Developing solution for lithographic printing plate precursor and method for making lithographic printing plate

Abstract

An alkaline developing solution for development of a presensitized plate for use in making a lithographic printing plate, which developing solution comprises a polyoxyalkylene adduct of alkylene diamine, a polyoxyalkylene compound having an acid radical, and an anionic surfactant; a method for making a lithographic printing plate comprising the steps of: light-exposing a presensitized plate for use in making a lithographic printing plate; and developing the light-exposed plate with an alkaline developing solution comprising a polyoxyalkylene adduct of alkylene diamine, a polyoxyalkylene compound having an acid radical, and an anionic surfactant.

1 . An alkaline developing solution for development of a presensitized plate for use in making a lithographic printing plate, which developing solution comprises a polyoxyalkylene adduct of alkylene diamine, a polyoxyalkylene compound having an acid radical, and an anionic surfactant.  
     
     
         2 . The alkaline developing solution of  claim 1  wherein the polyoxyalkylene adduct of alkylene diamine is selected from the group consisting of the compounds represented by the following formula (I):  
       
         
           
           
               
               
           
         
       
       wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7  and R 8  may be the same or different, and each independently represents H or —CH 3 , and R 9 , R 10 , R 11  and R 12  may be the same or different, and each independently represents H, —CH 3 , —COR 13  or —CONHR 14  (wherein each of R 13  and R 14  represents an alkyl, aryl, alkenyl or alkynyl group), a represents an integer of from 2 to 12, b, c, d, e, f, g, h and i may be the same or different, and each independently represents 0 or an integer of from 1 to 300, and (b+f)(c+g)(d+h)(e+i)≠0.  
     
     
         3 . The alkaline developing solution of  claim 1  which comprises the polyoxyalkylene adduct of alkylene diamine having a molecular weight of not more than 2000 and the polyoxyalkylene adduct of alkylene diamine having a molecular weight of not less than 3000.  
     
     
         4 . The alkaline developing solution of  claim 3  which comprises the polyoxyalkylene adduct of alkylene diamine having a molecular weight of not more than 2000 in the amount of 5 to 200 times that of the polyoxyalkylene adduct of alkylene diamine having a molecular weight of not less than 3000, by weight.  
     
     
         5 . The alkaline developing solution of  claim 1  wherein the polyoxyalkylene compound having an acid radical is selected from the group consisting of the compounds represented by the following general formula (II): 
         X—(CH 2 CH 2 O) n —Y  (II) 
       wherein X represents a group selected from R—O—, R—C(O)—O— and R—C(O)—NH— (wherein R represents an alkyl group, an alkenyl group, an aromatic hydrocarbon group or a heteroaromatic group), n represents an integer of from 4 to 30, and Y represents a phosphate residue or a carboxylic acid residue.  
     
     
         6 . The alkaline developing solution of  claim 5  wherein the polyoxyalkylene compound having an acid radical is selected from the group consisting of the compounds represented by the following formula (III):  
       
         
           
           
               
               
           
         
       
       wherein X represents a group selected from R—O—, R—C(O)—O— and R—C(O)—NH— (wherein R represents an alkyl group, an alkenyl group, an aromatic hydrocarbon group or a heteroaromatic group), n represents an integer of from 4 to 30, and M represents independently a hydrogen atom, an alkali metal atom or an ammonium.  
     
     
         7 . The alkaline developing solution of  claim 5  wherein the polyoxyalkylene compound having an acid radical is selected from the group consisting of the compounds represented by the following formula (IV): 
         X—(CH 2 CH 2 O) n —C p H 2p —COOM  (IV) 
       wherein X represents a group selected from R—O—, R—C(O)—O— and R—C(O)—NH— (wherein R represents an alkyl group, an alkenyl group, an aromatic hydrocarbon group or a heteroaromatic group), n represents an integer of from 4 to 30, p represents zero or an integer of from 1 to 30, and M represents independently a hydrogen atom, an alkali metal atom or an ammonium.  
     
     
         8 . The alkaline developing solution of  claim 1  wherein the anionic surfactant is selected from the group consisting of fatty alcohol sulfuric ester salts, alkyl aryl sulfonic acid salts, sulfuric esters of fatty alcohol having carbon atoms of from 8 to 22, aliphatic alcohol phosphoric ester salts, alkyl amide sulfonic acid salts, sulfonic acid salts of bibasic aliphatic ester, hydroxyalkane sulfonic acid salts, alkane sulfonic acid salts, alkyl diphenylether sulfonic acid salts, diphenylether disulfonic acid salts, dialkyl sulfosuccinate salts, olefin sulfonic acid salts, linear alkyl benzene sulfonic acid salts, branched alkyl benzene sulfonic acid salts, alkyl naphthalene sulfonic acid salts, alkyl phenoxy polyoxyethylene propyl sufonic acid salts, polyoxyethylene alkyl sulfophenylether salts, disodium N-alkyl sulfosuccinate monoamides, and petroleum sulfonic acid salts.  
     
     
         9 . The alkaline developing solution of  claim 1  which comprises the polyoxyalkylene adduct of alkylene diamine in the amount of from 0.001 to 10% by weight.  
     
     
         10 . The alkaline developing solution of  claim 1  which comprises the polyoxyalkylene compound having an acid radical in the amount of from 0.01 to 20% by weight.  
     
     
         11 . The alkaline developing solution of  claim 1  which comprises the anionic surfactant in the amount of from 0.001 to 20% by weight.  
     
     
         12 . A method for making a lithographic printing plate comprising the steps of: light-exposing a presensitized plate for use in making a lithographic printing plate; and developing the light-exposed plate with an alkaline developing solution comprising a polyoxyalkylene adduct of alkylene diamine, a polyoxyalkylene compound having an acid radical, and an anionic surfactant.  
     
     
         13 . The method for making a lithographic printing plate of  claim 12  comprising the steps of: light-exposing to infrared radiation, a heat-sensitive presensitized plate of a positive-working mode for use in making a lithographic printing plate, said presensitized plate comprising a substrate and an image recording layer which is formed thereon and comprises a novolak resin containing xylenol as a monomer component and an infrared absorbing dye; and developing the light-exposed plate with an alkaline developing solution comprising a polyoxyalkylene adduct of alkylene diamine, a polyoxyalkylene compound having an acid radical, and an anionic surfactant.  
     
     
         14 . The method of  claim 13 , wherein the xylenol used in the novolak resin is at least one selected from the group consisting of 3,5-xylenol, 2,3-xylenol, 2,5-xylenol and 3,4-xylenol.  
     
     
         15 . The method of  claim 13 , wherein the novolak resin containing xylenol as a monomer component has a weight-average molecular weight of 500 to 10,000.  
     
     
         16 . The method for making a lithographic printing plate of  claim 12  wherein the polyoxyalkylene adduct of alkylene diamine in the alkaline developing solution is selected from the group consisting of the compounds represented by the following formula (I):  
       
         
           
           
               
               
           
         
       
       wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7  and R 8  may be the same or different, and each independently represents H or —CH 3 , and R 9 , R 10 , R 11  and R 12  may be the same or different, and each independently represents H, —CH 3 , —COR 13  or —CONHR 14  (wherein each of R 13  and R 14  represents an alkyl, aryl, alkenyl or alkynyl group), a represents an integer of from 2 to 12, b, c, d, e, f, g, h and i may be the same or different, and each independently represents 0 or an integer of from 1 to 300, and (b+f)(c+g)(d+h)(e+i)≈0.  
     
     
         17 . The method for making a lithographic printing plate of  claim 12  wherein the polyoxyalkylene compound having an acid radical in the alkaline developing solution is selected from the group consisting of the compounds represented by the following general formula (II): 
         X—(CH 2 CH 2 O) n —Y  (II) 
       wherein X represents a group selected from R—O—, R—C(O)—O— and R—C(O)—NH— (wherein R represents an alkyl group, an alkenyl group, an aromatic hydrocarbon group or a heteroaromatic group), n represents an integer of from 4 to 30, and Y represents a phosphate residue or a carboxylic acid residue.  
     
     
         18 . The method for making a lithographic printing plate of  claim 17  wherein the polyoxyalkylene compound having an acid radical is selected from the group consisting of the compounds represented by the following formula (III):  
       
         
           
           
               
               
           
         
       
       wherein X represents a group selected from R—O—, R—C(O)—O— and R—C(O)—NH— (wherein R represents an alkyl group, an alkenyl group, an aromatic hydrocarbon group or a heteroaromatic group), n represents an integer of from 4 to 30, and M represents independently a hydrogen atom, an alkali metal atom or an ammonium.  
     
     
         19 . The method for making a lithographic printing plate of  claim 17  wherein the polyoxyalkylene compound having an acid radical is selected from the group consisting of the compounds represented by the following formula (IV): 
         X—(CH 2 CH 2 O) n —C p H 2p —COOM  (IV) 
       wherein X represents a group selected from R—O—, R—C(O)—O— and R—C(O)—NH— (wherein R represents an alkyl group, an alkenyl group, an aromatic hydrocarbon group or a heteroaromatic group), n represents an integer of from 4 to 30, p represents zero or an integer of from 1 to 30, and M represents independently a hydrogen atom, an alkali metal atom or an ammonium.  
     
     
         20 . The method for making a lithographic printing plate of  claim 12  wherein the anionic surfactant is selected from the group consisting of fatty alcohol sulfuric ester salts, alkyl aryl sulfonic acid salts, sulfuric esters of fatty alcohol having carbon atoms of from 8 to 22, aliphatic alcohol phosphoric ester salts, alkyl amide sulfonic acid salts, sulfonic acid salts of bibasic aliphatic ester, hydroxyalkane sulfonic acid salts, alkane sulfonic acid salts, alkyl diphenylether sulfonic acid salts, diphenylether disulfonic acid salts, dialkyl sulfosuccinate salts, olefin sulfonic acid salts, linear alkyl benzene sulfonic acid salts, branched alkyl benzene sulfonic acid salts, alkyl naphthalene sulfonic acid salts, alkyl phenoxy polyoxyethylene propyl sufonic acid salts, polyoxyethylene alkyl sulfophenylether salts, disodium N-alkyl sulfosuccinate monoamides, and petroleum sulfonic acid salts.