhibits a spectro-sensitivity only at a wavelength of about 400 nm. Therefore, to provide a electrophotographic layer having a satisfactory spectrosensitivity at a wavelength of about 780 nm, various sensitizing dye compounds are utilized. For example, Japanese Unexamined Patent Publication No. 62-220962 discloses sensitizing dye 35 material consisting of cyanine dye compounds having alkylsulfonic acid groups attached, as substituents, to nitrogen atoms located at both terminal portions of the compound molecule. An example of the cyanine dye compounds has the following formula: CH-,^^ 40 3 CH, \V \V 1 0 CH=CH -jy-CH=C 45 e (CH2)3S03l (CH2)3S03H.N(C2H5)3 The above-mentioned sensitizing dye compounds effectively enhance the spectro-sensitivity of the 50 electrophotographic layer when employed together with a chemical sensitizing agent, but this type of electrophotographic lithograph printing material is disadvantageous in that the electrophotographic layer exhibits an undesirably large dark decay in the surface potential thereof. The procedures for preparing a lithograph printing plate by using laser rays are usually carried out in a continuous system (note, an intermittent system is used by the camera system printing plate-making 55 method) without stopping the printing plate material. Therefore, the effect of the enhanced dark decay is not serious in the continuous printing plate-making method. Nevertheless, when the line speed of the continuous printing plate-making procedure is low, the enhanced dark decay does become a serious problem. 3 EP 0 488 51 1 A1 As an example of sensitizing dye compounds exhibiting a small dark decay and a high sensitivity, compound of the following formula: \V 3 10 wherein the nitrogen atoms located at two terminal portions of the dye molecule are substituted by alkyl is groups, is known, and this type of sensitizing dye compound is available under the trademark of NK 125, from Nihon Kankoshikiso Kenkyusho. This type of the sensitizing dye compound, however, has a disadvantage in that it causes the resultant lithograph printing material to exhibit a low heat resistance, and this has an adverse affect on the durability of the resultant lithograph printing material when transported or stored under high temperature conditions. 20 Namely, the commercial value of the lithograph printing material is often significantly reduced by the above- mentioned lower heat-resistance. Many attempts have been made to provide a sensitizing dye material capable of imparting an industrially satisfactory sensitivity, dark decay resistance and heat resistance to the electrophotographic layer, but these previous attempts did not succeed in obtaining a sensitizing dye material composed of a 25 single dye compound and having all of the above-mentioned properties. SUMMARY OF THE INVENTION An object of the present invention is to provide an electrophotographic lithograph printing plate material 30 having a high sensitivity to semiconductor laser rays, a high heat resistance, and a low dark decay. The above-mentioned object can be attained by the electrophotographic lithograph printing plate material of the present invention, comprising an electroconductive, water-resistant substrate and an electrophotographic layer formed on at least one surface of the substrate and comprising a photoconductive zinc oxide powder, a resinous binder and a sensitizing dye material, the sensitizing coloring material 35 comprising a mixture of a sensitizing dye component (A) consisting of at least one compound of the formula (I) and a sensitizing dye component (B) consisting of at least one compound of the formula (II): .'_"\-^"XT\'_^\-^"Xi\ /X0^-/'-\ . ' /X9^~-/'z N ©A C— t A- ^=c (B, } (I) 40 vr~"' xn^3 Rl R2 ''~\^X^ , v /X4~~~~ R3COO(Ml)in (Y2)n° R4COOM2 50 in which formulae (I) and (II), Ai and A2 respectively and independently represent a polymethine chain group having 5 to 7 carbon atoms, and non-substituted or substituted with at least one substituent, in which substituted polymethine chain group, two of the substituents may form, together with three carbon atoms in the polymethine chain group, a cyclic structure including 6 or more carbon atoms bonded to each other, Bi 55 , B2 , B3 and B+ respectively and independently represent a member selected from the group consisting of divalent benzene and naphthalene groups non-substituted or substituted with at least one substituent, Xi , X2 , X3 and X+ respectively and independently represent a member selected from S, Se and 0 atoms and -C(CH3)2 -group, Ri , R2 , R3 and R+ respectively and independently represent an alkyl group having 1 to 5 4 EP 0 488 51 1 A1 carbon atoms, Mi and M2 respectively and independently represent a member selected from the group consisting of metal atoms, organic bases and a hydrogen atom, Yi and Y2 respectively and independently represent an anion, and m and n respectively and independently represent zero or an integer of one but when n is an integer of one, m is an integer of one, and when n is zero, m is also zero and the -R3COO 5 group adjacent to the (Mi)m group in the formula (II) is anionic, the weight ratio of the sensitizing dye component (A) to the sensitizing dye component (B) being from 3:1 to 20:1. In the electrophotographic lithograph printing plate material of the present invention the sensitizing dye material to be contained in the electrophotographic layer must comprise a mixture of the sensitizing dye component (A) consisting of at least one specific compound of the formula (I) with the sensitizing dye 10 component (B) consisting of at least one specific compound selected from those of the formula (II), in a specific weight ratio thereof.
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