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    Vaithilingam Subbarayan
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    Present invention relates to a LITHOGRAPHIC PRINTING PROCESS involving on press development. Lithographic plate generally comprises a hydrophobic imaging area, which receives oily ink in a printing process. Conventional lithographic process usually comprises steps of masking a presensitized (PS) plate, exposing the PS plate to infrared light, and removing the image-forming layer.

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    Present invention relates to a LITHOGRAPHIC PRINTING PROCESS involving on press development. Lithographic plate generally comprises a hydrophobic imaging area, which receives oily ink in a printing process. Conventional lithographic process usually comprises steps of masking a presensitized (PS) plate, exposing the PS plate to infrared light, and removing the image-forming layer.

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    20 views30 pages

    10 902 161 Lithographic Printing Process

    Uploaded by

    Vaithilingam Subbarayan
    Present invention relates to a LITHOGRAPHIC PRINTING PROCESS involving on press development. Lithographic plate generally comprises a hydrophobic imaging area, which receives oily ink in a printing process. Conventional lithographic process usually comprises steps of masking a presensitized (PS) plate, exposing the PS plate to infrared light, and removing the image-forming layer.

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    {US 20050028697A 1 «i» United States « co) os), (sy en 22) 0) Jul. 30, 2003, LITHOGRAPHIC PRINTING PROCESS Inventors: Naonart Makino, Shizuoka (JP); Ryuki Kakino, Shizuoka (JP); Sumfaki Shizuoka GP); Yasuhito 1 Shizvoka (IP) Correspondence Address SUGHRUE MION, PLLC 2100 PENNSYLVANIA AVENUE, NW. SUITE 800 WASHINGTON, DC 20037 (US) FUJI PHOTO FILM Co Assigove: Appl. Nox 109902161 Fite ul. 30, 2008 Foreign Application Priority Data Py 2003-282716 054 Patent Application Publication co Pub. No: US 2005/0028697 Al Makino et al. (43) Pub. Date: Feb. 10, 2005 BaP 118. 101/ss0.1 (1) Incl? Gv. on ABSTRACT A lithographic printing process which comprises the steps fof: imagevise exposing to infrared light a presensitizd lithographic plate which comprises a hydrophilic support and a removable image-forming layer containing aninirared absorbing agent having the absorption maximum withia an infrared region and a visible dye having the absorption ‘maximum within a visible region 10 shift the absorption ‘maximum ofthe visible dye within the exposed area with a change of at feast 50 nm inthe wavelength snd a change of St least 15 in color in terms of AE, and to make the image-forming layer irremovable within the exposed area; removing the image-forming layer within the unexposed fares of the lithographic plate mounted on a eylindet of a printing press; and then printing an image with the litho- {raphie plate mounted on the eylinder of the printing press. The otber processes are also disclosed US 2005/0028697 AI LITHOGRAPHIC PRINTING PROCESS FIELD OF THE INVENTION [0001] The present invention relates to a lithographic Printing process involving on press development, The inven- tion also relates to lithographic printing process without ‘conducting development BACKGROUND OF THE INVENTION {0002} A lithographic printing pate generally comprises a hydrophobic imaging area, which receives oily ink in & printing process, and 2 hydrophilic non-imaging area, whieh receives dampening water. A conventional Iihographie pro- ‘cess usually comprises stops of masking a presensiized (PS) plate, which comprises a hydrophilic support and a hydro- phobic photosensitive resin layer, witha ih film, exposing the plate to light through the lth film, and then developing the plate to remove a non-imaging area with a developing solution. [0003] Nowadays » computer electronically processes ‘lores and oulpuls image information as digital data. A presensitized lithographic plate is. preferably scanned ‘directly with a highly directive active radiation such as a laser eam without use of a lth film to form an image according to 4 digital data, The term of Computer to Plate (CTP) means the lithographic process of forming a printing plate according to digital image data without use of a ith film [0004] The conventional lithographic process of forming a printing plate has a problem about CTP that 2 wavelength Fegion ofa lascr beam docs not match 3 spectral sensitivity ‘ofa photosensitive resin [0005] The conventional PS plate requires step of dis: solving and, removing a non-imaging area (namely, devel- ‘oping sip). The developed printing plate should be futher ‘subjected to postreatments such as a washing treatment using water, a rinsing teatment using a solution of a surface-actve agent, and a desensitzing treatment using a solution of gum stabic ora starch derivative. The ational wet treatments are disadvantageous tothe conventional PS ate. Even if an early step (image-forming step) in a thographic process is simplified according to 2 digital teeatment, the Tate step (developing step) comprises such troublesome wet treatments that the process as a whole ‘cannot be suficiently simplified [0006] The printing industey as well as other industries is, Interested in protection of global environment. Wet treat- iments inevitably influence global environment. ‘The wet ‘weatments are preferably simplified, changed into dry treat ments of omitted from a lithographic process to protect slobal environment, [0007] For example, a presnsiized lithographic printing plate comprises a hydrophilic layer comprising colloid such a silica provided on a lipophilic layer (described in Inter- rational Patent Application Nos. 94/1800S, 98/40212 and 5919143). The plate was imagewise exposed to Tight 10 abrade the hydrophilic layer within the exposed area, A heat-sensitive presensitized lithographic plate comprises a ‘water-soluble de hydrophilic overcoating layer provided! on the hydrophilic layer to prevent abrasion dust fom seatter- Feb. 10, 2005 ing (desecibed in Japanese Patent Provisional Publication [Nos 2001-096936 and 2002-086946), [0008] Further, a press development method comprises the eps of attaching an exposed presensitzed printing plate to a oylinder of a printer, and rotating the cylinder while supplying dampening water and ink tothe plate to remove «noa-imaging area from the plate. Immediately afer expos- ing the presensitized plate to light, the plate can be installed in a printer. A lithographic process can be completed whi ‘conklucting a usual printing treatment [0009] A presensitized lithographic printing plate suitable Tor the press development method must have & photosensi- tive layer soluble in dampening water or a solvent of ink ‘The presenstized plate should easily be teeated under roam light to be subjected to a press development in a prin placed under room light [0010] A conventional PS plate cant saisy the abowe- eseribed requirements. [0011] Japanese Patent No, 2,938,397 (corresponding to European Patent No. 0770494, and U.S. Pat. Nos. 6,030,750 and 6,096,481) discloses a method for making a lithographic Frintng plate The method uses an imaging clement (pre- Sensitized plate) comprising om a hydrophilic surface Of = lithographic based an image forming. layer comprising hydrophobic thermoplastic polymer particles capable of coalescing under the influence of heat and dispersed ia a hydrophilic hinder and a compound capable of converting Tight to heat. The method comprising the steps of imagewise ‘exposing to light the imaging element; and developing a thus ‘obtained imagowise exposed imaging element by mounting it'on a prin cylinder of & printing press and supplying an aqueous dampening liquid or ink tothe image forming layer ‘while rotating the printer cylinder. [0012] The imaging element ean be treated under ceom Tight beeause the element has sensitivity within an infrared region. [0013] Japanese Patent Publication Nos. 2001-27740, 2002-020162, 2002-046361 and 2002-137562 disclose pre- ‘ensitized lithographic printing plate in which microeap- Sules containing a polymerizable compound are dispersed in place ofthe thermoplastic polymer particles. [0014] A Computer to Cylinder (CTC) method has been proposed to advance digializaton from the stage of the CTP. method. The CTC method ean prepare a lithographic plate ‘on a cylinder of « press machine by merely exposing the Ff ht corresponding to digital image date without ‘ontlcting development or olher processes after the expos: ing step. The printing can be conducted immediatly al preparing the lithographic plate [0015] A presensitized lithographic plate for the CTC ‘method preferably has a hydrophilic image-forming layer that ean be changed hydrophobic within & heated area, or hhave a hydrophobic image-forming. layer that ean’ be changed hydrophilic within a heated azea [0016] When heating hydrophilic polymer having « cathoxyl group that can be decarboxylated (@.., a group forresponding. to sulfonylacetic acid), the polymer is, changed to hydrophobic by a decarboxylation reaction. A. prescasitized lithographic plate having a byeophilie image- orming layer that ean be changed to hydrophobie within a US 2005/0028697 AI heated area can be formed by using the above-mentioned hydrophilic polymer (described in Japanese Patent Provi- sional Publication Nos. 2000-12272 and 2001-33949). The hydrophilic polymer is preferably cross-linked or used ia ‘combination With 2 rost-Hinked polymer to prepare a litho- ‘graph plate without development [0017] A presenstized lithographic plate comprises a fmage-forming layer containing thermally fusible polymer Particles and « hydophilic polymer (dseribed in Japanese Patent Provisional Publication No. 2002-26597). The plate |s imagewise heated to fuse the particles to form a hydro- phobic area as well a8 a not heated hydrophilic area in the Jmage-forming layer. [0018] When heating 4 hydrophobic polymer having a ‘Sulfonimido, disulfone ofa sulfonate ester group, the poly mer is changed to a hydrophilic polymer having a sulfo rou. A presensitized lithographic plate having a hydro- phobic image-forming layer that ean be changed to bydro- Philic within a heated area can be formed by using the shove-mentioned hykeophobie polymer (desribed in Ja nese Patent Provisional Publication Nos. 14 1998)-28262, 10(1998)-282644, 10(1998)-282646, 10(1998)-282672 and 11(1999)-309953}, The hydrophobic polymer is preferably ‘qoss-linked or used in combination with a cross-linked polymer fo prepare a lithographic plate without develop- ment, [0019] A conventional presensitized lithographic plate has colored image-forming layer to conlim an image aller processing the plate (after development) and before printing {enounting the plate on a press siachine), [0020] According 10 « CTP of CTC method, an image ‘cannot be confirmed before printing (a the stage of image wise exposure or heating), even if the image-forming layer Js colored. In the CTP of CTC method, the entire image- forming layer is sill colored fore mouating the plate on & press machine, since the lithographic printing is developed fon a press machine or processed without development, ‘Therefore, a prnting-owt agent is usually added to a pre seositized lithographic plate forthe CTP or CTC method, ‘The printing-out agent has a function of forming a visible mage atthe imagewise exposing or beating sage to confi the formed! image [0021] Aa example ofthe prating-out agent is 2 combi nation of a compound forming an acid, a base or «radical ‘when the compound is heated with another compound hhaving a color that can be changed when the compound is reacted with the acid, the base or the radical (described in Japanese Patent Provisional Publication ‘No, 11(999)- 277027). Another example of the printng-ou! agent is @ thermally decomposable dye that is decomposed ata tem- perature of not higher than 250" C.(deserihed in European Patent Application No, 1300241), SUMMARY OF THE INVENTION [0022] _An object of the present invention isto confirm an Jimage after imagewise exposing a presesitized lithographic plate to light and hefore mounting the plate om a press ‘machine. Feb. 10, 2005 [0023] The present invention provides. a lithograph Printing process which comprises the steps of: [0024] imagowise exposing to infrared light @ pre= sensitized lithographic plate which comprises @ hydrophilic support and a removable image-forming layer containing an infrared absorbing agent having the absorption maximum within an infrared region and a visible dye having the absoeption maxim Within a visible region to shift the absorption ma mum ofthe visible dye within the exposed area with ‘change of atleast 50 nm in the wavelength and a ‘change of at least 15 in color in tems of AE, andl to make the image-forming layer irremovable’ within the exposed areas [0025] removing the image-forming layer withia the unexposed are ofthe lithographic plate mounted on ‘8 eylinder of printing press; and then [0026] printing an image with the lithographic plate ‘mounted on the cylinder of the printing press. [0027] ‘The invention aso provides a lihographie printing process which comprises the steps of [0028] imagewise exposing to infrared light a pre= seasitzed lithographic plate which comprises a hhyerophilic support and an removable image-form= ing layer containing an infrared absorbing agent having the absompion maximum within an infrared region anda visible dye having the absorption mai- ‘mum within visible region lo shift the absorption ‘maximum of the visible dye within the exposed area ‘witha change of atleast 50/am in the wavelength and 2 change of at leas 15 in color in terms of AE, and to make the image-forming layer removable within the exposed areas [0029] removing the imsge-forming layer withia the ‘exposed area ofthe lithographic plate mounted on & ‘elinder of a printing press; and then [0030] printing an image with the lithographic plate mounted on the cylinder of the printing press [0031] |The invention further provides a ithographic pri Jing process which comprises the steps of [0032] imagewise exposing to infrared light @ pre= sensitized lithographic plate which comprises a sup- port and « hydrophilic immage-forming layer conta ing an infrared absorbing agent having the absorption maximum within an ineared region and 3 ‘sible dye having the absorption maximum within & Visible region to sift the absorption maximum ofthe Visible dye within the exposed area witha change of at least 50 om in the wavelengtb and a change of at least 15 in color in terms of AE, and to make the imagesforming layer bydropbobie within the ‘exposed area; and then [0033] printing an image with the lithographic plate ‘mounted on a cylinder of a printing press. [0034] ‘The invention furthermore provides a lithographic printing process whieh comprises the steps of: [0035] imagewise exposing to infrared light a pre= ‘seasitized lithographic plate which comprises 4 Sup- US 2005/0028697 AI port and a hydrophobic aiming an infrared a having. the absorption maximum within aa infrared region and a visible dye having the absorption maximum within a visible region to shit the absorption maximum of the visible dye within the exposed area with change of at Teast 50 nm in the wavelength and 4 change of at Teast 15 in color in terms of AE, and to make the image-forming layer hydrophilic within the exposed ae and thea [0036] printing an image withthe lithographic plate mounted on a cylinder of a printing pres. [0037] The invention sill furthermore provides a litho= traphie printing process which comprises the steps of; [0038] imagewise exposing to infrared light « pre- sensitized lthographie plate which comprises a sup- ‘ort, an ink-receiving layer and a hydrophilic layer in order, said ink-roceiving layer containing a visible ‘dye having the absorption maximum within a visible region, and sui ink-receiving layer or said yo ‘philic layer containing an infrared absorbing agent having the absorption maximum within an infrared rygion to shift te absorption maximum ofthe visible ‘ye within the exposed area wih a change of atleast 50/nm in the wavelength and a change of at Feast 15, incolor in terms of AE, and to abrade the hydrophilic layer within the exposed area; and then [0039] printing an image with the mounted on a eylinder of a pri thographie plate ing press. [0040] The visible dye is preferably not decomposed when the dye is imagewise exposed to iafeared light [0041] The absorption maximum of the visible dye is preferably shifed by an intramolecular eycization reaction ‘of the dye when the dye is imagewise exposed to infrared light [0042] The visible dye preferably is a nitrogen-contaning heterocyclic compound substituted with a 2S-dicyanophe- aylthio group. [0043] _In the present specification, the change in eolor in lerms of AE means 4 geometrical distance between Iwo Points (one of which isthe original color, and the other of Which isthe changed color) in an L.*a"b" color space (CIE 1976 L*a*b*-color space). Accordingly, the color change of AE is represented by the following formula: AbiLsaet (ALF [0044] AE preferably is at least 20. DETAILED DESCRIPTION OF THE INVENTION [0045] [Visible Dye Contained in Pate] [0046] In the present invention, at least one layer (prefer ably image-forming layer) of a presenstized lithographic plate contains a visible dye having the absorption maximum ‘within a isible region, When the visile dye is heated of ‘exposed to light, the absorption maximum of the dye is ‘shifted with a change of at least 5O nm inthe wavelength and {change of atleast 15 in color in terms of AE. The visible ‘dye funetions as a printing-out agent to confirm the formed oacane Feb. 10, 2005 ‘mage or the kind ofthe plate, The visible dye is preferably fot decomposed! when the dye is imagewise exposed t0 ingtared lig [0047] Examples of the dyes include potythiophene ‘compound, a combination ofa spiropyran compenunl with a ‘metal salt, combination of diazonium salt with a coupler and compound causing an intramolecular cyclization reac- tie, [0048] The polythiophene compound has a molecular Structure in which two ore more thiophene rings are com- bined by a single bond. The thiophene rings are preferably ‘combined at 2-position and S-position, A substituent group ce be attached to positions ofthe thiophene ring other the sulfur atom (I-position) and the positions at which the rings are combined with each other (3-positon or 4-postion when rings are combined at 2-positon and S-position). Examples fof the substituent groups include a halogen atom, an alc phatie group, an aromatic group, a heterocyclic group, —O=R and —S—R. R is an aliphatic group, an aromatic group or a heteroeyelie group. Two substitvent groups ean be combined to Form a ring, whichis condensed with the thiophene ring [0049] The polythiophene compound has a aumber aver age molecular weight preferably i the range of 3,000 10 150,000, more preferably in the range of 5,000 to 130,000, further preferably inthe range of 7.00 100,004, and most preferably in the range of 10,000 to 80,000 [0080] ‘The spiropyran compound bas a molecular strue- ture in which « pyran rng is combined with anor ring (an Aliphati ring or a heteroeyelie ring) by'a spo bons stil ‘nother sing (an aromatie ring, an aliphatic ring, a hetero- ‘elie rng) ean be condensed with the pyran ring othe ring ‘comiined with the pyran ring by the spso bon. The pyran ‘ing, the ring combined withthe pyran ring by he spire bond And the condensed ring eam have a substituent group. [0081] The spico bond is 2-position (2H-pyran sing) or ‘positon ($H-pyran ring) of the pyran ring. 2position is preferred to 4-positoa, The ring combined with the pyran Fingby the spo bond preferably isa heterocyclic rng tather than ae aliphatic cing. [0052] _The meta salt comprises a metal ion and a counter ‘anion. The metal ion ean form a colored complex with the bovesmentioned spitopyran compound. The term “colored” ‘means that the complex his absorption within a visible region that can be confirmed with aiked eyes. [0083] |The metal preferably i an alkaline earth metal (Ca, Sr, Bs, Ra), a metal of the chromium group (Cr, Mo, W), ‘etal of he iron group (Fe, Co, Ni, a metal ofthe copper group (Cu, Ag), a metal of the zine group Za, Cay He), & metal of the carbon group (Ge, Sa, Pb) or a metal of the niteogen group (As, Sb, Bi). [0088] ‘The counter anion preferably i an inorganie ion rather than an organic ion (cg. carboxylate in, sulfonate ‘on. The inorganic ion preferably isa halide fon, sulfate ion or nitrate ion, more preferably is @ halide ion, and most preferably is chloride on [0085] The spicopyran compound is separated from the ‘etal salt in the image-forming layer. For example, one of the spiropyran compound and the metal salt can be eon- US 2005/0028697 AI {ained in microcapsules which are dispersed in the image- forming layer, and the other can be placed outside the microcapsules. [0086] The diazoaium salt usualy is salt of an aromatic lazonium ion (cation) and a counter ion (anion). The ‘coupler usually isan aromatic oxo compound (phenol), a0 aromatic amine of an active methylene compound, [0087] The reaction of the diazonivm salt with the aro= ‘matic oxo compound is illustrated below. [0088] In the formula, Ar‘ is a monovalent aromatic group; Ar isa divalent aromatic group; and X is an anion. [0059] The hydroxyl (OH) cam be hanged 10 3 keto- form (=0). [0060] The aromatic groups include an aromatic tetero~ ‘eyelic group as well as an aromatic hydrocarbon group. The Aromatic group ean have a substituent group. [0061] The reaction of the diazonium salt with the a1o- ‘matic amine i illustrated below. [0062] 19 the formula, Act is a monovalent aromatic pup Ar isa divalent aromatic groups es hydrogen or 8 monovalent aliphatic group: and X isa aon. mats seNX lA NR [0063] The aromatic groups include an aromatic hetero ‘lic group as well as an aromatic bydeocachon group. [0064] The aromatic group and the aliphatic group ean have a substituent group, [0065] The reaction of the diazonium salt with the active tan coop dasa Mogg artes (045 pe foal, om si fo at's daon hoa pore cata Zi tgs Rn yoga Sect Sade 100 [0067] The aromatic groups include an aromatic tetewo~ ‘eyelic group as well as an aromatic hydrocazhon group. [0068] The aromatic group and the aliphatic group can have 4 substituent group. Two or more substituent groups ‘can be combined to form an aliphatic ring (e-2, eyelopen- ‘ane ring, cyclohexane ring) or an aromatic ring (€2 benzene ring), [0069] The diazonium sat is separated from the coupler in the image-forming layer. For example, one ofthe dazonium salt and the coupler can be contained in microcapsules whieh are dispersed in the image-forming layer, and the ‘ther eau be placed outside the microcapsules. [0070] The visible dye preferably is a compound easing an intramolecular eyeization reaction. [0071] The absorption maximum of the visible dye is preferably shifted by an intramolecular eyelization action Df the dye when the dye is imagewise exposed to infrared Tigh Feb. 10, 2005 [0072] hbeteroeyelic compound substitute! with ylthio group. [0073] ‘The nitrogen-containing heteroeyelie ring prefer ably i a five-membered ring. The nitrogea-conlaning b eroeyelic ring preferably i an unsaturated ring, more prel- erably isan unsaturated ring having two unsaturated bonds. ‘One of the two neighboring atoms of the nitrogen atom in the ring preferably is carbon atom, The 23-dicyanophe- nylthio group is preferably combined to the neighboring chon stom, The otbeetheee atoms other than the above: ‘mentioned nitrogen and carbon atoms preferably are niteo- gen and carbon atoms, A substituent group ea be attached {o the carbon atom. Two substituent group attached t0 adjacent two carbon atoms can be combined to form benzene ring or a six-membered alipitic ring. In other words, a benzene ring ora sixmembered aliphatic ring € be condensed with the aitrogen-containing heterocyclic ring, [0074] A substituent group ean be attached w 4 S- of ‘-posiiton af the benzene ring contained in the 2.3-dicy- nophenylihio group, [0075] ‘The nitrogen-containing heterotic rng, the eon- ‘dense benzene ring, the condensed six-memnered alpha ring and the benzene ting contained in the 2,3-dieyanophe- fylihio group can have a substituent group, as is described above. Examples ofthe substituent groups include a halogen atom, cyano, ait, hydroxyl, mereapto, formyl, carboxsl, Amin, carbamoyl, an aliphatic group, an aromatic group, @ heterocyclic group, —O—R, SR, —CO—R, —CO— O-R, NHR, NR), —CO-NIR, —CO— N(R). R is an aliphatic group, an aromatic group or a heterocyclic group. [0076] In the present specication, the aliphatic group ‘means an alkyl group, a subsliuted alkyl group, an alkenyl ‘group, substituted alkenyl group, am alkynyl group or @ Substituted alkynyl group. The aliphatic roup preferably is the alkyl group, the substiuted alkyl group, the alkenyl group or the substituted alkenyl group, and more preferably Js the alkyl group, the substituted alkyl group. [0077] ‘The alipbatie group can have a cyeic or branched structue. The aliphatic wroup preferably fas 1 to 100 earbon atoms, more preferably bas 1 0 50 carbon atoms, further preferably has | to 30 carbon atoms, furthermore preferably bas 1 to 20 eabon atoms, ancl most preferably bas 110 15 cachon atoms, The visible dye preferably isa nittogen-containing 2dicyanophe= [0078] _ Examples ofthe substiment groups ofthe aliphatic group (the substituted alkyl group, the substituted alkenyl ‘group or the substitued alkynyl group) include a halogen atom, cyano, nitro, hydroxyl, mereaplo, formyl, carboxsl, amino, eubamoyl, suo, soamoyl, an aromatic group, 3 bbeterocyelie group, OR, SR, —CO—R, SO. R, —0—CO-R, —CO—O-R, —NH_R, NR) NH COR,” —CO—NI-R, —CO-N(—I —0-S0;-R, $0.0 R, NSO. R, Si NHAR, —S0,—N(—R),. R'is an aliphatic frou, aromatic group or a heteroeyeli group. [0079] In the present specification, the aromatic eroup means an aryl group of a substitued aryl group. The aryl group and the aryl moiety of the substituted aryl group preferably is phenyl or naphthyl, and more preterably is phenyl US 2005/0028697 AI [0080] Examples of the substituent groups ofthe aromatic group (the substituted aryl group) include an aliphatic group Jn addition to the substituent groups of te aliphatic gsoup. [0081] In the present specification, the heterocyclic group) ‘means « non-substituted heteroeelic group oa substituted heterocyclic group. The heteroeyclc ring of the heterocyclic group preferably i four, five, six or seven-membered ring, ‘more preferably is five or sixemembered ring. The hetero atom ofthe heterocyclic ring preferably is nitrogen, oxygen ‘or sulfur. Another heterocyclic rng, ao aliphatic ring oF a0 somatic ring can be condensed with the beteroeycic ring. [0082] Examples ofthe substituent groups of the heteno= ‘eyelic group include oxo (=O), thio (=) and imino (NH. ‘wherein R is an aliphatic group, an aromatic rou or a heterocyclic group) in addition to the substituent 1oups of the aromatie group. [0083] The aitroges-containing heteroeyelie compound ‘Substituted with a 2,3-dieyanophenylthio group is disclosed in Japanese Patent Provisional Publication No. 7(1995)- 2874, [0084] Examples of the nitrogen-containing heteroeyelie ‘compounds substituted with a2,3-dieyanophenylthio group fre shown below. [0085] (1) 2-2.3-dicysnophenylthio)imidazole [0086] (2) 2-2.3-dicyanophenylthio)4.5-dimethyti azole [0087) male [0088] (4) 2-2.3

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